A Feminist Book Review: The Double Life Of Billy Tipton

Meet Billy Tipton, a notorious jazz musician of the 1940’s, married five times, father to three adopted sons.

Oh, did I mention Billy was also a woman?

For those of you who don’t know, there is a great little bookstore under the parking garage downtown called (fittingly) Downtown Books. I once tried to sell some novels there that were in great condition and the owner told me he could give me 5 cents a piece. This guy has so much stuff that he marks some of it free and  leaves it on the sidewalk outside his shop each day – just to stop overflow! I go at least once a week, especially if I am headed to Finnigans with nothing to read, and it was there I found Diane Wood Middlebrook’s biography Suits Me: The Double Life of Billy Tipton.

Billy was born Dorothy Tipton in Oklahoma City in 1914. She was always, in the simplest terms, a tomboy. Dorothy kept short hair throughout her teenage years, and appears rigid and uncomfortable in the tight-fitting dresses that were the style of the time. Segregation was in full effect as Dorothy was growing up, but her piano playing mother often listened to and learned “race music,” that is, music written and popularized by black musicians. When she was 14, her parents went through a bitter divorce, and although her mother was awarded custody, she had no means to support Dorothy and her younger brother. The pair was sent to live with their Aunt in Kansas City. It was here that Dorothy would change her identity to Billy and become a popular jazz musician along the way.

At the age of 19, Dorothy began looking for a way to make money. Her only skill? The piano playing her mother had taught her and the ability to carry a note in a soft tenor tone. However, she quickly discovered that as a woman her skill was not taken seriously and she was paid less than men. She cut her hair even shorter than usual and started wearing pants instead of a skirt. She was soon mistaken as a man and didn’t correct anyone. It was a guise that continued until her death at the age of 74. And no one ever knew the truth.

Billy married five women, not one of whom ever suspected he was a really a she. He was a very private person, never completely undressing and always wearing wraps around his torso which he claimed were necessary to hide the injuries of a childhood automobile accident. Throughout his life he also wore what I can only describe as an “apparatus,” a clever one that made multiple women believe they were sleeping with a flesh and blood man. As most of his family were dead or estranged, there was no one to remember the “dainty daughter” Billy had once been.

At the time of his death, his sons didn’t know. His ex-wives didn’t know. He didn’t leave a written account of his feelings on the matter. All we can do is stand in awe of the strength it took to pull off a lifelong gender disguise, and of the loneliness Billy must have felt, not being able to share his secret or even true body with anyone. Although Billy is an amazing case, Middlebrook opens up the biography by noting that he was not the first to pull off such a feat. In the Civil War, one nurse alone documented over 400 cases of cross-dressing women among injured and dead in the Union Army. AND, the first successful caesarean was performed by a British physician that lived as a man her whole life. Whoa.

I am currently reading Louise Erdrich’s  The Last Report on the Miracles at Little No Horse, which (among a bunch of other awesome themes) explores gender issues through the life of Father Damien, a woman who lives the majority of her adult life as a Native American reservation priest. Erdrich thanked her friend in a post-script for sending her a copy of Suits Me as inspiration. As Billy left no account of his feelings, it has been interesting gaining the perspective of a character who has very mixed feelings about gender. For Damien, a woman is what (s)he is , but a man is what (s)he must be. Damien wouldn’t be whole without both aspects of gender, and I wonder if Billy felt the same.

But then, how different are we from Billy or Father Damien? How much of our gender is innate and how much is performance? Billy looks awfully comfortable to me.

As drag queen RuPaul said, “You’re born naked and the rest is drag.”

*Authors note: In this article, I chose to take the same approach to pronouns that Middlebrook employed in the Billy Tipton biography. In young life, Billy is referred to a she; after transitioning to a new persona, a he.