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All Or Nothing At All:
A Life of Frank Sinatra

Chapter 6

Frank Sinatra's comeback had been one of the most spectacular in the history of show business. His Capitol albums nearly all turned out to be classics of their kind, because his respect for musicians and for good songs was absolute. He had known since he was a teenager that his route to fame and fortune would depend first of all on his singing, and then he found within himself an ability to interpret his kind of songs which not even he perhaps fully understood; but the peak in the overall quality of his recorded work was now past. By 1960, Sinatra seemed to be winning all the games: the Westbrook Peglers and the Lee Mortimers were almost forgotten, and his pal John Kennedy was elected President of the United States. The studio system was collapsing and Hollywood, the world's dream factory, was Sinatra's playpen. What would he do with it? Like America, he floundered; but he floundered with energy and determination.

His Reprise record label was immediately successful. Sinatra had met Mo Ostin while he was trying to buy Verve from Norman Granz; MGM got Verve, but Sinatra hired Ostin, one of the most successful record men of all time, who subsequently oversaw Reprise and its sister labels for more than 30 years. Driving past the Capitol Tower with Ostin, Sinatra said, 'I helped build that. Now let's build one of my own.' The first five Reprise releases in 1961 included a Sinatra album; an instrumental set by Ben Webster, the great ex-Duke Ellington tenor saxophonist (The Warm Moods, with Johnny Richards and his orchestra); and Mavis! by Mavis Rivers, a highly rated New Zealand-born jazz-oriented singer who had made several albums on Capitol, including one with Riddle. On her Reprise debut Rivers was accompanied by eleven of the best West-Coast jazzmen, the Marty Paich Dek-Tette, as was Sammy Davis Jr on The Wham Of Sam!, and the fifth release was a comedy album, It Is Now Post Time, by Joe E. Lewis, the comic Sinatra had portrayed in The Joker Is Wild.

Other artists soon joining Reprise were Dean Martin, deep-voiced blues singer Jimmy Witherspoon, and the Hi-Los, the jazz-influenced vocal quartet, fresh from chart albums on Columbia. Comedy albums were very big in those days, when people still remembered how to listen to words without pictures, and cheap to make; Mort Sahl also recorded for Reprise. Some people in the industry had thought that Sinatra was indulging himself with his own imprint, but by the end of the first year it was clear that Reprise was capturing a large piece of the mainstream, or what would become MOR music, the middle of the road. Record distribution in the USA had long had its shady side, and it no doubt helped to have friends in certain places (a Federal wiretap caught mobsters including Sam Giancana talking about a debt of $14,000 that Reprise owed to somebody or other), but there can be no doubt about the success of Reprise's marketing and distribution.

As a label boss Sinatra was true to himself, first of all in freeing Reprise artists from the treatment he had received from the record industry: they retained ownership of their master recordings and owned shares in the company, they had complete control over their recording sessions, and their contracts were not exclusive: they could record for other labels if they wanted to. During the 1960s Bing Crosby and Rosemary Clooney recorded for Reprise, and there were three more albums by Mavis Rivers. From 1963 several Duke Ellington albums appeared on Reprise, not the peak of that great career to be sure, but including the lovely Afro-bossa. During the decade eight of Sammy Davis Jr's Reprise albums reached the Billboard chart. Only one of Dean Martin's Capitol albums had charted, but during the 1960s an incredible 20 Martin albums on Reprise made it. Arranger and conductor Don Costa, soon recording with Sinatra, discovered folk-pop singer and guitarist Trini Lopez performing in a Hollywood nightclub; his 'If I Had A Hammer' was the first big hit single on Reprise, in 1963, and 14 Lopez albums charted during the decade.

There had been expensive competition with Capitol, caused first of all by Sinatra himself, insisting on recording for his new label and his old one at the same time. Capitol objected to the title of one of Sinatra's first Reprise sets: Swing Along With Me, they successfully argued, was too close to Come Swing With Me, just released on Capitol, so the title of the Reprise album was changed to Sinatra Swings. Then Capitol started selling all Sinatra's albums on that label at reduced prices, and after Look To Your Heart in 1959, All The Way and Sinatra Sings Of Love And Things in 1961-2 were more compilations of Capitol tracks. He was now competing with packages of his old recordings on two other labels; but even so, Reprise was so profitable that in 1963, needing to divest himself of casino interests in Nevada, Sinatra sold two-thirds of it to Warner Brothers for a price said to be $3.5 million, far more than Sinatra had been willing to pay for Verve a few years earlier.

Warner Brothers was already successful with TV and film music, and comedy (Bob Newhart, the Smothers Brothers). Now Jack Warner acquired a lease on Sinatra's holdings in Nevada and got Sinatra as a member of the board, as well as his services in several films, and now that he had given up other interests and was concentrating on entertaining, Sinatra got what he had wanted at Capitol: his own label with somebody else putting up the money. Sinatra also obtained one-third of Warner Brothers Records, and Warner got Mo Ostin. Warner Reprise went on to become WEA (Warner-Elektra-Atlantic), one of the top three or four conglomerates in the international record business, partly because Ostin looked after his artists and let them do what they did best, signing up the best of the new era: Joni Mitchell, Emmylou Harris, Ry Cooder, Neil Young, the Grateful Dead and many more made albums in the Sinatra tradition: not many reached number one, but they are all still selling today.

Reprise itself was defiantly mainstream during most of the 1960s. Sinatra's daughter Nancy made a dozen flop singles before she finally convinced Ostin to let her record something rockish: her partnership with songwriter and guitarist Lee Hazlewood made a star out of her with 'These Boots Are Made For Walkin' ', a number one in 1966, and eight of her albums charted. (She couldn't swing a tune in a bucket, but the juke box liked her voice; somebody wrote that she looked like a pizza waitress, but so did a lot of other young women in that decade.) And the biggest star on Reprise was the boss, who had the mainstream sewn up almost by himself. He made a phenomenal six albums in 1960-1, three for Capitol and four for Reprise, which all went top ten in Billboard on release; a compilation album in 1991 became Sinatra's 38th Billboard chart album on Reprise, and the first was Ring-A-Ding Ding!

The ever-faithful Cahn and Van Heusen wrote a title song on Sinatra's catch-phrase, meant to be vaguely salacious. (He had already blurted it out on his recording of 'I Won't Dance', one of the less successful tracks on A Swingin' Affair in 1956, where it was evidently meant to refer to sexual excitement, followed by the line 'I feel so absolutely spunked out on the floor.') The lyric on 'Ring-A-Ding Ding!' was on the lines of 'Makin' Whoopee' and 'The Tender Trap': the swinging batchelor gets nabbed by the girl, which is what sexual excitement can lead to. Harold Arlen's 'Let's Fall In Love' uses one of a saloon singer's best tricks, starting with the bridge and then the verse (or introduction), which probably hadn't been heard since 1933, so that when we finally the familiar chorus, the recognition is a reward for listening. 'The Coffee Song' is also a highlight of the album, more fun than his 1946 recording on Columbia. Sinatra had embarked on a period of hiring arrangers for one-off projects: Axel Stordahl for Point Of No Return, and now Johnny Mandel for Ring-A-Ding Ding, a jazz musician who had worked with Mel Tormé, Hoagy Carmichael and Dick Haymes, and who was also blazing a path as a film composer (starting with I Want To Live! in 1958, a hit film which got Susan Hayward an Oscar). Mandel farmed out bits of arrangements to others, but the album had a secure overall identity, studded with solo bits by superb sidemen, and the theme of ring-a-dinging carried on throughout by orchestral chimes, triangles and xylophone. Ring-A-Ding Ding! made a sprightly beginning to Sinatra's career on his own label, and the next was Sinatra Swings, with Billy May, made at more or less the same time as the last album with May, Come Swing With Me! on Capitol. Once again everybody had a lot of fun, this time with a mix of standards, remakes, rescuings of weepies-turned-jokies ('The Curse Of An Aching Heart') and two tongue-in-cheek spectaculars, 'Granada' and 'Moonlight On The Ganges', which sounded like it employed every percussionist in Hollywood.

