I haven’t quite made up my mind about cross-dressing.
(Boy, that came out wrong).
I’ve yet to make up my mind yet whether cross dressing is funny.
I know it’s supposed to be funny. Men dressing as women. Women dressing as men. Big yucks.
It’s been part of the comedian’s bag of tricks for hundreds of years. Shakespeare used the gag constantly, in part because men played all the women’s parts anyway. Opera is full of “trouser roles”, young male characters played by young women.
I don’t know, though. The guys of Monty Python’s Flying Circus would regularly dress up as frumpy middle-aged housewives (known as Pepperpots, for some reason).

Though the joke got old eventually, the Monty Python cast in drag was definitely funny.
(And, I have it on good authority at a six-foot-three-inch bearded guy playing a clarinet while wearing a blue evening gown is hysterical. Of course, I had a better figure back then.)
On the other hand, women dressed as men? Not so funny. Partially because there really isn’t a lot of male clothing that isn’t also worn by women. Generally, when women DO wear men’s clothes, the results are, well, kinda sexy.
Remember that scene in Bull Durham when Jenny Robinson wears a catcher’s gear and almost nothing else? (Sorry I can’t find a picture of it, but if you’ve seen the movie, it’s pretty unforgettable.)
A friend of mine who has studied these things claims that it’s all about status. When someone of a high status takes a lower status position, we think it’s funny. When someone of a low status position takes a higher status position, it isn’t funny. Since men still hold a higher status position in Western Civilization—she argues—seeing them dress as women is funny. When women dress as men, they’re taking a higher status position, and that just isn’t as funny.
My friend could be right.
On the other hand, Terry Jones dressed as a man or as a woman is pretty funny looking. Even when he’s wearing nothing at all.

On the other hand, Jenny Robinson is pretty good looking dressed as a woman or a man. Even, one would imagine, when she’s wearing nothing at all. (Although once again, sadly, photographic evidence would appear to be lacking).
What do you think? Is drag inherently funny? Or, like a lot of things, is it all in the context?