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Portrait of the Artist as a Young Man

Gilles Pétard/Redferns/Getty Images
The young Frank Sinatra, early 1940s

At every step Sinatra was learning from everyone he encountered, perfecting himself as a performer, and savoring, on stage and off, the adulation of what his publicist George Evans called “a great herd of female beasts…all in heat at once.” (It was Evans who helped orchestrate the apparently random hysteria that swept over Sinatra’s audiences, and who certified his singularity by tagging him as The Voice.) He became a technician of breath control; a deeply informed student of the American songbook, with a singular capacity to discern hidden beauties in outdated or discarded material; a song interpreter who actually (in an era of pretty voices crooning lyrics presumed to be interchangeable) cared about what the words meant and how each played its part in a narrative arc.

A 1939 review in Metronome remarked on “the pleasing vocals of Frank Sinatra, whose easy phrasing is especially commendable,” but of course the phrasing had not been easily arrived at. He had realized early on that the relaxed fluidity of his role model Bing Crosby was not a style he could ever duplicate. His singing emerged from difficulties confronted. The carefully nurtured clarity of his diction, the precise accentuation by which he marked out the syntactic logic of the lyrics, insisted from the start that the words actually be heard. His singing could never be background music: something was being imparted, in a seamless wedding of word and tone, and attention had to be paid. He could afford to go easy on the schmaltz, and the emotional content of the songs came through all the more clearly.

It was as if he removed all obstacles separating the song from the listener. He did not so much express himself as expose, with objectivity and an almost oppressive clarity, the full measure of what the song had in it. Once he had sung a song—“Begin the Beguine” or “Autumn in New York” or “The Song Is You” or “A Foggy Day” or “Violets for Your Furs”—it stayed sung, in just his way, with every breath and rhythmic accent and knowing slur and catch in the throat permanently attached to it.2

The war years were Sinatra’s moment of early glory; he dominated the record charts, had his own radio programs where he hawked Vimms Vitamins and Lucky Strikes; signed a generous five-year contract with MGM; and headlined stage performances in front of ever wilder audiences, culminating in the so-called Paramount Riot of October 1944, a year in which he earned the then-enormous income of $84,000. George Evans’s publicity machine conjured up an appropriate storybook image of Sinatra as boyishly enthusiastic young husband and father, enjoying a cozy domestic life with his teenage sweetheart Nancy Barbato and their two children Nancy and Frank Jr. (a third, Tina, would be born in 1948). His 1945 hit “Nancy with the Laughing Face,” by Phil Silvers and Jimmy Van Heusen, became a convenient emblem of family happiness, whether its object was taken to be his wife or his daughter, and even though, as Kaplan reveals, the song was originally called “Bessie with the Laughing Face” and was retitled to curry favor with Sinatra.

In any event his private life was of a rather different character; he was rarely home and had established the pattern of sexual compulsiveness that provides the ground bass for Kaplan’s narrative, a compulsiveness fully in keeping with Sinatra’s insomnia, his fear of boredom, his fear of being alone. “In truth,” Kaplan writes,

there were probably even more affairs than the hundreds he’d been given credit for…. His loneliness was bottomless, but there was always someone to try to help him find the bottom.

Booze helped too—and books. He had developed the habit of reading on the long bus trips between gigs, and had by the mid-1940s evolved into a left-leaning intellectual of sorts, attentive to public affairs and a spokesman for racial and religious tolerance. His gorgeous interpretation of Earl Robinson’s “The House I Live In,” with its Popular Front resonance (“But especially the people—that’s America to me”), overwhelms by its impression of utter sincerity—but then, so does his interpretation of “Nancy with the Laughing Face.”3

In the midst of a life of desperate restlessness Sinatra managed to project, as needed, whatever personality the situation required. A New York Times critic, Isabel Morse Jones, was biased against Sinatra until she interviewed him in 1943 and came away writing things like: “He is just naturally sensitive…. He is a romanticist and a dreamer and a careful dresser and he loves beautiful words and music is his hobby. He makes no pretensions at all.” The sometimes vicious columnist Louella Parsons was persuaded that Sinatra was “warm, ingenuous, so anxious to please.” Sinatra had the ability to convince nearly everyone of his sincerity, let them down over and over, and still win them back. His relentlessly self-serving behavior could provoke disappointment tinged with disbelief, except among those intimates who knew him best and whose task it was to cater to his mood swings. They called him The Monster.

Sinatra’s irresistible ascent, coupled with the unlovely portrait Kaplan paints of him, begins to generate a certain monotony until the moment in the late 1940s when he starts to lose altitude, to the delight of so many who had been repelled by his perceived arrogance, skeptical of his having gotten out of the draft thanks to a perforated eardrum, and appalled by, or envious of, the “squealing, shouting neurotic extremists who make a cult of the boy.” The latter characterization was by the columnist Lee Mortimer, who would earn a role in Sinatra’s career crisis when Sinatra, enraged by repeated jabs in Mortimer’s column, assaulted him outside Ciro’s restaurant in Los Angeles in April 1947, administering an apparently fairly ineffectual beating while calling him (in one version) a “degenerate” and “fucking homosexual.”

The negative publicity attendant on this incident was nothing compared to the cloud cast by Sinatra’s presence in Havana during the notorious Mafia conclave at the Hotel Nacional in February of the same year. His unconcealed socializing with a group including Willie Moretti (an old New Jersey acquaintance of Sinatra’s) and Lucky Luciano caught the attention of the journalist Robert Ruark, who proceeded to draw national attention to Sinatra’s

curious desire to cavort among the scum…. Mr. Sinatra, the self-confessed savior of the country’s small fry…seems to be setting a most peculiar example to his hordes of pimply, shrieking slaves.

