Frank Sinatra on his private plane, 1962, from ‘The Rat Pack’ (Reel Art Press), a limited-edition book of many previously unpublished photographs
Frank Sinatra on his private plane, 1962, from ‘The Rat Pack’ (Reel Art Press), a limited-edition book of many previously unpublished photographs © Ted Allan/

Sinatra: The Chairman, by James Kaplan, Sphere, RRP£30/Doubleday, RRP$35, 992 pages

Sinatra’s Century: One Hundred Notes on the Man and His World, by David Lehman, Harper, RRP£16.99/Doubleday, RRP$24.99, 288 pages

Frank & Ava: In Love and War, by John Brady, Thomas Dunne Books, RRP$26.99, 304 pages

Hucksterism fuelled Frank Sinatra’s fame. In 1942, when he stopped being the “boy singer” for a jazz big band, the Tommy Dorsey Orchestra, and went solo, his New York publicist George Evans pulled every trick in the book to promote him. He devised a catchy nickname, “the Voice”, and fanned the flames of “Swoonatra” mania by coaching girls (“Sinatratics”) to scream at shows. When the singer went to California in 1943 to launch a movie career he was greeted at the railway station by thousands of young “bobby-soxer” fans. They had been corralled by Evans, too.

Success turned Sinatra into a publicist’s nightmare, a womanising, hair-trigger-tempered, Mafia-connected magnet for trouble. Poor Evans died of a heart attack in 1950 at the age of 48, reputedly after quarrelling with a reporter about Sinatra the night before. But the hyperbole continued unabated.

In his pomp, from 1954 to the early 1960s, when he released a series of classic albums with the arranger Nelson Riddle and lorded it over the Rat Pack in his desert stronghold of Las Vegas, the singer was treated as a tuxedo-clad deity. “He’s Here!” a billboard outside an Atlantic City nightclub would announce when Sinatra was headlining. “He Was Here!” it declared after the shows ended.

The boosterism followed Sinatra to his grave in 1998, where he lies under a headstone reading “The Best Is Yet to Come”, the title of the last song he sang in public. Perhaps in heaven — or, if the best hasn’t come to pass, the other place — the singer is keeping tabs on how the cult of Frank is faring today. If so, he will be glad to see the latest additions to the groaning shelves of Sinatrabilia, published to coincide with the centenary of his birth in Hoboken, New Jersey, on December 12 1915.

Sinatra: The Chairman is the final instalment of James Kaplan’s monumental two-volume biography, which began with Frank: The Making of a Legend in 2010. Sinatra’s Century is a whimsical potted history by poet and anthologist David Lehman. In Frank & Ava: In Love and War, John Brady relates Sinatra’s relationship with Ava Gardner, a union combustibly founded on shared enthusiasms for alcohol and hypersexuality.

They are dissimilar writers — Kaplan is zingier, Lehman is more self-consciously writerly and Brady is mechanical — but each shares the same outlook: an adulatory view of Sinatra, verging on hero worship.

The loaded term “genius” is sprinkled about like gold dust. The singer, Kaplan insists, was “indisputably” an “exquisitely sensitive genius”. Lehman asks: “What does Sinatra stand for? Above all, genius as a singer and performer.” Sinatra, thus garlanded, rises beyond mere mortal comprehension. Kaplan, with a shrug: “Geniuses contradict themselves.”

Overblown acclamations mount up, the literary equivalent of bobby-soxer fervour. “It was a dramatic relationship, full of the deepest kind of love and every extreme emotion imaginable,” Brady flannels of the Sinatra-Gardner pile-up. “Frank Sinatra”, Lehman gushes, “was the most interesting man in the world.” Kaplan, not to be outdone, marvels that “no human was more complicated than Frank Sinatra”. “Thank God!” he exclaims in reference to a last-minute improvement Sinatra made to the 1957 recording of “Come Fly with Me”, before correcting himself. “No; thank Frank.”

Like the best American products, Sinatra has always been sold with a generous helping of salesmanship. That’s not to detract from his extravagant talents, nor his significance; the same was true of Elvis Presley, whose hip-swivelling emergence appalled Sinatra, once the object of teenage screams himself. (Rock and roll, he fulminated in 1957, was “the most brutal, ugly, degenerate, vicious form of expression it has been my displeasure to hear”.)

But the sale is getting harder to make. When the notorious warts-and-all biographer Kitty Kelley published her hostile biography His Way in 1986, she was denounced as a muckraker by Sinatra fans. Yet her exposure of the extent of his misdeeds left an indelible stain, which subsequent chroniclers have been forced to either acknowledge or whitewash.

