The Billy Tipton Trio, Tipton pictured center.
The Billy Tipton Trio, Tipton pictured center.

Billy Tipton was a jazz musician and bandleader who gained a following in the Pacific Northwest during the 1940s and 1950s. He retired from music and adopted three sons with his common law wife. In 1989 at the age of 74, Tipton died due to complications from an untreated peptic ulcer. It was only after his death that Tipton’s family learned he was biologically female. The day after his funeral, his secret was revealed to the public.

Dorothy Lucille Tipton was born in 1914 and left home in the 1930s to pursue a career in music. Tipton initially began dressing as a man during performances to further his career, but was living full time as a man by 1940. He had many relationships with women over the years, keeping his biological sex a secret by telling his lovers he had been in a serious car accident that damaged his genitals and required him to bind his chest to protect broken ribs. He was able to keep his biological sex a secret from the world for almost fifty years. His biological family, however, was unaware of his double life–whenever he visited home he temporarily became Dorothy again.