If you’re reading this blog, you’re probably familiar with David Henry Hwang’s 1988 Broadway play M. Butterfly, the story of a French embassy official in Beijing who has a decades-long affair with a Chinese actress and singer. As anyone who’s seen the play or the 1993 film adaptation will know, the Beijing Opera performer was in reality a Chinese spy . . . and a man.
Hwang’s play is fictional, but it was based on a real incident and real people, including Shi Pei Pu, the singer who passed for a woman and even produced a son she told her French lover was the result of their liaison. Beijing Opera is an all-male form of theater—the female characters, known as a dan, are all played by male actors who specialize in them. (The famous Mei Lanfang was a dan actor and so was Bruce Lee’s father, Lee Hoi-Chuen.) Similarly, Japanese Kabuki, a related performance form, is also the domain of male performers and there are onnagata, specialists in female roles, who have lived their off-stage lives as women. But dan like Shi Pei Pu (who died in 2009) and the onnagata are actors, and they’re specially trained and practiced in the art of appearing and behaving as their opposite gender. (The Japanese contend that only a man can portray the ultra-feminine characters demanded by Kabuki, that no born female could be so dedicated and compelling.) These actors have made gender-shifting their life’s occupation and study, even when they take it outside the theater. What, then, do we make of Dorothy Lucille Tipton, a jazz musician and bandleader who lived in Spokane, Washington? Dorothy Tipton was better known as William Lee Tipton, or simply, Billy—and she lived most of her life as a man.
Gender, as the postmodern saying goes, is performance—an expression of the belief that “sex” is an anatomical and biological construct, determined by nature, while “gender” is cultural and social. We may have been born with determined sex differences (female; male), but gender differences (femininity; masculinity) are behavioral—that is, performed—and may be chosen, changed, and blurred pretty much at will or inclination.
Dorothy Tipton was born in Oklahoma City on 29 December 1914 (in Billy’s later account, he shaved six years off his age); her father, G. W. (for George William) Tipton, a machinist, built, repaired, and raced automobiles and airplanes. In the 1920s, G. W. Tipton, known as Billy, began designing planes and flying air mail in and out of Oklahoma City. Both Tipton’s parents, G.W. and the former Reggie Parks, played popular music on the piano and Tipton learned to play the violin and started giving concerts at 7; she later studied music in Kansas City. After her parents divorced in 1928, Tipton was taken to KC to live with her father’s wealthy sister, Bess, who introduced her to the piano. It was here, in one of the nation’s great jazz towns and during the nascence of the Big Band era, that Tipton, who took the nickname “Tippy” around then, began to become seriously interested in jazz and studied piano and saxophone, which remained Billy Tipton’s principal instruments. When she reached high school, Tipton wanted to join the school band, but was barred because she was a girl. Returning to Oklahoma City and her mother, Tippy Tipton finished high school in 1932 and went on to Connors State Agricultural College, a junior college in Warner, Oklahoma, where she was finally able to join the school’s band.
It was also at this time, about 1934 when Tipton turned 20, that she began appearing in male garb, in hope, she later asserted, that this would enhance her chances of being taken seriously in the largely all-male world of jazz bands. At several auditions, the club managers would say that though Tipton was very talented, they wouldn’t hire a woman musician. To pass as a man, Tipton cut her hair, padded her pants, and bound her breasts, a practice she’d later explain as support for the ribs fractured when a Buick crashed into her. She even obtained documents identifying her as a male, and at her next audition, Tipton got the gig. At first, Tipton dressed in male drag mostly for performances, but by 1940, the musician was living as a man off stage as well. She also adopted her father’s nickname, “Billy,” at the same time. Now permanently taking on the role of a male piano- and sax-player billed as Billy Lee Tipton, the jazz instrumentalist undertook the further daring step of dating a girl, Non Earl Harrell, a “horse,” or professional on the faddish walkathon circuit, who was soon known as “Mrs. Tipton”—a title eventually held by at least five women over Tipton’s lifetime. (None of his “marriages” was strictly legal: none of them, nor his “divorces,” was recorded.)
