Donald's Encyclopedia of Popular Music



(b Frank Sinestro, 12 December 1915, Hoboken NJ; d 14 May 1998, Los Angeles) Singer, actor, superstar. He was named after his grandfather; his mother had his birth certificate altered in 1945 to Francis A. (for Albert) Sinatra: the family had Americanized the name. His cousin Ray Sinatra was a bandleader in NYC. Influenced by Bing Crosby, then Billie Holiday and Mabel Mercer, he was the second pop singer after Crosby to transform the art. He had no obvious talent to begin with and had to work very hard at it; largely self-taught, he not only became a good singer but put his stormy and often painful emotional life into his art, not in any obvious emotive way but with great subtlety: together with his attractive and instantly recognizable baritone, his phrasing made him the greatest male interpreter of America's best songs. As he put it in later life, regardless of anything people may say about him, 'When I sing, I'm honest.' He quit school at 16 to sing at weddings, at the local Union Club, for anyone who would have him; on the Major Bowes Amateur Hour talent show on radio with three other boys as the Hoboken Four in 1935 they won, toured with Bowes and were filmed in blackface. He sang on the radio for free, worked '37-9 at the Rustic Cabin, a roadhouse near Englewood NJ where he doubled as headwaiter, valuing the job because the place had a radio wire. He married his sweetheart Nancy early '39; then was heard on the radio by Harry James, who had just left Benny Goodman to start his own band; he first sang with James mid-'39 after refusing to change his name. His first press notice (in Metronome) commended his 'easy phrasing'. His first record (uncredited) with James in July '39 sold 8,000 copies: 'All Or Nothing At All' was a no. 1 hit when reissued '43.

A CBS executive advised Tommy Dorsey to 'go listen to the skinny kid who's singing with Harry's band'; Dorsey made an offer and James, one of the nicest people in show business, let him go without a murmur. He recorded with Dorsey early '40, arranged by Axel Stordahl; made his first film with the band Las Vegas Nights '40 and by mid-'41 was named in a Billboard survey of colleges as the outstanding male band vocalist, displacing Crosby in the down beat poll late '41, although still usually uncredited on records. (Crosby later said, 'Frank Sinatra is the kind of singer who comes along once in a lifetime -- but why did it have to be my lifetime?') His first hit with Dorsey was 'Polka Dots And Moonbeams', number ones included 'I'll Never Smile Again' '40, 'Delores' '41, 'There Are Such Things' '42, 'In The Blue Of The Evening' '43. Dorsey allowed him to make four solo sides with arrangements by Stordahl in January '42 and in September he bought out his contract, hearing that Bob Eberly was leaving Jimmy Dorsey: he wanted to be the first singer since Crosby to make it big on his own.

From 30 December 1942 he appeared for four weeks at the Paramount theatre NYC with Goodman and was booked for four more, driving bobby-soxers wild: it is said that some girls were hired to scream, but many more screamed for free, and modern pop hysteria was born. Sociologists wrote about the phenomenon, but one of the bobby-soxers wrote many years later that 'the thing we had going with Frankie was sexy'. He was dubbed 'The Sultan of Swoon', 'The Voice That Thrills Millions', then 'The Voice'. On his second return engagement at the Paramount (12 October 1944, 'The Columbus Day Riot') 25,000 teenagers blocked the streets. Pop singers were a new phenomenon, taking over as the Big Band Era wound down, and he was the best of the lot; he gave Dorsey credit for lessons in breath control and phrasing. Critics and musicians knew he was a better than average singer, even then making a song his own by phrasing it in such a way as to make the listener feel that he or she was being sung to personally, yet never lachrymose or idiosyncratic, always in the service of the song. Jazz musicians appreciated him for this, though he did not recompose a song to the extent that many jazz singers did.

