Skip to content
Chicago Tribune
PUBLISHED: | UPDATED:
Getting your Trinity Audio player ready...

SUITS ME: The Double Life of Billy Tipton

By Diane Wood Middlebrook

Houghton Mifflin, 326 pages, $25

What do women want? Freud famously asked. Among his conclusions: to have a penis. What do artists want? Among the possible answers: to realize their talent and to honor their art. If a woman seems destined for disappointment, according to Freud, so much more so the aspiring female artist.

How to elude this trap? A number of female artists have found it necessary or useful to pass professionally-at least for a time-as men: Currer Bell (Charlotte Bronte) and George Eliot (Mary Ann Evans) are only two. Jazz musician Billy Tipton offers another, more contemporary and peculiarly American version of this solution.

Born Dorothy Lucille Tipton in 1914, Tipton discovered that she desired women and that she wanted to play jazz. Possessed of musical gifts, perseverance, a warm personality and a talent for self-invention, Tipton remade herself by the mid-1930s into Billy Tipton-pianist, saxophonist, leader of the moderately successful Billy Tipton Trio, a smooth-talking, deftly swinging jazzman. When Billy Tipton died in 1989, his long-sustained secret came out. The medics called to his home in Spokane, Wash., to revive him were the first people in decades to see his naked chest: He was a she. His astonished sons and several ex-wives, not to mention many fellow musicians, have had to rethink ever since what it meant to know Billy Tipton.

In this engrossing biography, Diane Wood Middlebrook takes up with verve and care the problem of knowing Billy Tipton. Drawing upon interviews with family members, three of Tipton’s five wives (wives of uncertain legal status), fellow musicians and friends from every stage of Tipton’s life, Middlebrook tells the compelling story not only of one artist’s life but of American social history in the Midwest and Northwest from the Depression through the 1980s.

The daughter of two passionate, talented narcissists, Dorothy Tipton grew up in Oklahoma City in the boom years of the 1920s. Her father, George William (whose middle name Dorothy would later swipe), cut a dashing figure as an aviator, inventor and crack mechanic. Her lively mother, Reggie, who had played ragtime for local dances, was Dorothy’s first piano teacher. After her parents divorced, the 14-year-old Dorothy and her younger brother, Bill, went to live with aunts in Kansas City, Mo., where Dorothy received more-formal piano training and soaked up the lively music scene.

By age 19, Dorothy had returned to Oklahoma City and was helping support her mother. It was in Oklahoma City that Dorothy undertook two apprenticeships, one in music and one in cross-dressing. She landed a job with the Banner Cavaliers, a band that pioneered western swing, a hybrid of country and jazz. She also cultivated her lifelong habit of dressing immaculately–as a man. What began as an improvised solution to the problem of finding work (female musicians were rarely hired, and the union frowned upon them) turned out to be the first stage of a thorough metamorphosis. While Dorothy’s cousins now prefer to recall this moment of Tipton’s career–this mimicry of masculinity–as a kind of forced choice, a Depression-era improvisation, Tipton’s subsequent trajectory suggests that what looked to be a response to hard times was actually Tipton’s bold seizing of an opportunity to realize her desire.

How did she pull it off? Such a story as Tipton’s almost inevitably incites a rather voyeuristic curiosity. Middlebrook satisfies our interest without pandering to sensationalism. On the nuts-and-bolts level, Tipton succeeded with the assistance of sharp suits, and, more intimately, with a dildo, a jockstrap, chest bindings and a fanatical insistence on privacy: His ex-wives who are still alive say they never saw him naked. On a more symbolic level, Tipton succeeded because he was a fantastic and convincing performer who could exploit the expectations of his audience, whether appreciative fans or sexual intimates.

If anything, the course of Tipton’s life offers a parable not of the sensational but rather of the progressive tyranny of the normal. In his early years, Tipton was a dashing kid: eager, able, omnivorous, a dapper and dedicated musician who squired around town his older, voluptuous girlfriend, the incredibly named Non Earl. The young Billy was one eccentric show person among show people; few of his fellow musicians found his persona or his lifestyle remarkable, although his father and his paternal aunts cut him off once he donned trousers and cropped his hair. But after Tipton moved to Joplin, Mo., solidified his career and moved through a few more women, he increasingly rigidified his simulation into a full-blown dissimulation. If his earliest wives and bandmates knew full well that he was a cross-dressing woman, his later wives and bandmates knew him as a straight up, gregarious, heterosexual man. What might have begun as deeply serious play became an even more serious secret. His body, with its ulcers, bore the cost.

Tipton’s story raises obvious questions about the social construction (and hence manipulability) of gender; it also illuminates what we might call the historicity of sex, sexual roles and sexual orientation. Middlebrook, author of a biography of poet Anne Sexton, handles the complexities of Tipton’s life without recourse to jargon but also without dumbing down the nuances. Most Americans today are familiar enough with RuPaul, Dennis Rodman and other celebrity gender-blenders. On any given day Oprah Winfrey or Jerry Springer might feature a cross-dresser, a transgendered person or a hermaphrodite (not at all, as Middlebrook and many theorists would tell you, the same thing).

Nevertheless, most of us implicitly and unreflectively operate according to what Middlebrook calls, in a striking phrase, “the gender fundamentalism of everyday life”: the idea that there are two and only two obvious genders, and that every person can be slotted easily into one or the other. Billy Tipton discovered that gender fundamentalism could work for him. In the middle and later years of his life, he made a wager that even his closest friends and intimates would assume that, because he presented himself as man, he was a man. Having backed himself into his own gender closet, Tipton was unable to take certain risks: In 1958 he refused, to the consternation of his bandmates, a potential breakthrough deal that included recording sessions in Los Angeles and a gig at the Holiday Hotel in Reno. As Middlebrook tells it, Tipton found himself confronted with the choice of developing as a musician or sustaining himself as a man. He chose the latter, more or less abandoning the jazz life as he became a conventional husband, adoptive father, booking agent and entertainer playing the local Elks Club. It seems a paler life, this; more importantly, given Billy’s deceptions of his last three wives and sons, it was an ethically compromised life.

Despite the book’s subtitle, Tipton lived something far more complex than a double life. In her efforts to reconstruct Tipton’s life, Middlebrook has written something both more and less than a biography. Her accounts of the regional music scenes, the youth culture of ’30s jazz and the prisonhouse of respectability are especially compelling; and from the numerous interviews she conducted she has generated a Rashomon-like version of the various Billy Tiptons and the contexts that made him possible. Having refused in his life to speak for himself, Tipton remains, even after more than 300 pages, an intriguing and emblematic Middle American cipher. In his very elusiveness, Tipton offers a parable of American self-fashioning–its pathos, successes and costs.