The Great Pretender


When a coroner in Spokane, Wash., yanked the covers off a private life in 1989, he unleashed a story line with legs. He phoned a local columnist and said the 74-year-old corpse on his table--known in life as a male jazz musician--actually was a woman. Nearly 10 years later, commentators continue to put fresh spins on the tale of Billy Tipton, a woman who passed for 50 years as a man.

Because Tipton never explained himself (the male pronoun is in keeping with how Tipton apparently wanted to be known), reporters, gender activists, playwrights, filmmakers, academics and historians all have rushed in to supply a reason for his cross-dressing. Even the family has split over motives, with Tipton’s former wives and three adopted sons selling two stories to movie companies.

Depending on which version you ascribe to, Billy Tipton did it for jazz, for sex, for identity or--as a new biography asserts--for art.

An acclaimed biographer and professor of English at Stanford University, Diane Wood Middlebrook has written the first full-length account of Tipton’s life: “Suits Me: The Double Life of Billy Tipton” (Houghton Mifflin).


Middlebrook is known for her bestselling biography in 1991 of poet Anne Sexton, a book that provoked controversy when it was revealed that the author had access to more than 300 hours of taped private sessions between Sexton and her psychiatrist. In the wake of that tempest, Middlebrook became something of a specialist on the challenges and ethics of biography.

“Suits Me” is likely to reinforce her credentials in this area, though the difficulties raised by Tipton’s story are different from Sexton’s. Sexton was a confessional poet who spilled her innermost secrets copiously. Tipton, on the other hand, left no diaries, journals or self-revelatory notes and, indeed, appears in Middlebrook’s account to be devoid of an inner life.

Yet, according to Middlebrook, both her subjects were motivated by the need to create.

“Anne Sexton created herself as an antidote to a fragmented sense of herself, and I think that was true of Billy as well,” Middlebrook said recently. “For artists, this [self-creation] endows life with a great deal of meaning and seems to be worth all the trouble they cause everyone else.”

On the Los Angeles stop of her book tour, Middlebrook’s high-brow professorial manner seemed at odds with the material she was here to discuss--a gritty tale populated with strippers, call girls and magicians and starring an unschooled main character fond of crude and homophobic jokes.


The biographer-subject match is easier to understand when one learns that the Tipton story came to Middlebrook, not she to it. Middlebrook had returned to her hometown of Spokane to give a public talk on Sexton in 1991 when a local woman slipped her a note proposing a book project.

“Since you seem not to fear the controversial,” the note read, “I feel this project may be of interest to you.”


The writer of the note was Kitty Oakes, a former stripper who had performed as the “Irish Venus.” Oakes lived as a wife with Billy Tipton for 18 years but claimed upon his death that neither she nor their three adopted sons had known that Tipton was a woman.

Middlebrook initially said no to the request. But later, after her mother died of lung cancer, she agreed to tackle the story.

“It was a way of returning to my mother’s hometown,” she explained “and getting to know it after her death.”

The quest to reconstruct Tipton’s life took her to Oklahoma City, where Tipton was born Dorothy Tipton in 1914, and to Kansas City, where Tipton grew up and began to play the sax and piano. The young musician first experimented with male attire at around age 20 and graduated to passing as a man some six years later.


For much of the 1940s and into the ‘50s, Tipton lived the life of an itinerant entertainer, playing Benny Goodman-style dance music in Elks clubs, Veterans of Foreign Wars halls and grange halls. Wherever he went, Tipton was accompanied by one of a series of good-looking “road wives.”

After years of touring, unrewarded by wealth or fame, Tipton settled into an obscure existence in Spokane, booking bands and raising the three sons he and Kitty Oakes adopted. Middlebrook shows Tipton trying hard to be a normal father during these years; he attends Boy Scout camp-outs and PTA meetings, pilots the family motor home and presides over backyard barbecues.

Tipton’s ability to pass as a man in 1950s small-town America may seem surprising at first glance. Actually, though, throughout history men and women have passed themselves off successfully in public as the opposite sex. During the Civil War, for instance, at least 400 women passed as male soldiers, according to accounts by gay and lesbian historians.

What’s unusual about Tipton’s story--the twist that gives Middlebrook’s account its juice--is not Tipton’s public passing but his alleged ability to deceive a string of intimate partners. Day in and out, year after year, in the midst of the intimacies of family life, Tipton supposedly went to dazzling extremes to keep his secret.


In “Suits Me,” Tipton’s life reads as one prolonged pulling-a-rabbit-from-a-hat act, leaving the reader to marvel at every new trick.

For instance, Middlebrook tells us that Tipton bound her breasts with Ace bandages and wore an elaborate prosthetic device to simulate male genitalia. The wives knew about the paraphernalia but said they believed various excuses: Tipton had been pinned by a Buick and had his pelvis crushed, or he’d broken ribs when he was kicked by a horse and the old injuries required binding.


