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The Great Pretender

For 50 years, jazz musician Billy Tipton passed for a man. A new biography says the artist kept up this facade, fooling even his wives and children, because of his need to create.


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.

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