By 1936, Billy Tipton was leading his own band and appearing regularly on radio stations in OKC. His talent was attracting considerable acclaim and by 1940 he’d joined Scott Cameron’s big band playing all around the Midwest and into Wyoming and Colorado. The next year, Tipton and Non Earl moved to Joplin, Missouri, a music town, and played for 2½ years at the Cotton Club and around the Midwest, followed by two years or so gigging in Texas. Tipton was sharpening his chops and gaining a rep as a talented pianist and sax-player—and nobody questioned his gender, despite his diminutive size (5’4”), wide hips, pink cheeks, baby face, and high-pitched tenor. In 1942, he broke up with Non Earl and had a liaison with an amateur singer named June. By 1946, he was “married” to pretty, 19-year-old Betty, a farm girl with a spectacular figure with whom he stayed for seven years.
In 1949, Tipton was asked to rejoin George Mayer’s Sophisticated Swing Trio, which planned to get in on the Pacific Northwest club circuit action. For a brief time in the 1950s, recorded Diane Wood Middlebrook, Tipton’s biographer (Suits Me: The Double Life of Billy Tipton, 1999), gambling in private clubs in Washington State was legal, drawing gaming tourists to the state from all over the country. Though the first dates weren’t very auspicious, they did have a benefit. One local radio station in Roseburg, Oregon, recorded the Thursday-night gigs at the club the Sophisticated Swing Trio was playing, and so four of their performances survive for posterity. During the three years that followed, Mayer’s trio played the northwest circuit in Oregon and Washington, and as far east as Idaho and Montana. Soon, Dave Sobol Entertianment Agency of Spokane began booking the trio’s gigs, putting the ensemble into some of the best clubs in the region, including the Boulevard Club in Coeur d’Alene, Idaho, where Tipton and his fellow musicians shared the stage with the likes of the Ink Spots, the Delta Rhythm Boys, and Billy Eckstine.
In 1951, in Longview, Washington, Tipton began to form his own group, the Billy Tipton Trio, which eventually included Ron Kilde on bass and Dick O’Neil on drums. Tipton started a professional association with Sobol who booked the trio into top-flight hotels in Spokane like the Ridpath and the Davenport where the combo played Dixieland and covers of poplar jazz classics. They were also not above a little slapstick and costumed gags: one report had it that Tipton slapped on a bonnet as the trio swung into Ella Fitzgerald’s famous 1938 rendition of “A-Tisket A-Tasket.” He was an accomplished emcee and showman for the little floor shows his band had to put on to please their customers, and he became popular for his convivial persona, spiffy attire, and boyish good looks. A natural mimic—as a musician and bandleader, Tipton was expected to sound as much like the artists he and his combo covered as possible—he created small vaudeville skits in which he enacted rubes, dunces, clowns, and kids; he played everything, in fact, except grown women and wrote punny blackouts and one-liners to keep the audience amused. In 1954, Tipton met his fourth wife, Maryann, a sometime call girl.
The trio still toured, however, and while gigging in Santa Barbara, California, in 1956, the combo was heard by a scout for Tops Records out of L.A. The label signed them to a contract and in 1957 issued two albums, Sweet Georgia Brown and Billy Tipton Plays Hi-Fi on Piano, which contained such jazz standards as “What’ll I Do,” “The Man I Love,” “Willow Weep For Me,” “Can’t Help Lovin’ Dat Man,” and “Don’t Blame Me.” The recordings sold respectably and brought the Billy Tipton Trio some renown and better offers, including the house-band spot at the new Holiday Hotel casino in Reno, Nevada, in 1958. Tipton disappointed his two bandmates, however, not only by turning down the lucrative chance at the big time, but also by declining four additional albums for Tops. Apparently he feared the spotlight would be too bright for his other performance.
Tipton moved to his last hometown, Spokane, in 1958 and the trio played weekly gigs in local clubs for the next decade, during which Tipton also acted as a booker for Sobol’s agency, helping younger musicians find work in the business. He ended up owning the agency, but retired from performing in 1973 when arthritis in his fingers and bursitis made playing painful. He also suffered from emphysema and ulcers, but declined to see a doctor.
