Anita O'Day began her career not as a singer, but a dancer. As a teen, she travelled the marathon dance circuit before deciding she would hang up the dance shoes in exchange for a microphone. O'Day's earliest recording success was in the early 1940s when she made sides with Gene Krupa's big band, and soon after, the Stan Kenton Orchestra. While rooted in the swing of these early bands, she was later cited as one of the early bebop vocal influencers and is considered part of the West Coast Cool Jazz sound.
Rather than position herself as another "girl singer," O'Day presented herself as part of the band. Her rhythmic approach and use of short phrasing set her apart from more traditional singers. Throughout her career she worked with Louis Armstrong, Thelonious Monk, and Oscar Peterson. Her 1958 performance at the Newport Jazz Festival was captured in the documentary "Jazz On A Summer's Day." Drugs would play a big part in O'Day's story: She was arrested several times for marijuana possession and fell victim to a heroin addiction, nearly dying of an overdose in 1968. Her resilience showed itself and O'Day recovered and continued to record and perform.