He served two stints in the top spot in Your Hit Parade, a popular network radio show since 1935, at one point having to sing 'The Woody Woodpecker Song' for several weeks. During the first part of his solo career the musicians' union was on strike against the record companies; he recorded '43 with a chorus a cappella but in November '44 the strike was over and he began recording with Stordahl, who'd left Dorsey with him; 86 hits on Columbia '43-52 (not counting 'All Or Nothing At All') included 33 in the top ten: 'Oh! What It Seemed To Be', 'Five Minutes More', 'Mam'selle' were all no. 1 '46-7; 'You'll Never Know' '43, 'Saturday Night Is The Loneliest Night Of The Week' '45, 'They Say It's Wonderful' '46, all at no. 2. The records with Stordahl defined the pop of the period, but he was also accompanied by the Page Cavanaugh Trio ('That's How Much I Love You' '47), James ('Castle Rock' '51), Mitch Miller ('Goodnight Irene' '50); sidemen/soloists over the years included Ziggy Elman, Chris Griffin, Bobby Hackett and Billy Butterfield on trumpets; Will Bradley, Si Zentner (d 30 January 2000 in Las Vegas aged 82) and Buddy Morrow on trombones; Tony Mottola and Dave Barbour on guitar; Herbie Haymer and Babe Russin on tenor sax. One of the first concept albums in history was The Voice '46, a number one album at the very beginning of the Billboard album chart, eight love songs purposely arranged by Stordahl to make a set of four 78s. George Siravo (d 28 February 2000 in Medford OR aged 83) arranged another album of eight uptempo tunes in the Swing Era style; Sing And Dance With Frank Sinatra came out on four 78s and on a 10-inch LP in October '50. (Siravo was still being commissioned many years later by Billy May to write for Sinatra when May was too busy to do it all.)

[Guitarists Al Viola (b 16 June 1919, NYC; d 21 February 2007) and Tony Mottola (b 18 April 1918, Kearney NJ; d 10 August 2004, Denville NJ) saw Bing Crosby on tour at the same time Sinatra did, at Leow's theatre in Jersey City in March 1933, when they were all kids, working at station WAAT for carfare. The guitarists were fans of Eddie Lang, Crosby's accompanist, and both later worked for Sinatra; Mottola came out of retirement in the 1980s to work for Sinatra again.]

Sinatra's films included Reveille With Beverly and Higher And Higher '43, Step Lively '44, Till The Clouds Roll By '46 (a cameo in a Jerome Kern biopic), It Happened In Brooklyn '47 with Jimmy Durante, and classic musicals with Gene Kelly: Anchors Aweigh '45, Take Me Out To The Ball Game and On The Town '49. He supported Franklin D. Roosevelt for President (naming his son after him), made a short film The House I Live In '45 (directed by Mervyn Le Roy) on behalf of religious and racial tolerance (the film received a special Oscar '46). He visited Cuba '47 and began to be accused of Communist and Mafia links. He left Nancy '50, married actress Ava Gardner '51, co-wrote and recorded 'I'm A Fool To Want You', since regarded as one of his all-time best records. The hopeless relationship with Gardner (who was just as strong-willed as he was) helped to define the rest of his life and helped him to his final maturity as an artist; the new marriage was publicly stormy and he had been too successful, too outspoken and too badly behaved for too long: the gossip columnists turned against him and the hits fell off, partly because of the junk forced on him by Miller (such as the novelty 'Mama Will Bark' '51 with the busty actress Dagmar). But the main reason his career faltered was the changes in the record business.

He began turning it around in 1953, making the most famous comeback in history: he fought for the part of Maggio in the film of the James Jones novel From Here To Eternity, winning the Oscar for best supporting actor '54, and switched to the Capitol label, then the most innovative in the USA. His first Capitol session was his last with Stordahl for nearly a decade; 'Lean Baby' was a top 15 hit, but his second session was the first with Nelson Riddle, including 'I've Got The World On A String' (by Ted Koehler and Harold Arlen '32), 'South Of The Border' (arranged in the style of Billy May, the song written by Jimmy Kennedy and Michael Carr '39, first sung that year by Gene Autry on a UK tour) and 'Don't Worry 'Bout Me' (by Koehler and Rube Bloom '39). When 'I've Got The World On A String' was heard on the radio everybody knew he was back. Good songs and recording technology together with Riddle's arrangements sold albums (then still a new phenomenon on long-playing records) to grownups who had been Sinatra's fans all their lives, while the singles business was soon abandoned to children; at a time when the album charts were dominated by film soundtracks and original Broadway casts, Sinatra was the only singer whose every album was a hit: 13 brilliant Capitol 12-inch LPs were top five '54-61, nearly all with Riddle. Some were compiled from 10-inch LPs, an example of Capitol's fearlessness in those days: they cost more because of the publisher's royalties to be paid on eight songs on each side instead of six, but the public bought them anyway. On Swing Easy '54 he was accompanied in chamber-jazz style; In The Wee Small Hours '55 was often called the first concept album, songs of aching love at the time of separation from Gardner; Songs For Swingin' Lovers! '56 used a big band with intelligent writing for strings, sidemen like Harry Edison on muted trumpet, George Roberts on bass trombone: 'You Make Me Feel So Young', 'It Happened In Monterey', 'You're Getting To Be A Habit With Me' etc were Sinatra's peak and Riddle's best work. Riddle knew that Sinatra was not a jazz singer, and how best to present him: the arrangements were not simply accompaniments, but compositions for orchestra and voice, as though a 20th-century Mozart had done it from scratch: the chart on Cole Porter's 'I've Got You Under My Skin' was done in a hurry the night before; it got spontaneous applause in the studio, with a trombone solo by Milt Bernhart that became famous, and was voted by thousands of Sinatra fans '80 as their all-time favourite. (Bernhart d 22 Jan. 2004 aged 77, in Glendale CA.) Further albums were Close To You, A Swingin' Affair (including Rodgers and Hart's 'I Wish I Were In Love Again'), Where Are You (with Gordon Jenkins), all '57; Come Fly With Me (with May) and Only The Lonely (arranged by Jenkins, conducted by Felix Slatkin) '58 (both no. 1 LPs); Come Dance With Me '59 (May) and No One Cares (Jenkins) '59; Nice 'N' Easy '60 (no. 1 album), Sinatra's Swingin' Session '60, All The Way '61 all with Riddle; Come Swing With Me with May and Point Of No Return with Stordahl '61 (thus his first and last Capitol sessions were with Stordahl).

