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. (more…)