It's a Mixed-Up, Muddled-Up, Shook-Up World

After I wrote about Stella Walsh a while back, commenter Volly mentioned the similar case of Billy Tipton, which inspired me to pick up a copy of Diane Middlebrook's Suits Me: The Double Life of Billy Tipton. The subtitle is a bit of a misnomer, because Billy Tipton didn't really lead a double life, but rather just a life as a man, although she was all girl.

S/he started out as Dorothy Tipton in Oklahoma, a kid saxophonist in a Western swing band, dressing in man's clothes although living her private life - she still lived with her mom at this point - as a woman. Eventually, Dorothy/Billy left her mom behind, split up the woman who had begun calling Billy her husband, and started living full-time as a man, wooing women who really did believe s/he could be a husband. There were four more wives, none of them ever legally married to Billy, and only one of whom eventually saw through the deception. There were also three adopted sons, who considered Billy only their dad, until that day in 1989 when Billy collapsed on the kitchen floor in his trailer, and Billy's son called the paramedics, who ripped open Billy's pajamas and immediately asked, "Son, did your father have a sex change?"

No, s/he hadn't, but had merely wrapped his upper chest in bindings, claiming that s/he had badly broken several ribs as a youngster (in either a car accident or as a result of getting kicked by a horse; it changed). Billy also always kept the bathroom door locked. Several of his/her ex-wives, when confronted with the truth after Billy's death, recalled clues they should have picked up on; one noted that when Billy went on the road with the Billy Tipton Trio, s/he packed a big box of sanitary napkins, which s/he claimed were excellent for filtering oil. Why s/he needed to filter all that oil, I'll never know.

After living for decades as a man, Billy went back to Oklahoma to see his/her mother one last time before she died, and was reunited with two female cousins s/he had grown up with. Eventually, the three of them sat down and talked about how Billy made it through the world, in one of the sweetest scenes in the book - two old Midwestern farm ladies talking with this she-male about going through the change.

Middlebrook thinks that Billy needed to become a man to have any sort of career in the world of jazz. And eventually, the need to be a man cost Billy his/her career: Later in his/her life, after years on the road, the Billy Tipton Trio declined a lucrative opportunity to become the house band in a hotel in Reno - because, Middlebrook surmises, Billy couldn't risk having such a visible post in the music world, where some of his/her old Oklahoma bandmates might run into him/her and give away the secret. Instead, s/he moved to Spokane. Sometimes it's hard to be a woman.