16. Billy Tipton
Billy Tipton was a famous jazz musician who played both the piano and the saxophone. Born in 1914 as Dorothy Lucille Tipton, she was told she could not have a spot in her high school band because she was a girl. Billy worked as a professional musician and one day decided to identify as a man.
By 1940, Tipton presented as a man and bound the breasts to conceal his sex. He performed along with various bands and had several long-term relationships with several women who never knew.