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All Or Nothing At All:
A Life of Frank Sinatra

Chapter 5

Among the noteworthy novels published in the USA in 1951 were The Catcher In The Rye (J.D. Salinger), The Caine Mutiny (a Pulitzer Prize for Herman Wouk), and From Here To Eternity (James Jones). Whatever their relative literary merits, all three were definitely post-war fictions: the Catcher, schoolboy Holden Caulfield, sought his own identity in a world that had become very confusing; Mutiny was about a paranoid super-patriot in the U.S. Navy, while Jones's novel seemed perhaps the most controversial of all at the time. With victory in the Second World War still very recent, the book was about bored and sexually frustrated military personnel in Pearl Harbor at the time of the Japanese attack: it not only featured sex, but adulterous sex at that, and few of the characters seemed to have anything heroic about them. Yet we knew that these ordinary people went on to win a war against the Japanese Empire.

One of the characters in From Here To Eternity dies before the end, missing out on the victory. Angelo Maggio is a skinny little guy, noisy and irritating, but full of energy and with a good heart; he is beaten to death by a bully because his pride will not allow him to submit. Frank Sinatra had campaigned in the past for non-singing roles, but Ronald Reagan played the returning serviceman in John Loves Mary, and John Derek was the slum kid on trial for murder in Knock On Any Door (playing opposite Sinatra's friend Humphrey Bogart); the role Sinatra did get was one he'd have been better off without: the priest in Miracle Of The Bells. But he knew beyond doubt that landing the role of Maggio would be the sort of timing that occurs once in an actor's career, if he's lucky. As he put it, 'I knew Maggio. I went to high school with him in Hoboken.' He had to do anything he could to get that role.

There were a couple of factors in his favor. For all their problems and notoriety, Sinatra and his bride were well-liked by other show folk; if his career seemed to be in trouble, her box-office success was increasing, and she went to work pulling strings on his behalf. Columbia Pictures had bought the rights to the novel, and both Frank and Ava were acquainted with the boss there, Harry Cohn. Ava went to see Cohn's wife, Joan, to beg for the part for her husband, while according to Arnold Shaw, Cohn actually owed Frank a favor. In 1949 Columbia had made a comedy with Lucille Ball, Miss Grant Takes Richmond, and Frank was booked to appear at the Capitol Theater; as a favor to Cohn, Frank requested that picture to be shown on his bill, so that it got a Broadway première. (Subsequently, according to Shaw, Sinatra fell ill before the engagement was completed and had to spend a few days in bed; Cohn kept him company while he recovered, but was then worried about his image as a tough bastard: he warned Sinatra, 'You tell anyone, and I'll kill you!')

But landing the part was more difficult than pulling strings. Sinatra looked like box office poison. Meet Danny Wilson had flopped (whether it was any good or not) and Universal had not exercised its option to use him in another film. He had ruined his own deal with the CBS television network, refusing to rehearse and making problems on the set, so that the sponsors had cancelled after 13 weeks instead of three years. He tried to keep Ava from going to Africa to make Snows Of Kilimanjaro, and threw a tantrum when the shooting lasted longer than ten days. (Incredibly, he even tried to blame the press for the failure of his marriage to Nancy.) The miracle is how anybody ever allowed him to make another film; but he knew his career was on the line, and he was not above begging. He pestered Buddy Adler, the producer, for a screen test for the part of Maggio. He went to see Cohn, and offered to do the part for $1000 a week for a few weeks of shooting, though he had been getting $150,000 per film. Cohn's wife put her case for Sinatra, and even Jonie Taps, Tommy Dorsey's favorite song-plugger, who was now a vice-president at Columbia, pushed for a screen test. Finally Cohn told Frank he might be considered for a test, and then it was a matter of seemingly endless waiting.

Sinatra's last recording date at Columbia Records (no connection with Columbia Pictures) was in September 1952; he was over $100,000 in debt for taxes, and somebody joked that the government would either put him in jail or recognize him as a foreign power. Columbia Records may have lent him the money to pay his taxes, because when he left there he was over $100,000 in debt to them. At the beginning of November, his career at rock bottom, he flew with Ava to Kenya, where shooting for Mogambo was to begin. They celebrated their first wedding anniversary on the Stratocruiser; he gave her a flashy diamond ring, and sent her the bill. (Later she cracked, 'It was quite an occasion for me. I had been married twice but never for a whole year.')

The film set, in the Kenyan bush, was hot and dusty, and Ava did not get along at first with director John Ford. When the British governor of Kenya and his wife visited the set, Ford asked Ava what she saw in her 'one-hundred-and-twenty-pound runt' of a husband, and she replied, 'Well, there's only ten pounds of Frank but there's one hundred and ten pounds of cock.' Ford was aghast, but the governor and his wife roared with laughter, and that was the beginning of Ford's respect for Ava, reinforced by her professionalism as an actress. But she did not feel well (it turned out she was pregnant), and Sinatra was bored and restless.

Sinatra went back to New York for a club date. His reviews were good, but a reporter who talked to him found him 'a restless unhappy man in his middle thirties who wants very much to re-establish himself and who wants to be an actor, not just a singer playing himself.' Back in Africa he finally received a telegram offering him a screen test for the part of Maggio. He jumped on the first plane to Hollywood (Ava paid for all the plane rides, too) and Adler was astonished to see him 36 hours after sending the telegram. When the test was arranged, Adler handed him a script, but he had read the part so many times he didn't need it. It was the last test of the day and Adler wasn't going to bother to attend, but then he got a call from the director, Fred Zinneman: 'You'd better come down here. You'll see something unbelievable.' Zinneman had already filmed the test, and made Sinatra do another take without any film in the camera; this time even Adler was impressed. But Cohn was out of town, and anyway they were also testing Eli Wallach, a first-rate Broadway actor who had never made a film. Sinatra flew to Africa yet again, knowing the he'd done a good test but worried that he'd lose the part to Wallach, and Ava and Clark Gable did their best to cheer him up.

They also tested a comedian, Harvey Lembeck, but he wasn't right. Wallach was the best of the three, everyone agreed, but then the money came through for the production of Tennessee Williams's new play, El Camino Real, to be directed by Elia Kazan, and there was no way Wallach was going to turn that down; he went back to Broadway (the play flopped, and Wallach made his first film a few years later). But Wallach's test for the part of Maggio was so good that Cohn, Adler, Zinneman and scriptwriter Dan Taradash couldn't make up their minds whether to go with Sinatra or test somebody else, so Cohn asked his wife for her opinion. She agreed that Wallach was a great actor, but there was no doubt in her mind. 'He's not skinny, and he's not pathetic, and he's not Italian. Frank is just Maggio to me.' And the picture was going to be expensive, with Burt Lancaster, Deborah Kerr, Donna Reed and Montgomery Clift already cast, and location shooting in Hawaii required, and Cohn could have Sinatra cheap. So Sinatra was offered the part of Maggio for $8,000.

[There has always been talk about the mob being involved: James Kaplan, in his definitive biography of Sinatra (two volumes, almost 1800 pages including the indexes), mentions Sidney Korshak in passing; Korshak (1907-96) began as a street punk in Chicago and became a mobbed-up lawyer in Hollywood, who probably helped Sinatra out of a tight spot or two. Then the ace investigative reporter Seymour Hersh, in his marvelous memoir Reporter (2018), wrote about his series of articles exposing Korshak in 1976: 'Korshak could stop a Teamsters strike on a Hollywood film set with a telephone call and had enough power to save Frank Sinatra's career by ordering that he be cast for a major role in From Here To Eternity.' So maybe Hersh uncovered the answer. But there were plenty of reasons to cast Sinatra.]

He knew this was a turning point in his career, and now all his arrogance came back. His relationship with Ava was always tempestuous, but it was most tolerable when he was down and he really needed her; the rest of the time he was unbearable and sometimes she hated him. He left Africa again, and a few days later, at the end of November, Ava flew to London for an abortion, making two of his children she'd aborted that year (there had been one in May). She already knew a thing or two about being unhappily married, and she must have felt that having children of this marriage would be a mistake, as well as a bad career move. She was as complicated and as temperamental as he was, but she had more self-knowledge. As Arnold Shaw put it, referring to one of his bouts of swearing loudly at newsmen in public,

It was at moments like these that the man she loved -- attentive and affectionate as Mickey Rooney had not been, outgoing and tender as Artie Shaw had not been -- reminded her of all the roughnecks she had ever known, from the vulgar tobacco workers and poor white trash of the North Carolina hamlet where she had been born to all the sharpies and wise guys of the Hollywood Hills.

He came back to Africa for Christmas, and they went to Paris together for a few days in January, but they squabbled constantly. He thought that everything would be all right as soon as he had finished shooting his part in From Here To Eternity, but the love of his life was hanging by a thread that would soon break.

In March and April 1953 the forty or so days of shooting took place. Montgomery Clift was a drunk and a drug addict, but he was also a very good and serious actor; Sinatra had never seen anyone work so hard on a film set, but the work habits didn't rub off. Nevertheless he learned a lot. He and Clift and James Jones spent a lot of time getting drunk together and crying on each others' shoulders. And at the same time, the other, even more important turn-up in Sinatra's fortunes was taking place.

His old friend Manie Sacks had tried to get him a recording contract at RCA, but the A&R department there didn't want him; the William Morris Agency had taken him on at the end of 1952, but couldn't sell him. Finally Capitol Records offered a contract. Capitol was then a ten-year-old independent label, so successful that it was virtually a major, the only important label located on the West Coast; such Capitol artists as Les Paul and Mary Ford, Nat Cole and Kay Starr were having hit after hit. Furthermore, the label was hip and cared about music, having been formed by two songwriters, Johnny Mercer and Buddy DeSylva, and a major West Coast record retailer, Glenn Wallichs. In the early days they had cramped offices upstairs from Wallichs's record store, and Paul Weston, one of Capitol's first music directors, has a great many stories about the joie de vivre there. Weston, Mercer and the others would be listening to test pressings of records they'd just made, and Wallichs, the businessman, would be on the telephone, saying, 'Hey, turn it down, you guys; I'm trying to set up a distributor in Philadelphia.' The others would say, 'Aw, forget about that; come and listen to this!' In the first half of the 1950s Capitol recorded the big jazz bands of Benny Goodman, Woody Herman, Stan Kenton and Duke Ellington at a time when such bands did not seem to have a future and almost never had hit records; and furthermore, Capitol's technology was first-rate: during this period its recordings were as good as any in the world.

Producer and music journalist Dave Dexter wanted Sinatra at Capitol, knowing what a fine singer he was and that only the right combination of songs and arrangements was needed. Even so, apart from Dexter, it took the influence of Axel Stordahl's wife, June Hutton, then a Capitol recording artist, and pianist Dick Jones, a Capitol producer who had played at the Sinatra-Gardner wedding, to bring off a deal. And Capitol wasn't taking any chances: the initial contract was for one year only, no advance was paid, and Sinatra would be responsible for the cost of the recording sessions. Having signed with Capitol, Sinatra angrily rejected Dexter as his producer, because Dexter had once made a mildly disparaging remark about one of Sinatra's Columbia disks in down beat magazine. (Dexter eventually co-produced a Sinatra session, and never stopped admiring him as an artist, but many years later still referred to him privately as an 'evil, foul-mouthed bastard'.) So it was former drummer Voyle Gilmore who supervised the Sinatra sessions in the early Capitol years.

Gilmore was not particularly a Sinatra fan at the time, but probably knew from the start that he wanted to get away from the lushness of the Stordahl-Sinatra classics. In Sinatra's last couple of years at Columbia he had used several other arrangers and conductors as well as Stordahl, but used Stordahl on his first Capitol session, early in April 1953, recording four tunes. 'Lean Baby' (arranged by Heini Beau) and 'I'm Walking Behind You' were issued back-to-back; the former was a nice riff by Billy May with dopey words added, and the latter was a new ballad from England by Billy Reid. Compiling the Billboard pop charts of the period (Best Sellers, Juke Box and Disk Jockey), the ballad was a top ten in May, but Eddie Fisher's recording of the same song was number one for seven weeks.

Even so, a hit with Sinatra first time out was not bad going, and by then there had already been two more recording sessions. The issue of Stordahl was soon resolved: with a pleasant boyish tenor voice, Eddie Fisher wasn't half the musician Sinatra was, but with five top ten hits in a little over six months, he was the hottest artist in the business, and Stordahl accepted an offer to conduct Fisher's new TV show. Sinatra then nominated Billy May to arrange and conduct his next sessions, but May had to cancel because he was on tour with his own band; and so it was that Gilmore brought together one of the greatest teams in the history of popular music. From the sessions of late April and early May, Billy May got label credit for 'South Of The Border', but it was the ex-Dorsey arranger Nelson Riddle who had done it in May's style, with a lasciviously slurping reed section. Of the eight tracks recorded, three made it into the top 20, but something new was happening. One of the nicest was a new ballad called 'My One And Only Love', which didn't chart at all, but it didn't matter; and the tune on the other side of the single changed a lot of people's listening habits.

In mid-1953 I was twelve years old, and crazy about music. I was interested in jazz, but there was none of that on the radio; I liked what we called 'popular instrumentals', like Percy Faith's 'Delicado', because I liked the sound of an orchestra (I was looking for classical music, though I didn't know it yet). I liked Fisher and Jo Stafford and the others well enough, but I didn't have much money to buy records anyway, and I was bored half to death, because I couldn't find enough music to listen to: in those days there were many fewer radio stations than now, and no FM at all outside big cities. In July I was hanging around in an ice cream parlor in the resort town of Lake Geneva, Wisconsin; a radio was playing, and suddenly there was the most amazing brass fanfare, some interesting harmony from the reeds, and then Sinatra began singing, slowly at first, but expectantly, a familiar old song:

I've got the world on a string...
Sittin' on a rainbow...
Got the string around my fi-i-inger...

(stringing out the word 'finger', teasing me, though I didn't know what I was waiting for) and then, Pow! the band came in swinging, two-beat style, perhaps influenced by Sy Oliver, and everything was all right: every note in the right place, the best kind of playing because it sounded like it was being improvised on the spot. I knew who Frank Sinatra was; I had heard him on the radio since I was little. He was somebody my mother liked, and the press didn't. He was supposed to be a loser, always in some kind of trouble, but now I knew that that must have been wrong. Sinatra has always cared what people say about him, even when it's his own fault, to the point of trying to stop people from writing about him; but with regard to his music, he said that, whatever people say about him, nothing matters except that when he is singing he is honest. I knew that, listening to his new record. He really did have the world on a string, because he said so, and that was that. Feeling sorry for myself the way only a frustrated poverty-stricken almost-teenager can feel, I nevertheless felt better for the rest of that muggy July day, having heard that record on the radio, and nearly 60 years later I still feel better every time I hear it.

