53. Billie Holiday
Band Or Solo Artist?: Solo
Genre: Jazz, Swing, Blues
Greatest Hit: "Strange Fruit" (1939)
One of the most revered singers of all time, Billie Holiday (or "Lady Day") changed American jazz/pop forever with tracks like "Fine and Mellow" and "Lady Sings the Blues." In honor of her legacy, the soulful and effervescent singer's songs were posthumously inducted into the Grammy Hall of Fame, the first being in 1976 and the most recent in 2010.
During the peak of her commercial career, Holiday pleaded guilty to possession of narcotics to try to get medical help. When she got out of prison, she sold out Carnegie Hall.