Sinatra's third album on Reprise was I Remember Tommy, a tribute to Dorsey, whose death in 1956 had been a shock (mixing heavy eating and drinking with a sleeping pill, he'd choked to death in his sleep, a surprisingly common accident among highly-strung show-business folk). Sinatra knew that a tribute album would be a good commercial idea; he reached back through the years for Sy Oliver to arrange it, and there were advance orders for 200,000 copies: word had got out and everybody was waiting for it. Thirty-five years later it never fails to disappoint. With this album it is suddenly clear that Sinatra was not as young as he used to be.

The words to 'I'm Getting Sentimental Over You', which Sinatra had never recorded before, are not up to much, but we know that Dorsey's theme is only an opener; then disaster strikes with the second track, Burke and Van Heusen's 'Imagination'. The original 1940 recording opened with the full band, but Dorsey's brass rarely blasted out as Oliver's do here; they sound like they're playing a gig in a nursing home for half-deaf Swing-Era fans leaning on their Zimmer frames. The gentle two-beat lilt of the original is gone, as though the bassist has to play four-to-the-bar or he'll turn into a pumpkin; but the worst part is Sinatra's vocal: instead of phrasing the song in a musical way as he did on the original, and which is the skill that made him famous, he drives the words down on the beat as though he hates the song. 'It's Always You' is dreadful in exactly the same way. 'East Of The Sun' is taken at much the same tempo as the original, but now used to toss the song off without any style to speak of. 'Take Me' is embarrassingly operatic: of all the songs from the Dorsey period, that was one they should have passed up; yet in general the ballads are the least objectionable tracks on the album. One of the best, 'In The Blue Of Evening', was not released until the CD edition.

Eight tracks were first recorded in March 1961, and rejected; the sessions had to start again in May. The rejected tracks sounded too close to the Dorsey originals, with a small string section (most of the originals had had no strings at all); Sinatra was now over 45 years old, probably doing too much recording and perhaps nervous about not sounding good, wanting more strings in back of him. 'In The Blue Of Evening' is the only track from March which was not remade, and it is clear that something was terribly wrong with the whole idea, beginning with the fact that Sinatra was effectively the producer of all his later records, and he needed some input from a cooler head. The tragedy is that the tribute idea was a sincere one. After Dorsey was dead, Sinatra could not stop talking about his erstwhile father figure; there are instances from the late 1950s onwards of him staying up all night with anyone who was willing to hear the old stories.

What went wrong with the album can only be fully understood with our hindsight. To begin with, the Swing Era could not be recreated by the original participants. There are those who think that rock'n'roll swept away mainstream music, but it's the other way around: rock could not have happened unless the Swing Era had been over, in the cultural sense. It would be easier to recreate that era today with a bunch of good young well-rehearsed musicians than it was with middle-aged men in 1962. Whatever combination of circumstances made Oliver such an innovating arranger in 1940 no longer existed 20 years later, and good a musician as he was, he was not the kind of artist who kept developing all his life. Nelson Riddle's work with Sinatra in the mid-'50s was successful partly because because it could not have been written in 1940; Riddle was to some extent celebrating the past, but was looking back with affection, not trying to enter a time machine. (Billy May is an exception that proves the point: he could always sound like the Swing Era, but he was not trying to recreate anything either; his object was to have fun, throwing in tuneable drums, slurping saxes or whatever he liked.)

James Fenton wrote in The New York Review in 1996 on the subject of embalmed culture:

There are paintings of famous moments in famous performances -- Edmund Kean as Richard the Third, on the night before the Battle of Bosworth -- and these paintings are always instantly recognizable as being depictions of theater rather than depictions of events. What comes across the centuries is the falseness of the gesture, whereas the whole reason for painting the scene was not for its falseness but for its truth. This was the moment when Kean froze the blood.

In film, too, when a director wishes to suggest that we are now watching a play, he will introduce a kind of lighting from beneath, the falseness of which will suggest footlights. But it was never the intention of the inventors of footlights to introduce a false, an 'alieneating' effect onto the stage. Everyone knew that they were dealing in an illusion, but nobody felt this implied that the whole project was a deception. It is when it is reproduced that theater seems so false.

So it was when Sinatra tried to recreate his years of glory, from the Song And Dance album of 1950 through the later years. What critic Stanley Dance dubbed 'mainstream music' was Swing Era veterans, like the Basie band, playing what they'd played all along, not a recording studio ghosting a band that never existed. The arrangements of the Swing Era are beautiful, many of them, but there was little that was original or innovative about the retro arrangements of two decades later; they imitated the half-remembered formula of jeek-jeek-a-jeek trumpets to please the middle-aged fans, which brings up another facet of retro music: the fans were easily pleased.

Charlie Barnet was one of the best leaders of the Swing Era, and no mean arranger himself; he tells the story in his autobiography (written with Dance), Those Swinging Years, of a series of tour dates in Texas in the mid-1950s. Barnet went to Dallas and rehearsed in the basement of a music store with a band of the best local musicians, but on the first date outside Dallas, none of the musicians showed up. They had wanted to play Barnet's charts, but did not want to tour, so they all sent substitutes. On the first gig of the tour, Barnet wrote,

... the completely unrehearsed band was awful. After some thirty minutes of playing, or whatever it was they were doing, I called an early break and repaired to the band room, where I downed a third of a bottle of scotch ... When I got back to the bandstand, here comes the committee, to give me hell. Instead, they said, 'Mr Barnet, we're so happy you brought the original band. We heard you on the air from the Palladium a few nights ago, and everything is just great.' That only went to prove my theory about the public being tone deaf and being unable to distinguish between good and bad.

During the Swing Era the bandleaders wanted to enjoy their own music, so they saw to it that the music was good, and everybody enjoyed it; the knowledgeable fans were ecstatic, and the rest got a bit of musical education. But when the power passed from the leaders to the record companies, and more recently to the accountants who run the record companies, most people couldn't tell the difference, and nobody's ears learned a thing.

There is even an element of hubris, and something symbiotic about the direction of American culture, in the recorded sound of Sinatra's reprising-the-past albums: I Remember Tommy has an absurdly wide stereo soundstage, and actually sounds better if you listen to it in mono (except most amplifiers nowadays don't have mono buttons). The effect is garish, like seeing the star on a huge screen, as though the technology will compensate for the fact that the music is not the real thing. The absolute integrity of the Capitol recordings with Riddle of 1953-6 was left behind in more ways than one as the record industry as a whole began to suffer from overdoses of technology.

Another aspect of this watershed in Sinatra's career is that he was now so rich and famous that he could do nothing wrong. There are not all that many artists whose work is vital right up into old age, like Haydn, Thomas Mann, Picasso; many reach their greatest fame only as they are passing their peak, or even after it, like Pavarotti, Maria Callas, or Duke Ellington. (Nobody likes to say so, but although Ellington often made beautiful music in his later years, there was little innovation or artistic progress after a certain point, which is why 1940-2 is still regarded as his peak.)

Similarly, when Sinatra was one of the most famous people in the world, not only did the quality of his recorded work begin to fall off, but he made several embarrassingly bad films: Ocean's Eleven, Sergeants Three, 4 For Texas and Robin And The Seven Hoods were all released 1960-4. 4 For Texas was a ludicrously unfunny comedy western, flabbily directed, casually acted and instantly dated, in which Sinatra and Dean Martin played themselves. Robin And The Seven Hoods started out as an interesting idea, a musical setting of the Robin Hood legend in Chicago during Prohibition days; Sammy Cahn thought they had got Gene Kelly to direct and Saul Chaplin to produce, but they had got Kelly to produce and Chaplin to supervise the music, and both soon dropped out. Cahn wrote what he regarded as one of his best-ever Sinatra songs, 'I Like To Lead When I Dance', and Sinatra loved it, but then didn't bother to perform it in the film. During this period Sinatra also made The Devil At Four O'Clock, co-starring Spencer Tracy, a melodrama that was too long, and The Manchurian Candidate, which is utterly remarkable, but as in the recording studio, he seemed to losing the ability to tell a good idea from a bad one.