When Frank Sinatra came out of the eight weeks of work on From Here To Eternity a new man, knowing he had done well in the best part he'd ever had, he also knew he was making good records.

In May he and Ava left on a tour of Europe; he had gigs booked in several cities, and she was shooting a film in England. They quarreled constantly. The picture, Knights Of The Round Table, was a turkey, with Robert Taylor, who should have played one of the horses; Ivanhoe, also with Taylor, had been a hit the year before, and the studio was trying to cash in. Such costume dramas showed a profit in those years, but Ava must have known that the work had little value, while Sinatra knew that he was back on top again. Journalists were impressed with the new sparkle in his eye, and he got good reviews in England, but his domestic life actually got worse. 'We were happy when he was on the skids,' Ava said in August, but the truth was that they could never get along. He was insanely jealous when she was out of sight, yet he could not resist being seen and even photographed with other beautiful women, to make her jealous. Their quarrels were so violent that the police sometimes had to be called, and neither could be the first to make a conciliatory move. They behaved like children, yet they must have been changed by their passion. They were each the other's greatest love, and if they could not stay together, at least they had clashed memorably, doing their best to conquer each other. Their marriage did not last until its second anniversary in November, though he chased her other around the world for a while longer; they were not divorced until 1957. But when they finally gave up the game, they each had some new, harder steel in their souls; having loved like that and lost is almost as good as having the world on a string. Many years later, Little Nancy asked her father if he would leave Big Nancy for Ava again, if he could do it over; and he answered that he would not. But that was whistling in the dark. He had never had any choice.

On the last day of filming From Here To Eternity, Sinatra had disagreed with the others over how a scene should be done, and Harry Cohn was so angry he sent Sinatra away before he'd even seen the final rushes; but he knew he had a hit on his hands. Sinatra returned to the USA to find showbiz agog over the film and his part in it. It opened in August in New York; it was unheard of to launch a major film during the summer holidays, but Cohn knew he didn't have to worry. It did record business at the Capitol Theater on Broadway, and Richard Watts wrote about Sinatra's performance in the New York Post, 'Instead of exploiting a personality, he proves he is an actor by playing the luckless Maggio with a kind of doomed gaiety that is both real and immensely touching.' A film guide now describes it as a 'cleaned up and streamlined version of a bestseller'; David Thompson, one of today's most interesting film critics, feels that the novel's robustness scared off the director -- he describes Zinneman as 'middlebrow' -- and that Sinatra's performance is superficial. Today's viewers can make up their own minds; the cultural artifacts of the past may look different each time we see them. But in 1953 the picture and all its performances were dynamite. The poster photo of Burt Lancaster and Deborah Kerr having an adulterous snog in the surf became a film industry icon; From Here To Eternity was nominated for twelve Oscars and won eight, the most any picture had won since Gone With The Wind before the war; and all this for a picture with no gimmicks: it had no wide screen, no 3-D process and it wasn't even in color. All it had was a good story, a good script and good acting. And among the Oscars was Best Supporting Performance (Male) for Frank Sinatra.

The night before the award ceremony, in March 1954, he had dinner with Nancy and the children. They gave him a little gold medal with St Genesius on one side (the patron saint of actors) and Oscar on the other. He was their Oscar, whether he won or not, and he knew it, but he had now reduced Big Nancy to the status of best friend; one can only try to imagine what she was feeling that evening. The next night his two oldest children accompanied him, and they had to sit through most of the awards: unlike nowadays, all the big ones came at the end. Some of the competition was stiff: other nominees for best supporting actor included Jack Palance for his demonic murdering gunfighter in Shane, and Robert Strauss for his scruffy, hilarious prisoner in Stalag 17. When Sinatra's win was announced, the ovation was one of the longest of the evening, because there's nothing Hollywood likes better than a comeback, and especially if it's a solid one: nobody voted for Sinatra because they felt sorry for him. Accepting the award he seemed to be at a loss for words, as though he really hadn't thought about what he would say: 'If I start thanking everybody I'll do a one-reeler,' was the best he could do.

Afterwards, he rang Nancy, and he rang his mother in New Jersey. Allegedly, he was overheard saying 'Yes Mama... No Mama...' over and over. Dolly had long since given up on Nancy, who didn't take any nonsense from her; she liked Ava (they no doubt admired each other's guts) and had engineered at least one reconciliation after a violent quarrel. But no matter who Sinatra was married to or separated from, he still needed his mother's approval. There was a telegram of congratulations from Ava. She had been nominated too, for her part in Mogambo, the only nomination she ever had; she hadn't won, but she certainly knew how important his win was, and that she deserved some reflected glory. He later joked about the Oscar: 'It was a dream that came true. It's quite a dream. I still have it three nights a week. I'd have it seven nights but I don't go to bed four nights a week.' But at the time, he was sharing a bachelor pad with Jule Styne, who often saw him sitting alone in a dimly lit room, surrounded by photos of Ava.

Already in February 1954, a month before the Oscar, a Sinatra record called 'Young At Heart' was a hit. The melody had been written by Johnny Richards in 1939 and called 'Moonbeam'; with new words by Carolyn Leigh, it was a song Sinatra didn't much care for, but four years earlier he had turned down 'Mona Lisa', which turned out to be an Oscar-winning song and a huge hit for Nat Cole, so this time he took somebody's advice, and 'Young At Heart' made no. 2 in the Billboard retail pop chart, his biggest hit in eight years. Meanwhile he'd been signed to do a picture called Pink Tights, co-starring with Marilyn Monroe, who never showed up; he spent some weeks cooling his heels on the set of a film that was never made. His pals Styne and Sammy Cahn had written some songs for that film, and were similarly sitting around doing nothing, when the studio needed a song in a hurry for a film that was finished but had only just acquired its final title: Three Coins In The Fountain. They wrote a soupy ballad in a couple of hours, and then needed a demo to send to New York: in a wonderful story which Cahn never tired of telling, he conned Sinatra into doing it. Thinking he was going to make a demo as a favor with Styne on piano, Sinatra walked onto a soundstage to be confronted with sixty musicians and conductor Lionel Newman on the podium, and that recording is said to be the one used in the soundtrack. Be that as it may, the song won an Oscar; the no. 1 hit version was by the Four Aces, a vocal quartet that yelled all their slow numbers with a shuffle beat, and all these years later I still dislike the song. Sinatra's Capitol studio version recorded with Riddle reached the top ten.

He continued having hits in the Billboard singles chart for over 25 years, but only nine more reached the top ten, and that didn't matter, because meanwhile something far more important and interesting was happening to the record business, something neither Mitch Miller nor Capitol Records nor Frank Sinatra could have anticipated. In 1947, when the long-playing record was introduced, Sinatra's biggest fans, the generation of the returning solidiers and their brides, were short of cash: some were going to college on the G.I. bill, and the rest were starting families. But by 1954 they were becoming more prosperous. Some of them still had their Sinatra 78s, but now they were buying albums, not singles. They were buying Frank Sinatra albums.

To put things in perspective, most of the number one albums in those days were film soundtracks: in 1954-5 the biggest sellers were the scores from The Student Prince and The Glenn Miller Story; in 1955 the only vocalists who had number one albums were Doris Day and Sammy Davis Jr, and Day's album was soundtrack-related (Love Me Or Leave Me). In 1956 album sales reached a new high; the number one albums included three soundtracks, a Broadway musical original cast album, and two albums each by Harry Belafonte and Elvis Presley: we were entering a new era. But between February 1954 and May 1957, Sinatra's first seven albums on Capitol, arranged and conducted by Nelson Riddle, all reached the top ten of the Billboard album chart; only This Is Sinatra!, a compilation of singles, did not reach the top five. In 1958 two Sinatra albums on Capitol spent a total of ten weeks at number one (each staying in the charts over 100 weeks), while a two-LP compilation on Columbia, The Frank Sinatra Story, reached number 12 (his debt to Columbia had been repaid quickly, and his royalties on that back catalog soon amounted to $50,000 a year).

The baby boom's orthodoxy is that album sales became more important than singles only in the 1960s, but this was never true. Long-playing records always made more money than singles, and at a time when more albums were being sold than ever before, Sinatra was beating the competition by a mile. In the 1954-7 period no other singer, not even Nat Cole, Perry Como or Bing Crosby, did as well; only Eddie Fisher had some hit albums. Back at Columbia, Mitch Miller's biggest artists, Frankie Laine, Guy Mitchell, Tony Bennett, Rosemary Clooney and Johnny Ray had no hit albums at all in this period; nor did Patti Page or Kay Starr or any of the other singles-sellers. Talk about a comeback: while Miller was having hit singles with noisy, witless junk and banjo-ridden 19th-century campfire songs ('The Yellow Rose Of Texas'), Sinatra was reckoned to be the biggest-selling album artist of all by a wide margin during 1955-59, and for the entire decade of the 1960s he was beaten only by the Beatles.

All this emphasis on chart comparisons would be merely vulgar and pointless today, but for the mid-1950s it is revealing. The markets for singles and albums had diverged completely; even the recording sessions were usually different. Albums were a lot more expensive then, relatively speaking, and they were not impulse purchases, so the music that was made for them had to be of more lasting value. Sinatra was making records for grownups, people who bought records carefully and kept them and continued playing them for many years, and replaced them when they wore out: records, in other words, that are still selling decades later. And it is not too much to say that Sinatra's enduring reputation as the greatest pop singer of the century could rest on these 1954-7 albums with Nelson Riddle.

Songs For Young Lovers and Swing Easy were both ten-inch LPs with four songs on each side, and both reached no. 3 in 1954; later they had tracks added and were reissued in the twelve-inch format with six songs on each side. That worked well enough, but the original albums had been well planned, so finally the original running orders were restored on one twelve-inch LP with eight songs on each side. Because of the way song royalties were paid by the USA record industry, albums with seven or eight songs on each side cost more than those with only six, but people bought Sinatra's anyway. The romantic Songs For Young Lovers began with 'My Funny Valentine', a song Sinatra had practically made his own, and was a nicely paced album, with two uptempo tracks ('A Foggy Day' at number three, and 'I Get A Kick Out Of You' halfway through), ending with 'Violets For Your Furs'. The lineup of the 'chamber group' Columbia sessions was revived, the band including just two horns, a rhythm section and four strings, but this time the four strings were the Hollywood String Quartet: Felix Slatkin and Paul Shure, violins, Paul Robyn, viola, and Eleanor Aller Slatkin, cello. With Capitol's first-rate sound quality and a group that was also making legendary chamber-music recordings for Capitol's classical division, the result was pure class.

And when you turned the twelve-incher over, you got a different set: the band on Swing Easy was a fourteen-piece swing band that never got in the way, because Riddle's arrangements abolished the artificial distance between the ballad and the swinger. If it had seemed in the 1940s that a pop record had to be either a soupy ballad or a novelty, now Sinatra and Riddle demonstrated that ballads with strings didn't have to be soupy, and that love songs could be nicely uptempo without being frenetic, from 'Just One Of Those Things' to a remake of 'All Of Me', which had been one of Sinatra's best swingers at Columbia. And the boyish enthusiasm of 1947 had been replaced by mature skill: the illusion of swing was now fully and effortlessly accomplished. Confirmation that Sinatra was back at the top came with wins in both Metronome and down beat polls, while Billboard named him as top male vocalist, 'Young-At-Heart' as best single and Swing Easy as best album.

In The Wee Small Hours came next, often described as the first concept album: in fact it was only further proof that Sinatra (and Gilmore and Riddle) were thinking in terms of albums far ahead of most other recording teams. It was first released on two ten-inch LPs (confusingly using the same number with different prefixes), but was soon squeezed onto one twelve-inch, and that was the end of the ten-inch era. The sixteen songs about unrequited love and loneliness were nearly all recorded in early 1955, when he knew beyond doubt that his marriage to Ava had failed. Sinatra knew how his fans felt in 1941, when they were all young together; by 1955 a lot of people in that generation were finding out that living happily ever after isn't so easy after all, and Sinatra knew how that felt, too, still there for the fans when they weren't kids anymore. For many years we have heard a lot about the baby boomers, but it was no picnic being the parents of the most privileged generation in history: no wonder they bought Sinatra's albums. And the songs! Some were remakes, like Rodgers & Hart's 'It Never Entered My Mind', which he'd recorded for Columbia, and there were others he hadn't got around to before, like Alec Wilder's 'I'll Be Around': he never seemed to run out of good ones in those years, and he sang them better than ever, because, like Billie Holiday, the older he got the more he knew what the words meant.

Often he inserted a syllable or dropped a word to make the song swing the way he felt it, and like all the greatest singers he often altered a melody line. Composers sometimes didn't like this; Cole Porter complained abou the way Sinatra did one of his tunes. Mel Tormé, in his book It Wasn't All Velvet, tells of singing 'Blue Moon' for the soundtrack of the Rodgers & Hart biopic Words And Music in 1948. The song as written goes like this:

Blue moon,
You knew just what I was there for,
You heard me saying a prayer for
Someone I really could care for.

This is a rare example of Rodgers & Hart writing a song that was hillbilly enough for Elvis Presley. Tormé wanted to sing: 'You heard me saying a prayer... /For someone I really could care for', using his own rhythm to make the extra syllable fit in the last line. Rodgers didn't like it, but Tormé had his way, so that it sounded as though the words meant something to him, rather than as if he were reading them off the page. This sort of singing reached its peak in the 1950s, just as the songwriting had passed its peak; and Sinatra, who had learned to talk before he ever heard a radio, let alone a television, was the acknowledged master of it.

The song had to be sung as it was felt. When Billie sang 'I'll Never Be The Same', she changed the words, singing 'I'll never be the same all day' (no wise guy was going to break her heart), but on Wee Small Hours Sinatra sang it the way it was written: 'I'll never be the same again'. He made the clumsy word 'again' sound perfectly natural spread across two notes, because he'd been a sucker for Ava and he'd screwed it up, and she would never be his again, and he would never be the same again. There was no room for bravado here: he could fool himself some of the time, but not when he had a song to sing.

