In March 1947, undercover officers arriving to raid a California house heard Dizzy Gillespie playing trumpet from a tree in the front yard. The homeowner was Anita O’Day, a singer who fundamentally altered American vocal music. This episode traces her fractured Chicago childhood, her escape into Depression-era walkathons where she once covered 4,000 miles in 97 days, and the stage name O’Day, pig Latin for dough, a daily reminder of her need to get paid.

We follow her into Gene Krupa’s integrated big band, where she refused to be window dressing beside trumpeter Roy Eldridge, scored the 1941 hit Let Me Off Uptown, and wore the same band uniform as the men while earning $7.50 a week. Then we look at how a childhood tonsillectomy that removed her uvula forced her to invent a percussive, snare-drum style of scat singing suited to bebop, her Verve years and 1958 Newport appearance, a heroin addiction that led to prison and a 1966 overdose, kicking the habit cold turkey on a Hawaiian beach, and a third act built on her own record label and a brutally honest memoir.

• What walkathon contests actually demanded of desperate contestants
• Why big band singers were classified as canaries and locked into meager salaries
• How a missing uvula turned her voice into a rhythm instrument
• Emily Records, named after her Yorkshire terrier, and the memoir High Times Hard Times
• Surviving a 1996 fall and medical misdiagnosis to record a final album called Indestructible