Sinatra was famous for his short temper; his friend Humphrey Bogart characterized him as 'tilting at windmills, fighting people who don't want to fight'. But his behaviour was not unusual for a working-class kid from an immigrant family in Hoboken; the other boys on the Major Bowes tour in '35 were just as bad, but did not subsequently become rich and famous enough to indulge themselves. Although his judgement was sometimes poor and his big mouth often got him into unnecessary trouble (he was the despair of his publicity people, who knew he could have charmed his way out of trouble any time he wanted), still Sinatra's rages had often seemed to stand for something: a lot of people cheered when Sinatra knocked down gossip columnist Lee Mortimer in a night club in 1947, and his struggle against the phony Hollywood moral code was a struggle against hypocrisy. A decade later however his temper had not improved while his standards began to slip. He attacked rock'n'roll as 'degenerate' in 1957 but three years later welcomed Elvis Presley home from the army in order to get big ratings on TV. He had wanted to produce a film of The Execution Of Private Slovik '60, the true story of the only U.S. soldier executed for desertion during WWII, but scriptwriter Albert Maltz had been blacklisted by Sinatra's old enemies the professional anti-Communists, and this time instead of coming out swinging he backed down because of his friendship with John Kennedy. He was part owner of the Cal-Neva Lodge, a gambling den with hotel rooms and music lounges, but was forced to give it up because he allowed mobster Sam Giancana to hang out there, which was simply foolish; the Nevada authorities could not allow it. Meanwhile he had formed his own Reprise label and began recording for it before he was finished at Capitol; Reprise had some hit albums (principally Sinatra's), but was expensive to run and suffered because Capitol began selling his old albums at a discount in a spoiling operation. Reprise was in turn sold to Warner Brothers '63 in a deal combining Sinatra's film work for Jack Warner, a job for him as a Warner executive and the off-loading of his Nevada leases. But he had what he wanted: his own record label with somebody else putting up the money (at Capitol he had suggested his own imprint, a concept years ahead of its time).

He had 36 more hit albums on Reprise '61-81, almost all top 40, including Ring-A-Ding-Ding! '61 (arranged by Johnny Mandel), Sinatra Swings (arranged by May), I Remember Tommy (remakes of Dorsey hits arranged by Sy Oliver), all '61; Sinatra And Strings (by Don Costa), Sinatra And Swingin' Brass (Neal Hefti) and All Alone (Jenkins), all '62. Sinatra made a world tour '62 for charity, partly because of his reputation as a wise guy with questionable friends, but typically he also saw to it that there was very little publicity in the USA about it, just as he tried to keep his private generosity a secret. Sinatra And Sextet: Live In Paris, with his regulars including Bill Miller on piano, Al Viola on guitar and Irv Cottler on drums, was finally released on Reprise after thirty years, making jazz fans and Sinatra fans wish he had done many more such albums; even better, the superb earlier concert set With The Red Norvo Quintet Live In Australia 1959 was also issued, on Blue Note. As he came off the '62 tour, Great Songs From Great Britain was made in London with Robert Farnon, but not issued in the USA for years: Sinatra thought he had been in poor voice, but it became a collectors' item. There was a set of Oscar-winning songs '64 arranged by Riddle; albums with Count Basie included Sinatra - Basie '63 (Hefti), It Might As Well Be Swing '64, two-disc live Sinatra At The Sands '66 (both arranged by Quincy Jones). Francis A. And Edward K. '68 with Duke Ellington was disappointing for several reasons, beginning with the fact that the Ellington band disliked playing outside arrangements (in this case by May).