There were better albums along with the less good. The last of six sets recorded in just two years was Sinatra With Strings, arranged and conducted by Don Costa. Costa was an self-taught producer, arranger, conductor and record company executive; he made a star out of 16-year-old Paul Anka and his ballads of teenaged angst in 1957 on ABC-Paramount Records, and then moved to United Artists, where his recording of the film theme 'Never On Sunday' is said to have sold 10 million copies around the world. Sinatra With Strings was his first and most successful project with Sinatra. Cahn thought that Costa was a substitute for Stordahl, and certainly the 'deep strings' style of the lushness seems to fill that gap. The twelve ballads were all familiar ones, including 'Misty', the Erroll Garner song which was then becoming one of the most recorded songs in the world, and a famous version of 'Stardust', on which Sinatra sings only the introduction, and never gets to the chorus at all. (Hoagy Carmichael was irritated, saying 'I wrote a whole song, not just a verse.' But the song as he originally wrote it was not the familiar smoochy ballad, but a sprightly mid-tempo instrumental for jazz band; and some think the verse or introduction was invented by Bix Beiderbecke.) There are too many bravura endings on the album, further evidence of Sinatra's moving away from the intimacy which was his great strength; yet curiously a remake of 'All Or Nothing At All' is a more vulnerable statement, with less bravura than the original; and a new version of 'Night And Day', though still less famous than the one with Riddle, is superb: slower than in 1956, and his only studio recording of the song that includes the introduction.

Next came All Alone, with Gordon Jenkins, recorded in early 1962. All the tunes were in 3/4 time, and 'Come Waltz With Me' was written by Cahn and Van Heusen, but didn't fit and was sensibly left off the album (though their movie theme 'Indiscreet' was included, the album's weakest track). 'Are You Lonesome Tonight' is a front-porch ballad from 1926, with which Elvis Presley had had a big hit single in 1960. There are no fewer than five songs by Irving Berlin, including his first heartfelt sentimental ballad, 'When I Lost You', written in 1912 when his first wife died after only five months of marriage. On the title track and the last track, 'The Song Is Ended' (both Berlin songs), an ethereal woman's voice (Loulie Jean Norman) sings a few phrases, sealing the nostalgia which seems to drench the album. Jenkins's arrangements are apposite, and Sinatra got in the mood, singing well behind the beat on every track, interpreting the songs with understated emotion, and on certain phrases allowing his voice to sound a bit worn, as though full of grief. The album was a success on its own terms, but did less well than any of his others in this period, reaching only number 25 in the Billboard chart.

Meanwhile, 'Everybody's Twistin' ' was recorded for a single with Neal Hefti, who had been hired as a producer at Reprise, where he made albums with Dean Martin and Alice Faye as well as Sinatra. The song was actually 'Truckin' ', written by Rube Bloom and Ted Koehler in 1935, with a nervous beat and altered lyrics; it was the kind of novelty that Mitch Miller might have thought of. Hefti made the most of it, but it didn't exactly mop up the pop chart. He was an experienced veteran of the Swing Era who later also became a composer of film scores; he had written an much-loved album in 1956 for Count Basie (The Atomic Mr Basie), and Hefti had led a good band himself in the early '50s, but gave it up when he saw how times had changed. He later recalled that he could be fined by the musicians' union if he allowed himself to be interviewed at a radio station where no musicians were employed, while Local 802 in New York City would no longer allow out-of-town bands to play at the Paramount Theater, where all the greatest bands had once played. Thus the union had done its best to strangle what was left of the Swing Era; apart from Basie, only a few ghost bands and Frank Sinatra kept trying to breathe life into the corpse.

Sinatra And Swingin' Brass was written by Hefti and recorded in April; both it and All Alone were released in the autumn that year, but the Hefti album was released first and barely made the top 20; perhaps the market was becoming saturated with Sinatra albums. Swingin' Brass had no more emphasis on the brass than on any other section of the band, but there were no strings; it was yet another retro Swing Era set, and unobjectionable on those terms, though again Sinatra's phrasing is sometimes choppy, and he sounds tired, as though some of the tracks called for too high a key. 'Goody Goody' is a silly jingle of a song that Helen Ward didn't like when it was a hit for her with Benny Goodman in 1936; its identification with the Swing Era was hackneyed. Sinatra was trying too hard to recapture his youth, but Hefti had not completely lost his touch; among the album's best tracks are Cole Porter's 'I Get A Kick Out Of You' and Ellington's 'I'm Beginning To See The Light' (Ben Webster plays some breaks on the latter, though the engineer has him so far off to the left that he's almost in another studio). 'Love Is Just Around The Corner' gets an amusing arrangement, and 'Ain't She Sweet', one of Oliver's best charts for Jimmie Lunceford, is almost recaptured. Swingin' Brass is one of Sinatra's most successful 'jazz' albums, but that's not saying a lot.

A month after President Kennedy had humiliated Sinatra by staying at Bing Crosby's house instead of Palm Springs, in April 1962 Sinatra embarked on a world tour at his own expense, raising money for children's hospitals. Allegedly, President Kennedy had asked him to do it for the State Department, but he had just bought his own jet plane and wanted to sponsor the trip himself. Sinatra's image needed some maintaining at this point, yet there was very little publicity in the USA at the time about the tour. He visited Mexico City, Hong Kong, Israel, Greece, Italy, France, England and Monaco, doing a total of 30 concerts and presenting large checks to local charities.

He traveled with a sextet of his regulars, including Bill Miller on piano, Al Viola on guitar and Irv Cottler on drums. Many of Sinatra's fans always wanted to hear him in the more casual context of a jazz-oriented small group, but whether he did not want to expose himself that way or his ego could not resist the prestige of larger and more expensive forces, he never recorded commercially with a small group after the era of the Page Cavanaugh Trio at Columbia (which included Viola). English record producer Don Norman once proposed a small-group recording project, and Sinatra's office looked into it, but nothing happened. During the 1950s Sinatra had performed regularly with a similar group led by Red Norvo, always one of his favorite musicians; he traveled with that group to Australia in 1959, where a concert was recorded and subsequently bootlegged; on the 1962 tour Emil Richards played vibes, and concerts in London on 1 June and in Paris on 5 June were recorded: the first was issued on JR for the world-wide Sinatra Societies; the second was bootlegged in 1992 and finally issued by Reprise. These concerts are especially precious to Sinatra fans, and the one from Paris is a good example of the saloon singer pleasing an audience in a setting that should have been his element. He even sounded younger than on his recent studio albums; that his phrasing is sometimes idiosyncratic and his jokes corny are part of the charm. Tossing off 'Goody Goody' as an opener for a live concert of 30 or so songs was allowable, especially followed by a version of 'Imagination' that is much better than the one on I Remember Tommy. 'Ol' Man River' was accompanied only by Miller, and 'Night And Day' was a duet with Viola, completely different from any of the other versions he recorded during his career.

