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.