The quality of the studio albums was falling off compared to the Capitol years; the loneliness concepts still worked (nobody knew more about that than Sinatra) but the attempts to re-create the Big Band Era were either garish or dull, yet Sinatra (along with Basie and Ellington) was so secure in the public's affection that all of the albums were hits. The best Reprise albums were September Of My Years '65 (with Jenkins), a thoughtful, moving song cycle by a man now turning 50; and Francis Albert Sinatra And Antonio Carlos Jobim '67 (Claus Ogerman), gorgeous treatments of the best bossa nova tunes with the subtle beauty they deserve. (Sinatra And Company '71 with Deodato also had Jobim on one side, tracks from an unfinished sequel to the '67 album.) But the quality of his material began to slip; he made an album of songs by poet Rod McKuen, and albums Cycles and My Way all with Costa, whose work also seemed to suffer because the pop of the period was not Sinatra's material. 'Strangers In The Night' was a no. 1 hit '66, a song whose success is a mystery, adapted from a film theme by Bert Kaempfert; not even Sinatra liked it. He had always performed contemporary songs, but his choice of this stuff revealed how much he had owed in the past to songwriters and arrangers, and how much country-rock songs like Bobby Russell's 'Little Green Apples' and John Hartford's 'Gentle On My Mind' (both on Cycles) depend on a different kind of sensibility, a sort of surrender to time of which Sinatra was incapable. This was the one area in which Sinatra never caught up with Crosby, who could cover country songs and make it work; it is still a mystery why Sinatra did not record more songs by the likes of Cy Coleman instead.

He threw tantrums in Las Vegas and finally swore he would never perform there again; at the same time his third marriage quickly failed (to actress Mia Farrow, many years his junior), his father died and his latest album and film were flops: Watertown '70 was a concept co-written by Bob Gaudio, who had earlier written hits for Frankie Valli and the Four Seasons, and didn't reach the top 100 albums in Billboard; the film Dirty Dingus McGee was a similar turkey. It seemed a good time to announce his retirement, which lasted less than three years. He couldn't stay away, and then became a concert artist, which was risky because the only places it could pay him to work with an orchestra were stadiums and big concert halls, and nobody had done that except the biggest rock acts. But promoter Jerry Weintraub managed it, and Sinatra conquered the world, the magic still working on stage; in the ensuing years probably more people saw Sinatra live than in his entire previous career.

But the albums were another story. Ol' Blue Eyes Is Back '73 with Jenkins and Some Nice Things I've Missed '74 (Jenkins and Costa) were California soft-rock, utterly unsuitable; Sinatra -- The Main Event '74 was better, from live concerts with Woody Herman, arranged by Riddle, Costa, May, 'The Lady Is A Tramp' by Billy Byers (d 1 May 1996, Malibu, on his 69th birthday). After many years of recording heavily, Sinatra albums became occasional events: Trilogy: Past, Present, Future '80 was a top 20 three-disc set and one of the strangest albums ever made. 'Past' was a triumph, the Swing Era far enough in the past to be approached without self-consciousness; Sinatra had revitalized himself on stage, the songs and Billy May's arrangements were superb and everyone involved obviously had a ball. 'Present' however (mostly Costa) was more twee contemporary pop, and the less said about Jenkins's 'Future' concept the better: 39 minutes of mush. L.A. Is My Lady '84 was arranged by Quincy Jones on Jones's Qwest label. Over 70 Hot 100 singles '54-75 included duets with Crosby, Keely Smith, Sammy Davis Jr, Nancy Sinatra; 'Three Coins In The Fountain' '54, 'Learnin' The Blues' '55, 'Hey! Jealous Lover' '56, 'All The Way' '57, 'Witchcraft' '58, 'That's Life' '66 were all top ten.