In 1962, Tipton left Maryann and “married” his fifth “wife,” a busty, red-headed former stripper named Kitty, and they raised a family including three adopted sons, John (b. 1963), Scott (b. 1963), and William (b. 1969). (He explained that the need to adopt was the result of his “sterility” from that encounter with the Buick which left him with severe damage to his ribcage and genitals.) The couple became active in the PTA, the Boy Scouts, and their community; Tipton was always the first to arrange a benefit for a cause or a friend in need. Tipton devoted himself to his boys: “He was always there for me,” said son John, and Scott declared, “He did a helluva good job with us. That's what mattered.” Though the musician was no athlete, he played ball with his sons and took them camping—but he never went swimming and he always wore a T-shirt and an athletic cup outside his underwear. Tipton seldom spoke of his private life or any of his personal problems, and he rarely saw a doctor and, though he had a Social Security number, he claimed no benefits in his later life. He and Kitty had separate bedrooms (“Kitty liked to stay up late,” explained John) and, according to one report, the musician only made love in a darkened room and usually only half-undressed; he “was deft at the use of a prosthetic device.”
After a quarrel, Tipton separated from Kitty in 1982. He and his sons moved into a run-down mobile home in a trailer park on the outskirts of Spokane. The boys left, his income dwindled, and he spent his last years broke. Refusing to see a doctor despite failing health, he collapsed and died of a perforated ulcer on 21 January 1989. He’d made a comfortable living for himself and his family as a musician—he called himself an “entertainer”—but his final estate was almost all debts.
At his death, when the coroner revealed Tipton’s anomalous sexuality, his ex-wives and sons all insisted that they had had no idea their husband and father had been born a woman and had disguised himself as a man—without surgical enhancement or hormones—for 55 years. (His aunts and cousins back in Oklahoma and Missouri, with whom he remained in contact, still knew him as Dorothy, but since he never let his former existence as a female and his present one as a male bleed into one another, neither camp knew of the other life.) He portrayed an exemplary citizen, a dedicated family man, an affectionate husband, and a loving father. If anyone had known, or even suspected, no one said anything in all those years. Dave Sobol, Tipton’s longtime friend and agent, remembered him as “a perfect gentleman.” The musician and bandleader may have begun impersonating a man for financial reasons, a ploy against the sexism of the industry, or even as a sort of joke—propositions most people who had something to say about Tipton’s deception after his death reject—but it became his life.
There remains considerable mystery about how the former Dorothy Tipton maintained the fiction, and no one’s talking, leaving it all up to conjecture and prurient imagining. (Kitty, who died in 2007, ordered Tipton’s body cremated, so the physical evidence is gone.) There remains a lot of speculation about Tipton’s motivation for his gender-bending life and the nature of his true sexual orientation. (The notion of transgenderism hadn’t been conceived in Tipton’s day; the term itself didn’t even appear until 1965 and at his death, the concept had barely been defined, much less come into common use.) “He got tired of keeping that secret,” lamented John. “That’s what probably gave him the ulcers and killed him.” His brother Scott added, “I think he probably never told us because he was afraid we might have rejected him. I could have accepted it. . . . He was my dad.” Youngest son William, however, acknowledges, “Now I feel that though I knew him for 18 years, I never knew him at all.” (Years later, William—who sometimes called himself Billy Tipton, Jr.—said, “He was a phenomenal person. He was a better man than most men could be.”) Curiously, though, he may have hinted at his double life through inside jokes that seemed insignificant . . . until you knew the truth. One of the sketches he wrote for his trio’s performances went like this: “How many sexes are there?” asked the straight man. Responded Tipton: “The male sex, the female sex, and the insects.”
Ironically, due to a split in the family after Tipton’s death, the musician’s ashes were divided between two family camps, one box going to John and Scott and the other to William. Diane Middlebrook reported that a local journalist reflected, “Even now, ironically, there are two Billy Tiptons.” Middlebrook observed that at Tipton’s death, no trace of the breast bindings and the jockstrap, what the biographer called his “sex-concealing gear,” was found in the trailer. “Billy,” Middlebrook speculated, “had prepared to emerge from behind his screen like the Wizard of Oz.”
