Billy Tipton (born Dorothy Lucille Tipton), 1914-1989

One Saturday morning in January 1989, an emergency call summoned paramedics to a trailer park on the outskirts of Spokane, Washington, the home of Billy Tipton, an aging white jazz musician. Tipton had been very ill, too weak to leave his bed, but had resisted all attempts to get him to a doctor. His adopted teenage son, William, had been looking after him. That morning, after carrying Billy to the bathroom, William had closed the door and, out of earshot, telephoned his mother, Kitty. They hadn’t spoken for nearly a year. Divorce had dispersed the family almost a decade earlier, and Kitty had remarried, but she could still be counted on in a crisis. She advised William to dial 911 and have Billy moved to a hospital. William made the call, then went to carry his father to the breakfast table. Billy Tipton gave a deep sigh and slumped against his son, unconscious.

That sigh was a secret escaping. The medics arrived almost immediately, lay Tipton on the floor of the trailer, squatted over him, and opened his pajamas to feel for a heartbeat. One of them turned to William and asked, “Son, did your father have a sex change?” William stepped forward and caught a glimpse of his father’s upper body, then stumbled back against the screen door and down the trailer’s steps. What had he seen? “I was in awe. I had no thoughts – just looked up at the sky, thinking it was some hallucination from drugs. If my father had lived as a woman, she would have had big breasts.”

Nobody but Billy had seen that nude torso for about forty years, not even the women who had lived with him as wives. Billy was a very private person, they explained later. He invariably locked the bathroom, where he washed and dressed. People who knew his habits knew that he always wore binding on his chest to support the ribs that had been fractured when the front end of a Buick had plowed into his body – or so he said.

And many, many people knew Billy Tipton. Spokane had been one of the regular stops on his trio’s circuit in the early 1950s, during the brief heyday of legal gambling in private clubs in Washington State, when a band could make a good living backing strippers, magicians, jugglers, tap dancers, any sort of variety act that would draw customers into the clubs to drink and play the slot machines. In 1958, Billy settled in Spokane, and the Billy Tipton Trio became the house band at a downtown nightclub called Allen’s Tin Pan Alley. Billy bought a house in the Spokane Valley and started earning a second income as an agent in the Dave Sobol Theatrical Agency, booking the musicians.

In Spokane, out of professional respect, Billy Tipton was referred to as a jazz musician. He referred to himself as an entertainer, for he had long before given up trying to make a living at jazz, though he smuggled it into floorshows he worked up with other members of his trio, playing a repertory of swing standards on saxophone and piano. Oklahoman by birth, he was attuned to the stingy provincial audiences he had to please in Spokane, and he had a flair for showmanship. As an emcee, he adopted the gregarious style of the businessmen who were regular customers at the clubs, and female fans were attracted by his boyish good looks and his meticulous style of dress.

After Billy married Kitty in 1962, they adopted three sons and involved themselves in the PTA and the Boy Scouts. In his work life too Billy was an exemplary citizen. If a charity wanted to hold a dance or a fellow musician was down on his luck, Billy Tipton was the one who would organize a benefit. He led an active public life in the community for thirty years.

But by the time of his death, Billy was almost destitute. Not much business walked through the doors of the booking agency, where he still worked on commission. He showed up in a fresh shirt every morning nonetheless, with a joke on the tip of his tongue to greet anyone who dropped by the seedy little office. He was a heavy smoker and chronically short of breath, and often quipped that ulcers and hemorrhoids were occupational hazards in the music business, but he brushed off questions about his health. Untreated, hemorrhaging ulcers finally killed him. Billy Lee Tipton was pronounced dead in the emergency room of Valley General Hospital that Saturday, never having regained consciousness, leaving a mystery as his most substantial legacy. He was dead. But who was she?

A buzz began after the autopsy on the Monday afternoon following Billy’s death. The autopsy report, written by a pathologist aware of Billy’s history, established that the body was that of a normal biological female past menopause. The coroner signed the pathologist’s report, then placed a call to a local journalist offering a scoop. “Get hold of Billy Tipton’s death certificate,” he told the journalist. Billy had been a prominent figure in the entertainment business in Spokane. Didn’t the public have a right to know?