It was immediately evident that Nelson Riddle deserved a lot of credit. His arrangements are equal partners with the singer, but never getting in the way. While the charts add up to a beautiful album, there is no sameness because they are also each tailored to the song. Here there's a muted trumpet solo from Harry Edison, there it's a reed section of Mahlon Clark, Skeets Herfurt, Babe Russin and Ted Nash, making a blend that any leader could have been proud of. 'Mood Indigo' is unique to start with because it's a Duke Ellington tune, basically an instrumental with words added, and the words aren't really up to much; so while Sinatra makes the best that can be made of them, Riddle takes a postmodernist glance at the music of the century: here and there the reeds (including flutes, and in one passage combined with muted trumpets) sound like an unanswered question by Charles Ives; there's a passage for plucked strings that might pay homage to Bartók, a short passage of double time that echoes New Orleans jazz, and then the writing for saxes is first in the style of Billy May and then (appropriately) Ellington. Yet on several tunes, such as 'Dancing On The Ceiling', there's only a quartet, because lying in an empty bed looking up at the movie in your mind is lonely.

There is enormous variety here, yet all adding up to an album with its own integrity. Startling evidence of the importance of Riddle's work is provided by comparing a session of 13 December 1954, with trumpeter and band leader Ray Anthony, and arrangements by Dick Reynolds, almost the only one of over 40 Sinatra recording sessions at Capitol between April 1953 and April 1957 that wasn't directed by Riddle. 'Melody Of Love' was a 1903 waltz with 1954 words added; it was not right for Sinatra. The other tune recorded that day was a hey-look-at-me anthem, 'I'm Gonna Live 'Till I Die', which Frankie Laine used in his cabaret act. The arrangement isn't bad, and it's well played, the studio band including many of the same people who played on Riddle's sessions; but it is one of those frenetic swingers that is somehow trying too hard. It would have made a fine souvenir of a stage show in some gin palace, but it would never have fit on the albums Sinatra and Riddle were making. It was the last gasp of the pre-modern Sinatra. Now, in his albums with Riddle, he had not only survived, but was singing better than ever.

Not that Sinatra's behavior in his private life had changed much. Also in 1954, Sinatra and Joe DiMaggio decided that Marilyn Monroe was having a lesbian relationship, so they hired a couple of goons and smashed down the door of an apartment in New York City, frightening some strangers to death: they were in the wrong apartment. A lawsuit resulted, and Sinatra swore that he had stayed outside while the others smashed down the door; he was suspected of perjury, but it was decided that there was not enough proof. An eyewitness who had claimed to see him actually inside the apartment was mysteriously beaten up. (Years later, Sinatra had an affair with Monroe and then passed her around to his friends; the former baseball hero DiMaggio never stopped loving his ex-wife, and never forgave Sinatra.) But the albums Sinatra was making in the mid-1950s transcended all that. Items from the gossip columns are as nothing compared to the flowering of the talent that had made him famous.

A song called 'From Here To Eternity' was a minor hit; written by Bob Wells and Fred Karger, it was published by Sinatra's Barton Music in 1953, and described by one reference book as 'inspired by' the film. Thanks to the Oscar, his film career was now revived; he was in demand as a freelance actor, if the level of inspiration was not up to that of the albums. His next picture was Suddenly, a tight thriller (over forty minutes shorter in its released version than From Here To Eternity) in which he played a would-be presidential assassin. Not As A Stranger was a slow hospital melodrama in which Robert Mitchum and Sinatra were wasted, but again a solid acting job; both these were for United Artists.

Meanwhile Jack Warner had an idea: he liked to raid his own locker, avoiding the cost of acquiring or developing a new property; Sinatra had a big hit record and Warner liked Sinatra, so he dusted off a piece of small-town hokum from 1938 called Four Daughters and turned it into a musical for Doris Day and Frank Sinatra called Young At Heart, with a ready-made title song. The original had been a sensational film debut for John Garfield, but the remake got a lukewarm reception, too obviously a heartwringer cobbled together for its stars. Sinatra's character, a singer who needed somebody to love him, was probably the best thing about it, but it wasn't enough.

The Tender Trap saw him back at MGM, this time as the star: no dancing and no singing (except for the hit title song, behind the credits), and no competition with the magic of a Gene Kelly. The picture was a romantic comedy in the mainstream Hollywood style of the decade, with Sinatra as a Broadway playboy opposite Debbie Reynolds. The song, by Cahn and Jimmy Van Heusen, fell into the same category; it was a top ten hit for Sinatra and nominated for an Oscar. Froth was big back then.

After the recording of In The Wee Small Hours Sinatra went to work on the set of Guys And Dolls for MGM, an incomprehensible failure. Sinatra and Marlon Brando were miscast in each other's parts: Brando couldn't sing but he had all the best songs; either of them could have acted through the Damon Runyon-style dialogue, but Brando should have been Nathan Detroit. (And Sinatra couldn't stand Brando's working habits. The method actor had to think about it all day and then do it ten times; Sinatra said to writer-director Joe Mankiewicz, 'Don't put me in the game, Coach, until Mumbles is through rehearsing.') But Ava was in town; they were seen together here and there, and friends noticed a change in them: they could not live together, and had begun to give up on each other, yet they could not doubt the passion they had known. He was the closest thing she'd ever had to a man she could rely on; she referred to him as 'Francis' or 'my old man', and he fondly called her Mrs Sinatra. The flame would never quite go out, but they had put down their torches; he had more time to spend with his children, and life went on. We have known love; we shall know love, or at least we can remember love. And the next album celebrated it.

Songs For Swingin' Lovers! was mostly recorded in January and February 1956, and became a hit album at the end of March: no time was wasted in those days. The title of the album has become mildly irritating; it was the beginning of swinging this and ring-a-ding that. Musicians who can swing don't have to talk about it, they just do it; and wasn't it around 1956 that 'swinging' became a euphemism for suburban wife-swapping? But never mind the title: the album itself is one of the great pop documents of the century, celebrating the existential hope of romantic love with another fifteen of the best songs, in arrangements that are the best of their kind. With this album Sinatra and Riddle made themselves permanently the masters of their trade. There are lovely individual tracks from almost all of Sinatra's career; but in retrospect it is impossible to exaggerate the importance of Nelson Riddle, because it was these albums and especially Songs For Swingin' Lovers that earned Sinatra his crown as our greatest singer of this kind of song. Henceforth he could have retired anytime, undefeated.

Among the many ways in which Sinatra had got older along with his fans, changing as they had changed, was that his voice had deepened and darkened. It had always been an attractive and distinctive voice, but had now become even more so, the instantly recognizeable Sinatra familiar now for so many years. Yet on Songs For Swingin' Lovers he actually sounds younger than he did in 1950. He taped the tracks for Sing And Dance With Frank Sinatra when his personal and professional lives were in a mess, while George Siravo's charts tried to recapture a Swing Era which was over; six years later, Riddle's charts were not retro music, but something new, and Sinatra was on his way up, not down, the love of his life behind him. A decade later a line would be written to describe his situation: 'I was so much older then; I'm younger than that now.'

Along with the greater emotional understanding and experience, some might conclude that there was a slight falling off of the technical mastery: but was there? During the 1940s his youthful intonation had seemed perfect; now the point was no longer to sing the songs perfectly, if it ever was. The more mature Sinatra was an even greater interpreter. Someone asked me, when I was starting to write this book, 'Why does he always sing flat? Crosby never did; why does Sinatra sing flat?' I was startled: flat? But when I thought about it, I was glad that I do not have perfect pitch to get in the way of my listening. In fact it is no accident that Sinatra warmed to Dorsey's trombone and to the violin of Jascha Heifitz (or that Riddle had been a trombonist): those are instruments that allow the player to make his or her own tonality, or microtonality. Henry Pleasants, a legitimate music critic who wrote a very good book about pop singers, put it like this:

While a note might not be, strictly speaking, out of tune, it could be just far enough off center for the listener to feel its resolution to be imperative, and to experience a sense of relief and satisfaction when it is resolved ... the variance from true pitch is microtonal, and, because it is too slight, the average listener may be unaware of any variance at all. But he reacts to it.

Thus if on the first half of 'Too Marvelous For Words' Sinatra sounds 'flat', that's because he's almost talking the words. He's remembering that she was so marvelous that she's gone now, but the remembering (and the arrangement) has a bravura ending, and by the time he remembers just how marvelous she was, you doubt neither his knowledge of her nor his knowledge of tonality. He sings flat at the start, if that is what he does, because he is laconic, until the full memory of her hits him; he sings flat for the same reason Dexter Gordon has his own intonation on the tenor saxophone: because he is a great actor as well as a musician.

Almost every singer has critical pitches in his or her range where smoothness is a problem, where there is a seam or a join that can be 'covered' by depressing the larynx. Pleasants points out that Sinatra knew how to do this, but usually didn't do it, not because the impression of the absence of technique sometimes seems central to pop music, but because the slight evidence of strain will suggest innocence, sincerety, loneliness, or whatever the song might call for. In other words, like every great artist, he knew how to use his own technical shortcomings in the service of the art. Al Jolson sang at you; Bing Crosby sang to himself, as though being overheard by the microphone; Sinatra used the microphone so well that it disappeared. The occasional sound of strain or tiredness, the touch of a New Jersey accent, what Arnold Shaw described as a counterpoint of toughness and tenderness: it is all there in Capitol's superb recorded sound of the mid-1950s, and honest mono at that.

During the 1940s the Sinatra vocal was like a jewel, and the Stordahl arrangement was a cushion of velvet or satin on which it reposed; during the Capitol years, the Sinatra version of a song became a modern work of art: now pointillist, now cubist, now abstract as the song and the mood demanded. Here he slipped across the bar lines like a magician; there he sang on the beat, sending the words home like hammer blows. The voice was smooth as smoke, but here and there allowed to crack with emotion. Sinatra has a great reputation as a swinger: if he is too much in control to swing the way a jazz musician swings, he is a great interpreter, and if a great arrangement allows him the illusion of swing, that is enough. (Are the songs not about an illusion, of love?) Riddle's studio band might sound on these tracks as though it was working hard, but Sinatra made it sound easy, and in that paradox is part of the illusion. Always there was that amazing ability to sing as many bars as he liked without breathing; and to continue the metaphor with visual art, the Riddle arrangement is the only possible frame for each picture. For Riddle was a designer, and each song is a story, with a beginning, a middle and an end; the frame is ornamented, yet never overstated (because Riddle is a master of dynamics), but reveals the song's structure. It is as though song and arrangement were composed together by a love-struck Beethoven of pop.

The hit singles on the radio in the early-to-mid 1950s may have been rubbish as the USA began to use its increasing prosperity to trash its own culture, but when it came to making albums for grownups, the veterans of the Swing Era (albeit confined to the recording studios) knew what they were doing: musical lessons had been learnt, so that (for example) the playing of studio rhythm sections in the mid-1950s was much better than that of the white bands of the 1930s and 1940s. The rhythm section on the 1950 album Sing And Dance With Frank Sinatra is not that much different from the albums of a few years later, but the arrangements are different, and Voyle Gilmore's studio was probably a nicer place to work than Mitch Miller's. More to the point, the years between 1950 and 1956 were crucial: a few more years to absorb the rhythmic lessons of modern jazz, and to get used to studio work in the era of tape recording; the arrangement wasn't limited to the playing time of a ten-inch 78. Also, Sinatra liked to have an audience of friends and hangers-on in the studio, who would have been appreciative of the band's playing. In some ways it must have been almost like being back on the bandstand at the Palomar, or Roseland, or Glen Island.

Riddle's studio band included the best of the Swing Era's survivors, who could play anything, and a good thing too: a map of one of the arrangements from Songs For Swingin' Lovers might look too crowded on a piece of paper, too densely populated, yet in the listening everything is cherishable. The bass clarinet, the bass trombone, the baritone sax are used as springboards for phrases; Harry Edison's muted trumpet became famous from these sessions, not a part of the trumpet section as such, but heckling fondly from the sidelines, 'filling in the windows' as Buck Clayton once did for Billie Holiday. (Sinatra reportedly insisted that Edison have his own microphone to play into.) Bassist Joe Comfort had played in Nat Cole's trio, later worked for Pérez Prado, Harry James and Billy May, and then played on most of the Sinatra-Riddle sessions, again and again lending harmonic sophistication as well as a superb beat: he played some well-deserved solo bits on 'Too Marvelous For Words'. The experienced pianist Bill Miller had joined Sinatra when he was at the bottom, in the early '50s, and was still with him in the '90s: his fills on celesta all over the Riddle albums are part of their beauty.

The celesta is an instrument that can easily become irritating, but not here. Similarly, flutes are often merely distracting in a jazz-based arrangement, but Riddle's flutes (in various registers and combinations) peep out from the shrubbery like a family of woodland creatures sneaking closer for a better look: indeed, the whole arrangement is like an affectionate audience, murmuring intelligent commentary. The sections of the band provide ghosts of counter-melody, teasing us: what are we going to hear next? Or they point out the harmonic sophistication of the tune: again and again Riddle reveals what it is that makes a so-called standard a high-class piece of work compared to most of Tin Pan Alley's output. And there's the strings: it always comes as a little surprise to remember that, yes, there are strings on these tracks, because Riddle uses them not as a tax dodge, nor to saw away slushily in order to impress some booking agent, but as another section in the band, an equal partner with every other section, and with the singer. Where the strings actually carry the melody, proudly, rightly, as in the middle of 'You Brought A New Kind Of Love To Me', far from intruding, they make you wonder why every band didn't have strings. There's all this stuff going on, and it's all a joy, because each detail is a joy, and nothing gets in the way.

In early 1956 when Songs For Swingin' Lovers was recorded, the average age of the fifteen songs was just under twenty years. The oldest, from 1923, was 'Swingin' Down The Lane', by Gus Kahn and bandleader Isham Jones, surely an early-modern use of that word 'swingin' '. Another old one, from 1928, was 'Makin' Whoopee', a song one would not have expected: isn't it slightly corny? But it was co-written by Walter Donaldson, one of Sinatra's favorite writers, many of whose songs can be effortlessly updated, as in this case. Sinatra's cooly knowing delivery and Riddle's setting, full of gentle joshing, was perfect for Sinatra's fans in 1956, who had made their whoopee and were now saddled with mortgages on houses in the suburbs: if their fathers had chuckled at Eddie Cantor's version in 1930, it was time for a new generation to see itself in the mirror.

