Top Five Historical Costume Movies About Cross-Dressing

One of my very favorite TV shows starts a new season on Sunday: RuPaul’s Drag Race! So drag queens and cross-dressing are on my mind. It’s not a new phenomenon, of course, either in history or in theater. Sometimes, it was meant to be serious — the character was supposed to be the gender they were cross-dressing as — and sometimes it was played as a joke. Either way, it’s always a bit transgressive and adds tension to the story.

So let’s take a look at some fabulous and fierce cross-dressing in historical costume movies, shall we?

Twelfth Night or What You Will (1996)

I could fill this whole top five with Shakespeare screen adaptations since cross-dressing is a well-used trope in the Bard’s plays. Instead, I just picked one I liked the crossplay look of best. This one works because not only does Imogene Stubbs make a relatively believable boy in drag, she also ends up with a passable similarity as Cesario to Stephen Mackintosh as Sebastian, so they work as twins.

Some Like It Hot (1959)

It would be impossible to make a list like this without including Some Like It Hot. It’s a justifiable classic, and the humor still holds up. The costuming on Tony Curtis and Jack Lemmon is surprisingly good — no, they aren’t good-looking women, but they are wearing historically accurate 1920s outfits (which is a lot more than you can say about Marilyn Monroe!).

Stage Beauty (2004)

I had a hard time finding historical costume movies that featured men dressing as women (so if you know of more, please tell me in the comments!). This is one of the few, and Billy Crudup does a nice job as one of the last men on the English stage who played women’s roles. The movie isn’t perfect, but it’s well costumed, and I found the topic fascinating. Crudup looks quite good in 17th-century female drag — he’s not totally passing as a woman, and he’s no goddess like RuPaul, but it gives you an idea of how the Restoration theater might have looked.

Tipping the Velvet (2002)

The main character, Nan, spends a lot of time in drag, including as a Victorian rent boy. In some of the scenes, she’s more hot-girl-in-boy-clothes but other times, she’s trying to pass and it works. Having read the book, I find that this adaption is more of a saucy romp than it needs to be (meaning, a little shallow), but it’s not bad by any means.

Victor/Victoria (1982)

We all remember Julie Andrews’ debonair turn as a woman who impersonates a man acting as a female impersonator in this 1920s flick. She looked awfully swanky in both a tux and in the sparkly “le jazz hot” cabaret number (when she removed the “female” wig to reveal her “male” status). But let’s not forget the hilarious finale where Robert Preston impersonates HER in female drag. It’s very camp and intentionally played for laughs within the film.

Do you enjoy drag performances? What are your favorite historical costume movies about cross-dressing?