I used to have an obsession with films where the main character changes gender, for reasons which might be kinda obvious. There’s a huge and somewhat bizarre subgenre of genre-swapping comedies—this was a huge trope in 1990s-2000s cinema for some reason.
Back in the early 2000s, a local indie newspaper hired me to review every new gender-flipping comedy that was coming out, and there were a lot during that time. I sat through tons of these films, so you don’t have to.
So here’s an incomplete guide to comedy films where boys become girls, or vice versa, based strictly on my memories of watching them back in the day. (Not including drag comedies, because come on. Drag is rather different, and we’d be here all day. Also, “incomplete” means I’m probably leaving some out. Don’t @ me.)
Nobody asked for this, but you’re getting it anyway!
Some Like It Hot (1959)
This is possibly the pioneer of the “fish out of gender” comedy film genre.
I saw Some Like It Hot when I was a kid, and I barely remember it? I thought it was cute back in the day. I remember that Tony Curtis and Jack Lemmon sort of look like adorable 1950s housewives and Marilyn Monroe is just at peak sexpot, and there’s a lot of riding around on a train. The important thing: it’s ridic easy for these two cis guys to transform themselves into ladies, and nobody questions it—which is a common motif for these films!
Tootsie (1982)
Another movie I saw as a kid. I just remember Dustin Hoffman seeming very grouchy and put-upon and kind of bitter—except when he turns into Tootsie, he’s suddenly perky and cute? I mostly remember Jessica Lange (who is the Marilyn Monroe in this film) being utterly radiant and alive, and much more interesting to watch than Hoffman. Where Lemmon and Curtis crossdressed (I think) to hide from some gangsters, Hoffman crossdresses to get an acting job—which sets a bit of a pattern, as we’ll see. Dudes in these films often crossdress for personal gain, to obtain opportunities that are only available to women. (Which, if you think about it, is a pretty fucked up trope that probably contributed a lot to transphobia!)
Victor/Victoria (1982)
This was one of my favorite movies as a kid. In fact, I had a whole rant about how Victor/Victoria was WAY BETTER than Tootsie, which I’m sure people really enjoyed being subjected to. But you know what? I still think that. Where I remember Tootsie as a film about a scowling dude who becomes a bubbly chick for personal gain, Victor/Victoria lives in my mind as a truly playful movie that—and this is important—embraces queerness at a fundamental level. Julie Andrews is just so lovable as a torch singer who pretends to be a man pretending to be a woman, with the help of her gay best friend, and then seduces James Garner. Victor/Victoria is a movie about how subverting gender is fun and wholesome, and I believe it helped make me the woman I am today.
All of Me (1984)
I saw this as a kid. Lily Tomlin is sharing Steve Martin’s body? It’s mostly an excuse for Steve Martin to do a lot of physical comedy, which—gender-wackiness is usually best served by physical comedy, as we’ll soon discover.
Just One of the Guys (1985)
I know I’ve seen this film but it’s kind of a blur. It’s worth mentioning because this is one of those films where a girl becomes a guy to get away with something, rather than the other way around. Just like Tootsie, the protagonist is trying to get an opportunity that’s only available to the “opposite” gender, though at least sexism exists and is a real thing to be upset about.
Switch (1991)
Something happened to Blake Edwards between 1982 and 1991. This movie is fucking weird. I was pretty stoned when I watched it in my twenties, but basically a shitty dude dies, and he begs for another chance, but in order to get another chance he has to make a woman fall in love with him. But then the Devil makes him come back to life as a woman? I don’t know. I vaguely remember Ellen Barkin has a fun time playing a womanizer who’s suddenly in a female body? I don’t think this is a good movie, folks.
Ladybugs (1992)
My friend Heather sent me info about this movie that I’d never even heard of. Rodney Dangerfield is coaching a losing girls’ soccer team, so he… recruits his stepson to play disguised as a girl, so Rodney can finally “get some respect.” It sounds… truly atrocious.
Mrs. Doubtfire (1993)
I never saw this one, sorry. It looked really annoying from the trailers, and I wasn’t yet being paid to review gender-swap comedies. You’ve probably seen it, right? Tell me what you think, but please only in haiku form.
Just One of the Girls (1993)
I don’t think I’ve seen this one either? I’m guessing it’s a remake of Just One of the Guys, but gender-swapped? Corey Haim becomes a cheerleader. According to Wikipedia, the director of this film, Gabrielle Beaumont, was the first woman to direct a Star Trek episode.
Dr. Jekyll and Ms. Hyde (1995)
Okay. Now we’re starting to get to movies I actually remember. I saw this one in theaters, and it was well worth the ticket. Basically, it’s Jekyll and Hyde, except that instead of a brute, Jekyll’s serum turns him into a smoking hot babe. Who is evil, if memory serves. There’s some fun stuff at the end where Jekyll is trying to banish his alter ego, but keeps turning back into her at the worst moments—morphing was new, so there’s a lot of morphing, and this seems like a better than average use for that technology.