Back in London in mid-June he made an album with Robert Farnon called Great Songs From Great Britain. Farnon began playing trumpet in Percy Faith's radio orchestra in Canada, and went to Europe during WWII as leader of the band of the Canadian armed forces (George Melachrino led the equivalent British band, Glenn Miller the American one, and to this day there are those who say that Farnon's was the best). Subsequently Farnon composed and recorded hundreds of short pieces for broadcast music libraries, as well as a dozen or so film scores; he backed Tony Bennett, Sarah Vaughan, Lena Horne, Eileen Farrell, Joe Williams and many others on albums, and his own compositions include the lovely tone poem 'A la Claire Fontaine', which critic Gene Lees (also Canadian-born) has described as Canada's 'Finlandia'. But most of all, Farnon made a series of instrumental albums for Decca in England in the early 1950s, orchestral versions of great pop songs, which have been used as teaching aids in music schools as an example of how to do it.

Sinatra's London recording sessions of June 1962 are still fondly remembered by those who were there; he is usually the soul of graciousness when he is surrounded by good musicians, and there were so many guests that even the control room was crowded, but Sinatra didn't mind. He was disappointed with the resulting album, though, which was briefly available in Britain, and not issued in the USA for 30 years. Nearing the end of his world tour he was tired and felt that his voice had suffered; in fact each track on the album is very well done, but the tempi are almost all very slow, and the overall effect of the album is soporific. Furthermore, some of the songs are simply not first rate. 'We'll Meet Again' needs to be trundled out only for documentaries about WWII, and some of the others are, as the British say, much of a muchness. Sinatra particularly disliked 'Roses Of Picardy', which was not released at all for decades; his voice is weak on that one, but the combination of his feeling and Farnon's arrangement turn a weak song into what some say is the best track of the lot. Others considered standout tracks are 'If I Had You' (relatively uptempo) and 'A Nightingale Sang In Berkeley Square'. At any rate, the album remained the most sought-after collectors' item in Sinatra's discography for many years.

Back in California, Hefti wrote Sinatra's next project, Sinatra-Basie, but the album that put Sinatra back in the top ten again was a big disappointment. 'I've waited 20 years for this moment,' he famously said at the beginning of the sessions, and he should have kept waiting. It is another example, like I Remember Tommy, of the big star doing something that is bound to make a few bucks, even though everybody involved sounds like they're just going through the motions. Not that the band doesn't play well: Basie's professionals of the period couldn't play any other way; Basie had the patent on four-to-the-bar swing (especially with Freddy Green laying down the best rhythm guitar in the business), and far from recapturing the swing era was the only band still successfully carrying it on. But the arrangements are not exactly inspired by the material; the best thing on the album is the rhythm section, and the tempi are so similar throughout that even that becomes a bore. Sinatra sounds, as he often does on the retro swing albums, as though he'd just wandered off the street into a toyshop. He sings well enough, though again he sounds as though the keys are too high, and we are reminded again that there is more to it than shoving a singer in front of a band. He pulls apart the lyric on the very first track as though he wonders why he's singing the song ('Don't you know each cloud contains [long pause] pennies from Heaven'). We don't need to hear 'The Tender Trap' played by Basie. We don't need to hear 'Looking At The World Through Rose Colored Glasses' played by anybody. We don't need to listen to this album; but the idea of Sinatra and Basie together was a commercial hit.

Yet he could still pull a trick out of the hat. The very next album, made in early 1963, was different from anything he had done since some of his sides with Stordahl at Columbia. The Concert Sinatra isn't perfect; the original edition (and the first CD version) is only 32 minutes long, with only eight tracks; except for Kurt Weill's 'Lost In The Stars', all the songs are by Rodgers & Hart, Rodgers & Hammerstein or Hammerstein and Jerome Kern, and I don't need to hear anybody sing 'You'll Never Walk Alone'. As befits show tunes, nearly all the arrangements have bravura endings (at least they are written by Nelson Riddle). Although 'Ol' Man River' is very moving, and the recording balance throughout is good, and Sinatra sounds himself again, singing in a comfortable register, 'Bewitched' is the last song that should have a bravura ending. Perhaps it is an album that few would want to listen to very often, yet here we have something tantalising.

Part of the reason Sinatra's retro Swing-Era albums don't work very well is that he should have matured into a dramatic singer, working as the singing actor he really was, rather than as a band singer. He served his apprenticeship as a band singer, but he needed a Harry James or a Tommy Dorsey to look after him; The Concert Sinatra is a hackneyed set in some ways, yet he sings better and sounds younger there than he does in the so-called 'jazz' albums.

Listening to a lot of different kinds of music, the question arises: why haven't legit singers ever been able to learn from pop singers, and vice versa? Some opera singers can act: Norman Welsby, playing the King in Henze's The Bassarids at the English national Opera in 1974, was electrifying; but good singing actors in opera are the exception rather than the rule: they often seem locked into convention to the extent of counting the number of oscillations in each vibrato, as though they are afraid to act. On original cast show albums it's the other way around: Ezio Pinza in South Pacific in 1947 brought his glorious bass voice from the Metropolitan Opera; but too many performers on Broadway sound like amateurs who can hardly sing at all. If only Sinatra, with his dramatic instinct and his powerful voice, could have inspired a new school of singing actors; if instead of chasing show-biz glory and spending money like a drunken sailor, he had commissioned original music drama, say for television. But he wouldn't have had the patience. Yet he had played the Stage Manager in Thornton Wilder's Our Town on television in 1955, for which Cahn and Van Heusen wrote songs (that's where 'Love And Marriage' came from); and The Concert Sinatra ended with his fourth recording of 'Soliloquy' (counting two versions at Columbia and an unfinished attempt at Capitol). It is over eight minutes of music drama, and maybe that was the limit of his attention span; yet he kept coming back to 'Soliloquy'.

As we shall see, when he did commission some original work, the result was a disaster; but we can wonder about what might have been. Also in 1963, Sinatra produced four albums recreating Broadway shows: Finian's Rainbow, Guys and Dolls, Kiss Me Kate and South Pacific were collectively known as the Reprise Repertory Theatre, with Sinatra, Davis, Martin, Crosby, Clooney, Jo Stafford and many others taking part, including the McGuire Sisters. These albums are virtually the only ones on which Sinatra allowed his name to appear as producer, but they remained obscure. Sinatra might have played opposite Barbra Streisand in the film version of Funny Girl, but the producer wanted Omar Sharif, a fine actor 'but no musical animal', said composer Jule Styne. It was one of the biggest disappointments of Styne's life (but of course Sinatra blamed it on Styne). In 1964 at MGM, Say It With Music would have celebrated Irving Berlin's career, with the ingenious idea of doing it backwards, ending up in the ragtime era; the film would have been produced by Arthur Freed, directed by Vincent Minnelli, and starred Sinatra and Julie Andrews. MGM pulled the plug because it was going to be too expensive. It might have cost half of what Sinatra was earning in a year, or half of what you have to pay just one of today's superstars to do a film, but it was too much. Freed retired, Minnelli left MGM and the studio never made another musical. And as for television, there too money was the only thing that counted. The USA had handed broadcasting to commercial interests in its earliest days; Britain's BBC could do anything it thought ought to be done, while American culture was abandoned to the mentality of the balance sheet.

Meanwhile, one thing Sinatra's life did not lack was drama. During this unsettled period in his life and career came The Manchurian Candidate, which has become a classic of a kind, the second film he had made on the theme of the assassination of a President, and one of those accidental films, rubbish on the face of it, which is still compulsively watchable many years later. Greil Marcus's essay on the film (collected in The Dustbin Of History, 1995) claims that it 'may be the most exciting and disturbing American movie from Citizen Kane to the Godfather pictures':

There's a special thrill that comes over you when you recognize an author working over his head ... and in The Manchurian Candidate everyone, from [director] Frankenheimer to Sinatra to the unnamed actor who flies across the stage in the midst of the carnage at the end of the film, seems like an author...

When you look at this 1962 black-and-white Hollywood movie made up of bits and pieces of Hitchcock and Orson Welles, out of Psycho and Citizen Kane, out of a lot of clean steals, workmanlike thievery, a second-class director using whatever he can get his hands on, what's so overwhelming is a sense of what the movie does that movies can no longer do.