He had conquered radio in the 1940s but was never really successful on TV, incapable of the kind of intimacy required and too self-centred to work at it. He made more than 40 films after From Here To Eternity, most of them less than masterpieces: as on TV he was incapable of teamwork, wanting just to learn his lines, do one take and go home. Musical films 1955-7 included Young At Heart and The Tender Trap, both '55. Frank Loesser's Guys And Dolls was seen as disappointing at the time, Sinatra and Marlon Brando seeming to be miscast in each other's roles, but it has aged better than one might have thought: Nathan Detroit is a small-time wise guy, a wanna-be gangster, a perfect role for Sinatra; Brando was taller and better looking as the romantic lead. Brando's voice was too small and too high; with today's technology it could have been tweaked, but in '57 he should have been dubbed. High Society was mushy, with Cole Porter past his best and co-starring Crosby; but Rodgers and Hart's Pal Joey was a success, Sinatra playing the gilt-edged heel Joey Evans: author John O'Hara said 'I don't have to see Sinatra. I invented him.' In The Joker Is Wild he played comedian Joe E. Lewis in the true story of a singer who turned comic after his throat was slashed by gangsters. Songs written for Sinatra films by Sammy Cahn/Jimmy Van Heusen included 'The Tender Trap', 'Love And Marriage' (no. 5 '55, for a TV production of Thornton Wilder's Our Town), 'High Hopes' (from A Hole In The Head '59) and 'Come Blow Your Horn' (title song '62). His best straight roles included Suddenly '54 (psychopathic would-be killer), Not As A Stranger '55 (Robert Mitchum's doctor chum in a hospital melodrama), The Man With The Golden Arm '55 (drug addict), thriller The Manchurian Candidate '62. There were 'rat pack' romps with buddies Dean Martin, Sammy Davis Jr, Peter Lawford, Joey Bishop; he later played detective Tony Rome. He directed the war movie None But The Brave '64 and narrowly escaped drowning in Hawaii, pulled from the surf by actor Brad Dexter.

He had become a Republican but continued to choose his friends badly: Vice President Spiro Agnew was convicted of corruption and President Richard Nixon also had to resign; Sinatra despised Ronald Reagan until Reagan began winning elections. He married Barbara Marx '76 (Zeppo's ex-wife) and this marriage lasted; they were active in charity work, especially for children. In early '94 he slowly collapsed while singing 'My Way' in a concert; he waved to the audience as he was carried off. His last two albums were Duets and Duets II '94-5; he seemed to be in good voice but he duetted with no one: his co-singers (most of them hopelessly unsuitable anyway) sang down digital telephone lines to the recording studio. By then he could neither remember the words to the songs nor read them on a prompter, and in '95 the concert career was over.

He was noted for private generosity to friends and strangers in need; he had shady friends, but the USA had created its organized crime and begun glamorizing gangsters when Sinatra was still a child. At any rate, his emotionally stormy life helped to make the singer-as-interpreter one of the best-loved of the century.

The studio recordings and broadcast air checks with Harry James from '39 have been transferred extremely well on Harry James And His Orchestra Featuring Frank Sinatra on Columbia Legacy, and it is clear that he was already a very good singer before he became famous. Tommy Dorsey/Frank Sinatra 'The Song Is You' is a five-CD set on Bluebird, four discs of the complete studio tracks and one of air checks, a fascinating document which is worth the price for 'Everything Happens To Me' and 'Without A Song' alone, and which also makes clear why the Dorsey band was so successful. The complete Columbia studio recordings were issued in a 12-CD set, and the wartime V-discs in a two-CD set; the Capitol and Reprise albums are nearly all in print. His youngest child, Tina Sinatra, produced Sinatra, a five-part TV mini-series on her father's life, starring Broadway actor Philip Casnoff, first aired on CBS-TV in 1992; it was accurate and honest as far as it went, surprisingly good as biopics go. Among many books, His Way: The Unauthorized Biography '86 by Kitty Kelley is exhaustive on the controversies and temper tantrums for those who want that; Sinatra! The Song Is You '95 by Will Friedwald is similarly exhaustive on the recording sessions, fascinating for music fans; All Or Nothing At All: A Life of Frank Sinatra '97 by Donald Clarke is a life-and-times, both the man and his music.


A great many albums, especially compilations and live concerts, are not very well put together for reasons that are unclear in retrospect. Producer Charles Pignone, who worked for Sinatra Enterprises and attended 500 Sinatra concerts, has been making amends with boxes of previously unreleased material. While Sinatra was making disappointing albums, some of his live shows were outstanding; a box called Sinatra: Vegas was followed in December 2009 by Sinatra: New York (four CDs and a DVD), which is a banquet for Sinatraphiles. It begins with a reunion with Tommy Dorsey, three superb tracks from 1955; there is a semi-private concert (for employees of the United Nations) of six songs from 1963, accompanied only by Skitch Henderson on piano; the highlight is a pair of complete concerts from 1974: April at Carnegie Hall and October at Madison Square Garden. The Main Event was a TV special and an album that was cobbled together from several shows; the October 1974 set here is from the night before the one chosen for the TV special, and the best of it all, according to Will Friedwald in the Wall Street Journal. There is also a 1980 Carnegie Concert on DVD and excerpts from two more shows in 1984 and 1990.