Suits Me: The Double Life of Billy Tipton

As Billy Tipton was dying he forbade his son to call an ambulance. He did anyway. As Billy lay on the floor, paramedics attempted to revive him. “Son, did your father have a sex change?” a medic asked. Billy Tipton had taken his secret to his death: that he was born Dorothy Lucille Tipton, and had lived for over fifty years as a man. Suits Me: The Double Life of Billy Tipton by Diane Wood Middlebrook tells his story. What would possess a woman barely into her twenties to masquerade as a man for the rest of her life? And even more incredulous, how could she deceive everyone, including five wives?


I had first heard about Billy Tipton after his death, when he had become the talk show topic du jour. Friends and relatives, among them any of his five ex-wives, went on the record to say that they had no idea that Tipton was a biological woman. Dorothy Tipton grew up in Oklahoma City in a musical family and mastered several instruments. Her passion was jazz and she hoped to become a professional pianist and sax player, but in the 1930’s, women weren’t members of bands. The only women one saw in bands were singers. Dorothy had a solution to this blatant sex discrimination: if she couldn’t beat ’em, she’d join ’em. She adopted the name Billy, naming herself after her father and brother, and from 1935 to her death in 1989, became both professionally and privately Mr. Billy Lee Tipton.

Her secret was known however among family members, some of whom disowned her. Two of Dorothy’s cousins, Eilene and Madeline, were in on the masquerade from day one:

“‘And Dorothy really tried to find work. She went looking for a job and just couldn’t find one.’
She couldn’t find one, but the cousins were there the day Dorothy finally figured out what to do about that. ‘Some way or another Dorothy heard about a band that needed a saxophone player,’ Eilene recalled. ‘Back in those days you know they didn’t have girls traveling with bands–it was just frowned on. Anyway, she wasn’t helpless and appealing-looking like you’d expect a woman to be. So she said, “Well, if I can’t go as a woman, maybe they’ll take me as a young man!” She took a piece of old worn-out sheet and wrapped it around her chest and pinned it real tight. I never will forget the big safety pin we used in it! Some way she had picked up some clothes. Dressed as a boy, she got this job and left with the band.’ Madeline added, ‘That’s what I admired and loved about Dorothy–she was so innovative! She didn’t cry or go around asking for help, she took responsibility for herself, and here she was, just a kid. She chose it out of absolute necessity.”

The disguise worked, and the new Billy Tipton became famous touring the American northwest and western Canada with jazz bands and later as the leader of his own trio or quartet. But the questions only multiply: how did Dorothy fool so many people? And five wives? The answer is so complex that one can’t give a few sentences and explain it all. The piano- and saxophone-playing of Billy Tipton was legendary, and musicians were in awe of him. His skills on the piano and saxophone brought him the respect and admiration of his bandmates, and although there were rumours about Billy’s sexual orientation based on his obviously feminine external appearance, these rumours were immediately put to rest. How disrespectful to talk of our Billy that way! Shame on you if you thought it made any difference. In the jazz world of the 1930’s and 40’s, if you played as well as Billy did, it didn’t matter what you looked like–as long as you were a man. Billy Tipton was a leader both onstage and off, and ingratiated himself with his fellow musicians by always looking out for his fellow band members and lending them money if they needed it. Thus Billy was seen as a caring and generous man who would stick his neck out for you, and you’d be a fool if you persisted in teasing him.  

In order to be more convincing in her masculine persona, Billy had to be seen with a female admirer. It solved the problem of dealing with crazy women fans at concerts, for if he had a steady girlfriend or wife on his arm, women fans would be less likely to want to rip his clothes off, exposing her secret. It also killed any rumours about his sexual orientation that were always swirling wherever he travelled. As Billy evolved from a small-town pianist to national jazz bandleader, his choice in women evolved as well. From his first wife, a mannish cross-dressing lesbian to his second (a pixyish singer) to his third (a voluptuous Rita Hayworth lookalike) to his fourth (a call girl) to his fifth (a burlesque artist and stripper), Billy’s women became more stereotypically exaggerated as feminine. The more famous he got and the greater exposure he received, the more womanly his wives had to be.

