There was a TV movie that came out in the 90s that I had on tape and still have today, my original recording, it was called "Mr Headmistress." It was on ABC I think, I remember an intro with someone from Disney talking abotu the tradition of men in drag. Harlan Williams plays this ex-con scam artist who impersonates a woman while running away from mobsters he owes money to, only to find out his victim is the new headmistress for a failing private girl's academy. It was cute, and not just because he sounded like a strange effeminate British parrot the whole time. I don't know whee anyone can find that now, though. I also saw a movie last year called "Sam" that was making the festival circuit about a lecherous player who gets turned into a woman, and I will give the movie credit, she doesn't change back. The lead actress was quite enjoyable, but the movie itself had a lot of issues. And I remember years ago, turn of the century, when I was toying with a gender bender idea in a SF story, I was going to have a character change from a guy into a girl, the "real" version, the boy, would be the actress in disguise and her voice would be modulated, so the girl version felt more natural. The actress I wanted? Amanda Bynes. So years later, "She's The Man?" Like someone read my mind. Anyway, regarding the topic... I think Shakespeare sort of set the standard for men-as-women, and I think it's because a) all the actors were men and didn't like wearing dresses on stage, and b) women are viewed as vexing and mysterious and complex, which they kind of are. Guys are straightforward, women are complicated, and a man assuming the role of a woman is a fun way of exploring that. When a man pretends to be a woman, at least in the movies, I think he has to act upwards, he has to affect changes, there's rules and extra clothing and accessories and so on, it feels additive. When a woman pretends to be a man, it feels subtractive, they have to slouch, to dress down, lower their voice, have baser thoughts, find crude jokes funny. Plus, there's something inherently funny and maybe empowering about a guy dressig up as a woman, see Channing Tatum's "Lip Sync Battle" song. Maybe it's about dropping the veneer and expectations of masculinity that's relieving and surprising. Women as men are... kind of sexy. I've heard the expression that "the ideal woman is man," that there are certain traits that men find attractive like height and so on that are typically thought of as masculine. I also remember a line from Wayne's World about women who dress as baseball players, it's sexy "because that which is feminine is underscored." I wonder if you can even get away with gender bender movies anymore. Androgyny is becoming a bit more mainstream (Tilda Swinton seems to be making a career of it), trans people are becoming more visible in real life and in media, and while that's a long way from mainstream acceptance, it feels like gender is becoming more fluid of an idea, less binary. And gender bender movies are rooted in that binary concept. In the same way that blackface or yellowface isn't acceptable anymore (even if you're making a comment on it), gender bender movies might be facing the same fate.