Billy Tipton

and the reality that women jazz musicians didn’t get jobs. But then the advantages became apparent. For the rest of her life, Tipton bound her large breasts, dressed like a man and made love to women. But when she visited her family, Billy always became Dorothy again. Was Tipton a lesbian? Was she truly female? Would it be accurate to call her a transsexual?

“I think the Tipton story is about the indeterminacy of gender identity,” Middlebrook says. It’s not that Tipton was born into the wrong body. Rather, her sexual identity became an exquisite act, a delightful invention that merged with her life on the stage. “You can understand her as someone who chooses her self-presentation in the face of options,” Middlebrook says. “You can’t draw a bottom line with her about identity, because she’s so adaptable. She could enjoy the fact that here, she’s this, and here, she’s that.”

Diane Middlebrook

Billy Tipton’s body was cremated, and so many questions about her will never be answered. But Middlebrook is certain Tipton wasn’t a hermaphrodite. And she wasn’t a transsexual. Rather, she was an actor, Middlebrook says.

“I believe Billy’s relationship to herself was female. She was the actor; he was the role,” Middlebrook says. “Billy clearly was a sexy man. There’s no question he was a heterosexual guy,” she concludes. ST

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