Anyone who dabbles in cross-dressing knows how much fun it is to explore a different side of yourself. So it should come as no surprise that some of cinema’s most feel-good comedies and musicals revolve around characters who play with gender.
Why not spice up your movie night with a cross-dressing classic? Some of our top 10 films have aged better than others, but they each hold an important place in cinematic history.
1. The Rocky Horror Picture Show (1975)
For many, a first viewing of The Rocky Horror Picture Show acted as a gateway into the world of cross-dressing. It’s hard to think of another film that makes genderplay look as fun and accessible as this. Who wouldn’t want to lace up a corset and step into a pair of high heels after watching Tim Curry strut around to “Sweet Transvestite”?
You don’t need to understand the absurd plot (a heteronormative couple find themselves trapped in the mansion of transvestite scientist Dr. Frank-N-Furter, FYI) to appreciate the film’s distinctively camp visuals and glorious musical numbers.
2. Mulan (1998)
When China is overrun by invaders, men across the country are summoned to join the military. In order to spare her father from serving, Mulan disguises herself as a man and goes in his place.
Of all the cross-dressing protagonists mentioned on this list, Mulan is arguably the strongest – physically and emotionally. She has an excellent motivation for becoming a Drag King, and the first transformation sequence is epic in itself.
3. Some Like It Hot (1959)
Two musicians – Tony Curtis and Jack Lemmon – witness a Mafia murder and seek safety from the mob in the most fabulous way possible: cross-dressing! The bewigged duo hop on a train to Florida, joined by Marylin Monroe and her all-female jazz band.
Some Like It Hot was revolutionary for its time, using screwball comedy to explore themes of gender norms and misogyny. Throw in a slew of classic Monroe moments (think “I Wanna Be Loved By You”), and you’ve got one of the finest comedies ever made.
4. The Birdcage (1996)
Robin Williams stars as Armand, a gay drag club owner who is in a committed relationship with his club’s main attraction, Albert AKA Starina (Nathan Lane). When the time comes to meet his son’s conservative future in-laws, Armand pretends to be straight and Albert masquerades as his wife. Campy hijinx ensues.Mike Nichols’s remake of the 1978 French farce La Cage aux Folles is sharp, playful and unabashedly queer, at least for a mainstream American comedy in the 90s.
A talented but struggling actor (Dustin Hoffman) reinvents himself as an actress and bags a role in a soap opera. While this new persona is a hit with audiences, things get complicated when he falls in love with his co-star (Jessica Lange).If you enjoy showbiz satire, Tootsie is a must-see. The jokes come thick and fast, but despite its farcical premise, the film treats its characters with respect and compassion, which is probably why it has aged so well. Plus, there’s something about Dustin Hoffman in that red sequinned dress that is positively captivating.
7. The Adventures of Priscilla, Queen of the Desert (1994)
Two drag queens and a transgender woman travel across the Australian Outback in a tour bus to stage a show in a rural town. Along the way, they perform dazzling song-and-dance numbers, encounter seething homophobes and – maybe, just maybe – open a few minds to the art of drag.
There is still much to love about this groundbreaking LGBTQ+ film. The jokes are infectious, the characters are rich and layered, and the Oscar-winning costume design lends itself to breathtaking imagery that imprints itself on the mind.
8. To Wong Foo, Thanks for Everything, Julie Newmar (1995)
This is truly America’s answer to Priscilla The Adventures of Priscilla, Queen of the Desert – from its “drag queens on the road” premise, right down to its lengthy, extravagant title.
To Wong Foo... struggles to match the emotional depth of its Australian counterpart, but it’s still a lot of fun. Patrick Swayze and Wesley Snipes give career-best performances, while the original Supermodel of the World, RuPaul, cameos in her iconic Confederate Flag dress.
9. Kinky Boots (2005)
The Full Monty with drag queens. That’s all you need to know about this tale of a failing Northampton shoe factory that starts producing erotic footwear at the insistence of transvestite cabaret singer Lola (Chiwetel Ejiofor).
Light-hearted fun with Ejiofor stealing every scene he’s in. The sex is in the heel, indeed.
10. Mrs. Doubtfire (1993)
Following a bitter divorce from his wife, Daniel (Robin Williams) impersonates a female housekeeper in order to interact with his children – with the help of a titanic brazier, a dodgy British-Irish accent and some Oscar-winning makeup.
Yes, Mrs. Doubtfire’s plot is a bit creepy on paper, and the film would most likely not be made today. But as the cross-dressing protagonist, Robin Williams brings exceptional comedic timing and a sense of tenderness that is crucial to Mrs. Doubtfire's enduring popularity.