All Mixed Up: Not Just Tipton, But Our Notions of Gender

Suits Me: The Double Life of Billy Tipton, by Diane Wood Middlebrook. Houghton Mifflin, 326 pages, $25.

Most of us have had unnerving fantasies about that moment, after death, when all our inconsistencies and white lies are revealed by the loved ones who meet at our funeral–and have a chance to compare their stories. How much more disturbed must have been the dreams of Billy Tipton, a jazz pianist and saxophonist whose career spanned five decades; who loved and left a succession of attractive women; who recorded the less-than-best-selling LP Billy Tipton Plays Hi-Fi on Piano ; who was known to his audiences and fellow musicians as a dapper, diminutive fellow, courtly and flirtatious with the ladies, raunchy around the guys. Billy must have intuited that after his demise (which occurred in Spokane, Wash., in 1989), his survivors–including three adopted children and his ex-wife, to whom he had been married for 18 years–would be extremely surprised when an autopsy revealed that he was in fact a woman: Dorothy Tipton, born in 1914 in Oklahoma City.

Actually, it’s hard to know what Billy would have thought. Among the challenges that must have confronted Diane Wood Middlebrook in writing the fascinating Suits Me is that Tipton left such scant evidence–few letters, no diaries or journals–of an interior life. It’s not a criticism of the book to say that, however deftly Ms. Middlebrook probes her subject’s actions and motivations, Billy’s decisions and desires remain something of an enigma. Nonetheless, this biography may make us think differently not only about the nature of gender but about our most basic perceptions of reality: about how much of what we see depends on what we assume we’re seeing. Believing that Billy was a man, the majority of his lovers, friends and colleagues chose to ignore all sorts of unsettling, contradictory evidence about Billy’s biological nature.

Set mostly in film-noirish nightspots through the Midwest and the West, Tipton’s life story features a cast of characters bizarre enough to challenge any idea that eccentricity and scrambled gender identity are recent phenomena confined mostly to downtown Manhattan. Few of the supporting players in the book turn out to be what they seem, or what we might expect, beginning with Billy’s paradoxically self-centered and devoted mother, Reggie, who–together with her otherwise highly conventional third husband–accepted Billy’s cross-dressing and welcomed her daughter home for visits with his current girlfriend, or wife. Among Billy’s early mentors was Oklahoma City radio host Buck Thomason, an enormous woman who also dressed as a man; a six-foot, 300-pound gay actor, Wayne (Tiny) Harrell, and Wayne’s sister, Billy’s first serious lover–a former marathon dancer with the improbable name of Non Earl.

Ms. Middlebrook guides us through the stages of Billy’s career, starting with his early association with bands such as the Banner Cavaliers and Louvenie’s Western Swing Billies, groups that played in bars and roadhouses, mostly in Oklahoma and Missouri. After a period of relative success in the 1950’s, recording and touring with the Billy Tipton Trio, Billy fell into poverty and obscurity when old age, arthritis and the pressures of a lifelong deception compromised his ability to earn a modest living. Meanwhile, we follow the parallel evolution of Billy’s sexual identification, beginning with some apparently casual cross-dressing in the early 1930’s–presumably because it was easier for males to find work in jazz bands–and shifting dramatically in 1937, when Billy began pretending to be a man. This subterfuge was facilitated by a variety of bindings and prosthetic devices, by references to old injuries that had resulted in chronic disabilities, and by the insistence that none of his lovers or wives touch him below the waist or follow him into the bathroom.

Ms. Middlebrook is consistently sympathetic toward, and respectful of, her subject–who could easily have been turned, by a more sensationalistic writer, into the ur- Jerry-Springer -guest. She’s conscientious about pronouns–”‘He’ and ‘his’ are used to refer to Billy’s professional persona and to the relationships he conducted with people who thought he was a man. Billy is ‘she’ in early life and in professional life when the people around her know she is cross-dressing”–and the author is tactful in her speculations about the nature of Billy’s sex life. No doubt anticipating that such questions will occur to even the least prurient of readers, she delicately quizzes Billy’s former spouses about their intimate relations; most claim to have been astonished to learn, after Billy’s death, that their husband was a woman–and are understandably amazed (as are we) by the fact that they never suspected the truth.

What’s almost as surprising is the range of responses to Billy’s gender. Many of his fellow musicians knew his secret all along–and displayed a degree of tolerance that one might not have anticipated in the early 1940’s, far from the presumably more permissive East and West coasts. “Now when you’re born and raised in Oklahoma,” said a musician who knew the facts about Billy, “you don’t question your elders and you don’t divulge secrets.” Another concurred: “He was a nice person, played well–what the hell difference does it make?”

Some, though not all, of Billy’s relatives accepted his male identity; two female cousins to whom he was close never abandoned their gentle attempts to persuade him to revert to being Dorothy. And in one of the book’s most telling moments, a member of the Billy Tipton Trio wanders into Billy’s hotel room, glimpses the body of a naked woman, and is so unable to reconcile the sight with his certainty that Billy would never cheat on his wife that he simply forgets the entire incident.

And, really–despite the evidence–why would anyone have suspected the truth, since so much of Billy’s behavior (not merely the flirtatiousness with women, the dirty jokes and on-stage patter) conformed to so many of the stereotypes that we tend to think of as “male?” Whoever would have imagined that a woman would abandon a supportive homebody spouse for a flashy, voluptuous former stripper–a trophy wife? Who would believe that a female cross-dresser, having opted for a stable domestic existence and three adopted children, would prove to be a “typically” distant, emotionally unavailable father? To its great credit, Diane Wood Middlebrook’s sensitive biography–like Billy Tipton’s life–raises as many profound and wonderfully puzzling questions as it answers. All Mixed Up: Not Just Tipton, But Our Notions of Gender