Play It, Billy! is based on the life of American jazz musician Billy Tipton (1914-1989). Born and raised as Dorothy Tipton, the young musician found it impossible to find work because of her gender, and so at the age of nineteen she decided to bind her breasts to her torso with a sheet, dress in a man's suit, and begin living as a man. Billy soon became a well-known jazz pianist and band leader whose charisma attracted many women who remained unaware of her biological gender. Billy was married altogether four times and adopted three sons. It was only after Billy's death that the boys or the general public would discover that Billy was, in fact, biologically female. Play It, Billy! tells the story of a person who gained everything because of a secret, but who was also deprived of everything because of that secret.