What Frank Sinatra and Billie Holiday Have to Do with Sam Smith’s Success

The American idols remain hauntingly relevant

Although F. Scott Fitzgerald famously wrote that there are no second acts in American lives, the greatest second act in American music began one night in November 1953, when songwriter Jimmy Van Heusen returned to his Manhattan apartment to find bleeding on his bathroom floor the 1940s’ most popular crooner. Dropped by his label and fired by his studio, jilted by the bombshell movie goddess for whom he’d left his family, alienated from everyone in show business and targeted by right-wing newspapers that despised his liberal politics, Van Heusen’s guest slashed his wrists a month after futilely sticking his head in another friend’s oven. The rush to the hospital that saved his life concluded—with dreadful near-finality—his first act, before an act two that would be scripted in capital letters, when the Voice made the Comeback and became the Chairman. Representing not just the resurrection of a career, 1953 marked 37-year-old Frank Sinatra’s creative emergence as the best singer of his century.

In defeat, Sinatra found his art. In survival, he was overtaken by a myth often at odds with that art. One hundred years after his birth, almost 80 years after making his debut in a talent contest (that he won), close to 20 years after his death, the Sinatra of our collective perception is the swaggering Rat Pack gangster whose ring-a-ding image is distinguished by bullying boorishness, runaway hedonism, and a frequent incapacity for locating the fairly vast middle ground between exalting women and demeaning them. So associated is Sinatra with certain musical traditions and their Vegas trappings, so saturated is the culture with his influence, that thinking of him as a revolutionary means remembering that he altered not only notions of modern masculinity and the nature of modern recording but, more fundamentally, the relationship between a singer and a song. Before Sinatra, a singer was the song’s vehicle; after Sinatra it was the other way around. Like Shakespeare rather neatly timing his life to take advantage of the printing press, Sinatra’s breakthrough coincided with technology in order to—by way of radio, the microphone, and the jukebox—advance to another level the intimate vocals of his predecessor and rival, Bing Crosby. A more momentous revelation, however, came in the ’30s at the Onyx Club on Manhattan’s 52nd Street, when Sinatra first saw and heard Eleanora Fagan from Philly performing under the name Billie Holiday.

Born the same year as Sinatra to an unwed, teenage African American mother, Holiday was raped at the age of ten. As punishment for having the temerity to be molested, she was sent to a girls’ reform school, where she spent at least one night confined to a room with a corpse. A prostitute in her early years, she auditioned badly and unsuccessfully as a dancer, which led to a gig as vocalist for the house band of a club in Harlem; she cut her first demo at 18. Given the limitations of a reedy voice that never stretched much beyond an octave, there was nothing else for Holiday to do but transform popular singing. What her vocals lacked in fullness, they made up for in autobiographical anguish: Long before every cheesy singer on vinyl, tape, disc, MP3, or American Idol made claims to being “soulful,” Holiday stormed the barricade of the blues, taking as hostage an intensity of feeling more profound than could be rendered a brand. Holiday’s play-list for the ages—“Lover Man,” “A Fine Romance,” “Fine and Mellow,” “Moanin’ Low,” “Gloomy Sunday,” “I Cover the Waterfront,” “Good Morning Heartache,” “Solitude,” “Lady Sings the Blues”—is a diary of victim-songs by a singer whose every note is resolutely defiant of victimhood. Though even audiences who have the most fleeting familiarity with Holiday tend to know her life was filled with bad men and worse drugs, often she gave as good as she got and chose the life she wanted to live as much as the constraints of racism and sexism allowed. “God Bless the Child” tells the story of forsaken youth and “Don’t Explain” of a wayward husband (Holiday cowrote both), while “Strange Fruit” bears witness to the dangling rope-bound doom of being black in America, the song so alarming to John Hammond—the pioneering producer who discovered her (as well as, later, Aretha Franklin, Bob Dylan, and Bruce Springsteen)—that Holiday had to record it for another, smaller label.

