Everyone's got a guilty pleasure (or seven), and mine happens to be teen comedies where the main character has to cross-dress in order to get revenge, or prove themself, or spy on the other school. It's usually a little petty and silly, but I enjoy the ever loving crap out of them.
Just one little caveat: I only really like them when it's a girl dressing up as a guy. Not the other way around. The other way around? Not very funny to me.
Now, I can probably predict what most people's reaction to that is. "Well, you are kind of a buzz-killing feminist. Of course you like things with women in them more than things with men in them." And you have a point, straw heckler. I, as a be-breasted member of society myself, can more easily related to movies and television shows about women. This is not news.
But it's not that I can't relate to movies about men dressing up as women that's the problem. I relate to men in other movies just fine. I related very strongly to Charles Xavier in X-Men: First Class. There are women in that movie--good ones. I just happened to feel most connected to Charles.
No, it really comes down to one simple concept: power dynamics.
Women have less power than men. Less power in society, relationships, physically, and monetarily, on average. This doesn't go for every situation, but in a cross-dressing comedy, that's usually what it's about. The men are dressing as women, and come to see the innate lack of power they have in that state. They hate it. They want it to stop. They also take a moment to crap on female hygiene (shaving your legs is sooooo hard, am I right, ladies?), sexism in dating (wherein our burly hero is somehow found insanely attractive by all men), and the secret world that women supposedly inhabit (initiation rites are held in the bathroom, that's why we all go together).
I don't like it. And I hate, I hate, how after this whole experience is over, the man comes out of it a "better person". He's realized that he needs to treat women as people, and respect them.
Good job. You've met the minimum requirement for being a person.
Want a cookie?
There's a codification that's inherent in those movies, one that I talked about a little bit before, in my article on why I hated the movie Sorority Boys. Namely, it's that it takes the experiences of a man in very bad drag, and allows them to substitute for all women everywhere. He understands women now because he was one.
No. No he wasn't.
It takes a lifetime to build up the kind of experiences that most women can refer to casually, experiences of sexism and discrimination that we encounter every day, and are so brushed off by our culture that we somehow stop seeing them as being anything other than what we deserve. When I was 17, a boy tried to force his way into my dorm-room at college and when I shut the door on him, he yelled that I was a cocktease. That wasn't a big deal for me then, and it's not really now, because I've been a woman for a long time, and I kind of got used to it. In grad school I was told that I would have trouble selling the story I wanted to write, and that I should consider doing something else, because it was too "masculine", and that producers would expect me to have a male co-writer. My professor wasn't trying to be sexist, he thought he was helping me. Just normal stuff.
But cross-dressing comedies where a man dresses up as a woman are almost invariably about that man learning something about women by "being one". Being a woman is not wearing a dress. It's not shaving your legs and being weirded out by how "hard" it is to put on a bra. It's a hell of a lot more than a costume that men can put on and take off with ease.
Okay, now, why do I like movies where women dress up as men?
For pretty much the exact same reason. Power dynamics.
As I said before, women hold less power in our society, and while male to female cross-dressing comedies are usually about men learning a lesson, female to male cross-dressing comedies are about women getting a power they lack. I find them very, very interesting.
Motocrossed is a re-telling of Twelfth Night, where a teenage girl who wants to be a professional motocross racer takes her twin brother's place when he breaks his leg, against the wishes of her uptight family.
Mulan is about a woman who chooses to impersonate a soldier in order to save her father from dying in battle and reclaim the family honor.
She's the Man is another Twelfth Night, about a girl who sees her women's soccer team cut, and without the option to try out for the men's team, impersonates her twin brother at another school, so as to get on their team and prove a girl can win.
Just One of the Guys is about a high-school journalist who is told that as a pretty girl she should do something more with her life than write, so she transfers schools, dresses in drag, and writes about the experience to show everyone that she can, in fact, write.
There are other examples.
On the male to female side, though, we have:
Tootsie, where a sexist male actor loses out on a part, and decides to get one back by showing that he can be a better woman than any woman can, and is right.
Sorority Boys, where three frat brothers have to hide out by dressing in drag and joining the "ugly" sorority, along the way learning about sexism and why women are actually people. (I hate this movie.)
The Hot Chick, where--you know what, I can feel my brain cells dying from here.
And so on.
Even Some Like It Hot, an amazing movie and one of my favorites, falls into this trap, of letting the male characters get away with slapping on some heels and padded dresses, then assuming that they understand everything about the "female condition."
It's not that female to male comedies are miraculously better written, or even above the same level of cheap humor (jock straps smell bad!, guys are gross!, etc). The importance of those movies lies more with the kind of messages they send. While female to male cross-dressing movies do send a troubling message, that women can only gain power in the world by acting like and dressing up as men, they spend the whole movie addressing that issue. And at no point in the movies do they stop and say that because the woman is dressed like a man, she now completely understands men.
Because that would be silly.
[For more on this subject, and a few more reasons why cross-dressing comedies suck, read Chris Bucholz' Cracked article on the subject.]