I’m on the far end with Bill from King of The Hill. As everybody knows, I love King of the Hill, I’ve watched it a million times and fall asleep to it every night. I firmly believe that Bill is an egg, or was at least written a few eggs. Normally wouldn’t declare a person an egg, but Bill is a fictional character so 🤷‍♀️ Bill has too many real emotional issues with gender in the show, and many aren’t immediately played for laughs.

His happiest moments are when he’s able to be comfortably “queer”, whether it was “pretending” to be queer to fit in with the other hairdressers at Hottyz, when he was put into dresses as a punishment as a kid and says how pretty the dresses were, or living with hippies at a national park. While part of this is fulfilled by Bill’s higher need for community, it’s because he needs a more queer community for him to truly feel comfortable as himself. Bill’s character is driven by gender dysphoria that he’s been alienated from over decades of living in a conservative south, with the alienation of the American conservatism being a huge theme among the other characters in the show.

Or the other times he’s shown to be happy is when he’s able to be an identityless do machine, giving up everything to the Harmonahollics, or being roped into an MLM.

So let’s go down the checklist. Bill is an extremely depressed man who is completely unable to take care of his own appearance, is super functional when he can separate from his own identity, references enjoying crossdressing as a kid even when it was used as a punishment, orbits queer groups he can’t fully be a part of because he doesn’t understand how he fits into it as a “man” whose attracted to women. That’s not even going into Lenore, whose full storyline with Bill is honestly just too depressing from the trans angle for me to want to go into.

Kurt Cobain | Kurt Cobain | Kurt Cobain

It’s not a specific character, but the Golden Compass series establishes that a person’s dæmon only has the same gender as their person in very rare cases.

I like the idea that they never share their person’s gender, actually. Just, by definition. Imagine that world.

transmasc revolver ocelot

There’s a girl from Diary of Our Days at the Breakwater, Makoto, who I have always headcanoned as being Glasses-kun from Non Non Biyori, post-transition. This started out as just a little joke between me and my mom about how these two characters looked kind of like gender-swapped versions of each other, but I kind of took a liking to the idea of them actually being the same person — at the very least because trans characters pog, and connecting two similar fictional works I like to each other is also pog. Keep in mind that I haven’t finished the NNB manga, never read the Breakwater manga, but have finished either anime (though I might not remember every detail from either).

As unlikely as my little “Makoto is Glasses-kun” headcanon is, it’s still fun. It’s still an exercise in imagination, to imagine how Non Non Biyori’s character who never spoke or smiled or really had any presence at all might’ve had some issues she was secretly working through in the background; and how the growing independence of high school life, where she was commuting to the city by herself and making friends outside her small town, might’ve facilitated her questioning and experimenting. How after her coming out to mother Yukiko went poorly, that she might’ve actually been disowned, and had to move in with some more progressive relatives, whose surname she took on for a “clean break” from the old life.

I guess another way to put it is that the most unlikely trans headcanons are also the most fun fanfiction prompts!

i started watching turn a based on one of your effortposts and even like 6-7 episodes in the trans energy loran gives off is enough to ignite a small star

i feel like this is as close as 1999 could get to an explicitly genderfluid/enby character and (having spoiled myself slightly) i can’t wait for what’s coming next