When Sinatra reflected that virtually all singers are “touched…by her genius,” he wasn’t captivated just by the anarchic sway Holiday held over a tune, toying with the beat like a kitten with a mouse and insisting that its arrangement conform to her. Rather “what she did,” Sinatra would recount to journalist Pete Hamill, “was take a song and make it hers…she lived inside the song.” For Holiday and Sinatra, the song was both slave and dominatrix; they submitted to it, serviced its lyric, and committed themselves to the song’s most forbidden agenda—seduction or sorrow, violence or vindication, recollection or regret—before, at an insurrectionary pivot, taking ownership of it. However different may be their respective renditions of, say, “You Go to My Head,” with Holiday’s a wary plea and Sinatra’s a languorous reverie, both plumb an eroticism the song barely admits is there. With the possible exception of Louis Armstrong, and with due respect to such estimable contemporaries as Crosby and Ella Fitzgerald, no other singer had this kind of impact on the essence of vocal interpretation, and if the personae of Holiday and Sinatra complicated or occasionally contradicted their accomplishments, identity and vision informed each other, as is the case with any monumental artist. Holiday was driven by an insubordination at once heroic and self-destructive, subsequently manifest in the likes of LaVern Baker, Janis Joplin, and Amy Winehouse, who took all the wrong cues from Holiday as well as the right ones. And notwithstanding whatever dim view he held of the music to come, there was something distinctly rock and roll about Sinatra that accounted for the admiration openly conveyed by David Bowie, Jim Morrison, Bono, Springsteen, and Dylan, who earlier this year issued an album of Sinatra covers. “He’s the mountain,” Dylan explained, “you have to climb.”


Regardless of whether the British singer Sam Smith knows it, his recent album, In the Lonely Hour, simply wouldn’t exist without Sinatra’s 1950s landmarks Only the Lonely and In the Wee Small Hours, which exorcised a love affair that drove him to razors and ovens. An erratic singles artist even in his ’50s prime, alternating between irresistible charmers like “Come Fly with Me” and “All My Tomorrows” and glop like “High Hopes” and “Love and Marriage” that Chuck Berry and Elvis Presley came to kill not a minute too soon (Sinatra savior Van Heusen cowrote all of them), Sinatra invented the LP as a quasi-narrative medium a decade before anyone heard Revolver or Pet Sounds. He also charted the sonic map of a masculine vulnerability that no straight man, anyway, dared to display before. Acknowledging the swing apotheosis of 1956’s “I’ve Got You Under My Skin” and his eternal association with the bombastic self-homages of “My Way” and “New York, New York” in the late 1960s and ’70s, Sinatra is at his most sublime on broken ballads, torch songs, saloon melancholia, autumnal reminiscences: “One for My Baby,” “Once I Loved,” “It’s a Lonesome Old Town,” “What’s New,” “What Is This Thing Called Love,” “When Your Lover Has Gone,” “I’m a Fool to Want You,” “Last Night When We Were Young,” “The Night We Called It a Day,” and his supreme moment, “Angel Eyes.” These constitute a noir soundtrack starring the object of his obsession, Ava Gardner, the steam rising off her as smoke curls from a gun, with the vocalist as murder victim singing from beyond the grave of desire like the dead body floating facedown in Sunset Boulevard. In 1957’s “There’s No You,” Sinatra is suspended at the intersection of a loss he can’t face and a memory he can’t relinquish. Watching a dream take flight on the sigh of trees, he feels a rapture that is almost not of this life and that he’s doomed to merely pretend he’ll ever feel again.

People make myths, but sometimes history conspires. When it does, both the greatest male vocalist and the greatest female vocalist share their centennials in the same year; life should always be so symmetrical. Just a few weeks prior to Sinatra’s suicide attempt in 1953, Holiday was the subject of a TV special celebrating her “comeback” from heroin addiction, a revival short-lived if it ever lived at all, her voice already filled with the rattle of mortality; an ex-convict barred from singing in New York clubs, she was caught in her one-act play’s final vortex. If Frank Sinatra endured to rebut the maxim about second acts in American lives—the Gatsby of American music, he returned from annihilation to reign over the ashes of his romanticism—Billie Holiday died to prove it. By the summer of 1959, with Sinatra at a peak unparalleled by his own previous stardom as well as that of any other singer, Holiday slipped in and out of a coma in a hospital room where police “found” a tinfoil of smack that they probably planted. She died under arrest and handcuffed to her deathbed, her legend the one thing that could never be taken into custody.