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Date: 2025-04-25 08:16 pm (UTC)a.) MOVIES: OG Twelfth Night is one of my favorite plays (also As You Like It but it is frankly a weirder and less coherent play and so gets done a lot less); She's The Man, the 90s rom-com starring Amanda Bynes, is not deep but IMO genuinely quite charming. There's also a Bollywood remake of She's The Man (and, by extent, Twelfth Night) called Dil Bole Hadippa! which I have been meaning to watch and could make a fun compare/contrast, but I do not alas expect it to be very queer. However, for another weirder queerer rec, the movie Dororo (based on a manga by Osamu Tezuka that I have not read) features a plucky cross-dressing thief as sidekick to a tragic Frankenstein baby (he gets better) and ends with the thief shouting "I still won't become a woman, I will be a man forever!"
b.) YA NOVELS: obviously Alanna is the one everyone remembers but I'm gonna second
c.) MANGA: and for another entry into 'we put a cross-dressing girl into this famously all-male group,' Kaze Hikaru is 'what if there was secretly a girl in the Shinsengumi?' Another one that I like a lot is Basara, which is another along the lines of 'girl has to pretend to be her twin brother' except in this case her twin brother is the dead destined saviour of their people and so now she has to lead a rebellion, while pretending to be her twin. Neither of these are particularly gay as I remember them but they're both quite epic and fun; Kaze Hikaru does a good job dealing with the Mores and Culture of Samurai Life and Basara is just nonstop balls-to-the-wall chaos.
d.) TELEVISION: Coffee Prince is the classic modern cross-dressing kdrama (she gets accidentally hired as the love interest's fake boyfriend, for reasons) and does deal very explicitly with the fact that the hero has gone through a whole coming-out arc before he finds out that the girl he fell in love with is, in fact, a girl, and is not in act relieved to learn her gender but hugely upset about it because he already went through this character development and now she's taking it back?! On the sillier side, You're Beautiful is maybe the most nonsense drama I've ever seen, in which a NUN has to join a KPOP BOY BAND pretending to be her IDENTICAL TWIN BROTHER because he's healing from COSMETIC SURGERY GONE WRONG. Is it good? Well, no. But is it very funny? oh, yes.
I am sure I have more but I'll leave it here for now and come back as they occur to me!