One person who didn’t think so was Billy’s former wife Kitty, now Mrs. Robert Oakes. She contacted a funeral director, swore him and his staff to secrecy, and arranged for cremation of the body. When she learned that the local newspaper was planning to publish the discovery of Billy’s hidden identity, she paid a visit to the managing editor and demanded privacy for the family. But one of Billy’s sons had already granted an interview, and this constituted sufficient family permission to override Kitty’s objections. The editor compromised by holding the story until after Billy’s memorial service the following Monday, and by keeping it off the front page. “Jazz Musician Spent Life Concealing Fantastic Secret” was published Tuesday morning, Jan. 31, 1989, in the newspaper’s regional section.

The wire services picked up the story at once. Even the New York Times carried a respectful, faintly marveling obituary for Billy Tipton. Media companies followed with proposals for feature films and made-for-TV movies, and Kitty and the three Tipton sons were greatly in demand for talk-show appearances.

The spotlights revealed a family at war, with the two older sons, John and Scott, allied against William, the youngest, and Kitty. A tabloid published a story called “My Husband Was a Woman and I Never Knew,” in which Kitty said she believed that she and Billy had been legally married and legally divorced and that she had never been physically intimate with Billy because of her own poor health. The two older sons claimed that they had not known Billy’s sex – “He’ll always be Dad to me,” said John – though before Billy’s death, both had begun using the family names of their biological mothers as aliases. But John and Scott did not believe Kitty’s claim to ignorance about Billy’s identity. Calling Kitty “a fake,” they assigned the rights to their story to a film company. The enmity between the two camps was poignantly expressed after Billy’s cremation by a division of his ashes into two boxes, one entrusted to John and Scott and the other to William. As a journalist observed, “Even now, ironically, there are two Billy Tiptons.”

As many of the articles written about Billy Tipton pointed out, Billy was not unique in solving an economic problem or seizing a tempting opportunity just by donning trousers. Throughout history, women had been putting on men’s work clothes in order to perform work reserved for men. Some went to sea, like the Pirate Jenny of Kurt Weill’s song, who had a number of real-life counterparts. Some went to war; a nurse who served during the American Civil War estimated that she had observed as many as 400 cross-dressing women in the Union army alone. Some wrote their memoirs. Among the most colorful on record is a Spanish nun named Catalina de Erauso, born in 1592, who fled the convent to become a soldier in Panama and, after disclosing her sex, received papal dispensation to continue wearing men’s clothes. In old age, she wrote a tell-all autobiography that was adapted for the stage. The French writers Georges Sand, in the 19th century, and Colette, in the 20th, also cross-dressed and told. But some of the cross-dressers we know about were exposed, like Billy Tipton, only after their death. James Miranda Stuart Barry (1795-1863), for example, served as a physician and surgeon for 46 years in the Medical Department of the British Army, where he rose to the rank of inspector general. The attendant who laid out the body for burial discovered Barry’s sex, but the information was suppressed in order to preserve the dignity of the army. Dr. Barry is credited with performing the first successful cesarean delivery in the British Empire and is now recognized as the first British woman physician, but of course conducted this medical career entirely in the guise of a man.

But Billy Tipton was not history, Billy was today, and with no credible explanation for his motivations coming from anyone close to the source, the world was free to make of Billy Tipton what it would. The world was ready. During the years in which Billy’s style of music had been going out of fashion in the entertainment business, gender had come into its own as a theme in art and politics. The very term “gender” was now a marker on the grave of venerable assumptions about the importance of sex difference. Billy Tipton literally became a poster boy for raising consciousness about the confusion of sex (biological) and gender (culturally meaningful physical and social attributes) when, shortly after his death, his image appeared in San Francisco on the cover of a how-to book addressed to cross-dressers and transsexuals. Artists, too, appropriated Billy as a symbol. A group of avant-garde female jazz musicians from Seattle dubbed themselves the Billy Tipton Memorial Saxophone Quartet; Billy’s obituary provided the story line for an opera titled “Billy,” produced in Olympia, the capital of Washington State. Thinly disguised versions of Billy’s story also formed the plots of several plays that received wide critical attention. One, titled “Stevie,” by Eduardo Machado, was staged at the Mark Taper Forum in Los Angeles by the British actor and producer Simon Callow. Another, “The Slow Drag,” by Carson Kreitzer, was produced Off Broadway in New York and as cabaret theater in London. Academic researchers immediately took an interest in explaining Billy, while on the Internet, Billy’s name became shorthand for a whole host of issues among groups with list names across a range of identifications from “sappho” (lesbians) to “boychicks” and “f2mlist” (female-to-male transgenderists).

