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.
Tipton recorded two albums of jazz standards in 1957, and the songs included “Can’t Help Lovin’ Dat Man,” “Willow Weep For Me,” “What’ll I Do” and “Don’t Blame Me.” It was reported that the albums sold more than 17,000 copies, which was considered a respectable sum for an independent record at the time.
Tipton adopted three sons with Kitty Oakes, and neither Oakes nor their sons knew Tipton’s secret until the death in 1989 at age 74. Tipton’s life inspired an opera, a play, a musical and others.
