On May 2, 1929, 14 years old Billie Holiday was arrested for Prostitution along with her mother after a raid of the Brothel they were employed at in Harlem. In  1947 she was arrested for a narcotics violation and spent a year in a rehabilitation center called Alderson Federal Prison Camp in West Virginia. Her cabaret license to work in nightclubs was revoked, but did not stop her from selling out Carnegie Hall ten days after her release.

Billie Holiday was arrested again January 22, 1949 in San Francisco for drug possession.