What are some (non-trans) movies where one or more characters cross-dressed to portray a character of the opposite sex?
Ladybugs is a comedy starring Rodney Dangerfield from the 1990s. Although Rodney does dress up in one scene, most of the movie features Johnathan Brandis as Martha (aka as Matthew) who pretends to be a girl on a girls soccer team that Rodney coaches. As usual, Dangerfield has numerous opportunities to poke fun when he unleashes one-liners aimed at various people.
Chrissy
Some Like It Hot and Tootsie. I don't know if you'd consider Birdcage a trans movie or not, although Albert is certainly a legitimate trans character.
Mrs Doubtfire
Sir Les Patterson Saves The World.!
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Bosom Buddies
Just One of the Girls, also titled as Anything for Love, is a 1990s movie starring Corey Haims.
Corey as Chris in the movie, is enamored with Mary. So Chris becomes a female student to avoid bullies and to make friends with Mary. It is a fun movie with a high school setting.
Chrissy
Shakespeare in Love