“I think he probably never told us because he was afraid we might have rejected him. I could have accepted it. He did a helluva good job with us. That’s what mattered. He was my dad.”

-Scott Tipton

Billy Lee Tipton was a jazz musician who managed to marry five times without anyone finding out that he did not have the genitals a cisgender man is expected to have. Managing to carve out a life in a famously competitive field, Tipton had a relatively quiet life, followed by a legacy that was complicated by the discovery of his assigned gender at birth.

Gender is strange, and when looking back in history it can seem doubly so. Between constant language shifts, the erasure many transgender people suffered from cisgender historians, and—for safety and privacy reasons—trans people themselves staying hidden, it can seem impossible to identify transgender people in history. With transgender men, there is an additional wrench thrown in the works. Historically, sexism has barred women from many professions. Fortunately, women have been incredible as long as there have been barriers, so there have always been women finding ways around them. One such tactic was passing as men in order to pursue their dreams with less interference. The problem that arises for historians when looking at this phenomenon is, of course, finding out if the person with a vagina and/or breasts is dressing in traditionally masculine clothing as a means to an end, or if they are actually a transgender man.

Tipton was born in 1914 and spent most of his childhood in Missouri, USA. He discovered his fondness for jazz at a young age but soon after hit up against the cold reality of sexism. He was turned away from pursuing music multiple times because of his assigned gender at birth.

This obstacle continued to come up as he continued to pursue a career in jazz music, so with the help of his female cousins, he began to show up to auditions dressed in traditionally masculine clothes. He introduced himself with his father’s name, Billy. In addition to this, he began binding his chest with a bandage and padding his pants. This strategy saw immediate success; Tipton began to get jobs and played at a number of venues, even becoming the leader of a band, gathering enough fame to keep his pocket lined but never so much that his personal life was overly scrutinized.

As such, his personal life was surprisingly quiet for a musician. He was well-liked by his friends and upon later review was very strategic in the people he surrounded himself with. He often chose to maintain relationships with people who were more self-focused, leaving him with the space to keep the nature of his genitals a secret. In his sexual encounters with women, he was able to keep the bandage on and explain his lack of a penis by telling his partner he had been in a car accident when he was younger, and the rest was managed by keeping the lights off.

While five women used the name Mrs. Tipton while in a relationship with him, and a couple of relationships he found himself in counted as common law, he never sent in the paperwork for an official marriage so there was never any major scrutiny in that regard. Later in his life, he met Kitty Oakes, a sex worker at the time, known as the “Irish Venus”. The two quickly settled down. They adopted three boys, William, Scott, and John, all of whom loved their father dearly. Only ten years after their relationship began, Tipton was forced to retire from music due to his arthritis.

While the relationship between Tipton and Kitty lasted for some time, it eventually dissolved, in part because Kitty had become physically abusive with their children. Tipton moved into a trailer park where he worked as a talent agent, and his sons moved back in with him after running away from home earlier to get away from Kitty. For a while, they lived like that, in poverty, with Tipton refusing to go to a doctor’s despite his growing pain and ever-present shortness of breath.

In 1989 at the age of 74, Billy Tipton died. Shortly after his death, it was revealed that he had genitalia that did not correspond to what people expected a cisgender man to have. Though Kitty tried to keep this fact from the press the press did find out and it became a national story, and Tipton’s carefully maintained privacy ended shortly after his life.

To say Tipton was transgender seems easy, but it quickly becomes more complicated. While in his later life the evidence is clear, within his early life the evidence is almost non-existent. It must be remembered that he did begin dressing as a man to pursue a career in music, which is a clear indication that this may have been more of a means to an end. But in counter to that, he also continued in his transition long after his career in music was over. Another thing to be noted is that during his time on stage, he would dress up in female clothing. In the end, all of these pieces of information are by no means conclusive one way or the other, and that seems to be the case for most reasons why people consider him to be a woman who dressed as a man to pursue a dream. While there is evidence to support that claim, none of it is conclusive.

On the other hand, Tipton spending all of his time as a man seems like a pretty convincing point. No matter how close his relationship with someone, he never revealed that he was assigned female at birth. The only people who knew this were those who knew him before he transitioned. It seems prudent now to note that while the question of his gender may be up in the air, there is no doubt of his attraction, as he dated and maintained long-term relationships with women even before he transitioned, so his identity as a man was not maintained to keep having relationships with women. From the point of his transition on, he dated heterosexual women, and many of them were shocked to find out that he was not, in fact, a cisgender man.

Though it is unquestionable that he was queer, there are many things left unanswered, and that is something that has to be accepted in the study of queer history. Not everything is clear and obvious. In fact, most things aren't. Historical figures are complex, messy, and nearly impossible to pin down because they are human. And when looking at Tipton’s life it is clear to see that his path did not follow exactly what the mainstream transgender narrative dictates, but to be fair at that point there wasn’t a clear mainstream transgender narrative. The mainstream transgender narrative as it exists today is not entirely accurate to even the time it serves, so it seems like a lot to ask for other time periods to correspond to it. It is entirely possible that setting these expectations of how Billy Tipton should have lived to be deserving of the title transgender is in itself completely unfair and slightly ridiculous. So even the pathway to finding the answer to the question of Tipton’s gender is as complex as the answer itself.

In the end, Billy Tipton, who was full of contradictions and left the world with so many unanswered questions, left one answer startlingly clear. If the people around him knew he was queer, would they have still loved him? His son Scott Tipton had an answer for that.

“I think he probably never told us because he was afraid we might have rejected him. I could have accepted it. He did a helluva good job with us. That’s what mattered. He was my dad.”

[Disclaimer: some of the sources may contain triggering material.]

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