(Kaplan makes somewhat less of such mob ties than other writers have done, chalking them up in large part to the adulation of a lifelong wannabe, while acknowledging the likelihood of many favors given and received.)

Bad news piled up. A trade journal asked in 1948: “IS SINATRA FINISHED?” He was having vocal problems and at times losing his voice altogether. Audiences at his shows had already been shrinking; his record sales were off; newcomers like Perry Como and Eddie Fisher were eclipsing him. His recent movies had been bombs, and when The Frank Sinatra Show debuted on CBS in 1950, Variety took note of its “bad pacing, bad scripting, bad tempo, poor camera work and overall jerky presentation.” After his first marriage ended in divorce, he had to give up his Palm Springs house and was often broke. The IRS was after him for unpaid taxes.

Right-wing columnists who had always despised him redoubled their attacks in a rapidly changing political climate. (Sinatra’s demoralization can be gauged from an internal FBI report from 1950 which claims that he offered the agency his services in providing confidential reports on “subversive elements” in the entertainment field; the offer was rejected.) Estes Kefauver called him before his committee investigating organized crime, although he was permitted to testify in secret. (Did he know Frank Costello? “Just to say hello.” Joe Adonis? “Just ‘hello’ and ‘goodbye.’”) Within a few years Sinatra had lost his movie contract with MGM, his radio contract for Your Hit Parade, his television contract with CBS, his agency contract with MCA, his recording contract with Columbia.

At the same time that his career was apparently falling apart, his affair with Ava Gardner had gone public and by 1951 they were married, a marriage that would last just under two years (a good deal longer than Ava’s two previous marriages). This well-publicized and subsequently much-analyzed debacle—a series of violent quarrels and passionate (and, eventually, not so passionate) reunions, punctuated by a number of apparently halfhearted suicide attempts or threats on Sinatra’s part—has become the crucial episode in capsule lives of Sinatra, in which he plumbs the limits of suffering and emerges a great artist, boyish seductiveness burned away into a harsher and more rueful emotional realism. (“Ava taught him how to sing a torch song,” in Nelson Riddle’s formulation.)

Kaplan dutifully chronicles the endless comings and goings of a marriage marked mostly by separation, and sums up Ava’s contribution to Sinatra’s life:

Like Frank, she was infinitely restless and easily bored. In both, this tendency could lead to casual cruelty to others—and sometimes to each other. Both had titanic appetites, for food, drink, cigarettes, diversion, companionship, and sex…. Both distrusted sleep…. Both hated being alone.

It might suffice to say that he had met the female Frank Sinatra—a woman he could neither dominate nor leave alone—and leave it at that. In a cold light this pair of ennui-ridden insomniacs might seem a poor substitute for Antony and Cleopatra, but who would want to see them (any more than Antony and Cleopatra) in a cold light? If they exist for us at all it is as figures of myth, or what in this latter era has passed for such. Ava Gardner persists as a presence made numinous by the cinematographers who so lovingly framed and lighted her in The Killers, Pandora and the Flying Dutchman, and Mogambo. However indifferent she may have been to movie stardom as a career, she was clearly not indifferent to the power she was able to exert just by being there, and still exerts: just as The Voice continues to create an idealized world through its reverberations, resistant to even the most squalid of biographical details.

To get at anything like an anchored sense of reality in that maze of reflections and echoes—that peculiar arena where their inner lives were parsed on a daily basis by the odious likes of Walter Winchell and Louella Parsons and George Sokolsky—must have been as difficult for Gardner and Sinatra as for the audience of the open-ended public spectacle in which they played out their roles.

One closes Kaplan’s book with a dark and sodden sense of the world in which those lives were improvised, a world neatly summed up in an offhand remark attributed to the agent “Swifty” Lazar: “Losers have the time to be nice.” The glittery splendor of Sinatra’s Oscar-winning moment of redemption for his performance as Maggio has little warmth in it, to say the least. “\Then, turning up the volume on one of the records he made not long afterward, after he had recouped his losses and settled into a second and more lasting preeminence, it all gets washed away by a wave of upbeat insouciance—

When skies are cloudy and gray
They’re only gray for a day
So wrap your troubles in dreams
And dream your troubles away

—as Sinatra works with Nelson Riddle to create a separate reality invulnerable to ordinary suffering, the reality of song at the heart of his maze.4 And then, again with Nelson Riddle, at the end of one of those ballads that he seems to slow down to a pace almost intolerably slow, so as to sound the very bottom of each note and each thought, he inscribes in the final phrase what might be taken as a symbolic suicide note, a record of inner transcendence, or a demonstration of how deeply he had lost himself in his art: “‘Scuse me while I disappear.”5


Correction March 24, 2011

  1. 2

    For “Begin the Beguine,” “Autumn in New York,” and “The Song Is You,” see the box set A Voice in Time, 1939–1952 (Sony, 2007); for “A Foggy Day” and “Violets for Your Furs,” see Songs for Young Lovers (Capitol, 1954). 

  2. 3

    The House I Live In,” as recorded for the 1945 short film directed by Mervyn LeRoy, can be found in the box set Sinatra in Hollywood, 1940–1964 (Warner Bros./Reprise, 2002). 

  3. 4

    Wrap Your Troubles in Dreams,” Swing Easy! (1954). 

  4. 5

    Angel Eyes,” Frank Sinatra Sings for Only the Lonely (1958). 

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