Lehman takes the latter course. “How’s this for machismo?” he chuckles, relating an anecdote about Sinatra bedding an actress. He chooses not to mention, even to repudiate, Kelley’s claim that Sinatra, in a drunken rage, threw an unnamed woman through a glass window at a party in Palm Springs, almost severing her arm. How’s that for machismo?

Kaplan is more nuanced. Despite his worshipful view of Sinatra, he doesn’t airbrush the worst extremes of his volatile personality. A 1966 assault on the real estate magnate and art collector Frederick Weisman in a bar (Kelley’s book is Kaplan’s source) begins with Sinatra making an anti-Semitic remark to Weisman and ends with the victim in intensive care with a fractured skull. “If this guy croaks, I’m fucking finished,” Sinatra frets. No wonder even his closest friends called him “the Monster”.

With most of the principals in Sinatra’s life dead, Kaplan relies on a vast bibliography of previous books and articles: there are no new revelations. The first of his two volumes is the best. It charts Sinatra’s big-band apprenticeship and his rise to the top as a solo act, starting with the hit “All or Nothing at All” in 1943, until checked by a career slump in the early 1950s amid falling record sales, movie flops and the scandal of his adulterous relationship with Gardner.

“He’s a dead man,” the Hollywood talent agent Irving “Swifty” Lazar said in 1952. “Even Jesus couldn’t get resurrected in this town.” (Everyone in Sinatra’s circles seems to have spoken like characters in a dime-store novel.) Yet Sinatra made what Kaplan typically terms “the greatest comeback in show-business history” when he won the Oscar for best supporting actor in From Here to Eternity in 1954.

Sinatra: The Chairman resumes the story in the aftermath of the Oscar win. Sinatra is on the verge of 40 and about to embark with the “genius” arranger Nelson Riddle on “the string of groundbreaking recordings that would revolutionise popular music in the 1950s”, starting with Songs for Young Lovers in 1954. The timespan covers the singer’s Rat Pack heyday, joshing about with Dean Martin and Sammy Davis Jr, and his undignified role as President John F Kennedy’s friend-stroke-procurer. The last decades of his life, dominated by fading powers and his fourth wife Barbara (an echo of his domineering mother, Dolly), are dispatched in a brisk 100 pages.

The narrative arc is less dramatic than the first volume, and the writing doesn’t have the same swing. Kaplan tones down the novelistic brio he brought to bear before, as though counteracting Sinatra’s Jack Daniel’s sprees with a more sober style of his own. However, there is enough incident to keep the reader turning through almost 900 pages of text. At times the hard-living mythologising works its old magic, as with a passage in Sinatra’s 1,275-page FBI dossier referring to high-jinks at the singer’s Atlantic City hotel suite during a run of shows: “The party referred to lasted approximately two weeks . . . ”

Kaplan’s weakness is his reliance on a hackneyed “great man” approach to history. Sinatra, we are told, was responsible for “single-handedly bringing the primacy of the big-band era to an end and ushering in the age of the solo vocalist”. He “was far more than just a singer: he was an artist shaping his medium.” In Sinatra’s Century, Lehman really cuts loose: “He was a one-of-the-kind, a maverick, the ultimate nonconformist, and as such a monument to Emersonian self-reliance.”

This heroic mode of biography — brilliant underdog bends the world to his will and becomes top dog — is not confined to Sinatra. Other compatriots from his era have been given the same treatment. Marlon Brando, whom Sinatra disliked and called “Mumbles”, is an example. JFK, whom Sinatra idolised until being expelled from Camelot due to Mob links, is another.

Pop music is particularly prone to the style: the writer Greil Marcus is its high priest, lionising Elvis Presley or Bob Dylan as outsiders who changed everything. In an echo of the 19th-century historian Thomas Carlyle (“The history of the world is but the biography of great men”), they are held up as the unconventional “founding fathers” of postwar America, remaking the world anew through force of individuality.

Sinatra wasn’t averse to casting himself in the same light, as with his brassy anthems of self-fulfilment, “That’s Life” and “Theme from New York, New York”. “My Way”, released in 1969, is the prime example, sung by Sinatra with the gusto of a bull in a china shop. But Sinatra actually disliked the song, written for him by the singer Paul Anka. It “really had nothing to do with my life whatsoever”, he complained. “I know it’s a very big hit — and I love having big hits — but every time I get up to sing that song I grit my teeth . . . ”

Musical to his fingertips, he was aware of his place in a tradition. He idolised the Broadway and Tin Pan Alley standards that were the bedrock of his work and paid tribute to vocalists who influenced him such as Billie Holiday and Mabel Mercer. He did not “single-handedly” end the big band era. Other factors were involved, most importantly a musicians’ strike between 1942 and 1944.