The tempo of each tune is exactly right. If you notice that you've been seeing rather a lot of a certain person, and you think to yourself, 'You're getting to be a habit with me', it should be a sort of expectant stroll, almost (but not quite) fast enough for a tap-dance: happiness might be just around the corner, but you don't want to hope too much. Milt Bernhardt plays a famous trombone solo on 'I've Got You Under My Skin'; that arrangement, said to have been written in a hurry and greeted by applause in the studio, is the most successful of all, rising to a controlled frenzy before it is over, halfway through the album. It is followed by 'I Thought About You', a little slower; then 'We'll Be Together Again', the slowest track on the album; then 'Makin' Whoopee' picks it up again: the perfect tempo of each track is matched by the programing of the set as a whole. Songs For Swingin' Lovers is one of those albums on which entire careers could have stood or fallen, and there was a lot more to come.

The month after Songs For Swingin' Lovers was recorded, and not quite fourteen years after the Capitol label had been formed, the famous Capitol Tower opened in Hollywood: the label was now so successful that it was able to build its own landmark, and the first Sinatra session in the new building was an instrumental album called Tone Poems Of Color. He conducted a set of twelve original pieces suggested by colors, written by Riddle, Victor Young, Billy May, Gordon Jenkins, Alec Wilder, Elmer Bernstein, Jeff Alexander and André Previn. This is the rarest of all Sinatra albums, even less well known than his 1945 recordings of Wilder's music. (On Capitol he also conducted an album by Peggy Lee in 1957,The Man I Love, with arrangements by Riddle, and one by Dean Martin in 1958, Sleep Warm, written by Pete King.)

Then, recorded in March and April 1956, together with a session from the following November, came Close To You, an album of ballads, again featuring the Hollywood String Quartet. With only a few additional solo musicians in addition to the quartet and the rhythm section, the chamber-music feeling was even more intimate than on Songs For Young Lovers. On that album there was a fresh and youthful feeling as the horns occasionally played chirpy bits in unison; on Close To You there is only one solo instrument on each track, no chirpy bits and no uptempo tracks at all. On In The Wee Small Hours the tempi were all slow, but with a full-sized orchestra; on Close To You, with a much smaller, yet tightly arranged group, the string quartet almost dominates the arrangements. Sinatra and Riddle were not only concentrating on making albums, but each album was different; they were too intelligent and restless to copy themselves, and Close To You took longer to make than any of their other collaborations.

Songs For Young Lovers was romantic; In The Wee Small Hours was about loneliness; now Close To You combined elements of those albums to make one about various unsettling aspects of love. Again there were a few remakes; the title song was revived from 1943 and 'Everything Happens To Me' from the Dorsey years, but all the songs represented snapshots of emotions: 'Love Locked Out', 'It's Easy To Remember'. 'P.S. I Love You' was a Gordon Jenkins song from 1934, a hit for Rudy Vallee; it had been revived for a 1953 hit single by the Hilltoppers (another of those vocal groups with a slow shuffle beat) and was then recorded by Billie Holiday in 1954, and now by Sinatra. He would have remembered the Vallee hit; he knew about all the tunes: for this album he rescued another Walter Donaldson song, 'I've Had My Moments', from a forgotten comedy film (Hollywood Party, 1935). The most unusual track on the album, at the end of the first side, was 'Don't Like Goodbyes', by Harold Arlen and Truman Capote, from House Of Flowers, a show that flopped on Broadway in 1954. Gerald Bordman has written, 'An intangible gossamer grace rendered the show somehow untheatrical', and the same could be said of the song (arranged by Riddle without any rhythm section, just four strings and an almost inaudible French horn), and about Close To You as a whole: too good for the market. Close To You is a lovely album, and it was a number five hit in the Billboard chart early in 1957, yet compared to the other Riddle-Sinatra albums it remains obscure and often unavailable. The Hollywood String Quartet were credited on the cover, and to the average punter, 'string quartet' means 'classical': a fair number of fans may have been put off over the years thinking that the album was another of Sinatra's high-toned experiments. Which of course it was: a wholly successful one.

Two songs from the recording sessions could not be fitted onto the original album, 'If It's The Last Thing I Do' and 'Wait 'Til You See Her', as well as a joke: 'There's A Flaw In My Flue' (with the line 'Smoke gets in my nose') was allegedly recorded as a prank, but nobody at Capitol noticed. All three were included on a CD edition of Close To You, itself out of print by 1995.

Meanwhile, Songs For Swingin' Lovers had hit the charts early in 1956 the same week as Elvis Presley's first album, which hogged the top spot for ten weeks. Presley was seen by much of the music business of the time as a fluke, a carnival sideshow freak, while his album marked the beginning of a wider market for albums: kids, country music fans and African-Americans bought Presley, all people who had not bought many albums until then. (And remember that that was the last decade to see an appreciable number of hit musical shows and films: Presley was dislodged from the top by the original cast album of My Fair Lady, which stayed there for 15 weeks.) This Is Sinatra! was the compilation of singles (including film songs) which went top ten, but Songs For Swingin' Lovers actually stayed in the charts longer than Presley's debut, and as soon as Close To You had been recorded a sequel to Songs For Swingin' Lovers was on the way.

Arranging, or orchestrating, has always been one of the most important yet unsung jobs in popular music. Few people have heard of Robert Russell Bennett, for example, who was not only a prolific American composer, but was responsible for the sound of Broadway, orchestrating many of the biggest hit shows between 1923 and 1960. During the Swing Era the arrangers for the big bands, whether writing a chart for a pop song or composing an original tune, would create what was effectively a tone poem, a musical miniature, except it was the kind of piece you could dance to. Jerry Gray, to name just one arranger, created two of the classics of the era: Artie Shaw's version of Cole Porter's 'Begin The Beguine' (1938) and Gray's original 'A String Of Pearls' for Glenn Miller (1942). In classical music, Mahler, Strauss and Shostakovich memorably orchestrated some of their own songs, but in that music the melody, harmony and orchestration are all part of an integral work of art, whereas in commercial music the chores were parceled out. Significantly, Duke Ellington was almost the only Swing Era bandleader who was also the composer and the arranger, and he is generally considered to have been the greatest of all. Nelson Riddle had started in the Swing Era, working for Tommy Dorsey, but in the 1950s it was still the case that the arranger was paid a flat fee for each chart: Riddle was probably paid around $50 for Nat Cole's 'Mona Lisa', one of the biggest hits of 1950, and a hundred dollars a chart for Songs For Swingin' Lovers: $1500 for writing an album that is still a legend over 50 years later.

A Swingin' Affair was recorded in November 1956 (except for 'No One Ever Tells You', made in April) and hit the Billboard chart in May 1957. It is the first of the Sinatra/ Riddle projects that is not a masterpiece qua album: it is a marvelous set, beloved of Sinatra fans, and almost any track on it could have fit on Songs For Swingin' Lovers, yet as an album it doesn't hold up as well, perhaps because Riddle was working too hard. But perhaps Sinatra knew that he had made a masterpiece with Songs For Swingin' Lovers, and didn't exercise his usual judgement over the songs and the arrangements on the followup album; with Sinatra there was always the danger of the attitude that he could do no wrong.

A Swingin' Affair opened with 'Night And Day', a song that has been associated with Sinatra since the 1942 session with Axel Stordahl, and he would record it again, but this Riddle arrangement became a famous one. (Sinatra's diction is incredibly good, as always: at the very beginning you can hear two separate letter 'd' sounds in 'and' and 'day'.) 'I've Got You Under My Skin' from Songs For Swingin' Lovers had made such an impression that by this time the fans' favorite cliché was that Sinatra sounded like he was swinging hard, but it was the band that was doing all the work; 'Night And Day' is a good example of this, but the new album was made with the cliché too much in mind: on half a dozen tracks the arrangement starts off interestingly, but the band works harder and harder only to stop rather suddenly, as though Riddle had run out of manuscript paper. 'I Got Plenty O' Nuttin' ' is one of these; indeed it almost harks back to the Swing Era: Sinatra sings the song, then George Roberts's bass trombone introduces an exposition for the band which takes a third of the track before Sinatra comes back. 'I Won't Dance' and 'From This Moment On' also suffer from a too-relentless application of the formula, now become a two-beat treatment with the drummer playing a loud back-beat, as if they were trying to turn these standards into rock'n'roll.

'Lonesome Road' was the opener on the second side of the LP; at nearly four minutes it is one of the longest tracks on the album, but it is a song from another era by Nat Shilkret and Gene Austin, and should have been left there, with its repetitious tune and corny lyric about 'weary totin' such a load' (it had been shoved into the 1929 film version of Show Boat, mimed by Stepin Fetchit). What is this doing on an album called A Swingin' Affair? On 'Stars Fell On Alabama', Sinatra changes the melody line a bit in a pleasing bit of interpretation, but also changes the lyric: 'stars fractured Bama' should have been confined to live gigs; listening to it over and over on the record becomes tedious. But Rodgers & Hart's 'I Wish I Were In Love Again' is right up Sinatra Street, with its unforgettably sardonic lyrics:

When love congeals
It soon reveals
The faint aroma of performing seals
The double-crossing of a pair of heels
I wish I were in love again.

'No One Ever Tells You' was a new song in 1956, and a good one; 'If I Had You' was a remake from 1947 and 'Oh! Look At Me Now' from the Dorsey years; both are fine, along with 'I Guess I'll Have To Change My Plan.' Altogether, A Swingin' Affair seemed to mark the end of the beginning of Sinatra's Capitol albums; in some places it is a brash showing-off kind of set. There is nothing terminally objectionable about it, but it is not as fine an album as it might have been, either.

During the recording sessions two versions of 'The Lady Is A Tramp' were made, one for the soundtrack of Pal Joey and one for a single or an album; this was finally added to the CD issue of A Swingin' Affair, to make 16 tracks altogether. Sinatra played with the lyric on 'Tramp' too; it has always been one of my favorite Sinatra tracks, and I am not one of those who objects to the word 'broads' for women. We took it for granted as slightly vulgar slang in the '50s, and when you met a woman in a bar you hoped she would have a sense of humor. But again, it begins to jar after you've heard it a few dozen times, and might have been better confined to the club act. Meanwhile, Riddle wasn't the only one who was working hard. While he was arranging nearly 140 tracks for Sinatra between April 1953 and March 1957, Sinatra also made a dozen movies, including From Here To Eternity but not counting cameos in Meet Me In Las Vegas and Around The World In Eighty Days, both in 1956. With around sixty film roles altogether during his career, after From Here To Eternity he had become one of the biggest box office draws in Hollywood's history. Some of the later ones weren't very good, but every single one of them made a profit, which is all that matters in Hollywood.

After Guys And Dolls, Sinatra's next film was one of his best, a controversial picture about drugs called The Man With The Golden Arm. Sinatra had wanted the part of Terry Malloy in On The Waterfront in 1954; producer Sam Speigel and director Elia Kazan wanted Sinatra, but Harry Cohn at Columbia was putting up the money, and he wanted Marlon Brando. Sinatra was furious. Then Brando got the better of the two male leads in Guys And Dolls, one of the worst mistakes Sam Goldwyn ever made; but now, in Otto Preminger's version of Nelson Algren's novel about a small-time gambler who becomes a drug addict, it was Brando's turn to be furious: Sinatra snatched The Man With The Golden Arm from under Brando's nose by agreeing to do it without even seeing the entire script. Preminger liked working with Sinatra, and in a postscript to the story, many years later Preminger was offered The Godfather by Paramount, and in turn offered the part of Don Vito Corleone to Sinatra, who turned it down. So Preminger turned the film down too, and of course when the film was finally made by Francis Ford Coppola, it was Brando who turned in one of the best performances of his career.

There is something strange about the careers of Frank Sinatra and Marlon Brando being so intertwined; except that they both appeared in Guys And Dolls, one wouldn't think of them at the same time. Brando can't sing, but is no doubt the greater actor; as many films as Sinatra made, we think of him primarily as a singer. Yet both men have serious character flaws which kept them from doing much of the best work they might have done on the screen. Brando's absurd ego and his disgust with himself and with his profession meant that only a handful of his films turned out to be really first-class work; Sinatra was too impatient with the nuts and bolts of filmmaking to become the first-rate actor he might have been. If Brando is the greater actor, some of his disgust with Hollywood was justified; his self-directed western, One Eyed Jacks (1960), might have been a masterpiece, but we'll never know: it was butchered by the studio before it was released. But the film industry does not make allowances for egos like Brando, Orson Welles or Frank Sinatra. Brando described his own profession as empty and useless; Welles was described as 'an active loafer, a wise madman'; Sinatra could do as he wished, but the overall result of his film career was disappointing. Movies have to be made on an assembly line, like any other mass-produced product; they have to be movies that the public wants to see, and it was during the 1950s that Hollywood, competing with television, came up with the slogan 'Movies are better than ever'. As the competition for the mass audience became keener, movies were worse than ever, and there was even less room for the destructive ego.

It is really quite remarkable that some of Frank Sinatra's films are still watchable, and given the nature of film-making in the 1950s, even the best of them are touch-and-go. The chores in film-making are broken down and parceled out even more than in the recording studio, and Sinatra's nature would not allow him to take part in a collaborative process. He wanted to be the studio boss, telling everybody else what to do; but at the same time, he wanted to come in, walk through his role and go home, and if the film flopped, as with everything else in his life except his singing, it would be someone else's fault. Preminger liked working with Sinatra because Sinatra was reliable when it came to learning his lines and turning up on time; but when Sinatra wanted to fire an electrician who'd somehow got in his bad books, Preminger was the sort of professional who could quietly make it clear that he was the one who did the firing. Sinatra admired Preminger, and talked about how much he'd learned from him, but as with Montgomery Clift on From Here To Eternity, what he learned from the professionals never seemed to seep into his own attitudes.

The Man With The Golden Arm benefited from a score by Elmer Bernstein; the soundtrack was a hit album in 1956, and there were several hit versions of the driving main theme, the biggest by bandleader Richard Maltby. Preminger's treatment of heroin addiction was controversial at the time, even though he watered down the story and gave it a happy ending. (Nelson Algren was a writer who was deeply suspicious of Hollywood, but he loved the way Sinatra played his character, Frankie Machine, whose golden arm, by the way, had nothing to do with the drug, but the way he dealt cards.) Sinatra's acting, including succumbing to heroin (with Darren McGavin wonderfully creepy as a pusher) and later going cold turkey, seemed like dynamite in the mid-'50s, but he never fully absorbed the lesson that he was at his best playing characters who were not quite in control of themselves.