Written by George Axelrod, adapting a thriller by Richard Condon, The Manchurian Candidate is nonsense based on Communist 'brainwashing' of American prisoners during the Korean war, but the film transcends its origin. The twists in the plot and the details in the finished film all seem inevitable in retrospect, as though some sort of once-truth had been captured. Laurence Harvey plays a character who is programmed to commit murder; Angela Lansbury was nominated for an Oscar in her role as his mother, an American fascist who is in league with the Chinese Communists, and whose husband is about to be elected Vice-President, then President; Sinatra plays a sort of ineffectual hero who figures it all out at the very end, when the plot is resolved and the bad guys are all dead. But he can never reveal what he knows, because no one will ever believe him.

The Korean war had made Americans uneasy; they did not feel comfortable waging war for what seemed to be ideological reasons. The plot of the film is nonsense, but what it is really about is paranoia, and the fact that fascism and communism are really two sides of the same coin; as Marcus's essay was called, it is 'A Dream of the Cold War'. It is also about patriotism, and about politicians who are not what they seem to be, and about our own complicity in the Cold War. Historians would deny that history can be determined forever by a single bullet, yet that seems to have happened subsequently, and more than once. According to Condon, the film was only made after President Kennedy approved it (the president of United Artists was prominent in the Democratic party and didn't like the idea of the film, but JFK was a fan of Condon's novels). Then in November 1963 John Kennedy was murdered in Dallas, and the ironies proliferate as fast as we can count them. At Sinatra's request, Chicago crime boss Sam Giancana had used his influence to deliver the trade union vote in the West Virginia primary, so that Kennedy got the Democratic nomination; and then Giancana probably helped Chicago mayor Richard J. Daley steal Illinois at the national election itself. Ginacana didn't care who was President, but hoped to get the Federal government off his back, and the Kennedy White House double-crossed him: Bobby Kennedy pursued the Mob with a vengeance. Giancana was a psycopathic murderer who ended up hating the Kennedys; we will probably never know whether the Mob was involved in the assassination.

When Kennedy was shot, Sinatra was shattered, secluding himself in his grief; for three days, Nancy Jr wrote in 1995, he stayed in his bedroom in Palm Springs, the only room that was unchanged since Kennedy had visited there. The Manchurian Candidate was not immediately withdrawn from circulation, contrary to popular belief; after the assassination, in fact, it was shown on television. But then it was withdrawn, and not re-released until 1988. Marcus recites the assassinations and near-assassinations of our time, from Medgar Evers through Ronald Reagan, and concludes, 'There must have been a feeling, as the film was withdrawn, as year after year it, too, stayed hidden, that our real history, our history as we live it out every day, the findamental premises of all our work and leisure, love and death, might be a kind of awful secret we will never understand.' There was certainly a lot that Frank Sinatra never understood. During this period he was hanging out with mobsters who hated his precious Kennedys, and who thought nothing of kidnap and murder; then the culture of violence and easy money struck close to home.

Frank Sinatra Jr had embarked on a career as a singer, and he certainly couldn't have had a better teacher. In 1963 Frank Sr scolded him backstage after a set, saying 'Don't ever let me catch you singing like that again, without enthusiasm. You're nothing if you aren't excited by what you're doing.' Sixteen days after John Kennedy was shot, Frank Jr had been singing in Lake Tahoe with a Tommy Dorsey ghost band, and was kidnapped for ransom. Still grieving for his dead brother, Robert Kennedy put 248 men on the kidnapping. A ransom of $240,000 was paid, and Frank Sr went to a pickup point, but Frank Jr wasn't there; it must have been the lowest point in his life. Frank Jr was eventually found stumbling along a highway barefoot, and the kidnappers were caught within a few days. Taking a cue from the gossip industry, they claimed in court that they had been hired to do it as a publicity stunt, and Frank Sr famously said, 'This family needs publicity like it needs peritonitis.' The kidnappers went to the slammer; Frank Jr's singing career never recovered, and Frank Sr continued hanging out with mobsters.

That was the worst experience any Sinatra kid ever had, but bearing that name was never easy. Jilly Rizzo, a New York restaurateur who became Sinatra's right-hand man and was close to the whole family, used to say with a sad grin, 'We can't go dere.' He meant that being famous the way a Sinatra was famous did not confer freedom. When Nancy was a teenager, if she went to a party where marijuana was being smoked, she had to leave, because she knew that if there was any trouble the headlines would link 'Sinatra' and 'drugs'. Nancy married singer Tommy Sands in September 1960; Sands is said to have wanted to move to New York to avoid becoming one of the Clan's mascots. In any case, the marriage lasted less than four years.

The parade of Frank Sinatra's albums and movies continued. After The Manchurian Candidate, and not counting the Rat Pack films and several where he played cameos, usually as himself, Sinatra made 12 more feature films, all now fodder for late-night TV. Come Blow Your Horn was based on a Neil Simon play; None But The Brave and Von Ryan's Express were WWII adventure yarns, the former with a part for Sands; Marriage On The Rocks was a romantic comedy with a part for Nancy Jr (they were shooting it when Tommy left her). Assault On A Queen was a caper movie involving the ocean liner Queen Mary, with music by Duke Ellington; The Naked Runner was a spy picture; Dirty Dingus Magee was a burlesque western; Contract On Cherry Street was a TV movie, and The First Deadly Sin, Sinatra's last starring feature, in 1980, was a disappointing cop movie.

Journalist Pete Hamill once wrote, 'A Sinatra film never reached down into the darkness the way the songs did. He never cheated on the songs.' Along the way, in 1967-68, there were three other cop/ private eye movies, to which Sinatra seemed to bring something of himself. In Tony Rome he played an aging, cynical and world-weary character with something of Bogart in it, solving an old-fashioned murder mystery; the script had a touch of the amorality of the 1960s. In The Detective he carried a badge through a good script, with Robert Duvall one of the supporting players; then Lady In Cement was another Tony Rome story, but the return to the Bogart-type thriller had already run out of steam: this time the script just wasn't good enough. Despite Sinatra's obvious potential as an actor, he did not develop a true film star's instinct for what he was doing; most of the films turned out to be, as Pauline Kael described The Naked Runner, 'a good movie to read by if there were light in the theater.'

During the filming of None But The Brave in Hawaii in May 1964, Sinatra and a few others went swimming in the surf; Sinatra and Ruth Koch, the wife of executive producer Howard Koch, were swept out to sea, became exhausted and almost drowned. For 30 years the story has been that brawny actor Brad Dexter saved their lives, swimming out to their rescue and keeping them afloat until more help arrived on surfboards. Dexter and Sinatra became close for a while; Dexter had a part in Von Ryan's Express, and became a vice-president of Sinatra Enterprises in charge of production. Dexter told Kitty Kelley many years later that he tried to interest Sinatra in better movie material, which was a matter of trying to get Sinatra Enterprises to acquire properties. Sinatra was interested in Harper, but his lawyer Mickey Rudin didn't like the deal, and Sinatra turned down Clockwork Orange, which he didn't understand. (Harper became a better-than-average private eye film starring Paul Newman, Stanley Kubrick made Clockwork Orange, and both pictures made a lot of money.) Finally Dexter came up with The Naked Runner, the spy film in which Sinatra was to play an unwitting assassin.

