5. Billy Tipton, Musician (1914-1989)


Billy Lee was a bandleader and jazz musician in America, having lived from 1914 to 1989. Born Dorothy Tipton, he lived his entire adult life as a man until his death. In fact, it wasnt discovered until after his death that he had been a woman living as a man. Tipton took company with women throughout his life, identifying himself as straight.