
I first became aware of her when he died in Spokane, the city where I grew up, and where the truth was discovered.
Billy Tipton was a woman who lived as a man for 53 years, from 21 years old until his final curtain call at 74. His three adopted sons never suspected a thing. Here is the fun part: Tipton lived with five women over five decades, all of them attractive females, even va-va-vavoom hot. He had intercourse with all five, and yet none of them noticed that her man was a woman, although number four figured it out eventually. Like his thousands of fans, Tipton’s girls were hoodwinked by one of the greatest performances of all time.
Dorothy Lucille Tipton decided to become Billy Tipton in 1935, ostensibly because it was the only way an aspiring female jazz musician could get work in a nearly exclusively male avocation. The ruse wasn’t really all that difficult. Tipton had a boyish face and a figure that wasn’t what they used to call “curvy”. She did have a big bust, but no waist. With a sheet wrapped around her chest, padding in the crotch, along with a man’s wardrobe, she passed for male. Tipton was even boyishly good-looking. Girls found him adorable, plus Tipton was in a band as a talented pianist, horn player, and singer. Girls liked that.
At the start, Tipton was strictly a crossdresser, making no effort to hide his assigned gender during those times when he wasn’t making music. He lived as a lesbian with a woman with the nutty name of “Non Earl” Harrell. They were based in Oklahoma City, but by 1940 the couple had moved to Joplin, Missouri, unbelievably, at the time, the entertainment center of the Midwest. In Joplin, Tipton began to pretend to be a male full-time, a pose he adopted for the rest of his life.
Tipton and Harrell split-up in 1942. After a relationship of a few years with a singer named June, Tipton met Betty Cox, a pretty 19-year-old. They were together for seven years. Cox later claimed that they had a particularly passionate heterosexual relationship. She even believed that she’d had a miscarriage. I sometimes I think I don’t really know my husband, but after the first seven years, I think I figured out which sex he was. Just like my husband and I, Tipton and Cox only made love in the dark. Don’t most people?
Tipton never removed her underwear and he wore a jockstrap that was fitted with some sort of special stuffing. He wore massive chest bindings at all times, supposedly for an “old injury”. He never allowed himself to be touched below the waist. He refused to share a bathroom. Cox may also have been distracted. She dated other men while she was with Tipton.

In 1958, Tipton had his own jazz trio with a growing reputation. He was on the verge of a successful career as a musician. A Reno nightclub offered to book the trio as their house band. But instead, Tipton took a job as a booking agent in Spokane. He also got a regular gig playing with the house band at a club called The Tin Pan Alley (it is still there, but it has been renamed The Bing Crosby Theatre after Spokane’s most famous native).
The band played swing standards rather than the jazz that Tipton preferred. His performances also included sketches where he imitated celebrities like Liberace and Elvis Presley. In some of these sketches, he played a little girl, but he never impersonated a woman, and he made jokes about queers. Perhaps he feared fame would lead to his unmasking and he felt he’d gone as far as he dared.
In 1960s Spokane, Tipton married a pretty, but troubled stripper named Miss Kitty Kelly. She later claimed that she and Tipton never had a sex life, but in other respects they lived a stereotypical working-class Spokane life. They adopted three boys, but neither could handle the kids when they became teenagers. After a bitter fight in 1980, Tipton moved into a trailer with his sons. From there it was all downhill. The boys split, Tipton couldn’t find work, and he was afraid to go see a doctor.
This is when I read the astonishing story of Billy Tipton in an article in the Spokesman Review newspaper, sent to me by my parental units who still lived there. It seems that Tipton had remained in Spokane, living in poverty, until he collapsed and died in 1989. It was the paramedics who were trying to revive her who uncovered the truth about Tipton. Death must have come as some sort of relief; at that point, Tipton had been pretending for 54 years.

After her passing, Tipton literally became a poster boy for raising consciousness about the confusion around biological sex and gender. His image appeared in San Francisco on the cover of a how-to book for cross-dressers and transgender people. Artists appropriated her as a symbol. A group of avant-garde female jazz musicians from Seattle called themselves The Billy Tipton Memorial Saxophone Quartet.
Tipton’s obituary provided the story line for an opera titled Billy. Thinly disguised versions of her story also formed the plots of several plays including Stevie, by Eduardo Machado, that was first staged at the Mark Taper Forum in Los Angeles by gay British actor, Simon Callow; and The Slow Drag by Carson Kreitzer, produced Off-Broadway. Talented singer-songwriter-cabaret artist Nellie McKay performed her biographical show about Tipton, A Girl Named Bill:The Life And Times Of Billy Tipton at New York City’s 54 Below in 2014.
Tipton’s life demonstrated that gender is a performance; he was an actor, and Billy was his role. His initial act of cross-dressing was a brilliant, problem-solving prank, but Tipton soon discovered that being taken for a man provided access to almost everything she wanted: music, travel, adventure and the love of good women.