From the roaring twenties all the way through to the early 1960's, jazz was king. One group that personified the royalty of the genre was Billy Tipton and the Billy Tipton trio. But there's a incredible secret about Billy that wasn't revealed until after his death. He was in fact born a her.
The group gained a local following in the Pacific Northwest throughout the 1940's and 1950's, starting out at the local Elks club in Longview, Washington. As they rose to prominence, Billy maintained his public presence as a man by binding his breasts and using padded pants to exude a male bulge.
Initially, Billy pursued women who were lesbians, meaning they knew full and well that he was born a woman (and still had the parts). But over time, Billy began courting straight women who thought he was male.
To do this, Billy invented a story that he was involved in a gruesome car accident which resulted in damaged genitalia and busted ribs, forcing his chest to be permanently compressed.
Over the years, Tipton wouldn't get formally married but would later have countless women come forward identifying themselves as his wife. He adopted three sons along the way, named John, Scott, and William. By all accounts, Billy was a good father.
After a long career of entertaining crowds along the west coast, Billy was forced to retire from music in the 1970s, due to worsening arthritis. His best year musically was in 1957 when his group's albums sold 17,678 copies despite being signed to a small, independent record label. They'd go on to perform as the house band at Allen's Tin Pan Alley in Spokane, Washington. Billy performed skits as characters ranging from Elvis Presley to Liberace.
In the late 1970s, Billy left Kitty. She was his spouse for many years through the adoption of their sons. Sadly, she had abused the boys, forcing two of them to run away from home. Billy was forced to move into a mobile home park with an ex-girlfriend named Maryann, where he would live in poverty until his death.
In 1989, at age 74, Billy passed away from a hemorrhaging peptic ulcer that had been left untreated. Paramedics rushed over to try and save his life, and while doing so, Billy's son William learned that his father was a transgender man.
Immediately following his death, Kitty returned to try and cremate Billy's body before the press realized the truth of his sexuality. But she was offered a ton of money from the press to go public about him, prompting her to do so.
The story ran in nationwide newspapers, and the family appeared on talk programs to discuss it.
In 74 years of life, the secret of Billy Tipton was likely only revealed to a handful of family members. Did his fellow musicians know all along and choose to say nothing? Probably.