Believe it or not, the 2005 remake of King Kong contains crossdressing.
After Kong is brought to New York City, Jack Driscoll (played by Adrien Brody) attends a Broadway play, a comedy titled Cry Havoc. In the scene of the play that appears in this film, a male actor is crossdressed for some convoluted reason in order to win over the girl of his dreams.
(Yup! When I was dating and wanted to win over a girl, I always got crossdressed and drank tea with her.)
He wore a very pretty outfit, but he was not very pretty.
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