Stories as juicy as jazz musician Billy Tipton’s don’t come around often. Tipton, a much-divorced father of three adopted boys, was at best a minor figure in the music world, but he became world famous in 1989, when he died and it was discovered that he was a she. For more than 50 years, he had strapped down his breasts and slipped a little something extra into the jockstrap he always wore. He was taken by almost everybody as a man. Even most of his wives said they thought they’d married a man–and had intercourse with him, often.

It’s hard to imagine anyone writing about Tipton’s life without some amount of sensationalism–you have to get down to the nitty-gritty. But in her new biography, Suits Me: The Double Life of Billy Tipton, Diane Wood Middlebrook tries to take the high road. She’s a Stanford professor, after all, not some hack from the tabloids. When Middlebrook exploits Tipton, it’s for academic purposes.

With a bit of work, Billy Tipton’s life can be hammered into a test case of haute gender theories, increasingly common suppositions that “male” and “female” are arbitrary categories distinguished more by performative acts than genitalia. The story pretty much has to be spun that way: its author is an English professor with a career to look out for. But Middlebrook makes a compromise with the reader–we’ll let her drop in a paragraph of classroom lecture here and there as long as she tells us a good story. It turns out to be a worthy exchange. Middlebrook is light-handed in her professorial role and a gifted storyteller who sees beyond the obvious points of interest.

Suits Me finds a context for Tipton in a detailed evocation of the small-time music scene. He seldom recorded; he made his living playing in house bands for radio stations and by touring Oklahoma and the midwest in combos that specialized in imitating Benny Goodman’s sound. Middlebrook researched the times and places, then filled in the blank spots with educated guesses. “Billy did not write a memoir or leave a letter marked with the instruction ‘To be opened after my death,'” Middlebrook notes. “We will have to substitute imagination for the absent documentation. Perhaps what happened went something like this.” And away she goes. Most of the time she convincingly passes off her hunches as facts, and all but erases the line between biography and novel. Though it’s clearly calculated not to seem blatantly exploitative, Suits Me has all the suspense and voyeuristic kicks of a true-crime book.

The early parts of Tipton’s life were the most difficult to research since so much time has passed, and as a result his youth is the liveliest part of the book–Middlebrook makes up for what she lacks by turning out a thorough and entertaining piece of ethnography. Delving into our purportedly simpler past, she finds in Prohibition-era Oklahoma City a thriving, populous lesbian community, though she notes that such terminology belongs to our age, not Tipton’s. In Billy’s time, “invisibility was promoted by the very absence of such categories. An individual could therefore be regarded merely as eccentric, rather than as a member of a social minority or, worse, as pathological.”

Billy himself was among the eccentric invisible, but Middlebrook still manages to unearth many details. Born in 1916 to an Oklahoma City couple with its own hint of gender subversion–mom was called Reggie while dad was named Billie–Dorothy Tipton was raised by two aunts from the age of 14, when her parents divorced. Middlebrook tells us that Tipton initially dressed as a man at 19 to break into the male-dominated music business. Dorothy, now known as Billy, was cross-dressing but not always passing as a man when she started getting regular sax-playing gigs. Surrounded by a gallery of supporting characters with their own quirks of identity and sexuality, Tipton might not have been an anomaly. First among these characters is Non Earl Harrell, Billy’s first “wife,” a married woman 14 years older than Billy. (Her name “sounds like a joke on the difficulty of keeping the sexes opposite,” Middlebrook points out, in case you hadn’t noticed.) Though she eventually returned to her ex-husband–coincidentally named Earl–for several years Non Earl and Billy passed themselves off as man and wife. Like Tipton, Non Earl was a show person, having made a name for herself as a “horse” in the sadistic dance-marathon craze of the 1930s. Unlike Tipton’s future brides, Non Earl knew Billy was a woman. Cross-dressing wouldn’t have fazed the inveterate rule breaker Suits Me shows Non Earl to be. A divorcee in a time and place where that was still uncommon, Non Earl not only broke ground as a club dancer but she had the nerve to try to pass off her much-younger, inexperienced cross-dressing girlfriend as a husband. She and a cross-dressing female radio station owner who gave Billy an early break are aptly used to suggest Tipton’s unconventional life was not entirely without precedent.