Some of the film was shot in England, where Sinatra had a temper tantrum about a helicopter ride; the weather, the air traffic over southern England, and the daily business of Britain's armed services should have been subordinate to Siantra's comfort. Dexter had to coax him into going back to work. The next location was to be in Denmark, after Sinatra went back to California to dabble in politics, campaigning for a third term for Governor Pat Brown (who was beaten by Ronald Reagan). Sinatra decided not to go to Denmark, and Dexter was ordered to bring all the footage back to California. Dexter complained that he had production commitments in England; he and the director, Sidney Furie, no doubt fed up with Sinatra, rewrote the script and edited the film so as to finish the picture without him. Thus Sinatra had agreed to make a film as a shareholder in Warner Brothers, and then ensured that a hash had to be cobbled together after he'd shortchanged everybody. No wonder it turned out to be the kind of film that made Pauline Kael wish for a book to read. Dexter delivered the finished picture to Jack Warner, and never received the rest of his fee as producer. Dexter had tried to help rescue Sinatra's film acting career, and once told someone 'I'd kill for him.' In Nancy Sinatra's first book (Frank Sinatra: My Father, 1985), she tells the story of the near-drowning in Hawaii in 1964 and mentions Dexter's part in it, but then Dexter told Kitty Kelley stories about Sinatra's manic-depressive behavior (for Kelley's book, His Way, 1986), and in her next book (Frank Sinatra: An American Legend, 1995), Nancy tells the story without mentioning the name of the man who saved her father's life.

Actually, Dexter's days as a Sinatra intimate were already numbered, and the disaster of The Naked Runner was probably caused in part by Sinatra's mid-life crisis over whether or not to marry the 21-year-old actress Mia Farrow. Sinatra and Dexter had just flown to London to start work on the film when he asked Dexter whether he should marry Mia; Dexter told him to go ahead and marry her if he wanted to, but he didn't think it was a good idea because of the huge age difference. Sinatra threw a tantrum, and married Mia two weeks later, in July 1966. He wanted her to quit show business; when she refused to walk off the set of Rosemary's Baby, one of the biggest hit films of the decade, the marriage crumbled. It was the best role she ever had, but then she already knew what it was like to sleep with the Devil.

When the marriage was over, Sinatra's valet of many years, George Jacobs, met Mia in a nightclub and danced with her; and of course this was reported in some gossip column, and Sinatra fired Jacobs. Jacobs later talked to Kitty Kelley too, of course; he had nursed Sinatra through a suicide attempt, he said; he had helped him get over Ava, waited on Sinatra's gangster friends, made John Kennedy laugh so hard he fell in the pool, had a plate of spaghetti shoved in his face by Sinatra, drove Sinatra's women to their abortionists and all the rest of it, and his reward for many years' of loyal abuse-taking was sudden summary dismissal, and without any explanation. For Sinatra could not fire Jacobs himself any more than he could fire Dexter. That's what Mickey Rudin was for.

And through all the melodrama the work continued, albeit of decreasing value. There were an incredible 20 more Reprise albums between The Concert Sinatra in 1963 and his temporary retirement in 1971. There were good things on almost every album, but nearly all of them were spoiled by a kind of self-indulgence: cabaret singers from Bobby Short onwards are still mining the century's obscure but worthwhile songs, but the man who had once chosen the standards for us no longer tried hard enough; clearly his albums would have sold well and made a profit even if they had been better ones, yet he aimed too low. Sinatra's Sinatra was entirely remakes, including 'Young At Heart', which he hadn't particularly liked in the first place, and the dreary 'Second Time Around'; Days Of Wine And Roses, Moon River And Other Academy Award Winners had the kind of tunes that come out of the ceiling at the airport, including 'Three Coins In The Fountain', 'Love Is A Many-Splendored Thing', and the two Henry Mancini songs (but it was interesting to compare Sinatra's 'Secret Love' to Doris Day's virginal original); and Moonlight Sinatra was what the concept album had now come to: 12 songs with the word 'moon' in the title. At least these three albums were all with Nelson Riddle, who made as much as could be made of them. America, I Hear You Singing was made with Fred Waring and His Pennsylvanians, a mish-mash of Christmas songs, patriotic songs (including a remake of 'The House I Live In') and two tracks with guest Bing Crosby. Maybe there was something Sinatra admired about Fred Waring, who had made jazz-influenced records in the 1920s, was enormously successful on radio in the 1930s, and ended up essentially a choral conductor, having grown mellow as his fans grew older, and distracted from music by his business interests. In 1966 Waring said, 'We don't sing music, we sing songs,' which could be translated as 'Nice songs, shame about the production.'

Softly As I Leave You marked the end of an era: the first Sinatra album to have three different arrangers, and the CD doesn't even bother to tell you who arranged what. The opening track, 'Emily', is a sickly sweet movie song (from The Americanization Of Emily, which was coincidentally another novel by William Bradford Huie), while 'Here's To The Losers' is more fun, but there isn't one really first-class song on the album, so while the singing is good, it doesn't matter. It Might As Well Be Swing was another album with the Basie band, this time arranged by Quincy Jones; it included 'Hello Dolly', hardly material of Sinatra quality, and a country song, 'I Can't Stop Loving You'. (I try to imagine a Sinatra country album: he might have mopped up Nashville if he'd tried, but not with the Basie band; and he was probably not capable of choosing the right songs.) My Kind Of Broadway was a compilation album, including the 'Hello Dolly' with Basie; not Sinatra's kind of Broadway, but a marketing job. Speaking of marketing jobs, A Man And His Music was a two-LP compilation, with most of the tracks edited, and narrated by Sinatra. It went top ten and won a Grammy as Album of the Year in 1966, but by then the market had changed utterly: everybody was buying lots of albums, and anything might float to the top, and by then it should have been clear that the reason Sinatra was still king of showbiz was by default. It was too soon to offer the title to Mick Jagger, and there had been a lost generation between the two, except for Elvis Presley, whose hit albums during this period were the soundtracks of movies that were even worse than Sinatra's.

An album which Billboard called Frank Sinatra (aka The World We Knew, after the first track, a Bert Kaempfert song) was a compilation that included the dreadful (Oscar-winning) movie song 'Born Free', as well as a no. 1 hit single, a duet with Nancy on 'Somethin' Stupid', a dumb song with a kling-kling-kling beat. A Man Alone And Other Songs of Rod McKuen is some kind of nadir: from the man who once choose our standards for us, a set of 'songs' by the most banal McPoet who ever schmoozed Hollywood. This was 1969, and Sinatra was so eager to be loved that he had now sunk as far as he could into the mass market; he had managed to make some of the best and some of the worst vinyl LPs ever pressed. But it is hard to choose a nadir, really. That's Life includes the stereotype title track, which became a Sinatra anthem, as well as 'Winchester Cathedral', one of the dumber pop songs of the Swinging Sixties. Strangers In The Night was a number one album on the strength of the nasty title song, arranged by Ernie Freeman and produced by Jimmy Bowen, who'd started as a Texas rocker in the same recording studio as Buddy Holly, and later became a successful producer of country music at MCA; 'Strangers' is another Kaempfert song, and Sinatra openly professed to dislike it, so why did he sing it? The single won four Grammies; probably the industry was grateful to Sinatra for his capitulation to kitsch. But the rest of the album is arranged by Nelson Riddle, and has some good things on it that completely overshadow the title track, especially 'Summer Wind', and a completely new treatment of 'All Or Nothing At All', Sinatra's third recording of the song. Sinatra At The Sands is a 2-LP set with Basie released in mid-1966, almost the only live set Sinatra ever authorized; fans regard it as better than either of the studio sets with Basie.

Francis A. & Edward K. is an album with Duke Ellington, arranged by Billy May, and at first you think it's going to be saved by the sound of the band, especially as the first track is the best: 'Follow Me', from Lerner & Leowe's Camelot, swinging at a slow tempo, and obviously heartfelt. (Was that Cootie Williams? There's Paul Gonsalves.) But Ellington did not like sharing the spotlight, and his men had not bothered learning the arrangements, which were not very inspired anyway. (To be fair to May, no one could write for the Ellington band; they hated to play arrangements from outside.) The album had to be pulled together in the studio, with lead players added (Al Porcino in the trumpets) and three pianists in the end: Ellington, Jimmy Jones and Milt Raskin. Ellington's amanuensis, Billy Strayhorn, virtually the band's co-leader, might have played piano and done the arrangements, and the band would have played them happily; but Strays, the beloved Swee'Pea, had died of cancer earlier that year. The result was a shambles, one of the nadirs of both careers. Even the songs were badly chosen: the worst is 'Sunny', a dreary country-pop dirge of the period. Most of the album was very slow and the last track absurdly fast; even the engineering was awful, as though echo could cover up the sloppiness of the ideas.