In general, the richer and more powerful Sinatra became the worse his movies got. Each film has to begin with an idea, a proposal from someone or other; Sinatra's knack of picking good ideas of his own (such as it was) did not outlast the 1950s by much. It is interesting that many of Sinatra's best pictures were in black and white. Producers liked monochrome because it was cheaper than color and kept the budget down (the reverse is true now, when everything is made in color). It may be that the extra pizazz color added to a picture was at odds with the sort of characters Sinatra played best. Golden Arm was in monochrome, and so was Johnny Concho in 1956, a well-made small-scale western for United Artists.

Also in 1956 came MGM's High Society, which must have seemed like a good idea at the time, with Cole Porter songs, starring Grace Kelly, Louis Armstrong and Bing Crosby, with Sinatra and Crosby together on screen singing a duet. This was a musical version of a play, Philip Barry's The Philadelphia Story, and it doesn't hang together at all, as though they all knew it was fluff. 'Now You Has Jazz' with Crosby and Armstrong was merely insulting, 'Well, Did You Evah' was reclaimed from Porter's trunk for Crosby and Sinatra, and 'True Love' for Kelly and Crosby was a hit single and nominated for an Oscar, but it must be the weakest song Porter ever wrote: the world in which he was at his peak was long gone. The Pride And The Passion in 1957 was another bad idea, for United Artists, a star-studded costume melodrama about a bunch of people dragging a big cannon across Spain in 1810, 45 minutes longer than Johnny Concho, in blazing color, with Sinatra, Cary Grant and Sophia Loren all wasted.

But also in 1957 there were two better films. Pal Joey was in some ways a typical Hollywood version of a Broadway musical, tinkered with and mauled a bit, but the original show in 1940 (revived in 1952) had been controversial, because the hero was a heel and one of the two female leads was past her prime. The book was by novelist John O'Hara (from his stories first published in the New Yorker), the music by Rodgers & Hart, and the whole thing was ahead of its time. The original songs included 'I Could Write A Book' and 'Bewitched, Bothered and Bewildered'; the latter had made little impression in 1940, except that it was regarded as daringly suggestive. But suddenly in 1950 there had been nine hit singles on it, the first and biggest a fluke: an instrumental version by pianist Bill Snyder on a tiny independent label was the sort of serendipity that we used to get in popular music now and then, establishing the song as a standard and perhaps encouraging the show's Broadway revival in 1952. Gene Kelly had played Joey in the original, Harold Lang on stage in 1952, but it is hard to imagine anyone other than Sinatra in the part now. In fact, in his tempestuous private and public lives and in his art since sometime in the 1940s, among other things he had been helping to establish the anti-hero at the heart of popular culture: Joey is a shallow, selfish gigolo who wants to run a nightclub, but somebody else has to put up the money; in the film, Rita Hayworth plays the hard-bitten femme fatale, and Kim Novak the younger woman who loves Joey. It was typical of a Hollywood studio (in this case, Columbia) to drag in songs from other Rodgers & Hart shows: 'The Lady Is A Tramp', 'I Didn't Know What Time It Was' and 'There's A Small Hotel' all came from other sources, while an appropriate but lesser-known song from the original, 'Take Him', was dropped. But the result was a soundtrack album that spent 27 weeks in the Billboard chart.

The other interesting Sinatra film in 1957 was a monochrome effort for Paramount, The Joker Is Wild. It was much too long (nearly 20 minutes longer than Pal Joey), but it was the true story of another wise guy, with songs added: Joe E. Lewis was a nightclub singer in the 1920s whose throat was slashed by gangsters, whereupon he became a comedian. Given all the rumors about Sinatra's involvement with the Mob over the years, here is a picture in which the hoodlums are definitely the bad guys; his acting job was creditable, although he does not make a convincing comic. Among the songs in the picture was 'All The Way', by Cahn and Van Heusen, which won an Oscar.

In the mid-1950s Sinatra was a member of the Holmby Hills Rat Pack, whose ringleader was Humphrey Bogart. Other members included Lauren Bacall (Mrs Bogart), Mr and Mrs Sid Luft (Judy Garland), Swifty Lazar, David Niven, restaurateur Mike Romanoff and Jimmy Van Heusen. They were iconoclasts who got together for the purpose of laughing, drinking a lot and staying up late; and being an iconoclast was essential in the 1950s. The USA was making more films and records, and broadcasting more entertainment than had ever been seen before, and most of it was junk; television was famously described by a Federal official as 'a vast wasteland.' Teenagers who were jazz fans (or Sinatra fans) in the mid-1950s were hipper than those who listened to the Crew-Cuts (this was the era when mainstream pop music finally got so bad that Stan Freberg couldn't satirize it anymore), and it was necessary to know that Ernie Kovacs and Sid Caesar were funnier than I Love Lucy or Ozzie & Harriet. This was the sort of thing the Rat Pack would have been good at. In-jokes, teasing and funny names for everybody were also de rigueur; Sinatra was called The Pope, or El Dago.

Not just anybody could call Sinatra a dago. Some people in Hollywood disapproved of the Rat Pack, perhaps because they were not included, but most of its partying was probably done in private, and Bogart was always in charge. He was a well-read man who was absolutely secure in himself, and was held in such affection that the more he insulted Sinatra or the press the better they liked it. When Ava Gardner was driving Frank crazy by playing around with a bullfighter, Bogart said to her, 'I'll never figure you broads out. Half the world's female population would throw themselves at Frank's feet, and here you are flouncing around with guys who wear capes and little ballerina slippers.' (She told him to mind his own business.) Bogart liked Frank, but considered him immature, describing him as 'a kind of Don Quixote, tilting at windmills, fighting people who don't want to fight.' When he remarked that Sinatra would define paradise as a place where there were plenty of women and no newspapermen, he added that 'He doesn't realize it, but he'd be better off if it were the other way around.' He also knew that Sinatra would be a better actor if he paid a little more attention to business.

Sinatra had been anxious to go to Spain to make The Pride And The Passion, because that's where Ava was; his contract stipulated that no one could be paid more than he was, but when he got to Spain he hated it and behaved obnoxiously the whole time, squabbling about things like the type of car that would take him back and forth to the set. Sinatra probably admired and looked up to Bogart as much as any man he ever knew, but show biz would have to take Sinatra as he was. Billy Wilder liked Sinatra but refused to work with him, knowing that it would probably drive him crazy; Wilder was one of those who thought that if Sinatra stopped spreading himself so thin and concentrated on acting, 'his talent on film would be stupendous. That would be the only word. Stupendous.' Shirley MacLaine speculated that perhaps Sinatra was afraid to put everything he had into it, the way he did singing, because then he wouldn't have anyone but himself to blame if it wasn't good enough. The way he always wanted to go with the first take may also have been a sort of gambling, effectively a roll of the dice with each scene; in fact he was always word-perfect on the first take (he clearly took film more seriously than television), but it is the nature of film-making that there are a large number of things that can go wrong on a take. Some directors could cope with Sinatra well, and when he appeared in a film with Spencer Tracy in 1962 he was in his element, because Tracy was another one who wanted to get it over with on the first take. But on the whole Sinatra's attitude was never going to to allow him to realize his potential as an actor.

Bogart died in 1957, the same year Sinatra had his last stab at a TV series. He was even worse in a television studio than on a film set; he probably didn't even like television, but the whole country was watching TV, so he wanted to be a star there too, and the money was very good. He signed a three-year contract with ABC which included tax advantages and a majority ownership in 36 half-hour variety programs, as well as complete control over the content of the shows, saying that this time he wouldn't have anyone to blame but himself if he flopped, and that was the way he wanted it. The result debuted in October, and was a disaster to equal that of 1952; again he refused to rehearse or cooperate in any way. He would not even learn his lines, but read them off the teleprompter. Television skits depend entirely on ensemble skills (which is what made Cheers so successful 30 years later, for example), and the shooting schedule for a weekly program is even tighter than that for a film. But Sinatra behaved like a hooligan, as though he willed himself to fail; indeed, some of the critics thought that Sinatra despised the whole business and was effectively insulting the audience. On one program his guest was his crony Dean Martin, and the pair of them stood around making in-jokes that might have gone down well in Las Vegas. The series was cancelled, and as the director Jack Donohue put it, 'There are quite a few performers who have no business on television each week, and Sinatra is one of them.'

Nelson Riddle had done all of Sinatra's musical arrangements in his films; but back in the recording studio, Sinatra turned to Gordon Jenkins for his next album, Where Are You?. He may have concluded simply that he and Riddle needed a rest from each other, and that he did not want to fall into a rut, as he had in the previous decade with Axel Stordahl. Or he may have been jealous of the amount of credit Riddle was getting for the quality of their albums together. Crosby allegedly advised Sinatra not to rely too much on one arranger, but if so, Crosby should have kept his mouth shut: he recorded countless duets and one-offs with everybody under contract to Decca, but he never made an album with anything like the stature of Songs For Swingin' Lovers. Riddle's feelings were allegedly hurt, but it was certainly not the end of their work together. Sinatra wanted to make an album lush with strings, and in that area Jenkins had quite a track record.

Serving various apprenticeships with bands and on the radio during the Swing Era, Jenkins had then become a managing director at American Decca, making hits with Louis Armstrong, Peggy Lee, Dick Haymes and the Andrews Sisters, as well as Pete Seeger's folk quartet, the Weavers. His hit songs (apart from the previously mentioned 'P.S. I Love You') included 'When A Woman Loves A Man' (memorable recorded by Billie Holiday) and Benny Goodman's closing theme, 'Goodbye'. Jenkins probably made more money from these few hits than Riddle made from all his arrangements; he was a composer manqué, and his Manhattan Towers was a landmark of the LP era, a corny impressionistic suite with songs (including 'Married I Can Always Get'), instrumental passages and narration. He first recorded it for Decca in 1945 and for Capitol a decade later, and there were other recordings, as well as concert versions (one for Las Vegas added comics, dancers, everything but the hat check girl). Manhattan Towers remains very much a period piece, but by the mid-1950s Jenkins had gone freelance, and his arranging was in demand. When it came to albums with strings he was as highly regarded as Percy Faith, Paul Weston and Robert Farnon. In April 1957, just as Jenkins began recording with Sinatra, his album with Nat Cole, Love Is The Thing, entered the Billboard chart and stayed at number one for eight weeks: 'When I Fall In Love' and 'Stardust' from that album were so sumptuous that they sounded like little symphonies, and 'Stardust' got so much radio play that it took a 45 EP into the singles chart.

Made in April and May, Where Are You marked several milestones in Sinatra's recording career. Voyle Gilmore was replaced as producer by Dave Cavanaugh, and this was Sinatra's first stereo album; the vastly improved sound quality over what Columbia could do ten years earlier with Stordahl is important. If you are going to use a large string orchestra, the arrangement, the song and the vocalist must complement one another, with nothing getting in the way, and the balance of the sound is crucial. Jenkins's orchestra included three French horns, some woodwinds and 20 or 22 strings, with no trumpets or trombones; not only was the studio full of the best string players on the West Coast, but the sound and the balance were virtually perfect. Before long, a great many stereo recordings would be over-produced, often putting the vocalist too far forward; one thinks not only of some of Sinatra's later albums, but of Billie Holiday's Lady In Satin, made only a year later at Columbia: the recording emphasised the harshness in her voice at a time when her health was failing.

For my taste, there is often a problem with the use of such lush string orchestras anyway. The arrangements are too likely to become settings of no value in themselves; this is the opposite of Riddle's best work, in which the charts are an integral part, so that each track becomes a miniature work of art. The arrangers for strings were rarely adventurous at all; the object was always to be in the best possible taste, which means not to offend anyone. The two Jenkins arrangements mentioned above, on the Nat Cole album Love Is The Thing, are relatively impressive precisely because they are more listenable than such arrangements usually are. Another notable arrangement of this type is Percy Faith's chart on 'The Song From Moulin Rouge (Where Is Your Heart)', a big hit in 1953 (sung by the Canadian Felicia Sanders); it is interesting that Faith was primarily an instrumentalist, and allegedly disliked accompanying singers. At any rate, Jenkins's arrangements on Where Are You do not draw attention to themselves. Sinatra's vocals make it a very beautiful album, for listening late at night; Nick Fatool on drums can hardly be heard, and the bassist (John Ryan) does a superb job of playing ever so slightly behind the beat. The album could also be used for romantic dancing, because the lesson of Tommy Dorsey's band playing so well at slow tempi fifteen years earlier had been learnt, and this was one of the things that Stordahl, Faith, Weston, Farnon and Jenkins all had in common: they always drew superb playing from their studio bands.

Once again the songs are well chosen. Where Are You is an album by a middle-aged man who knows that he is a failure at love; he has gone past loneliness now. Ava Gardner said that she knew their marriage was over when he rang her up while he was in bed with another woman, saying that as long as he had the name he was playing the game: it passes understanding how such an insensitive man could reveal so much self-knowledge just by singing popular songs, but that is sometimes the way; the artist can't help it. 'Where Are You' itself came from a so-so musical film called Top Of The Town in 1937; it was co-written by Jimmy McHugh, who had spent a few years writing shows at the Cotton Club for Duke Ellington's band. Several of the tunes are remakes: 'The Night We Called It A Day' from the Dorsey years, 'I'm A Fool To Want You' and Alec Wilder's 'Where Is The One' from the Columbia period. 'Lonely Town' by Leonard Bernstein, with lyrics by Betty Comden and Adolph Green, is from On The Town (1944), and it is gratifying to see it reprised here: not only is it a lovely song, but MGM had foolishly dropped it from the score when Sinatra's 1949 film was made. The only quibble I would make, listening to this album nearly 40 years after it was made, is that 'Laura' and 'Baby, Won't You Please Come Home' should each have had a slightly quicker tempo, which would have lent the album just a touch more variety; they could have been nearly twice as fast without destroying the mood. In the case of 'Laura' the melody itself seems to demand more tempo, but the choice of 'Baby' for this album is itself remarkable. This classic of dixieland cabaret was co-written by Clarence Williams, who was born near New Orleans nearly sixty years before this recording was made, and as a closer for the album more could have been made of the tongue-in-cheek fact of having it there at all. But on its own terms Where Are You must be counted as a successful Sinatra recording project.