As for sex, one wife, Betty Cox, says she and Tipton always had sex in the dark and she had to keep her hands to herself.


“You just never got out of line with Billy,” she told Middlebrook. “You didn’t touch Billy.” (Kitty Oakes was the only wife who claimed she and Tipton never had sex during their 18-year marriage. Yet Middlebrook quotes letters from Tipton to Oakes suggestive of a shared sex life.)

Some questions are never answered. How did Tipton manage the mechanics of menstruation in a household with four other family members? (It’s never explained.) And didn’t anyone in Tipton’s house ever burst through a closed door without knocking?

In any case, the intimate deception may make for an intriguing plot--or a potential movie, as Kitty Oakes has hoped it would--but it has troublesome implications for people whose lives most resemble Billy Tipton’s today: female-to-male transsexuals.

In Middlebrook’s interpretation, Tipton was not a transsexual, but an actor who pulled off a lifetime charade for the pleasure of the act. An entertainer’s challenge is to create a believable image from costumes, posture and props, so Tipton’s ability to pass as a man was the ultimate showman’s coup, according to Middlebrook.


Yet contemporary female-to-male transsexuals clearly see in Tipton an earlier version of themselves.

“I don’t want to put words into Billy Tipton’s mouth like everyone else does, but when I look at the pictures in the book I see female-to-male written all over them,” says Jamison Green, president of a support group called FTM (female-to-male) International.

Because there are so few public portrayals of females-to-males, the Tipton biography may serve as many people’s introduction to this little-known population, says Holly Devor, a University of Victoria sociology professor and an expert on female transgenderism.

“I’d be concerned with what impression this book will leave,” says Devor, who interviewed 45 transsexuals in depth for her book, “FTM: 20 Female-to-Male Transsexuals in Society” (Indiana University Press, 1997). “Diane Middlebrook seems to say this was just a really good con game and that Billy Tipton was a consummate actor. I don’t see it that way. Billy Tipton needed to be a man. He paid very highly for that need by dying, in the end, because he wouldn’t go to a doctor (for a bleeding ulcer) and be found out.”



Like Devor, Jamison Green objects to the book’s continual references to deception, masquerade and fraud.

“This is a very, very sore point for us,” he says. Transsexuals don’t see themselves as fooling anyone, says Green. They’re just trying to be who they authentically feel themselves to be.

Further, contemporary female-to-male transsexuals, as a group, are opposed to defrauding intimate partners, says Green. Yet, he says, few mainstream accounts of female-to-male lives capitalize on the deceit theme. In particular, the female-to-male transsexual community is feeling stung by news stories about Brandon Teena, a 20-year-old youth who passed as a man in Falls City, Neb.


Teena apparently deceived teenage girls into having sex on the pretext that she was a biological male. Angered by the charade, local youths raped and murdered Teena in 1993. The tragedy has spawned a rash of magazine articles, a book and an upcoming film, to be produced by Diane Keaton and Drew Barrymore and starring Barrymore.

Because of the Teena story and now the Tipton biography, Green says, “people might assume (female-to-male transsexuals) routinely engage in deception. Now we have to defend ourselves andsay we are not masquerading.”

Adding to Green’s frustration over the misperception is the possibility that Billy Tipton really wasn’t the intimate deceiver Middlebrook paints him to be. Female-to-male transsexuals have on occasion passed themselves off as anatomical males in brief encounters with young, inexperienced partners. But Green says it is unlikely that Tipton--who was 5-foot-5 and broad-bottomed, with a soft, hairless face and a high voice--could have fooled so many mature, sexually experienced women for so many years.

“I find it hard to believe they were all deceived,” Green says.


Yet Middlebrook says the wives’ denials have the “smell of truth” to her.


“Billy Tipton was a shrewd psychologist and surrounded himself with people who were not very observant,” she said, explaining why the wives might not have known the truth.

Authenticating a dead subject’s life is never easy. But complicating the biographer’s task in this case is the fact that nearly all Middlebrook’s main sources accuse each other of lying. Two of Tipton’s sons have said their own mother, Kitty Oakes, lied about not knowing Tipton’s sex. Oakes accuses Tipton’s other wives of lying. The wives accuse Oakes.


And Billy Tipton himself lied constantly about his family history, his age, past relationships, his professional accomplishments and his Air Force career (he borrowed his brother’s military service and claimed it as his own.)

How does an earnest biographer make peace with all this? Over the course of writing two demanding biographies, Middlebrook says she has learned that a biography is ultimately more a work of literature than of history, and that her task was to make sense of Billy Tipton’s life the way a novelist might.

At the same time, she added, she tried to be true to her motto, taken from Voltaire: “We must respect the living, but only truth is good enough for the dead.”

“Finally,” she concluded, “it’s my story of Billy Tipton. It’s as close as I could possibly get to making sense of this stuff. From my point of view, that satisfies the Voltaire standard. That’s the ‘good enough’ truth.”