In life, the two may have been miles apart in circumstance and success. But as each other’s great influences, they’ll be forever one.
BILLIE HOLIDAY, née Eleanora Fagan, was born in Philadelphia, 100 years ago this past April 7. Eight months later, on Dec. 12, 1915, Francis Albert Sinatra arrived, about 95 miles up the coast in Hoboken, N.J. The birth of these two great — arguably, greatest — popular singers, in the same year, a century ago, might be deemed a cosmic fluke, an accident of history. You could also call it history in action. They were born into a still-primitive pop music universe, but changes were afoot. By the time they turned pro, as teenagers in the 1930s, American music had been reshaped by modernity: by the blues and jazz and suave Broadway pop, by electrical recording and microphones and radio. This new brand of music and set of technological tools were ideally suited to Holiday and Sinatra’s talents — an artistry based on uncommon musical and emotional intelligence and expressed through miraculously shrewd and subtle vocal phrasing. Had Eleanora and Francis been born in another year, had they come of age in a different musical world, they might never have become Lady Day and the Voice.
They were linked by more than just the coincidence of their birth year. We associate Holiday and Sinatra with other muses and collaborators — she with the saxophonist Lester Young, he with the arranger Nelson Riddle — but throughout their careers, the singers exerted a powerful pull on one another. Their paths crossed early. Sinatra first saw Holiday perform sometime in the late ’30s; he became an instant devotee. In 1944, Holiday told columnist Earl Wilson that she’d offered Sinatra advice on his singing. ‘‘I told him certain notes at the end he could bend. … Bending those notes — that’s all I helped Frankie with.’’ Sinatra made no secret of his debt to Holiday: ‘‘It is Billie Holiday … who was, and still remains, the greatest single musical influence on me,’’ he said in 1958. In ‘‘Mr. S: My Life with Frank Sinatra,’’ from 2003, George Jacobs, the singer’s former valet, writes that Sinatra visited Holiday in her New York City hospital room in July 1959, shortly before her death from drug and alcohol-related liver and heart disease. When Holiday died, Sinatra holed up in his penthouse for two days, weeping, drinking and playing her records.
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The Holiday-Sinatra bond, in other words, was a classic relationship of guru and disciple. Certainly, Holiday was the more precocious of the two. She began singing in Harlem jazz clubs at age 16 and cut her first records as an 18-year-old in 1933. By the time she returned to the studio in 1935, she was a revelation — neither the white balladeers who dominated the Hit Parade nor the black blues queens from whose ranks she emerged provided a precedent for her. By traditional measures, she didn’t have much of an instrument. Her voice was small and slight. She delivered songs in a midrange drawl that cracked and creaked when she ventured north and south — a bit shrill in the upper register, a touch hoarse on the low end. Yet the result was inviting and beguiling. Like a cool enveloping mist, it was a sound to get lost in.
Her approach to rhythm was cunning. She meandered around the beat, slyly elongating and truncating syllables, gliding down for a landing in surprising places. Sinatra was captivated by the third song she ever recorded, ‘‘I Wished on the Moon,’’ a stock-standard Tin Pan Alley ballad that Holiday, with deft tugs at the melody, transforms into something deeper: a celebration of ecstatic new romance tinged with the melancholy awareness that love fades.
On that record, as on so many others, you can hear Holiday batting bedroom eyes. She was a beautiful woman, but it was her husky voice, and the knowledge of earthly pleasures that it conveyed, that made her a sex symbol. As for Sinatra, even as a tyro — a babyfaced 25-year-old fronting Tommy Dorsey’s band in a bow tie too big for his string-bean frame — the throb in his song was unmistakable. From Holiday, he’d learned that, ideally, musical seduction was a subtle art. His come-ons were staked on telling details: minute vocal shading, delicately dabbed colors, the teasing extra half-beat pause before the headlong plunge into the chorus. Those notes that Holiday told him to bend — they bent toward the boudoir.
Of course, the message of Holiday and Sinatra wasn’t just sex. It was pain. To put the matter in genre terms: Both Holiday and Sinatra were torch singers. In Sinatra’s case, this was a novelty. Torch singing had traditionally been women’s work, but his records made the case that a bruiser in a fedora could love as hard, could hurt as bad, as any dame. He proclaimed himself an ‘‘18-karat manic depressive,’’ and you could hear it even in up-tempo songs like his tumultuous 1956 version of ‘‘I’ve Got You Under My Skin’’: the singer gusting from ecstasy to despair and back again, along the crests and crashes of Riddle’s orchestrations. His ballads cut even deeper. On albums like ‘‘In the Wee Small Hours,’’ Sinatra cast himself as a noir gumshoe, pursuing an insoluble case: ‘‘What is this thing called love? … Who can solve its mystery?’’ Holiday played a more traditional role. In ‘‘My Man,’’ ‘‘Don’t Explain’’ and other torch ballads, she was the bruised diva, doomed to masochistic love with callous men. But there was more: a spirit of resiliency and unflappable cool in the face of cruelty you could detect in all her music, from the most standard pop-jazz genre fare to the anti-lynching anthem ‘‘Strange Fruit.’’ In Holiday’s hands, a torch song was also a protest song.
The fates of the two singers can stand as a parable about race in 20th-century America. Holiday was an adored cult artist who never reached superstardom during her lifetime. When she died, at age 44, she had 70 cents in her bank account. She spent her last days in Manhattan’s Metropolitan Hospital under police guard; she’d been placed under arrest in her hospital bed, on drug possession charges. Sinatra outlived his hero by 39 years. He released dozens of albums, including a few of the best ever made, and a handful of duds, too. He was feted by presidents and died a multimillionaire.
Today, Holiday and Sinatra are so shrouded in myth it can be hard to see them clearly. But when you listen to their records, the clouds part. Frequently, you find them playing against type. Sinatra is often celebrated as the swaggering Rat-Packer, Holiday as a tragic balladeer. Yet it’s Holiday’s music that percolates with greater joie de vivre, and Sinatra’s that scrapes darker depths. One of my favorite parlor games is to listen to the singers’ versions of the same songs: to hear the hay that they both made of ‘‘All of Me’’ or ‘‘Day In, Day Out,’’ to observe their different angles of attack on ‘‘Night and Day’’ — Holiday’s playful and insouciant, Sinatra’s grand, booming, brooding. Then there are those moments when the two giants directly address one other. Sinatra was the acolyte, but the flow of influence reversed on Holiday’s lavishly orchestrated ‘‘Lady in Satin’’ (1958), an homage to Sinatra’s Capitol Records concept albums. Holiday made the connection explicit by opening the LP with a tremulous version of ‘‘I’m a Fool to Want You,’’ Sinatra’s signature torch song, co-written by the man himself. A few years later, Sinatra answered back on a recording of the standard ‘‘Yesterdays,’’ a Holiday staple. At the 1:11 mark of that song, Sinatra sings the word ‘‘then,’’ unleashing a dramatically low and rumbling descending vocal line. Keen-eared listeners picked it up right away: This was Ol’ Blue Eyes doing his Billie Holiday impression. A century after their births, Holiday and Sinatra are still talking to each other. What a privilege it is to listen in.
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