Next came the Pal Joey soundtrack album, with arrangements by Riddle, then a Christmas album with Jenkins (complete with 'Jingle Bells'), and then Come Fly With Me, one of Sinatra's most famous albums, with yet another arranger, Billy May. The concept album was already becoming old hat; anyone could throw together twelve songs after girls' names, or (in this case) twelve about travel, and Come Fly With Me contains a measure of banality: the fair view to take is that much of it was meant to be tongue in cheek. The market was also changing: in the mid-1950s the old-fashioned 78rpm record represented one-quarter of sales but less than 20% of dollar volume, so the record companies began squeezing it out, and by 1958 Americans were prosperous enough so that most people had up-to-date record players and could buy albums as impulse purchases. Deejays were paying more attention to albums: there was more profit in promoting an album, so there were 1,800 deejays receiving free copies, compared to only 50 a few years earlier. The number of albums released each year was multiplying, and all this meant that quality began to slip. A lot of people would buy an album because their neighbors had bought it, and deejays were playing the title track of Come Fly With Me.

Sinatra was becoming seriously rich, and had a reputation as a ferocious swinger in his private life; or to put it another way, he was living the fantasy life that a great many Americans envied, the American dream coming true: the invitation to jump on his jet plane and hop down to Acapulco was not to be resisted in a country where we were increasingly encouraged to remain adolescents as long as possible. 'Come Fly With Me' itself was of course written by Cahn and Van Heusen; their film songs were instant fodder for Muzak, the '50s equivalent of Bert Bacharach in the following decade, but 'Come Fly With Me' was too light-hearted to offend. The next track on the album, however, was a dreary waltz: Victor Young's 'Around The World' (In 80 Days), from the '56 film. 'Isle Of Capri', 'Blue Hawaii' and 'On The Road To Mandalay' are simply silly; the latter had to be left off the UK edition of the album because the words were by Rudyard Kipling and his estate objected. Ary Barroso's 'Brazil' is thrown away: the opportunity to turn a samba into a four-to-the-bar swinger is lost because of the way Sinatra mostly chants the words instead of floating over the beat. 'Moonlight In Vermont', 'Autumn In New York', 'Let's Get Away From It All' and a few others are fine, the latter revived from the big production with Dorsey in 1941; 'April In Paris' is lovely, while it is tempting to speculate that 'London By Night' reminded Sinatra of a few weeks in that city with Ava that should have been idyllic, but weren't. Then the closer, 'It's Nice To Go Trav'ling (but it's oh, so nice to come home)' is a risible novelty by Cahn and Van Heusen:

And the Hudson River
Makes you start to quiver
Like the latest flivver
That's simply drippin' with chrome.

Adolescents quivered over American cars in those days, and they were dripping with chrome, but a flivver was Henry Ford's original Model T, from two generations earlier. What can these words possibly have been about? In fact this was a throw-away album, as American culture was becoming a throw-away culture. Sinatra indulged himself with kidding around: in one song a girl is wearing a meatball on her finger; in another he's going on a cruise for some exotic booze all the way to a bar in Bombay, but in a third he can hardly wait to get home to make a pizza. Voyle Gilmore was back as producer; stereo was still a new technique, and the early stereo sound of Come Fly With Me is loud and brash: people liked that in those days; it made their hi-fi sets sound good. Entering the chart in early 1958, Come Fly With Me was number one for five weeks, and in the top 50 for over seventy weeks. Among the number one singles in the USA in 1958 were 'Witch Doctor' ('Ooo! Eee! Ooo Ah Ah! Ting! Tang! Walla Walla Bing Bang!'), and Danny and the Juniors' 'At The Hop' ('Let's go to the hop!' repeated endlessly to a frenetic beat): the singles chart had been turned over entirely to children, and Sinatra's first number one album since 1946 was an album for older kids.

Whatever you thought of the album, however, you could listen to the band. Sinatra and Billy May had known each other for nearly 20 years before they finally worked together, and nobody was more likely to arrange a tongue-in-cheek album than May. As a trumpet player and arranger he had contributed to the happiest of all the white swing bands, that of Charlie Barnet, in 1939-40, leaving to go with Glenn Miller because Miller could pay more, but working for Miller was not as much fun: May's chart on 'Ida, Sweet As Apple Cider' was supposed to have a jive vocal by the band, but Miller wouldn't allow it. Miller's delightful version of 'I Got Rhythm', recorded live in early 1942, is almost certainly a May arrangement, the band loping along and having such a good time with it that one wonders if Miller hadn't taken the night off. In the early '50s May and saxophonist Al Klink liked to make wisecracks such as 'Adolph Hitler is alive and well and playing Fender bass for Glenn Miller in Argentina.'

But also in the early 1950s, May became something of an institution at Capitol, perhaps the only dance band leader to have four top ten albums in 1952-5, including Sorta-May, with such unusual fare as 'Donkey Serenade' and 'In A Persian Market'. He also took care of all the little bits of musical humor and fill-in on the records and radio programs of satirist Stan Freberg, who memorably described May in his Hawaiian shirt at a recording session as looking like a porpoise at a luau. May admired the Sauter-Finnegan band, run by two of his colleagues from the Swing Era, Eddie Sauter and Bill Finnegan: it had a lot of humor and unusual instrumentation in its music, but it was a concert band rather than a dance band; May's arrangements for Sinatra's Come Fly With Me seem to have been inspired by it. The trademark Billy May slurping saxes make an appearance here and there; the muted trumpets sometimes squeak like mice, there's a vibraphone on one track, and tuneable drums can be heard, as well as a huge gong on 'Mandalay'. If the album is largely fluff, it is fun to listen to every ten years or so.

Sinatra appeared on the cover of Time magazine in 1957 as the highest-paid entertainer in the history of show business, said to be earning $4m a year. He may have been able to take anybody to Acapulco who wanted to go, but his jet-set love life was not going so smoothly. Also in 1957 an actress he had been seeing took an overdose of sleeping pills, but recovered; and his pal Humphrey Bogart died of lung cancer. Bogart was the screen's favorite tough guy, but in fact had the kind of confidence allied with wit that meant he could do or say almost anything he wanted and get away with it. Sinatra had a much thinner skin. Before long he was running around with the widow, Lauren Bacall. He took her to the openings of The Joker Is Wild and Pal Joey, but he was afraid of getting serious, and so he should have been, after the disaster with Ava, who had only recently divorced him.

Bacall later wrote that when she first met Sinatra in 1945 she said, 'They tell me you have a voice that makes women faint. So make me faint.' He had to like that; her kind of attitude was what had made the Rat Pack work. In March 1958 they became secretly engaged, but Hollywood agent and professional party animal Swifty Lazar was in on the secret and shot his mouth off (perhaps getting his own back at last: for years Sinatra had played unmerciful pranks on the neurotic Lazar). The next day the engagement was in all the papers, whereupon Sinatra dumped Bacall and did not speak to her for several years. He not only rejected one of the most attractive, desirable and intelligent women in Hollywood, but did it in as humiliating a way as possible. Ava was amused, and teased him about it. Two months later he began recording Only The Lonely, with Nelson Riddle, an album that was back up to standard.

Sinatra was getting used to loneliness, a fact of his life, and he now made an album dedicated to his fellow losers (allegedly, it was almost called For Losers Only). The practice was now established of having Cahn and Van Heusen write a title song, but this time the normally glib Cahn had some trouble. 'Session after session without the glimmer of a line,' wrote Van Heusen, who offered to change the melody here and there, but Cahn wouldn't allow it, and said later that he usually refused to write a lyric that came hard, but was glad he'd persevered with 'Only The Lonely', and it is certainly one of their better ones. After a rest from each other, once again Riddle and Sinatra broke new ground together, and later when Riddle was asked which were his favorite albums he'd made with Sinatra, he unhesitatingly named Songs For Swingin' Lovers and Only The Lonely. There is a large orchestra, with lots of Riddle's instrumental felicities, French horns, woodwinds, trombone solos and so forth, yet the album has a minimalist feeling. After the line 'Pardon me, but I gotta run' in 'Angel Eyes', two bassoons make what can only be described as a muttering sound, startlingly apposite; Joe Comfort is back on bass, and nails down 'What's New?' with wonderful grace notes, while the same track (well over five minutes long) also has a pair of trombones, then an oboe during the instrumental bridge. And on the bridge in 'It's A Lonesome Old Town', the strings behind the trombone solo are surreal in the upper reaches of the harmony: the town is not only lonely, it is empty and cold. Carroll Lewis on muted trumpet plays the role Harry Edison played on earlier albums, but he is his own man, more detached, resigned rather than sardonic.

'Willow Weep For Me' could have had a slightly quicker tempo; all the tempi are very slow, as on Where Are You, and in fact the first recording session for this album was aborted after three tracks: at the end of May they were remade and four more were successfully got down with Felix Slatkin conducting (Riddle was allegedly not that good a conductor, and a slow tempo is more difficult to conduct than a swinger). It was at the second session that Sinatra famously failed to negotiate Billy Strayhorn's 'Lush Life', a difficult tune; after three attempts, he can be heard on the master tape walking out of the studio and slamming the door.

Riddle was back on the podium in June. To me, Gordon Jenkins's 'Goodbye' always sounded simply dreary when Benny Goodman played it (but that may be the influence of the awful Goodman biopic of 1955); here Riddle's arrangement starts with a fat English horn sound (which can be the most mournful sound of all), followed downwards by a cello, then a string bass played arco (with the bow): we think, what song is this? And then Sinatra reveals that it might be a pretty good song after all. (There were two basses at the session, Comfort and Edward Gilbert, probably to do the bowing here and there.) 'Blues In The Night', by Harold Arlen and Johnny Mercer, had six memorable hit versions in 1941-2, and Sinatra may have recorded it with Dorsey, but if he did that version is lost; Rosemary Clooney revived it in 1952. In 1958 Sinatra and Riddle have all the familiar accents in the arrangement, but they are now definitive: it is as though we know what the song means at last, and there is resignation instead of melodrama. Cahn and Styne's 'Guess I'll Hang My Tears Out To Dry' is revived from the Columbia years, with a very affecting solo guitar accompaniment; and the somewhat lugubrious 'Ebb Tide' gets a more convincing performance than one would have thought possible. 'Spring Is Here' and 'Gone With The Wind' are followed by a classic: the first recording of 'One For My Baby' (Arlen and Mercer again) with Bill Miller's piano and minimal orchestral backing. Sinatra had recorded the song in 1947, but here it became his own; it was actually recorded in the studio with a single spot on Sinatra, just as he did it in clubs.

Listening to the CD edition of Only The Lonely all these years later, one would like to remix it; Sinatra's voice is too far forward, a little boomy here and there, which isn't fair to anybody. Capitol has added a couple of tracks to the CD edition of each Sinatra album to pad out the playing time; one appreciates that they would be criticized if they didn't do that, but the original albums were thoughtfully arranged and compiled, and in many cases they should be left alone. In this case, 'Sleep Warm' from a session of September '58 would work as a new closer by itself, but 'Where Or When' from the same session has a bravura ending which doesn't belong on this album at all. Only The Lonely remains one of Sinatra's mature classics, made at a time when Capitol still displayed a lot of good judgement. But Sinatra wanted still more control over his affairs, and began to resent being under contract to Capitol.

He never liked not being in complete control. When Columbia began reissuing Sinatra's old records on long-playing albums, he seemed to resent it. The old Columbia sides made successful albums, but selling in a different market than the original 78s, a grownup market, which should have vindicated Sinatra; but by that time rock'n'roll was making inroads into all the markets, and Sinatra's old hatred of Mitch Miller was rekindled. There are plenty of reasons to regret Miller, who hastened the process of turning the singles market into wallpaper for the ears, but Sinatra tried to blame all his troubles in those years on Miller, which was nonsense. The memory of the painful period when his career seemed to be on the skids still rankled, and he had to blame it on somebody.

Rock'n'roll was just another genre, a fusion of hillbilly music and black rhythm and blues, but Sinatra loathed Elvis Presley and his like, writing for publication about this 'most brutal, ugly, degenerate, vicious' form of expression, saying that 'it smells phony and false'. (It is interesting that 'vicious' was one of Sinatra's favorite adjectives, while it would also be the best word to describe some of his own behavior.) The best rock'n'roll was musically simplistic, but anything but phony, a joyous, raucous, uninhibited music allowing people who would not have been welcome at one of Sinatra's shows their own form of expression; furthermore, to the extent that rock'n'roll rhythms and songs were sexually suggestive, they were at least not hypocritical about it. Sinatra's type of song was very often about sex, but obliquely so, while the sheer number of women in Sinatra's life represented a standard of vulgarity that the most jaded rock'n'roller could not hope to exceed. Sinatra had done a great deal in the 1940s to break down the hypocrisy of the studio system and its morals clauses, but when the urban working class (both black and white) began to express itself through R&B and rock'n'roll, he turned out to have a good line in hypocrisy of his own. The ABC network got some of its money back from the fiasco of the 1957-8 TV series when Sinatra hosted several one-hour specials; on the last of these, in 1960, he finally got high ratings by welcoming Elvis Presley home from the army. Presley's ten-minute appearance brought Sinatra's program the highest TV rating recorded in five years; but perhaps this was an early example of a kind of confusion that began to affect his artistic decision-making.

Meanwhile, Miller also disliked rock'n'roll, but had the good sense to declare that there was no such thing as immoral music. In a speech at a disk jockey convention in 1958, Miller accused the deejays of abdicating their responsibility, of pandering 'to the eight to 14-year-olds, to the preshave crowds that make up 12 percent of the country's population and zero percent of its buying power.' In fact Elvis Presley was setting sales records, and a lot of his output was purchased by adults, while Miller had done as much to cheapen pop music as anyone. But Miller's point was that the broadcasters were chasing the Top 40 and ignoring most of the music that was available in the marketplace, which was bad for music, and he was right. The deejays gave him a standing ovation, but the Storz broadcasting chain (sponsoring the convention) then banned Columbia records. Broadcasters who were chasing the largest common denominator did not want to be called upon to separate the gems from the dross.

In those days Columbia was clean and was not bribing deejays (the practice known as payola), nor did the company have any direct connection with music publishing. But when Congress decided to investigate payola in 1958-9, Sinatra stuck his oar in, claiming that he had been forced to record substandard stuff at Columbia because the parent company, CBS, had some connection with BMI (Broadcast Music Incorporated). In fact, when the music licensing organisation ASCAP (the American Society of Composers, Authors and Publishers) went on strike against the broadcasters in 1940, trying to force them to pay a much higher royalty rate for each piece of music broadcast, it lost the strike ignominiously; the broadcasters had clubbed together to set up a competing agency, and BMI saw to it that black and hillbilly songwriters and publishers, always ignored by ASCAP, got a fair piece of the action; and all this still rankled 20 years later. Congressmen were trying to get votes by investigating 'dirty' songs, and the industry tried to use public concern about rock'n'roll as a stick with which to beat BMI. But Miller had only to point out that Sinatra's contract at Columbia had given him complete control over what songs he recorded; that of 57 tunes Sinatra recorded for Miller only five had been BMI songs, and two of those were published by Sinatra's own BMI company; and that 'Young At Heart', the soppy ballad that had been one of Sinatra's biggest hits ever, on Capitol in 1954, was a BMI song. The truth is simply that there was something in Sinatra, his childhood loneliness, his awful mother or whatever, which meant that if anything went wrong it must have been somebody else's fault, and when he shot his mouth off he often demonstrated poor judgement.