Cycles, recorded in late 1968 with Costa, was a set of ten of the decade's folk-rock songs, and a good example of a later Sinatra album that could have worked, but didn't. It is interesting to hear him sing Joni Mitchell's 'Both Sides Now' and Bobby Russell's 'Little Green Apples'; if anyone could have bridged the gap between the songwriting of two or more generations, it might have been Sinatra, but those two tracks are the best ones on the album. Sinatra was simply not the sort of artist who could let his hair down. There is a clue in Sinatra's version of John Hartford's 'Gentle On My Mind'; lyricist Gene Lees put his finger on it in 1969:

At the end, he 'corrects' Hartford's grammar: he sings 'the rivers flowing gently on my mind,' and it kills the mood. Hartford's use of 'gentle' as an adverb is an Americanism, parallel to 'Drive Slow', which bothers none of us any more. We are in the process of dropping a lot of adverbial endings on this continent, and the English language in another fifty years is going to be radically different than it is now. As Chaucer used a lot of 'low' English only to have it become standard English, Hartford uses the peoples' English of our time, and Sinatra makes a serious error in tampering with it. As a matter of fact, he doesn't do the song at all well. He tries to make it swing in the manner of jazz, and country-and-western music swings in quite another way. By punching out the time, he kills the swing and diminishes the depth of the song ...

This goes straight to the heart of why Sinatra was never going to make a success of this kind of material. He was a jazz-oriented artist; the songwriters he loved best were influenced by jazz; and jazz had come indoors and got respectable: in the 1960s it was being regularly played in concert halls. To be sure, the best of it always includes freedom of interpretation, but the musical values are sophisticated ones. There have been a lot of good songs written in country music and country rock, but the values are entirely different: they call for a kind of resignation, a capitulation to timelessness, and Sinatra, as an artist or as a man, could never be resigned to anything. His kind of passion would not allow it.

And most of the songs on Cycles are badly chosen. 'Rain In My Heart' (the album's opener) is absurdly overwrought, while 'By The Time I Get To Phoenix' is too laid back: Sinatra got stoned on Jack Daniels, not the other stuff. Yet if he was going to make an album of this sort of material, the biggest hits of the type had to be chosen rather than songs that might have been better suited to him, and again a lack of judgement is evident from someone who once seemed never to fail. He doesn't sound fully engaged; the photo on the cover of the album is apparently supposed to portray him in a thoughtful mode, but the way he's holding the bridge of his nose he looks like he needs an aspirin. Finally, the songs are over-arranged and too prettified; Costa was a talented man without genius, trying to do too many things, and the album jangles with too much soft-rock rhythm section, as though to make things easy for the middle-aged.

My Way in 1969 is perhaps the strangest tragedy of all these late albums, because he is in such fine voice and sounds like he's giving it all he's got. But there are only ten songs, and they do not make a coherent album. On Jimmy Webb's 'Didn't We', the Jacque Brel/ Rod McKuen 'If You Go Away', and especially on 'A Day In The Life Of A Fool' (Luiz Bonfa's 'Manha de Carnaval' with English words), once again he makes the songs better than they are. But on Lennon & McCartney's 'Yesterday' he seems to have trouble with the word 'Yesterday' all the way through, and Paul Simon's 'Mrs Robinson' is a bad joke, overarranged by Costa, and Sinatra forcing himself to utter lyrics like 'wo wo wo' and 'hey hey hey'. The album was memorable chiefly for a sleeper: 'My Way' was a French song with English words by Paul Anka, and reached the top 30 as a single, eventually included on at least five Sinatra albums; it would assume more importance in the following decade.

The best of nearly 40 albums on Reprise are undoubtedly two very different ones: September Of My Years, an unusual admission of the passage of time, and Francis Albert Sinatra & Antonio Carlos Jobim. These two are treasurable, almost up to the level of the best Capitol sets, making comparison with the rest of the Reprise output all the more stark.

September was made mostly in April 1965, just before he got involved with Mia Farrow, and a year before the final descent into 'Strangers In The Night'. Arranged and conducted by Gordon Jenkins, it is nearly Sinatra's last and certainly his most personal concept album; in fact it is the logical conclusion to all the loneliness concept albums: the would-be, has-been lover can see the end of the road in the distance, and is looking back with affectionate amusement, as well as regret. The first (title) track is one of Cahn and Van Heusen's best, the gentle modulations coming as mildly pleasant surprises rather than being telegraphed. (It is also the best-sounding track on the album, recorded all by itself in May, with a different engineer; the rest of the album deperately needs remixing to match it as closely as possible: Sinatra's voice is too far forward and the tinniness of the background doesn't do anything for Jenkins's fiddles.) There are two songs by Jenkins, a handful of standards (Alec Wilder, Arlen and Harburg, Rodgers & Hammerstein); and the rest were all surprises.

'The Man In The Looking Glass', by Bart Howard, who wrote 'Fly Me To The Moon', is completely disarming. Sinatra got in the news when he had a hair transplant, and at one point he allegedly paid a woman $400 a week to look after his 40 toupees (his hair loss is the reason he wore so many hats on the record covers). But now he sang 'I knew that dopey guy/ When he didn't know how to tie his tie/ He stood right there/ And he had hair/ Galore'. The same fellow 'seems so much wiser now/ Less lonely, but then/ Could be he's only pretending/ Again.' But the album's centerpiece is 'It Was A Very Good Year', written by Ervin Drake, who wrote Billie Holiday's 'Good Morning Heartache', and was also one of those who wrote words for instrumentals to make them more saleable: 'Castle Rock', 'Perdido', 'Tico Tico'. Here he outdid himself and received one of Jenkins's best symphonic-style arrangements; in fact the opening oboe tune, reprised at the end, sounds like it could have been snatched from Sibelius. 'It Was A Very Good Year' has been attacked by feminists as implying a catalog of conquests, with its 'small-town girls', 'city girls' and 'blue-blooded girls of independent means (We'd ride in limousines/ their chauffeurs would drive/ When I was 35)'. But the work of art exists independently of what we know about Sinatra; and in any case what we know about him is that he had believed in love, just as the women did, even if he ultimately couldn't stand to be in the same room with it. The song is about memories of love, not sex; it is about the happiness that ran through his fingers like sand. The longest track on the album, it is also an example of the singing actor at the heart of Sinatra's work: you can't dance to it; you can only listen. The last perfect concept album ends perfectly, with another piece of dramatic magic, Weill's 'September Song', including both verses of introduction. Sinatra would soon be 50 years old, and he never made a more revealing document.

September Of My Years is the only Sinatra album on Reprise that did not disappoint on first hearing except for the one with Jobim, made in early 1967, arranged and conducted by Claus Ogerman; Sinatra abandons himself to the bossa nova beat, one of the nicest things to happen to post-war pop, and the result sounds like memories of love and jazz heard through the prism of the tropics. Seven tunes were Jobim's; the other three were two standards lending themselves to the treatment, and another recording of 'Baubles, Bangles And Beads', easily surpassing the earlier one with Billy May. The gentle Jobim joins in vocally on four tracks. Gene Lees wrote the lovely English words to 'Corcovado', which then became 'Quiet Nights Of Quiet Stars', and Lees published a memoir of his friend Jobim in his Jazzletter in 1995. Talent and genius are not the same thing, Lees reminds us, and in the same way that we can tell a Gershwin song within a few bars,

If you examine the song 'Dindi', you'll find that it's not terribly unusual, harmonically or melodically. The problem is that it is unusual, and I can't tell you why. It has a distinct but ineffable quality; it is one of the most beautiful songs I know.