Generalizations and symbols will take us only so far in thinking about an individual life, however. What could be learned about Billy’s reasons for adopting men’s clothing and a masculine identity? Billy, it turned out, had left plenty of clues, beginning with a legal will. Early in their marriage, Billy and Kitty Tipton had owned a certain amount of property. With a lawyer’s assistance, Billy had drawn up a will in 1965, after the adoption of their first child; updated it in 1971, after the adoption of their youngest son; and updated it again in 1982, after he and Kitty separated. In every version of the will, Kitty was named executor of the estate. By the time Billy died, his estate consisted mainly of debts, plus the alto and soprano saxophones he had never pawned and the diamond ring he had always worn while playing the piano. Those relics of his career in show business went to William. The older sons, John and Scott, were acknowledged with one dollar each.

The other documents found in Billy’s files revealed mainly how shrewd he had been in avoiding the attention of officialdom. He had a social security number but lived in poverty during his last years rather than claim benefits. No marriage or divorce was ever recorded for the William L. or Billy Lee Tipton in question, though, as would later be discovered, a sequence of women had called themselves Mrs. Tipton on their driver’s licenses. Wisely, Billy had generated few medical records, since the intention to pass as a man would have been diagnosed as pathological during most of his lifetime. Not much evidence of Billy’s inner life was to be found, either. There was no personal journal among his papers, and only a few letters survive from among the hundreds written to family members during the years Billy spent on the road, traveling with various bands.

Nor had much of Billy Tipton’s art been recorded for posterity: a couple of demo tapes from the 1940s, a couple of LPs on generic labels produced during the late 1950s. Billy had not made a serious effort to become a recording star and had mainly earned his living playing dance music of the kind popularized by small jazz ensembles in the 1930s and 1940s. At his best, he sounded as much as possible like Benny Goodman’s piano player Teddy Wilson. If Billy Tipton possessed a measure of Teddy Wilson’s talent, however, he did not strive for Teddy Wilson’s visibility. On the occasions when success approached, Billy retreated.

Yes, Billy had covered her tracks. Yet a collection of personal letters found among her professional memorabilia suggests that at the end, Billy decided to let her accomplishments be known. She had been in contact with two affectionate women cousins, whom Kitty had never even heard about before Billy’s death. The cousins, it turned out, had been actively corresponding with Billy for years and knew all about Billy’s family life: the marriage to Kitty, the adoption of the children, the divorce. For the past several years, they had been trying to persuade Billy to join them in the Midwest and take up life as a woman again – the woman they still called Dorothy. Why had Billy turned down the opportunity to slip away once her sons were grown? Wasn’t it because she wanted to take a posthumous bow? The young musicians Billy booked at the Sobol agency recalled Billy’s stories about the old days in the music business, traveling with the likes of Jack Teagarden, Bernie Cummins, Russ Carlyle, Scott Cameron. The stories were not always true, but they show us that Billy hoped to be remembered as belonging to a legendary era in American music, even though her participation required a lifelong disguise. The dramatic way she surrendered her secret at the time of her death suggests that she wanted the disguise to become part of the record too.

Billy Tipton had come of age as a musician at the same time that technology was inventing ways to separate the musician’s body from the musician’s sound. Take the case of Teddy Wilson, Billy’s idol, one of the first black men to play with a prominent group of predominately white artists. Benny Goodman’s integrated orchestra reached its huge audiences over the radio and on records. The music flowed right into the bodies of white listeners without rousing the necessity to condemn this kind of intimacy with the black man. Billy Tipton probably made the acquaintance of Teddy Wilson’s elegant piano style in 1936, listening on a car radio to Camel Caravan, broadcast over CBS from New York. Billy studied Wilson’s recordings until he could imitate Wilson’s style, and later, when he had a small group of his own, adopted the Goodman quartet’s “Flying Home” as a theme song. For Billy, the title of this song was loaded with private meanings that reached back into her childhood as Dorothy and evoked her relationship with her father, an aviator. But the Billy Tipton Trio’s imitation of the Goodman group’s “Flying Home” was purely practical, for bands like Billy’s succeeded best when they most closely duplicated the recorded sound of jazz celebrities. At the peak of Billy’s career, every successful small-time musician was to some extent a skilled impersonator. For instance, Billy’s trio often performed “Exactly Like You,” made famous by Louis Armstrong. Billy caught the multiple meanings of this clever title early in her career as a musician, and improvised on it for the rest of her life, in undetected drag.