Capitol Records had been sold to EMI in 1955, a move which Johnny Mercer later regretted; Glenn Wallichs was still chairman, but the sale freed Sinatra from any feelings of loyalty he should have had to the company which had re-launched him as one of the most successful recording artists of the century. From early 1956, when recording began at the Capitol Tower, Sinatra's masters were produced by his own Essex Productions: Capitol still owned them, but Sinatra's royalties were paid to his corporation, which was a tax advantage. (There was a Bristol Corporation that served the same purpose in his film work.) In 1957 he had signed a new seven-year contract with Capitol, but immediately regretted it: he had realized that the way to have complete control and to keep more of the profit was to start his own record company. He wanted Essex to become his own subsidiary label, but he was ahead of his time once again: nobody had such a deal in 1958. So he began agitating to be released from his contract. He was no longer happy with Gilmore as his producer, and switched permanently to Cavanaugh, a saxophonist and arranger whom Sinatra had known for some years; and he began to threaten to withdraw his labor -- to stop recording -- which was really the only weapon he had.

But recording continued for the time being. The next album, made in December 1958 with Billy May, was Come Dance With Me!, in a straightforward Swing-Era style: no fancy bits or knobs on, just brass and reed sections answering each other, as in the good old days. With Conrad Gozzo and Mannie Klein in the trumpet section, Milt Bernhardt back on trombone, old friends Babe Russin and Skeets Herfurt in the reeds and Shelly Manne or Irv Cottler on drums, the crew was well-equipped, and the whole thing is reminiscent of the 1950 Columbia album Sing And Dance With Frank Sinatra; except that the rhythm section is less stiff; in fact some of the new arrangements were by Heini Beau. Along with George Siravo, Beau had often written this type of thing for Axel Stordahl to conduct at Columbia; he could write in the style of Billy May or whoever he was helping out, and May himself was often very busy and only too happy to buy a few charts from Beau. (May was also a self-confessed procrastinator: he often came to recording session with work unfinished, but always pulled it off in the end.)

The trouble with Come Dance With Me was that, like all retro pop music, the main purpose of it was nostalgia. There is not a single solo on the whole thing, despite all the fine musicians on hand. If the rhythm section is less stiff, it also does not sound very involved. On most of the tracks there is a two-beat feeling on what are clearly supposed to be recreations of the peak of the Swing Era, but it has none of the unique flavor of Sy Oliver's best work, while the driving four-to-the-bar rhythm section of a Charlie Barnet or a Woody Herman is missed, as though the cast were all too aware that they were recording for fans who were now pushing middle-age. The combination of corn and May's wacky sense of humor on Come Fly With Me is also missing. 'Saturday Night (Is The Loneliest Night Of The Week)' and 'The Song Is You' were remade, and 'Day In, Day Out' was Sinatra's fourth recording of that tune for Capitol; he could do this sort of thing in his sleep by now, and all the accents are in the right place, but he does not sound terribly involved either. 'Baubles, Bangles And Beads' has some words added ('Them cool, cool beads') to fill out the dull originals. Cahn and Van Heusen wrote the title opener, which isn't up to much, and the closer, 'The Last Dance', which is better, the only slow one in the set. Come Dance With Me is eerily out of date, the same way the earlier Columbia album missed the boat: the Swing Era, an era of bands on the road and playing for live audiences every night, was over. Still, a lot of Sinatra's long-time fans must had a good time dancing to this album; Come Dance With Me won a Grammy as Album of the Year in 1959. Like the album itself, the Grammy might have been a bow to yesteryear.

Four appropriate tracks have been added to the CD edition of Come Dance With Me: all had been made a few months earlier for release as singles. DeSylva, Brown & Henderson's 'It All Depends On You' had been recorded for Columbia, while 'Same Old Song And Dance', 'Nothing In Common' and 'How Are Ya Fixed For Love' are better than average Cahn & Van Heusen ditties, the last two duets with Keely Smith, who brings plenty of the right chirpy spirit. In fct, the irony is that the four added tracks are more fun than the rest of the album, without the labored feeling that comes with cranking out tracks for a retro concept.

Look To Your Heart was a Capitol compilation, top ten in mid-1959; then it was back to Gordon Jenkins for another loneliness concept, No One Cares, made in March 1959. No One Cares is similar to the earlier Where Are You: tasteful strings, choirs of harmonising reeds and/or French horns, a firm rhythm section and (again with Cavanaugh producing) very good sound balance. The songs are lovely and Sinatra's delivery heartfelt, more evidence that Sinatra's artistry was instinctive or it was nothing. The songs on Songs For Swingin' Lovers were all standards that he loved to sing and that perhaps made him feel young again, and on that album he had Riddle's best work to inspire him. But 'Why Try To Change Me Now', 'Here's That Rainy Day' and the rest of the songs on No One Cares are simply better suited to him than 'Something's Gotta Give', 'Too Close For Comfort' and the rest of the jivers on Come Dance With Me. He is now a 44-year-old who has loved and lost, and knows that he has lost for good. Anybody who tried to best Sinatra in a business deal (or tell him what to do or drink him under the table or take his photograph without permission) would find out what a loser was, but when it came to love he was the prince of losers, and he knew it; there is no other explanation for the way he sings these kinds of songs, so that we do not need to hear anyone else sing them. Billie Holiday sang sad songs, but her sadness was existential, as though maybe it wasn't her fault, and anyway her bravery shone through. Sinatra is simply bereft.

'Cottage For Sale' and 'Ghost Of A Chance' are just lovely; 'I'll Never Smile Again' is remade, after nearly 20 years. It is nice to hear the intro to 'I Can't Get Started' ('Superman turns out to be flash in the pan'), and the verses are updated: 'I've flown around the world in a plane/ Designed the latest IBM brain ...' Indeed, another line seems to hark back to the corny Mandalay pretense:

In Cincinnatti or in Rangoon,
I simply smile and all the gals swoon;
Their whims I've more than just charted,
But I can't get started with you.

Now there's an admission: he's got all the broads he wants, and he wants them and likes them and charts their whims up and down, but the one he wants most of all has been and gone, or maybe hasn't turned up yet, and he knows she won't, and maybe he even begins to suspect that she doesn't exist.

On this album there was no sense of the customer getting his or her money's worth. There were only eleven tracks on the original edition of No One Cares, none of them as long as four minutes, and one of them was Tchaikovsky's 'None But The Lonely Heart', which should have been left in the previous century. The CD adds some interesting things: a slow version of 'The One I Love (Belongs To Somebody Else)', which had been a semi-jiver in the Dorsey years, had already been added to some later LP editions; and 'You Forgot All The Words (While I Still Remember The Tune)' is an obscure but thoughtful song co-written by Bernie Wayne, a craftsman responsible for 'Laughing On The Outside (Crying On The Inside)', and 'Blue Velvet', which turns up every few years like a bad penny. Sinatra was always one to give a good song a chance, but it was becoming harder to find them.

Then he laid down his gauntlet in the dispute with Capitol. He was rich and famous enough so that his arrogance had begun to manifest itself outside the saloons of Hollywood and Las Vegas; Sinatra and his friends in what came to be called the Clan were providing much of the spice in the show-biz columns. In April 1959 he visited Australia, and was completely unprepared for the sheer feistiness of the Australian press; he did not make a good impression. (Ava Gardner was there, shooting On The Beach, and she did not make a good impression either, saying 'I'm here to make a film about the end of the world and this sure is the place for it.') Sinatra redoubled his effort to take complete control of his professional life; between May 1959 and March 1960 he did not make any recordings except tracks for the musical film Can-Can; and then his dispute with Capitol was settled: they agreed to let him go before his contract ran out in return for four more albums.

Nice 'N' Easy, made in March and April 1960 with Nelson Riddle, had an informal photo of a smiling, comfortable, informal Sinatra on the cover, instead of a garish artwork or a designer's idea of hipness, and twelve songs, nearly all remakes that everybody liked to hear him sing: 'That Old Feeling', 'How Deep Is The Ocean', 'Fools Rush In', 'Embraceable You', 'Mam'selle' (his number one hit from 1947) and so forth; the album was irresistible and the biggest chart success of his career (in the nick of time, while Elvis Presley was in the army and the Beatles were popping pills in Hamburg). The title song was a new one, not by Cahn and Van Heusen for a change; it seemed to be about premature ejaculation ('The problem now of course is/ To simply hold our horses'). It did not fit terribly well with the rest of the album, but got a fair amount of airplay as a single, which helped: the album was number one for nine weeks and in the chart for 86 weeks.

The following year, 1961, he would have no fewer than six chart albums: all in the top ten, four in the top five. He paid off some of his obligation to Capitol with remakes of the songs he had recorded for the Columbia album Sing And Dance With Frank Sinatra in 1950. Sinatra's Swingin' Session!!! with Nelson Riddle (and three silly exclamation points) included six of the eight tunes from the '50 album (with more interesting arrangements), and Come Swing With Me! with Billy May included another. The album with May was a retread of Come Dance With Me, but a more appealing album, with a smoother rhythm section (Joe Comfort back on bass), some medium tempo and a couple of slower tracks for variety (e.g. 'Sentimental Journey'). Again, several tunes are remakes from the 1940s: 'Five Minutes More', 'American Beauty Rose'. More than half the tracks were arranged by Beau, including 'That Old Black Magic', which swipes its intro idea from Artie Shaw's 'Begin The Beguine', and 'Lover', with a pungent bass trombone in its intro. The CD adds five appropriate tracks with May, Riddle or Skip Martin, and on the whole the album's bow to the Swing Era was less self-conscious than most such efforts.

All The Way was a Capitol compilation album, and no fewer than three Sinatra chart albums in 1961 were the first three albums on his new label, Reprise, for which he had already started recording in December 1960. Sinatra had tried to buy Verve Records from Norman Granz, but the deal fell through; then he had already made two albums for his new label before he made his last original album for Capitol, which he didn't really want to make at all. Point Of No Return, made in September 1961, saw the return of Axel Stordahl, whose skill had been so important to Sinatra from the Dorsey years right up until 1953; Sinatra was in a hurry, and most of the tracks were done in one take (there is a very audible tape splice at the end of 'These Foolish Things', on the last word Sinatra sings: 'remind me of you'). But a miracle happened. The songs, of memory and regret, were well chosen, such as 'As Time Goes By', 'September Song', Noël Coward's 'I'll See You Again'; 'I'll Remember April' is particularly fine, introduced with a unique rhythmic pattern set down by Comfort on bass, and delicate percussion, almost Chinoiserie. The tracks vary in length from two and a half minutes to more than four for 'September Song', and one is glad for tape recording and the long-playing record: no doubt there is something about not being limited to the playing time of a ten-inch 78 that can help to set the music free. These arrangements of Stordahl's somehow sound less self-conscious than the old Columbia 78s. Sinatra may have been feeling impatient, but he was incapable of not turning in a professional job in the recording studio, while Stordahl was glad to be working with his old chum once more.

Stordahl was ill with cancer, and died less than two years later, just 50 years old; he had spent four years in the mid-'50s with Eddie Fisher and made some other albums, but he hadn't done a lot of the kind of writing he had been used to doing with Sinatra. Yet their old working relationship re-established itself immediately, and if anything, Stordahl had actually improved. His string writing was as reliable as ever, but everything else fell into place as well; even the rhythm section, rarely audible on the Columbia sides, had a reason for being, and the arrangements are more fun to listen to than the lushness of Gordon Jenkins. With producer Cavanaugh and Capitol's recorded sound deserving some of the credit, the album was a great success, remembered with pride by everyone who was there. The CD edition includes the four tracks from April 1953, including a forgotten early version of 'Day In, Day Out', combining Sinatra's first and last Capitol sessions and all his Capitol work with Stordahl on one disk.

Meanwhile, Sinatra was still making two films a year. Kings Go Forth in 1958 was a wartime melodrama; Some Came Running a postwar melodrama the same year, like From Here To Eternity from a novel by James Jones. Sinatra saw to it that his friend Shirley MacLaine's part in Some Came Running was made more dramatic, by way of solving a problem that Sinatra himself had caused: when the film got behind schedule, he tore twenty pages out of the script and said to an assistant director, 'There, pal. Now we're on schedule.' The writers and the director had to pull the story together somehow, and Sinatra had thrown out one of MacLaine's scenes, so she received the dramatically rewritten ending, which resulted in an Oscar nomination for her.

Next was a Frank Capra movie. Capra's feel-good films were thought to be out of fashion: Americans could no longer be jollied along by the likes of Mr Deeds Goes To Town and You Can't Take It With You (both from the 1930s); even It's A Wonderful Life had fallen flat in 1947, and Sinatra was no James Stewart. But he had discovered a property that he liked, and hired Capra to direct an easy-going comedy of the Capra-corn type. Capra had a hard time dealing with Sinatra's work habits, and some scenes had to be improvised to keep everybody fresh, but A Hole In The Head was a box office hit and revitalized Capra's career. (The theme song from Some Came Running, 'To Love And Be Loved', was nominated for an Oscar, and 'High Hopes' from A Hole In The Head won the following year: both were written by Cahn and Van Heusen, and 'High Hopes' was Sinatra's third Oscar-winning hit single in six years.)

Never So Few in1959 was about wartime jungle action in Burma, while Can-Can in 1960 was a dull musical: the 1953 Broadway version had established 'It's All Right With Me', 'I Love Paris' and 'C'est Magnifique' as new Cole Porter standards, but musicals don't always translate well to the screen, and Hollywood often botched it. The set of Can-Can was visited by Soviet premier Nikita Krushchev and his wife, and the newspapers got a chance to describe Sinatra's charm for a change instead of his bad manners.

