So here’s the latest facet of American culture that I’ve been pondering: cross-dressing. Specifically, cross-dressing as either a comedic or non-comedic element of movies and television. While watching a comedy sketch in which a man was playing a female character, Jim and I got to discussing the popularity of men playing women in comedy sketches and the relative unpopularity of women playing men.

Certainly this phenomenon can be partially attributed to the disproportionately high number of men in comedy groups – when you’re using your entire female cast in a sketch and still need another female character, or when your entire cast is male, the obvious solution is to have one of the male cast members dress up as a woman. But this can’t be the sole explanation, since there have been plenty of times on SNL when a man has played a female character and there was no shortage of available female cast members. Furthermore, when a man dresses up as a woman for a sketch, he is rarely simply playing a woman; he is mugging for the camera, playing a grotesque caricature.

The fact is, there is something intrinsically funny (at least to most Americans) about a man dressing up as a woman, but the same is not true of a woman who dresses up as a man. If this statement doesn’t seem intuitively correct to you, I think I can demonstrate it by cataloguing some of the more popular instances of cross-dressing in films.

Before I do that, I think it’s important to make a few distinctions between different “types” of cinematic cross-dressing. There are movies in which characters of one gender are played by actors of another — for example, Hairspray. Then there are movies in which a character of one gender has to pretend to be the other gender for some kind of instrumental reason — for example, Mrs. Doubtfire. Finally, there are movies that feature transgendered characters who actually want to be the other gender, transvestites who derive sexual pleasure from cross-dressing, and mentally ill characters who manifest their sociopathy by dressing like the other gender — e.g. Boys Don’t Cry, Psycho. (Note: I’m not equating transgenderism and transvestitism with psychosis here, I’m just putting them all in the same category of non-instrumental cross-dressing.) For the purposes of the current analysis, I am only looking at the middle category, within-the-movie instrumental cross-dressing, although I’ll probably talk a little about the first category sometime in the future.

Now, gathered from the Wikipedia page on Cross-dressing in film and television, here is a list of American movies that fit into the instrumental cross-dressing category, along with whether it is a male or female cross-dressing, and whether the movie is a comedy or a drama. (Note: I am ignoring Victor, Victoria because it’s way too confusing to categorize. Also, this is in no way a complete list; if you have anything to add, leave it in the comments.)

So, we’ve got 14 movies in which men dress as women, 13 of which are comedies (the lone drama is a James Bond film in which the villain apparently dresses as a woman to escape capture) — that’s about 93 percent. And we’ve got 9 movies in which women dress as men, 4 of which are comedies (if we count Shakespeare in Love, which I consider more of a romance than a comedy, but whatever). You know what, let’s be generous and include Motocrossed as a comedy as well, since it’s a Disney movie. So that would be 5 out of 9, or 56 percent. (Update: After I posted this article, a friend who has seen Thunderball informed me that it shouldn’t even be on the list, since the cross-dressing is transient and irrelevant. So let’s make that a whopping 100 percent of male cross-dressing movies that are comedies.)

I think it’s safe to say that this supports my argument that, in mainstream American culture, cross-dressing men are inherently funny in a way that cross-dressing women are not. In fact, the only argument this data supports even more persuasively is that cross-dressing men are essentially never not funny.

Rudy Giuliani dressed as a woman? High comedy. Nancy Pelosi dressed as a man? Confusing. An obvious explanation is that men have less leeway when it comes to gender conformity — woman are free to wear pants, and tomboyism is accepted if not encouraged — which means that male gender transgressions are viewed as far more taboo (and therefore far more hilarious). But I don’t think this fully explains the phenomenon, and I think that looking more closely at the motives behind cross-dressing in these films will show that.

Let’s discount the dramas for now and just look at the comedies. In the female cross-dressing comedies, the main character dresses up as a male so that she can participate in some activity off-limits to women: journalism (Just One of the Guys), acting (Shakespeare in Love), motocross (Motocrossed), soccer (She’s the Man), paid work (Twelfth Night). That is, there is something disadvantageous about their femaleness given their interests or needs, and so they need to pose as men in order to be allowed to participate. The comedy arises from the trouble they have posing as men (since they have no experience acting “tough” and manly) and the inevitable confusions that arise when they fall in love with men who are unaware of their buddies’ true identities.

In the male cross-dressing comedies, on the other hand, the main character dresses up as a woman because he is in trouble and has to hide his real identity in some way, and the only option he has is to dress up as a woman. Robin Williams’ character needs to disguise himself in order to see his kids because his custody was revoked; the only way he can become part of their lives again is to become a (female) nanny (in Mrs. Doubtfire). Three guys get kicked out of their frat, and in order to get back into the Greek system they have to pretend to be ugly girls and pledge the ugly girl sorority (Sorority Boys). Michael Dorsey has been blacklisted by directors due to his difficult nature, so he has to disguise himself as a woman in order to get acting parts (Tootsie). Two musicians who witness a murder have to get out of the town in which they live, and the only job they can find that will help them escape is an all-girl band (Some Like it Hot). (In the few male cross-dressing movies that don’t fit this mold, the male usually has to dress up like a specific person, not a generic female — it is the particular identity that is important, not just that he be disguised as a woman.) And the comedy arises from, yes, the characters’ difficulties acting “feminine” and the threat of accidental homosexuality, but also from the constant humiliation and degradation that the men-disguised-as-women experience at the hands of the men around them.

So for the women, dressing up as a man is a privilege; their newfound masculinity empowers them, enables them to do things they were unable to do as women, although it may temporarily prevent them from getting the guy. But for the men, dressing up as a woman is a punishment of sorts, a necessary evil that they must withstand if they are to accomplish the goal that has been jeopardized by a previous misdeed. After all, why would someone want to be a woman if he can be a man?

And that is my theory as to why male cross-dressing is funny while female cross-dressing isn’t necessarily: as the zeitgeist sees it, a man who dresses as a woman is essentially demeaning himself, and as the past popularity of minstrel shows and current popularity of comedians like Kathy Griffin and the Wayans brothers can attest, there is nothing America finds funnier than a person demeaning himself or herself.

This is all a half-baked theory, of course, and I hardly think this is the entire explanation; as I hope I’ve made clear, there’s never only one reason for any cultural phenomenon. For this particular phenomenon, there’s probably an entire web of intertwined factors, each exerting influence on the others. I’d be interested to hear alternative theories, so if you have something to contribute, post it in the comments below. Try to keep it constructive.