9.
But I'm a Cheerleader
(1999)
This may not teach you as much about queer history overall, but it is one of the few film depictions of so-called conversion therapy, albeit a humorous one. The story follows Megan, played by Natasha Lyonne, as she's thrown into the heterosexual world of True Directions, where she must learn the "root" of her abnormal behavior, then address it through performing super-feminine tasks. True Directions' plan goes awry when Megan falls in love with one of her bunkmates.
While the film is a humorous take on a serious subject, it's also a deft exploration of gender roles and how they have forced people of all gender identities and sexual orientations to hide who they really are.
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