Anita O'Day only ever wanted to be a singer and the film showcases performances that date back to the 50's with such artists as Gene Krupa, Roy Eldridge, Stan Kenton, Louis Armestrong and Hoagy Carmichael. She is shown teaching Billy Taylor how to be a jazz vocalist. Bert Stern comments on Anita performing "Sweet Georgia Brown" for his film JAZZ ON A SUMMER'S DAY while George Wein, legendary impresario, states it was the greatest rendition of the song ever made.

She speaks candidly, always candidly, with Dick Cavett, Bryant Gumble and David Frost, and in interviews on 60 Minutes and CBS This Morning. Anita was a woman who lived her life the she wanted without every looking back and was a musical genius and pioneer who broke race barriers. She talks openly about how she had to overcome great adversities, including a 20-year addiction to heroin and alcohol. The film shows Anita on tour in Europe well into her eighties and making her final recording shortly before her death, the death of an icon.