So ended the most successful decade, in artistic terms, of Sinatra's career. He was now one of the most famous people in the world, both as a singer and an actor, but much of his best work was behind him. Dean Martin and Peter Lawford, two of his Hollywood pals, had co-starred in Some Came Running and Never So Few respectively; his next film, still in 1960, was Ocean's Eleven, an overlong caper movie featuring his own Rat Pack, soon known as the Clan: Sinatra, Martin, Lawford, Sammy Davis Jr and comic Joey Bishop, with the action periodically stopping for in-jokes. Sinatra would become richer and more famous, but he would also show more bad judgement as his power to do as he pleased began to coincide with a general decline in the quality of American popular and political culture. In 1960 he made a mistake which in retrospect signals this decline, and ironically the mistake lay in not doing as he pleased.

The object of the Holmby Hills Rat Pack had been to have a good time, but when Sinatra had assembled his own team of acolytes, there was no Bogart to keep an eye on him, and the only object was to follow the leader. Not as well-read as Bogart, Sinatra's Clan invented its own school-boyish vocabulary: all women were of course broads; death was 'the Big Casino'; an act that flopped was 'bombsville'. The -ville suffix could be added to anything, as in Sinatra's famous quote about his own work: 'The audience is like a broad -- if you're indifferent, endsville.'

Sammy Davis was a talented crowd-pleasing singer and dancer who adored Sinatra, with plenty of reason to be grateful: they had already been close friends for a decade, since Sinatra had plucked Davis from obscurity in a trio act with his father and his uncle and helped him to become the biggest black star in American entertainment since Nat Cole. Dean Martin had known Sinatra since 1948, and was one of the few people who never took any nonsense from him, eventually retiring with his integrity more or less intact. Joey Bishop was a successful stand-up comic useful for his one-liners. Peter Lawford was a second-rate actor, a drunk and finally a self-confessed pimp for the rich and famous, but he had some social cachet, apart from his English accent: in 1954 he had married a sister of John Fitzgerald Kennedy, a Democratic member of the House of Representatives from the state of Massachusetts, who looked increasingly like a successful candidate for the White House. The Clan period became legendary; Shirley MacLaine has described it:

When we made pictures at the same time the the Clan was appearing in Vegas, there was an energy there that has never been duplicated since. Two shows a night, seven days a week, for three months -- while shooting a picture. Granted, these pictures were not award winners ... but the spontaneous humor on the stage and the set was unparalleled. The director never knew what was going to happen or how a scene would be played on a given day. But it didn't matter.

No doubt it was fun at the time, but it did matter. In retrospect, all these years later, all that jive looks and sounds like self-indulgence. And the spontaneous humor was not as free and easy as it seemed. The fact is that Dean Martin, for example, was a lot funnier than Frank Sinatra. The jokes were corny, many of them around the subject of booze: 'Frank, do you know how to make a fruit cordial?' 'No, Dean, how do you make a fruit cordial?' 'Why, be nice to him!' But Martin could pull off this sort of thing; Sinatra could not. MacLaine goes on to describe how Sinatra got tired of Martin getting all the laughs, so one night they exchanged roles; and instead of laughing at Sinatra's punch lines, the audience laughed at Martin's straight man. Martin's easy persona and his sense of comic timing is the reason he was a success on television and Sinatra was not; it is remarkable that they remained friends for so long. But as Joey Bishop said after Martin's death at the end of 1995, 'I remember him most of all for his honesty. He hated anything that was phoney and would not partake of it. He was one in a trillion.' Martin and the others were having fun; one suspects that even when he was trying to be funny, Sinatra took it all too seriously.

When Sinatra was at the bottom in the early 1950s, the story goes, he was walking down the street when he came across a gaggle of teenaged girls who recognized him, and poked fun at him, making it clear that they were Eddie Fisher fans. He took it well, allegedly telling them that he liked Fisher's singing, too. But a decade later, Fisher was a sort of mascot of the Clan, and one of their favorite pastimes was climbing on stage during his performance, making a shambles of it with their pranks. Fisher did not have the wit to take part in the shambles, and looked out of place in his own act.

In November 1959 John Kennedy stayed at Sinatra's Palm Beach home for two nights after a big fund-raiser in Los Angeles, according to Lawford; in January 1960 Kennedy, by then a Senator and running for President, attended a performance by the Clan at the Sands in Las Vegas during the filming of Ocean's Eleven. Relaxing away from the campaign trail, he enjoyed japes about race, booze, Italians and the mafia, as well as a cake pushed in Bishop's face and some of the others running around on stage in their shorts. Both Kennedy and his father, Joseph P. Kennedy, were fascinated by Tinseltown and its inhabitants; and both Kennedy and his father were incorrigible womanizers, who liked to hang out in Hollywood picking off film stars.

The Irish-American Joe Kennedy had got very rich over the years in shady activities of various kinds, including bootlegging liquor during Prohibition, which no doubt brought him into contact with even shadier characters. One of the great ironies in the history of American showbusiness was the fate of the Keith circuit: Benjamin Franklin Keith and Edward Franklin Albee had a stranglehold for decades on vaudeville venues in the USA, cheating the performers the whole time; after Keith's death, and when the death of vaudeville was written on the wall in the late 1920s, Albee was bamboozled out of his empire by an even bigger crook. Joe Kennedy made several million dollars from mergers that became RKO Pictures, including Keith's vaudeville palaces, which were already showing films. (There is even a story that the threat of a phony paternity suit helped the deal along, and that the woman involved later died mysteriously.) Actress Gloria Swanson was one of Joe Kennedy's mistresses; later he was a Nazi sympathizer as Ambassador to the Court of St James in London on the eve of the Second World War; and later still, he was intent on buying the White House for his second son, as the first had been killed in a plane crash. Joe Kennedy and Frank Sinatra had something in common apart from shady friends and chasing skirt: emotionally they were both immigrants, getting even with the establishment, and winning the White House would be the last laugh. But in 1960 something almost came between them.

Sinatra had already survived the wrath of the paranoid anti-Communists of the late 1940s, but there were other victims who were not unscathed. The House Committee on Un-American Activities had been formed in 1938, partly in reaction to Franklin Roosevelt, whose radicalism during the Depression had extended to creating the Works Progress Administration, for example, to give some of the unemployed some useful work to do. This sort of thing was seen as creeping socialism, which in the USA was thought to be the same thing as communism. In 1947 the Chairman of HUAC (or the House Un-American Activities Committee, as it became familiarly known) was J. Parnell Thomas of New Jersey, whose education in the arts had begun with the question, 'Which WPA payroll is Christopher Marlowe on, New York or Chicago?' The Committee's ranking Democrat was John E. Rankin of Mississippi, fond of using words like 'kike', 'nigger' and 'Jew-boy' in debate on the floor of the House. In 1947 the Committee was investigating the film industry, one of the best ways of attracting column inches in the newspapers, and a group of craftsmen who refused to answer questions about their politics past or present were cited for contempt of Congress and sent to prison for a year. Only the most fanatic of film buffs ever would have heard of them, except that they went down in history as the Hollywood Ten. (J. Parnell Thomas, by the way, was soon sent to prison for taking kickbacks from Federal employees, serving time in the same Federal slammer as some of his victims.)

Seven of the ten were screenwriters; the others were directors and producers. All were blacklisted on release from prison and could not work at their chosen professions, although blacklisting itself was supposed to be against the law. Director Edward Dmytryk recanted and went back to work, but all had paid their dues. One of the screenwriters was Dalton Trumbo, who published a pamphlet in 1949 called 'The Time Of The Toad', from an article by Emile Zola, in which Zola claimed that he purchased a toad in the market each morning and swallowed it whole and alive, in order to make himself immune to the mendacity of the French press of the 1890s. The time of the toad in Germany, wrote Trumbo, began in 1933, when the new Chancellor in that country decreed the discharge from the civil service of all 'who have participated in communist activities ... even if they no longer belong to the Communist Party or its auxiliary or collateral organizations', and those who have 'opposed the national movement by speech, writing or any other hateful conduct' or have 'insulted its leaders'.

Those were the days in Germany when respectable citizens did not count it a disgrace to to rush like enraptured lemmings before the People's Courts and declare under oath that they were not Communists, they were not Jews, they were not trade unionists, they were not in any degree anything which the government disliked -- perfectly aware that such acts of confession ... rendered all who would not or could not pass the test liable to the blacklist, the political prison, the crematorium.

'As a matter of general policy,' Trumbo went on, the House Un-American Activities Committee

has flouted every principle of Constitutional immunity, denied due process and right of cross-examination, imposed illegal sanctions, accepted hearsay and perjury as evidence, served as a rostrum for American fascism ... acted as an agent for employer groups against labor ...

And on and on, all too true. Informer Harvey Matusow had named many names, including those of the Weavers, the folk group discovered by Gordon Jenkins; having wrecked their career, he later confessed that he'd made it all up, and got five years for perjury. The unfreedom and the lies could not live forever, though; Trumbo subsequently won Oscars for his original story for Roman Holiday in 1953, allowing somebody else to take the credit, and under a pseudonym for his work on The Brave One in 1956, a story about a boy and his pet bull. In 1960 Kirk Douglas and Otto Preminger produced Spartacus and Exodus respectively, both insisting that Trumbo's name appear in the credits; the American Legion picketed the films, but nobody cared much, and the reign of HUAC's ignorant crooks seemed to be over.

Another of the blacklisted screenwriters was Albert Maltz, who had scripted a wartime documentary in 1942, Moscow Strikes Back, which won an Oscar, and was nominated himself for his work on a 1945 flagwaver, The Pride Of The Marines. He also wrote the screenplay for Sinatra's short film about tolerance, The House I Live In, which won a special Oscar in 1945. Opposition to HUAC and everything it stood for must have sounded good to Sinatra. In 1960 he decided to produce and direct a film of The Execution Of Private Slovik, by William Bradford Huie, about the only soldier executed for desertion by the United States Army since the Civil War. He hired Maltz to write the screenplay, because Maltz would have made a good job of it; helping to consign the blacklist to history would have been a plus. But instead of waiting until the picture was shot to become a hero, Sinatra lost his way and finally made what I would describe as one of the biggest mistakes of his life.

Maltz was anxious; he knew that Sinatra was playing at politics, supporting Kennedy, but he wanted the blacklist ended by discrediting it as soon as possible, so he asked Sinatra if they couldn't make an announcement. Any suggestion that Sinatra needed to wait on the Kennedys or anybody else was like a red rag to a bull; at any rate the news got out in an article in the New York Times in March 1960, and all hell broke loose. It was the Hearst press all over again: The New York Mirror described Maltz as 'an unrepentant enemy of his country'; The Los Angeles Examiner accused Sinatra of 'making available a story wide open for the Communist line.'

All-American hero John Wayne said, 'I wonder how Sinatra's crony, Senator John Kennedy, feels about him hiring such a man?' Henry Fonda, James Stewart and many others had served their time in uniform; Gene Autry lost his title as King of the Cowboys to Roy Rogers while he was flying supply aircraft in Burma; but John Wayne did everything he could to avoid losing any career momentum, pretending to win the war single-handed on screen and spending the rest of his life wrapped in the flag. He was proud of having driven Carl Foreman out of Hollywood (Foreman had also refused to answer HUAC's questions) because he disliked Foreman's film High Noon: a movie about a real hero made Wayne too uncomfortable.

Sinatra defended himself, using adverts in the Hollywood trade papers. Hank Sanicola, Nick Sevano and lawyer Mickey Rudin were running a production company that had TV specials lined up sponsored by General Motors, who were threatening to pull out; they begged Sinatra to change his mind: he shrugged and said, 'There'll be other specials.' Sevano kept pleading until Sinatra got sore and fired him, and the production company broke up. But then the Cardinals (not the baseball team, the old men in funny hats) told Joe Kennedy that the furor was going to hurt JFK with Catholic voters, and the biggest problem JFK faced was the fact that he was a Catholic: no Catholic had ever been elected President. It only took one phone call to solve the problem. 'It's Maltz or us,' said old Joe Kennedy, and Sinatra caved in to the Kennedy glitz. He published a statement that was almost sarcastic:

I had thought that the major consideration was whether or not the resulting script would be in the best interests of the United States. Since my conversations with Mr Maltz had indicated that he has an affirmative, pro-American approach to the story, and since I felt fully capable as producer of enforcing such standards, I have defended my hiring of Mr Maltz.

But the American public has indicated it feels the morality of hiring Albert Maltz is the more crucial matter, and I will accept this majority opinion.

He paid off Maltz and gave up Private Slovik. (The story was made into a TV movie a dozen years later, starring Martin Sheen, with a different writer.) Sinatra had had a good idea for a movie and a scriptwriter that might have been one in the eye for the elderly Roosevelt-haters who were still running the newspaper business, but he took his cue from an elderly bootlegger who happened to be a candidate's father; and he knew he had made a mistake. A few days later he got drunk, almost started a fight with John Wayne, and did start a fracas in a Los Angeles parking lot; some goon beat up a parking attendant, and yet another suit against Sinatra's temper had to be settled out of court. His temper was all he had left. He had sold out for nothing.

The American working class as a whole always despised Communism, which was never a domestic threat in the United States, but the politicians and the John Waynes capitalized on it. After Franklin Roosevelt's death the political parties locked themselves into a historical trap of each having to be more anti-Communist than the other, so that during his presidential campaign Kennedy invented a phony 'missile gap' between the USA and the Soviet Union, touching off a grossly expensive and dangerous arms race, and before long Kennedy was sending advisers to Vietnam. But at least he wasn't embarrassed by his Hollywood friend hiring a blacklisted scriptwriter.

Sinatra campaigned for John Kennedy; at old Joe's suggestion he asked his gangster friends to help steal the election, and he continued passing his cast-off women JFK's way. Sinatra then remodeled the Palm Springs place at vast expense, figuring it would turn out to be JFK's favorite hideout; but his own tasteless horsing around put paid to that. He had passed a brunette called Judith Campbell both to John Fitzgerald Kennedy and to top mobster Sam Giancana, and FBI chief J. Edgar Hoover knew it. Hoover and Bobby Kennedy, who was now Attorney General of the United States, did not have much use for each other, but Hoover passed the information about Campbell to Bobby, and when President Kennedy came to California in March 1962 he stayed at Bing Crosby's house instead. Sinatra was devastated, and blamed Peter Lawford, for reasons known only to himself; meanwhile the Mob grew disillusioned with Sinatra, who did not have enough influence to get the Feds off their back after all.

The 1950s had been a fantastic decade for Sinatra, and there would be more good music and more partying to come, but the real glory had peaked.

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