I started to say this in a comment on the Some Like It Hot discussion, but decided to make it a separate post so I could find it later, if the subject ever came up again.
I can't explain why so many people find men dressed as women to be so very funny. But I have figured out why I don't. It can lead to some situations that are amusing to me, like the scene in Some Like It Hot where Jack Lemmon as "Daphne" has to share a cozy late-night drink and chat with Marilyn Monroe and the girls in the upper berth of a railroad car while pretending he isn't half-crazed by Marilyn's proximity.
But the thing in itself: not very funny. The reason is that the clothes, makeup, hair, and general vibe of women are meant to be sexually attractive–not necessarily in a crude way, but at least in a general way. They are meant to enclose and heighten the appeal of the female body. And this is a very pleasant and powerful thing.
But the male body is not a sexual thing to me; just the opposite, in fact. So a male body with the accoutrements that signal "female" is jarring and unpleasant. It's like finding something like grass or twigs in your ice cream; somewhat more off-putting, really, because of the repelling effect of the like poles of two magnets.
Light On Dark Water 
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