Billie Holiday was a true original. Her voice welded the improvisation of jazz and the soul-searching expressiveness of the blues, and her delivery was distinguished by unique phrasing and an idiosyncratic sense of rhythm. Jack Kerouac dubbed her "The Heroine of the Hip Generation"; U2 celebrated her as the "Angel of Harlem." Saxophonist Lester Young provided her best-known sobriquet: Lady Day.
Holiday, nee Eleanora Fagan, was born in 1915. To say that she survived a troubled youth would be an understatement: her parents were neglectful, she was sentenced to reform school after she was raped at age 9, and was imprisoned for working as a prostitute when she was 14. Her lot in life improved at 15, when she first sang at a nightclub in Harlem following a failed audition to be a dancer. She took her stage name from the actress Billie Dove and her father's surname, Halliday, which she soon changed to Holiday.
In 1933, the famed producer John Hammond first heard Billie at a speakeasy in Harlem. "I just absolutely was overwhelmed. She had an uncanny ear, an excellent memory for lyrics, and she sang with an exquisite sense of phrasing. She always loved [Louis] Armstrong's sound and it is not too much to say that she sang the way he played horn...I decided that night that she was the best jazz singer I had ever heard." He soon helmed the 18-year-old's first recording session, with Benny Goodman.
Holiday enjoyed great success over the next decade, highlighted by performances with bandleaders Count Basie, Fletcher Henderson, and Artie Shaw, and recordings for Columbia (and its subsidiary labels), Commodore, and Decca. Holiday's signature songs included "God Bless the Child" (co-written by Billie), "Lover Man," “I've Got My Love To Keep Me Warm,” "Crazy He Calls Me," and "Strange Fruit," the chilling and controversial 1939 dirge (written by Abel Meeropol, a Jewish teacher from New York City) which protested lynchings in the South. (For a deep dive on that song, watch Strange Fruit: The Biography of a Song on Kanopy.)
Holiday's intemperate personal woes — failed marriages, addictions, bouts with depression, and the death of her mother — weighed heavily throughout her career. In 1947, she was arrested for heroin and served eight months in prison; she was prevented from performing in nightclubs when she lost her NYC Cabaret Card because of her conviction, which closed a significant source of income. In the '50s, Holiday's drug and alcohol abuse had weakened her voice, though she recorded acclaimed discs for Clef and Verve and did a heralded tour of Europe in 1954. Her fact-challenged autobiography (ghostwritten by William Duffy), Lady Sings the Blues, was published in 1956 (and was the source for the 1972 biopic starring Diana Ross); two concerts at Carnegie Hall are regarded as her last great performance. Nat Hentoff noted, "Throughout the night, Billie was in superior form to what had sometimes been the case in the last years of her life." In May 1959, she was hospitalized in New York with heart and liver disease; her room was raided by the Federal Bureau of Narcotics, and she was arrested for possession of heroin. She died on July 17, 1959.
But Holiday's often-tragic life doesn't overshadow her towering musical achievements and legacy. In Billie Holiday: The Musician and the Myth, John Szwed notes, "Holiday was the singer she was because she knew how to rise above the easy pathos of so many of the songs that came her way and to bring a dignity, depth, and grandeur to her performances that went far beyond simply displaying the bruises she suffered...[But] the focus on the emotional power of her interpretations has tended to reduce her artistry, creativity, and enormous influence on the history of jazz to merely her ability to express feelings through music."
Billie addressed the essence of her instinctual genius in Lady Sings the Blues: "If you find a tune and it's got something to do with you, you don't have to evolve anything. You just feel it, and when you sing it other people can feel something too. With me, it's got nothing to do with working or arranging or rehearsing. Give me a song I can feel, and it's never work. There are a few songs I feel so much I can't stand to sing them, but that's something else again."
All of the songs cited in this essay – and many more classsics – are on the 2019 collection, Gold.
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