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She began singing in clubs in 1930, and was discovered by record producer John Hammond three years later. Hammond arranged several recording sessions for her with Benny Goodman. She later worked with such jazz legends as Lester Young, Count Basie, and Artie Shaw, breaking the color barrier along the way by becoming one of the first jazz singers of that era to perform with white musicians. Nevertheless, she was still forced to use the back entrance and described being forced to wait in a dark room away from the audience before appearing on stage. Once before an audience, she was transformed into Lady Day with the white gardenia in her hair. She explained the sense of overpowering drama that featured in her songs, saying, "I've lived songs like that".
Even when she was young and singing trivial pop songs, however, her unique tone and emotional commitment made her performances special.
Holiday's success was marred by a growing dependence on drugs, alcohol, and abusive relationships. This affected her voice as well, and in her later recordings youthful spirit is replaced by overtones of regret, but her impact on other artists was substantial in all phases of her career. Even after her death she influenced such singers as Janis Joplin and Nina Simone. Diana Ross played her in a movie version of her autobiography, Lady Sings the Blues.
Her late recordings on Verve are as well remembered as her Commodore and Decca recordings of 20 years before. Several of her songs, including her signature song "God Bless the Child", George Gershwin's "I Love You Porgy" (covered exactly by Simone), and the rueful blues "Fine and Mellow" are jazz classics.
Her anti-lynching song on Commodore, "Strange Fruit", with the lyric "Southern trees bear strange fruit" gave her a place, not just in musical history, but in American history.
Holiday's final years were a tragedy. She was swindled out of her considerable earnings and died with only 70 cents in the bank and $750 dollars hidden about her person.
Billie Holiday is interred in St. Raymond's Cemetery, Bronx, New York.