Sorority Boys (2002)
So this is the first one I was paid to review for the paper, and I still have the review I wrote back then. This is the synopsis I wrote at the time: “Three fraternity brothers, expelled from their sexist boys-club paradise, must take shelter in the ultra-feminist sorority across the street.” Basically, if you ever wanted to watch Smallville‘s Michael Rosenbaum transform into an astonishingly pretty girl, alongside two other stars of WB shows at the time, then this is for you. This is definitely one of those comedies where the protagonists learn a Valuable Lesson, in that they start out as sexist douches and learn to become (a bit) more feminist. There’s a dildo fight, and a feminists-vs-jerks football game, and I guess the physical comedy rescues an otherwise heavy-handed film. I’d watch it again.
Juwanna Mann (2002)
It’s basically Tootsie, if Dustin Hoffman was Black and played basketball. Jamal Jeffries loses his pro basketball career due to his obnoxious antics, so he decides to play women’s basketball in disguise, as Juwanna Mann. The past few years’ moral panic over trans women in sports has really changed the meaning of this film in a profound way, and it already wasn’t a very good film. As with Sorority Boys, Jamal learns a Valuable Lesson, but there’s no dildo fight in this one. According to the review someone paid me to write back in 2002, this movie goes through the motions, but comes to life in some slapsticky scenes. (See above, re: All of Me. Gender-swap comedies work best with a lot of slapstick.) There’s also a weirdly gonzo bit where a rapper named Puff Smokey Smoke hits on Juwanna Mann. (No, I’m not kidding. His name is Puff Smokey Smoke.)
The Hot Chick (2002)
Okay, I’m going to praise a Rob Schneider film. Basically, in this film, Rob Schneider and Rachel McAdams swap bodies due to (checks notes) a cursed pair of earrings. The thing I like about this film is that once Rachel McAdams is in Rob Schneider’s body, she’s still herself. She still identifies as a girl, and at no point does she say, “Well, now I’m in a dude’s body, so I guess I’m going to enjoy life as a dude.” Nope. If anything, if memory serves, this movie shows the protagonist working hard to still present as a woman while being in Schneider’s body. (Which is not shown to be as easy as Dustin Hoffman made it look.) It’s a weirdly pro-trans film, which makes it an outlier for the genre, at least based on my twenty-year-old memory.
White Chicks (2004)
This movie is… kind of a lot. But I honestly love it. Basically, Shawn Wayans and Marlon Wayans are FBI agents who are supposed to protect Brittany and Tiffany, two spoiled white socialites who are expected to be kidnapped. But the girls disappear, and these FBI agents can’t afford another failure on their records. So… they use cutting-edge technology to turn themselves into the spitting image of these two Paris Hilton-wannabes. Just to be clear: the Wayans brothers don’t just disguise themselves as random women, they disguise themselves as two specific women whom a lot of people know. And then they hang out constantly with Brittany and Tiffany’s best friends, who don’t notice anything different. This film goes places. I remember a scene where the Wayans brothers, in white-girl drag, coax the other white girls into saying the “N” word because there’s only white girls here. It gets very, very weird, and I still can’t believe I didn’t dream it. Honestly, after this film, the gender-swap comedy genre had reached its furthest limits, and I think they had to kind of stop making them. Except…
She’s the Man (2006)
Okay so here’s the other girl-disguised-as-a-boy comedy that I’ve seen off the top of my head. This one is explicitly a Twelfth Night retelling, except with boarding school and soccer and stuff. Amanda Bynes wants to play soccer but they cancel the girls’ soccer team, so what is there to do? She has to dude it up and impersonate her twin brother. I saw this one in the theater when it came out, and I remember it being a genuinely good movie—probably the best movie on this list besides Victor/Victoria. Amanda Bynes is utterly charming, and the whole thing is kind of joyfully silly.
It’s a Boy Girl Thing (2006)
I’m pretty sure I’ve seen this one but I remember literally nothing about it. Nerdy girl and jock boy switch bodies thanks to (checks notes) an Aztec statue, and have to live each other’s lives, Freaky Friday style. I feel like it kind of goes through the motions? The nerdy girl and the jock boy are opposites in every way, not just gender, so there are hijinks as they become kind of a nerdy boy and a jock girl? I think there’s some slut shaming in there. I remember going to this film, but remember literally nothing about it. According to Wikipedia, this film was produced by Elton John and distributed by Mel Gibson, so that’s… interesting.
Please tell me about any gender-reversal comedies I missed—but only in haiku form, please.
This article was originally published at Happy Dancing, Charlie Jane Anders’ newsletter, available on Buttondown.
