Billy Tipton was a hell of a ladies' man, for a lady. She was also a gifted musician, a loyal friend, an indulgent father of adopted boys and -- according to many women who lived with her at different times during the 50 years of her deception -- a satisfying lover. Few of her paramours, not to mention colleagues, had an inkling of her true gender. But that's the main question posed in Diane Wood Middlebrook's biography of the cross-dressing jazzman: What was Billy Tipton's true gender?
She was born Dorothy Lucille Tipton in Oklahoma City in 1914. Her mother, Reggie, gave her piano lessons and dressed her in ruffles. Her inventor-father, G.W. Tipton, was a daredevil pilot who took her up in airplanes. When, at 19, Dorothy began to live as a man, she took her father's nickname, Billy. By then, her parents were divorced and her father had faded from her life. But Billy Tipton, the self-made man, kept up a clandestine relationship with his/her mother and other relatives throughout his life.
What did Billy Tipton want? She wanted to make a living as a jazz musician during a time when women in the business were treated as freaks and novelty acts. She loved women, and wanted to live with them. So she cut her wavy blond hair, bound her breasts and wore a codpiece under full-cut suits. At first she was accepted among show people as a cross-dresser. But after she left Oklahoma for the life of a road musician, Tipton assumed a male identity. Tipton was intensely private, always locking the bathroom door, never turning on the lights in bed or letting her lovers touch her. She wore bindings, she said, because of an unhealed rib fracture. She was a small but lively character who told dirty jokes and played big brother to young musicians. This might not have worked in a more sophisticated place or time, but in the Dust Bowl of the '30s and '40s, and later the second-tier club circuit in the Pacific Northwest, Tipton passed with flying colors.
Tipton's cover was blown only after her death from bleeding ulcers in 1989. She hadn't seen a doctor in more than 50 years, but her autopsy showed that her body was that of a normal 74-year-old woman. Her fifth and last wife, Kitty Tipton Oakes, with whom she lived for 18 years, claims she was taken by surprise, as were their three adopted sons. Oakes approached Middlebrook, a poet and biographer, at a reading in Spokane and asked her to research Tipton's past, and perhaps to find an explanation for a lifetime of lies.
At first Middlebrook, whose last book was a biography of poet Anne Sexton, seems flummoxed by the lurid aspects of Billy Tipton's story. She tries to compensate for the lack of solid information about her early years by posing breathless questions ("Wild Billy Tipton! Why on earth did she do it?") or with sociological musings ("Possibly Billy was able to undertake this masculine role-playing with such self-confidence because she had entrusted the hidden female identity to her mother's keeping"). But as Middlebrook gains more authority with her subject matter, the book swings into life. Eventually we come to see Billy Tipton as a full human being, heroic and flawed, funny and tragic, motivated by love as well as fear.
Amazingly, even the "straight" women whom Tipton deceived didn't hold it against her. Betty Cox, who lived as Tipton's wife from 1946 through 1953, only learned Tipton's true identity after her death. She was "disturbed" to realize she had been sleeping with a woman, but still declared Billy "the most fantastic love of my life!" Billy Tipton the male jazz musician was generous to a fault. He would shower his wives with gifts, buy meals for his sidemen and later, when he went into the booking business, waive his fees if the bands needed money. The only thing he wouldn't share was his secret self. He died divorced and broke in a trailer outside Spokane. Under different circumstances, Tipton might have become a star. But in the end he chose privacy over money and fame.
Was Tipton a man trapped in a woman's body, an ambitious lesbian with a taste for straight women or a consummate actor playing the role of a lifetime? Middlebrook concludes that she was perhaps a blend of all that and more. Tipton left no diaries and no explanations -- just a stack of old 78s and trail of people who loved her for what she was: a good person and a gentle soul.