There is nothing Hollywood likes more than a man dressed like a chick. Except maybe animals that talk. Or Jessica Alba. Same thing. (Hi-yo!) Put a guy with a five o’clock shadow in a skirt and stockings, mix in some zany misunderstandings and you have the potential for movie gold.
No, they don’t always get it right – sometimes you get Mrs. Doubtfire or Sorority Boys – but, other times, you get some real cinematic brilliance. In honour of this week’s release of Hairspray – a.k.a. John Travolta Is a Fat, Fat Lady – let’s look at some of the best crossdressing films.
To Wong Foo, Thanks for Everything, Julie Newmar (1995)
Premise: Drag queens Vida Boheme (Patrick Swayze) and Noxeema Jackson (Wesley Snipes) take drag princess Chi-Chi Rodriguez (John Leguizamo) with them on a cross-country drive. Their car breaks down in a small, sheltered town and amusing culture clashes ensue.
That’s a dude? John Leguizamo makes a pretty believable woman, but the real joy in this film comes from watching Patrick Roadhouse Swayze and Wesley Demolition Man Snipes sashay across the room in pantyhose and heels. It starts off being only slightly entertaining because they are very manly men in real life, but it becomes very entertaining because they end up making very graceful ladies, despite the Adam’s apples.
The Adventures of Priscilla, Queen of the Desert (1994)
Premise: Another drag queen road trip movie, but this time it’s in Australia and stars Hugo Weaving, Guy Pearce and Terrence Stamp, who bring far more depth and nuance to their roles than did To Wong Foo‘s Swayze, Snipes and Leguizamo.
That’s a dude? Priscilla features the most magnificent wardrobe of any movie ever, with a dress made out of flip-flops and feathered headdresses as far as the eye can see. Remember how awesome Weaving looked as an elf in Lord of the Rings? Here, it’s like he’s the most fabulous elf in the forest. Extra points for the dress made entirely out of American Express cards that Lizzy Gardiner wore to the Academy Awards when she won for Priscilla’s costume design.
Premise: Michael Dorsey (Dustin Hoffman) can’t get work as an actor, so he disguises himself as a (rather ugly) woman and gets hired to play a woman on a soap opera, where he begins to fall for his (actually) female co-star.
That’s a dude? OK, so Hoffman might not make an attractive woman, but he does play a pretty convincing woman. You wouldn’t want to date her, but you’d probably let her knit you a sweater. And has anyone noticed that the only people who can pull off sequined gowns are men in drag?
Some Like it Hot (1959)
Premise: On the run from the mob, Jerry and Joe (Jack Lemmon and Tony Curtis) dress up as women and join a women’s band, where Joe falls in love with a beautiful singer (Marilyn Monroe) and Jerry has to fend off the advances of Osgood, a love-struck millionaire.
That’s a dude? Lemmon and Curtis reportedly got all gussied up in their costumes and then went into women’s bathrooms to fix their makeup; when no women complained about their presence, they knew their costumes were perfect. The film is also the source of one of the best lines of all time: when Jerry reveals to wannabe suitor Osgood that he’s a man, Osgood nonchalantly replies, "Well, nobody’s perfect." Chortle! Guffaw!
The Rocky Horror Picture Show (1975)
Premise: After their car breaks down in the rain, lovebirds Janet (Susan Sarandon) and Brad (Barry Bostwick) end up in a bizarre castle populated by even more bizarre characters, specifically Dr. Frank-N-Furter, the sweet transvestite from Transexual, Transylvania. Add in some delightful musical numbers, and you have one splendid, tenacious cult movie.
That’s a dude? No movie makes people feel as rad about crossdressing like Rocky Horror does. While each character looks fantastic in a corset and garters, Tim Curry, who plays Dr. Frank-N-Furter, is the only one who looks truly comfortable and sexy in the getup.