(The bandleader’s biographer also found double meaning in some of the songs the Billy Tipton Trio played, such as “Exactly Like You”; “All of Me”; “The Way You Look Tonight”; and “It’s Only a Paper Moon,” with lyrics that plead, “It wouldn’t be make-believe if you believed in me.” But, of course, these were also just the jazz standards the trio’s audiences expected to hear.)
Many years after Tipton’s death, Brook Ellingwood, a staff writer at KCTS-TV, the PBS outlet in Seattle/Yakima, Washington, described the musician’s life as “a set of Russian nesting dolls,” with “a talented girl wanting to play” jazz inside “a cross-dressing woman” inside “a pleasant yet unremarkable heterosexual man.” I don’t see Tipton as a set of dolls, though. That’s way too passive and rigid for what he did. In my perception, the life of Billy Tipton was a concurrent array of performances, like Charles Spencer Chaplin playing Charlie Chaplin playing The Little Tramp playing The Lone Prospector (his character in The Gold Rush) playing various roles (explorer, waiter, valet, millionaire, dancer, lover, and so on). Dorothy/Billy Tipton was, simultaneously or serially, a young, jazz obsessed girl; a talented musician and bandleader; a female musician dressed as a male for professional reasons; a woman living as a man; a husband and lover; a father; a community-oriented gentleman. To borrow (and slightly misapply) words from William Shakespeare: “All the world's a stage, / . . . / And one man in his time plays many parts.” Whenever Billy Tipton ventured forth, at home or in public, he wore several (if not all) of these costumes.
Of Dorothy’s relationship to Billy, Middlebrook put it aptly: “[H]er sexual identity became an exquisite act . . . . [S]he was the actor; he was the role.” All we can say for sure is that Dorothy Lucille Tipton took on the part of Billy Lee Tipton in 1934 and made it the longest-running—and arguably the most successful—performance of all time. After all, even The Fantasticks only ran 42 years—13 years fewer than Billy! (Okay, London’s The Mousetrap has run 62 years to date—but both Fantasticks and Mousetrap changed casts—Billy Tipton never did. So there!)
[Like many actors and screen personalities during their lifetimes, Tipton became a symbol after his death and his photo was used as an iconic image. He appeared on the cover of Lou Sullivan’s Information for the Female to Male Cross-Dresser and Transsexual (Ingersoll Gender Center, 1990). There have also been many adaptations of the Billy Tipton story—I wonder how Tipton himself would feel about that, having worked so hard to keep his private life to himself for so long. Aside from the biography by Diane Middlebrook (who died in 2007) and countless articles (including nationwide obituaries) both in print and on line, there are:
- Stevie Wants to Play the Blues by Eduardo Machado, a 1990 play based on Tipton’s life, performed at the Los Angeles Theatre Center
- “Tipton” by folksinger Phranc, a 1991 song in tribute to the musician
- The Opposite Sex Is Neither, a theatrical revue by Kate Bornstein, featuring Tipton, premièred at the Fourth Annual National Festival of Lesbian and Gay Performance (Highways, Santa Monica, California), 1992
- Billy by Timothy Brock (music) and Bryan Willis (libretto), an opera based on Tipton’s life, staged in Olympia, Washington, in 1994
- Can't Help Lovin' Dat Man by Alix Umen and Prisco, a 1995 eight-minute film based on Tipton’s life and career
- The Slow Drag by Carson Kreitzer, a 1996 jazz musical based on Tipton’s life, performed at the American Place Theatre, New York City, and the Whitehall Theatre, London
- Trumpet by Jackie Kay, a 1998 novel based on Tipton’s life
- “The Legend of Billy Tipton” by the punk band The Video Dead, a song about Tipton’s story on the 2003 album Shogun Sessions
- “Kill Me, Por Favor” by Ry Cooder, a 2011 short story including a section about Tipton in the collection Los Angeles Stories
- A Girl Named Bill – The Life and Times of Billy Tipton by Nellie McKay, a 2014 cabaret act drawing on the story of Billy Tipton]