These women accepted Billy’s excuses for his disguise. He told them he had to constantly wear tight binding around his chest in order to keep his ribs in place following an accident. I can see the plausibility of this excuse: after Andy Warhol was shot and nearly killed, he had to wear a girdle around his torso for the rest of his life. Billy also claimed that a car accident rendered him sterile: that explained to them in advance why he could never father children. In interviews Middlebrook conducted with his ex-wives, they claimed that they engaged in sexual intercourse with Billy, yet over the duration of a conjugal relationship, wouldn’t a wife ever want to see her husband nude? Even if he had to leave his chest binding on? One of Billy’s wives claims to have felt his erection through his pants, but this could have been a prosthesis, and he could have used a dildo for intercourse. But still, sterile or not, is it not normal for a married woman to be curious about her husband’s nude body? These are questions Middlebrook raises, yet the wives are evasive. They feel that the author’s questions are too personal and prying, or they claim that the love and affection they received was all that they wanted, and they were not concerned with the physical side of sex. I can read D-E-N-I-A-L between the lines, and the wives are not being entirely open and honest with Middlebrook.

This reaction leads Middlebrook to wonder if any of Billy’s wives were themselves closeted lesbians. In mid twentieth-century America it was common for lesbians in relationships to comprise a “femme” and a “butch”. Were Betty, the Rita Hayworth lookalike, Maryann, the call girl, and Kitty, the stripper, all femmes to Billy’s butch?

Middlebrook devotes some space to explaining the different clinical classifications of hermaphroditism, in order to disprove the doubts of skeptical readers. It is unfathomable for any of us to understand the extent to which Dorothy had to disguise herself in order to pass as Billy. As he gained fame, his tangled web grew larger and grew more barbs, ready to snare him at any moment. As her cousin Eilene explains:

“Mother always thought she should change back as soon as she got a job and could change back. But I think she was talented and good-looking and had a great personality, and once the ball started rolling, I don’t think there was any turning back for her.”

Billy was born female; she was not a hermaphrodite or anywhere on the spectrum of intersexual. As a woman, she menstruated, yet explained the blood stains in her underwear as caused by hemorrhoids, an unfortunate side effect of having to sit long hours behind the wheel travelling from gig to gig, and also from sitting while playing the piano. Upon one wife’s shocking discovery while packing supplies for their life on the road:

“Betty remembered that the first thing into the trunk was Billy’s collection of jazz records, which were nested in a big cardboard box and surrounded by boxes of dishes, pots and pans, extra bedding, first aid supplies, spare cans of motor oil, and a big box of sanitary pads–useful for filtering oil, Billy said.”

When Billy retired from touring and accepted a job in an entertainment booking agency, he realized that setting down roots was detrimental to maintaining his secret. Whenever rumours about his true identity started to spread during his life on the road, it was only a matter of time before he and his band would be off again. Settling down was a risk, so late in life he and his fifth wife decided to start their own family. Billy and Kitty adopted three boys, and created an instant traditional nuclear family: a perfect solution to anyone who doubted Billy’s manliness or virility.

Suits Me became most interesting as Middlebrook told of Billy’s final years. Billy’s two cousins, who had been in on his cross-dressing secret from the very beginning, were not afraid to ask him questions that anyone would have had. Billy was always welcome at the homes of his cousins Eilene and Madeline, whose own families looked to Billy as the coolest aunt/uncle who lived–and was still living–an incredibly fascinating double life. They had heart-to-heart talks:

“But Billy told Madeline that she was content. ‘She was determined to be happy. That was the night she told me, “Some people might think I’m a freak or a hermaphrodite. I’m not. I’m a normal person. This has been my choice.”
“Yet Billy wanted to keep the secret from her boys. On that visit, Billy asked Madeline to promise that if she got sick, Madeline would come and get her, take her away from Spokane to die. ‘Then, after I die, you have my body cremated so I’ll just disappear.’ And Madeline agreed that she would.”


“You don’t know what fear she lived under that she’d be found out.”

The tangled web would not release Dorothy from Billy’s persona. However in her final years, as her ulcers and emphysema worsened, Billy made the following admission to Eilene:

“But at the motel, when we had a chance to talk, I asked her if she was ever going to change back. William [Billy’s youngest son] was still at home, and she said when she got him grown she was going to disappear and change back.”

Billy never had the chance. He died with his secret intact. Middlebrook has written a scholarly biography of the double life of Billy Tipton, and Suits Me is intelligent and honours the woman who gave up her female identity in order to play the music she loved.

Billy’s second album was Billy Tipton Plays Hi Fi on Piano. A collector’s item now, I picked it up for a dollar at a charity store:


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