As the years progressed, more documentation of Tipton as an entertainer accumulated, but the act he ultimately became famous for was still going unrecorded. There are really two biographies in the middle of the book: the on-the-record career of Tipton the jazzman and the inferred career of Billy the gender trickster. Middlebrook even uses two sets of pronouns: “‘He’ and ‘his’…refer to Billy’s professional persona and to the relationships he conducted with people who thought he was a man.” For the most part the split approach works, because the material is interesting, whether it involves Tipton’s illusion or less spectacular matters. In Middlebrook’s hands, Billy’s career as a road musician is almost as intriguing as his prolonged act of disguise. But writing two histories leads her to sometimes think of Tipton as two distinct personalities: the real Dorothy and the fictitious Billy. Such a classification makes things easier for her and the reader, but it greatly oversimplifies the mechanics of assumed identity. Tipton lived as a man 24 hours a day, and was a man in the eyes of everyone, including himself. It seems unlikely that Billy wasn’t the real deal, or that Dorothy was watching from a distance while using her body as a puppet.

The Billy Tipton of Suits Me is, by necessity, mainly Middlebrook’s creation. Not surprisingly, the author is rather protective of her boy. For most of the book, this seems like genuine empathy for Tipton, but as Billy ages it becomes unrealistic. Sadly, in the end, Tipton turned out to be the kind of man you’d call a pantywaist, or a pussy–a guy with no balls. Having insinuated himself as the head of a business and a family, he turned out to be a failure at both, due to a pitiful inability to assert himself. He briefly owned a talent agency, but never tried to collect from the deadbeats who comprised his clientele and who mocked him as “the little old lady” behind his back. His adopted sons ran up debts that he always got stuck with, and they also took over his home. Billy’s fourth wife, Maryann, remembers one afternoon when she and Billy were edging toward a reconciliation. He drove her to his home, and they waited in the driveway until his sons’ fistfight broke up before they went inside. Being “gutless”–as Tipton’s final bride, Kitty, describes him–is an unbecoming trait in any gender, but it’s especially sad to find in a literally self-made man.

Middlebrook argues that Billy’s ending was a happy one, for he got to keep up the illusion he so loved, and because he died a man, making “no deathbed conversion to gender fundamentalism.” But she also believes that when Tipton–who never saw a doctor in order to maintain appearances–died of hemorrhaging from untreated ulcers, he “had prepared to emerge from behind his screen like the Wizard of Oz, to dissolve the magic into wisdom, revealing by her nakedness in death that the ‘difference’ between men and women is largely in the eye of the beholder.” This is gender studies hagiography. The trickier case to be made is that Billy Tipton wasn’t a saint: he was a man. The proposition that he relished the idea of having his life picked over once he was dead is dubious; it seems at least as likely–and more human–that he didn’t know how to explain and, with characteristic passivity, resigned himself to not trying. If he’d really wanted to leave a hot trail for a posthumous biographer, he could have done a better job of it.

Maybe Middlebrook doesn’t want to concede Tipton’s failings because they might somehow suggest that gender roles really are biologically determined after all. Suits Me would seem a more honest book if it wasn’t so preoccupied with political positioning. But maybe honesty is the least appropriate approach to the story of Billy Tipton, who had such a selective way with the truth. Because he rarely recorded, his artistic legacy survives mainly through the scripts for skits he performed in his act. “When did you first begin to like girls?” one of his sidemen would ask. “When I found out they weren’t girls,” came the answer. Another gag ran “How many sexes are there? The male sex, the female sex, and the insects.” Suits Me is at its best when, like Tipton onstage, its wisdom about gender doesn’t stop the show.

Suits Me: The Double Life of Billy Tipton by Diane Wood Middlebrook, Houghton Mifflin, $25.

Art accompanying story in printed newspaper (not available in this archive): Tipton photo courtesy W.T. Tipton; Tipton and his wife Betty, circa 19522 photo courtesy Betty Cox; uncredited album cover.