The gift of writing melody is a mysterious one. Not every educated musician has it; Nelson Riddle and Gil Evans didn't. Nor does lack of education preclude it: Irving Berlin had no musical education whatsoever, and Harry Warren didn't have much, but each of them had an inexhaustible gift of melody.

Lees goes on to describe the uniqueness of the the bossa nova rhythm, which came from the samba, and was something new that Jobim and others were doing in Brazil in the 1950s. (For example, the songs were notated in 2/4 rather than the 4/4 of American ballads, but when they were brought to the USA, northern publishers had them re-notated in 4/4.) It is a gentle yet inexorable beat, timeless and evocative; it was a fad in the USA for a while, yet it was more than a fad: it has never really gone away, and retains its timeless beauty. 'Dindi' was one of the songs on the first Sinatra/Jobim album, which was recorded halfway through the marriage to Farrow. Lees wrote about 'Dindi' in 1967: 'It is filled with longing. It aches. Somewhere within him Frank Sinatra aches. Fine. That's the way it's always been: The audience's pleasure derives from the artist's pain.'

The Sinatra/Jobim album was something special, and they recorded ten more tracks together, in early 1969, arranged by Eumir Deodato and conducted by Morris Stoloff, but the second album was never released properly. One of the tunes was 'Off Key', the English version of the lovely 'Desafinado' ('Out of Tune'), a response to early Brazilian critics of bossa nova, who didn't understand it. Nine of the tracks were scattered across compilation albums (seven of them on one side of Sinatra & Company in 1971), and 'Off Key' was not released at all, until all 20 of the Jobim tracks were finally compiled on a cd in 2010.

Sinatra never seems to have been interested in doing 'songbook' albums, perhaps because Ella Fitzgerald did it first; Sinatra may have been another, like Ellington, who didn't like to share the spotlight. On the basis of what he did with the songs of Cole Porter, Irving Berlin and others, to say nothing of Jobim, we may wish that he had done songbooks; but apart from the Jobim (a masterpiece) and the Rod McKuen (dreck), virtually the only such album Sinatra ever released was a compilation of Van Huesen songs on CD, because most of them were associated with Sinatra and some were Oscar-winners: another marketing job. (And it is interesting that some of the best songs on the album were written by Van Heusen and Johnny Burke, rather than with Sammy Cahn.)

And then came the worst boondoggle of all, or the biggest tragedy, depending on how you look at it. Watertown was not a bad idea: a middle-aged man in a small town watches his wife leaving him. Maybe she's bored, maybe he's taken her for granted, but he doesn't know why she's leaving; all he knows is that a part of his life is over. It is virtually the only time Sinatra commissioned anything like dramatic music or a song cycle for himself, and the project was bungled badly.

Goodfellas (1990) is one of the all-time best gangster movies, written and directed by Martin Scorsese. It has a scene in a neighborhood nightclub where the thugs and their women are being entertained by one of those Italian-American singers who had brash hit records in the late 1950s-early 1960s, and it is perfectly judged: the banality of the entertainment is matched by the banality of the people, the men all pointing their suits at one another and the woman all looking like retired pizza waitresses. The singer in the film is Bobby Vinton (who was actually of Polish descent, played by his son in the movie), but it could have been Dion DiMucci (of Dion and the Belmonts), or Frankie Valli. Frankie Valli and the Four Seasons (named after a bowling alley in New Jersey) had over 40 hit singles starting in 1956, many of them co-written by Bob Gaudio (a former member of the Royal Teens, as in 'Who wears short shorts') and Bob Crewe, who'd come from Swan Records, one of those labels like Cameo and Parkway that came from nowhere to have so many hit singles in that era that they helped trigger a congressional investigation into payola. Apparently Frankie Valli had bragged to Frankie Sinatra that the reason they had so many hits was that Gaudio had written them; and Bob Gaudio was hired to co-write, co-arrange and produce Watertown.

It was going to be done for television, but an album was all that resulted. The backing tracks were recorded in July 1969 in New York, and overdubbed by Sinatra later in Los Angeles. According to John Ridgway's Sinatrafile, the recording sessions used over 30 musicians including strings, but they sound like a cabaret bar-band, with a thumping electric bass and banal rhythms throughout. The writing for strings may as well have been an off-the-shelf synth program, except that hadn't been invented yet; the first song has a choo-choo sound in it as the wife leaves, a device that thankfully wasn't available for Schubert's song cycles. Nearly all the ten songs are faded out at the end, a first for a Sinatra album, and the sure sign of an arranger who can't think of anything to do.

Watertown is so hard to listen to that one wonders if something might have been done with the songs; Gaudio had had a number of years practicing as a writer, after all, and Nelson Riddle might have made something of it, we'd like to think. But there was not enough inspiration on this team. The fact is that Gaudio was one of those who helped turn rock'n'roll into what we now call 'pop music', elbowing other musics out of the marketplace. Rock was supposed to be a gloriously raucous and uninhibited pig's ear, at its best retaining its country-music heritage as a superb vehicle for a troubador's story-songs; but no matter how many hacks try to make a silk purse out of it, that's never going to work. The tunes on Watertown are simple and repetitious rockaballads, and the words are banal; not even Sinatra can make the word 'tragedy' rhyme properly with 'in the tea'. At the end of the last song, the singer thinks his wife is coming back, but apparently she doesn't get off the train. Maybe she's in New York listening to Bobby Short.

Gene Lees, who attended one of the recording sessions for the first album with Jobim in 1967, was glad that Sinatra refused to record with headphones on. People who recorded with Tommy Dorsey in 1940 know that the headphones belong on the engineers, not the musicians; they also know that the singer sings in the same room at the same time with the band. Why did Sinatra agree to overdub Watertown? Why did he surrender to this rubbish two years later after the Jobim album? Who was behind this, who benefitted? Sinatra sounds terrible on Watertown; his diction sticks out because it is wasted on the material. I think he tried to get into this stuff, but couldn't manage the plaintive, self-serving whine that this kind of music requires; if he was trying to sound like Frankie Valli, he failed. Having divorced Mia, he should not have tried to dabble in the music of her era.

Sinatra had campaigned for Hubert Humphrey in the 1968 Presidential election, in his last act as a Democrat from Hoboken. (Humphrey lost to Richard Nixon, who Sinatra seemed to despise.) In early 1969, Marty Sinatra finally succumbed to complications of the asthma that had bothered him all his life. Marty's medical problems overwhelmed him, and nothing could be done; Dr Michael De Bakey in Houston, Texas, was deeply moved: 'I saw the way he kissed his father.' In April 1970 Watertown was released, and didn't even make the top 100 albums in Billboard; in November the film Dirty Dingus Magee opened, and was generally agreed to be one of Sinatra's worst movies. On his birthday in December something good finally happened: his Little Nancy got married again, this time happily (until Hugh Lambert died of cancer in 1985.) During this period, as we'll see in the next chapter, he washed himself up in Las Vegas. There were a few more benefits and TV specials; in January 1971 Sinatra opened a Medical Education Center in Palm Springs, named after his father; and in March, he announced his retirement from public life.

In June, at yet another benefit, he made his farewell performance; the last song performed was an intimate saloon song, 'Angel Eyes', and on the song's last line, 'Excuse me, while I disappear', the spotlight went out. And Sinatra was gone. But not for long. He tried to relax in the desert, he looked after his bank accounts and he made new friends among the social and political glitterati, but of course he could not stay away from performing, even while the world changed around him. In the following decades he would become more famous than ever as a concert artist, a new king of showbusiness, and the fact that he could not stay away from the spotlight is an endearing quality. It is not given to many of us to know what we do best.

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