Undoing Billy’s disguise raises intriguing questions. Billy worked almost exclusively with men, in close quarters, for years at a stretch. Happily, the plot of Billy’s story lets us watch one woman’s bold solution to gaining a certain amount of recognition in what was largely a man’s world. But how did she compensate for being raised as a girl and trained to play music as a girl? Would a professional career have been possible if Billy had lived openly as a woman? After all those years of playing a man, was Billy a woman, or just female?

Other questions rise in the wake of what can be learned about Billy’s sexual practices. His former wife Kitty assumed that because there was no sex in their marriage, there was no sex in Billy’s story. “Everybody wants to know the wrong thing,” she often said in response to intrusive questions about their private life. But Kitty was only the last woman in Billy’s life to be called Mrs. Tipton – the last of at least five. At least one of these women knew that Billy was a woman; at least two of them made love with Billy for years thinking that Billy was a man. What is really the “wrong” thing in Billy’s story, then – deceitfulness? Gaining erotic satisfaction from women who would not have permitted the same intimacies if they had known Billy’s sex? And what did Billy want? What was in it for her when she chose not only to adopt the role of a man but to play it in every scene, including those we think of as the most confiding?

Precisely because we can gain so little access to Billy’s thoughts and feelings, to answer such questions we have to direct our gaze toward Billy’s skills as an artist. The most important of these was a gift for mimicry. Billy deployed well-worn vaudeville traditions of impersonation in the nightclub skits he wrote. He parodied Elvis Presley and Liberace, and he played rubes (“Goofus,” “Cindy”) and kids (“Little Playmate,” “All I Want for Christmas Is My Two Front Teeth”). Billy never impersonated adult women, but he frequently donned a sunbonnet to play the role of little girl in acts such as “My Wubba Dolly” and “Little Nell.” Hidden under the broad comedy of these standard routines was an actor’s talent for adopting and using the body language of another person. Billy was both acting the role and acting the actor who played it.

Billy’s near-lifelong stint of male impersonation seems on first impression akin to the overt use of drag by contemporary performance artists, such as David Bowie’s androgynous persona Ziggy Stardust. Or transvestite supermodel RuPaul’s how-to interviews on his personification of a glamour queen. Or Madonna’s impersonation of Michael Jackson. Or Laurie Anderson’s cool, technologically assisted, sporadic appropriations of masculinity onstage. All of these artists make visible the stylizations by which gender is communicated as “natural.”

But Billy is different. A perpetual improviser, never out of character, Billy drew her material from the gender fundamentalism of everyday life: the general belief that gender difference arises from anatomical sex difference in human beings and that gendered behavior is the natural outcome of sex difference. Playing a sequence of roles historically reserved for the “opposite” sex, Billy demonstrated by her accomplishment that gender, unlike sex, is in large part a performance: she was the actor, he was the role. And if her first act of cross-dressing was a brilliant, problem-solving prank, Billy quickly found that being taken for a man provided access to almost everything she wanted – music, travel, the love of adventurous and caretaking women.

Inevitably, death ended the act and exposed the actor. Billy was prepared. An adept illusionist to the end, she had done away with her sex-concealing gear, for the trailer was empty of the jockstrap and bindings familiar to Billy’s wives and sons. Billy 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. And locked away in Billy’s office closet, along with the carefully worded and updated will, was the record of a lifetime’s achievements: clippings and photographs documenting the transformation of Billy from she to he and the annotated routines, musical arrangements, and program notes in which Billy makes eye contact with posterity. These professional files show how, night after night, Billy scattered clues and riddles about the drag she wore, including risque gags about homosexuality and jokes that called attention to the costume. Some have been placed at the heads of chapters and on the endpapers of this book, as though they were Billy’s own comments on the story, for her handwritten versions convey an artist’s pride in craft and discipline. They suggest that Billy was anticipating our admiration of her skill, our curiosity about her strategies, and, yes, our pursuit of her secrets.

Diane Middlebrook (1939-2007) was an American biographer, poet and teacher. This essay was excerpted from her book “Suits Me: The Double Life of Billy Tipton.” Reprinted with permission from the publisher. See www.DianeMiddlebrook.com.

This article appeared in the April 2013 issue of Allegro, the magazine of the New York City musicians’ union (AFM Local 802). For more information, see www.Local802afm.org.