Once upon a time there was a bandleader named Billy Tipton. He played piano and saxamaphone and recorded albums and was generally a success at that.Not a big success, but a reasonable one. He played with Sinatra and Duke Ellington, which is pretty bad ass. As one is wont to assume about jazz musicians of that day, and musicians in general, he got a lot of ass and was married a bunch of times. One chick described him as the best lover she ever had.
But..... Billy had a secret. In his pants. And, um, his shirt.
Billy Tipton was born female, born into this world as Dorothy Tipton. See, back then, people weren't so hep to female jazz musicians. Her school wouldn't let her play in the school band on account on the whole having a vagina thing. Jerks. I can relate. I did not make it into my high school vocal jazz choir, apparently because my I didn't sing through my nose and my voice was too deep. You know, for jazz. The sort of music in which everyone sings in soprano, duh. Remind me, someday, to do my impression of the WonderBread Jazz Choir's interpretation of "I've Got Rhythm" for you. It's special.
I digress. After Dorothy graduated, she figured it would be easier to have a serious jazz career if she dressed as a man. So... she did. She binded her breasts, chopped off her hair, put on a suit, changed her name to Billy and set out on her way. At first she only dressed as a man for shows, but soon began living as one full time. Because Billy was so secretive about this aspect of his life, it's impossible to know if he was a transgendered person or if she was just a lesbian with a passion for jazz, doing it the only way he knew how. Sadly, it wasn't altogether uncommon in those days for women wanting more success in life to attempt to pass as men. I'm not going to speculate.
He began having affairs with women, telling them that he'd been in a terrible accident in which her genetalia had been maimed and her ribs broken (to explain the bandages keeping the boobs in). He even got married and had three kids (adopted), who all say he was an amazing father and a great boy scout troop leader.
Now, back in the golden era of wacky talk shows (I miss you, Jenny Jones. I truly do.), this was a pretty common trope. Usually more in the "Guess what, husband? I used to be a man!" vein of things. And like, with those, maybe you could sort of see how they might not catch on- because at the very least they'd had surgery or hormones or something. But Billie Tipton never had surgery or hormones. I don't mean to brag, but I am fairly sure that I would have been swift enough to catch on to something like that. I mean, what kind of accident would you be in where only your junk and chest area are affected? How can you be married to someone forever and never see them naked? Even if the lights are off, you'd think at one point you'd peak. You'd get curious. You would have to get curious. You would have to "accidentally" barge in on them in the bathroom or something.
Anyway, the story goes that no one found out about Billy's secret until the day he died, and that his ex-wife (he got divorced) was shocked and tried to have him cremated so no one would find out. But people did find out and it was a giant tabloid scandal, as such things are wont to be. The sad thing is that, part of the reason he died was that he refused to see a doctor due to fear of being outed.
It's sad, though. I mean, even when I was in elementary school it seemed like musical instruments were gendered. I don't remember too many girls playing saxaphone, or too many boys playing the flute. To boot, it's not like society is that much more accepting of transgendered persons these days either. I don't personally know how I could cope with that big of a secret without going totally insane, but I have a big mouth and am way too excited to tell people things that should technically be my deep dark secrets (they're more interesting than what I did at work that day). However Billy coped with that shit, it's pretty safe to say that dude had one bad ass life.