By then the era of the crooner was under way, with Bing Crosby as its biggest star, a precursor with whom Sinatra had a respectful but rivalrous relationship. The younger man enhanced Crosby’s easy style of singing, adding feeling to it. Crosby, more reserved, had instructed one of his lyricists not to put the words “I love you” in his songs. Sinatra had no such qualms.

He used to speak the lyrics of a song before singing them in order to get the inflections right. The result was a conversational delivery with impeccable phrasing and a winning sense of personality. He was a master of tempo rubato — Italian for “stolen time” — the singing technique by which a vocalist plays around with, but ultimately obeys, a song’s timing: a perfect illustration of his mix of conservatism and rebelliousness.

The style he honed was the product of science as well as art. Sinatra’s favourite microphone, the Neumann U47, came on the market in 1949; its sound quality remains almost unmatched today. Advances in vinyl production, studio equipment and high-fidelity stereo systems lay behind his recordings in the 1950s, allowing him to murmur sweet nothings from the turntable in the nation’s living rooms. When he sang “I’ve Got You Under My Skin”, the real meaning lay the other way round. It was his voice charming the ears of millions, getting under their skin, a physiological seduction brought about by recording technology.

The illusion of intimacy was painstakingly created. Whereas Sinatra took idle pride in his “one-take Charlie” label on Hollywood film sets, he laboured over his recordings. His success can be gauged in the way his biographers call him Frank or Frankie, like aspirant Rat Pack hangers-on. Yet in person Sinatra had a horror of closeness. He hated to be touched by strangers and lambasted reporters who called him Frank (“I am Mr Sinatra”). His relationship with Ava Gardner was volatile but shallow, a to-and-fro of soused arguments and what Sinatra’s Century insists on calling “the world’s greatest make-up sex”.

“’Cause it’s witchcraft, wicked witchcraft,” he sang with a knowing twinkle in “Witchcraft” in 1957, when he was at the height of his powers. The sense of intimacy that his songs created lay in those lines, somewhere between an act of enchantment and a con trick. As time goes by, to use the refrain from another song he sang, the outline of the con trick grows clearer.

Sinatra and the writers

Frank Sinatra’s background was not bookish; the closest he came to literature in his youth was a brief job unloading crates at a Manhattan publisher’s office. But as an adult he became a keen reader.

The habit began during long bus journeys touring in his big band days. From pulp novels he graduated to weightier fare, such as Gunnar Myrdal’s immense 1944 survey of US race relations, An American Dilemma, a book that bolstered Sinatra’s advocacy of civil rights. (Although he ended up as a Reagan supporter, as a young man he had a leftwing reputation. In 1945, FBI director J Edgar Hoover was sent a typically inaccurate memo alleging the singer was a Communist sympathiser.)

Frank Sinatra reading at home in Palm Springs, California, in 1965
Frank Sinatra reading at home in Palm Springs, California, in 1965 © Getty

His best films were based on novels, including Nelson Algren’s National Book Award-winning portrait of a drug-addicted hustler, The Man with the Golden Arm, and Richard Condon’s cold war thriller The Manchurian Candidate, which Sinatra loved. When James Jones’s US army bestseller From Here to Eternity was published in 1951, the singer became so fixated with the character of a savvy Italian-American from Brooklyn that he offered to play the role for nothing.

In 1965, he found himself shadowed by a New York journalist for an Esquire magazine feature. Gay Talese was refused an interview with Sinatra, who was nervous about his organised crime links being raised. But Talese was able to observe the singer and his entourage for several weeks, during which he gathered material for a celebrated profile.

“Frank Sinatra Has a Cold”, newly republished by Taschen, depicts the mercurial singer in his natural habitats, carousing in Las Vegas casinos, engineering a tense confrontation with a screenwriter in a Beverly Hills club and singing beautifully in the studio. It was written in a novelistic style, an early example of the freewheeling approach to reportage that became known as “New Journalism”.

When Talese encountered Sinatra at a party several years later, the singer blanked him. But Mario Puzo, author of Mafia epic The Godfather, suffered a worse fate when he bumped into the singer in a Hollywood restaurant in 1970. Angry to be rumoured as the model for the character of Johnny Fontane, the crooner who cravenly seeks Mob help to further his career, Sinatra’s advice to Puzo was curt. “Choke,” the singer told him. “Go ahead and choke.” Don Corleone couldn’t have put it better.

The ‘Rat Pack’ is published by Reel Art Press. Limited Edition available as Master RRP£650, Deluxe RRP£1250 or Heritage RRP£2500.

Photographs: Ted Allan/; John Domanis/Getty Images

Ludovic Hunter-Tilney is the FT’s pop critic

Copyright The Financial Times Limited 2022. All rights reserved.
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