Billy Tipton (1914-1989) got his start in the predominantly masculine world of jazz during the 1930s. He made a name for himself playing the saxophone and piano, and during the 1950s formed his own group, the Billy Tipton Trio. Throughout his life he had a number of wives and adopted three sons. Therefore, when he died at the age of 74 on January 21, 1989, it came as a surprise to almost everyone to discover that Billy Tipton was really a woman. Even his wives claimed not to have known his secret during their marriages to him.
It is not clear why Tipton chose to conceal his gender. Some speculate that it was the only way for Tipton to make it in the world of jazz during the 1930s, although by the 1950s a number of women had established careers in that field. Others theorize that Tipton was simply more comfortable living as a man.
Regardless of Tipton’s motivation, it was certainly a secret that he rigorously guarded. Apparently he chose not to seek medical treatment for the bleeding ulcer that killed him because that would have required disclosing his gender to the hospital staff.
Ironically, by the 1980s the revelation that a male musician was actually a cross-dressing woman would no longer have been shocking to most people, given that this was the decade in which musicians such as Madonna, Boy George, Prince, David Bowie, and k.d. lang all made careers out of bending gender norms.