10 Best: Movie Cross-Dressers

“Did you ever find Bugs Bunny attractive when he put on a dress and played the girl bunny?” asked the noted thinker Garth Algar in Wayne’s World. It’s a question that’s been posed by inquiring audiences for generations now, and not just in reference to lady-like lepus; many a young filmgoer’s notions of sexual identity and societal roles have been scrambled by the on-screen spectacle of gender swapping by men and women — and sometimes other species, too, as anyone who recalls seeing E.T. dressed as a woman for the first time will confusingly attest. Occasionally it’s depicted as a serious exploration of gender politics (you saw White Chicks, right?) but frequently it’s played for broad comedy, and more often than not it will involve somebody going undercover to hide from, or infiltrate some contrived high-concept plot. Used to be that cross-dressing acting was the norm, of course; at least in the old theatrical days, when men, albeit barely boys, would play the parts of women on stage because ladies weren’t permitted to act (the movie Stage Beauty documents it nicely). Now in the era of Big Momma’s House and Norbit it’s mostly a source of would-be guffaws, but it hasn’t always been the case — as these fine and fearless folks have shown.

10. Mrs. Doubtfire (Robin Williams), Mrs. Doubtfire (1993)

Never one to miss an opportunity for full-blown schtick, Robin Williams swapped his chest hair for a generous old maid caboose in this family comedy about an actor who disguises himself as an elderly housekeeper so that he can spy on his ex-wife and kids from within their home. Nothing creepy about that at all. Surprisingly, the manic comic makes for quite the convincing old lady, the disguise restraining his indulgences and allowing him to tug some heartstrings at the same time. Even when his breasts are on fire.

09. Norman Bates (Anthony Perkins), Psycho (1960)

A boy’s best friend is his mother; or, as is the case here, his mother’s wardrobe. Never leave your best dresses to your only son in your will, ladies, because in all likelihood he’ll become a sinister, cross-dressing motel caretaker with a penchant for shower homicide — or so it is with Anthony Perkins’ troubled young Norman Bates, anyway. We can’t help but think had the Bates Motel hosted a weekly drag night, this might have all been easily avoided.

08. Mitzi and Felicia (Hugo Weaving and Guy Pearce), The Adventures of Priscilla, Queen of the Desert (1994)

No list of movies’ cross-dressing clientele would be complete without Australia’s very own queens of camp, the loudly outrageous drag performers Mitzi and Felicia; played by the otherwise very mannish Hugo Weaving and Guy Pearce. Where to begin describing those Oscar-winning costumes, which run the rainbow gamut from intergalactic plumage to a gown of, well, thongs? Co-star Terrence Stamp summed it up nicely: “Just what this country needs: a cock in a frock on a rock.”

07. Ed Wood (Johnny Depp), Ed Wood (1994)

Infamous for directing the so-called worst movie of all time, Edward D. Wood, Jr also enjoyed shooting his stuff in drag; his film Glen Or Glenda even made a sincere, if notably inept, case for transgender tolerance. As played by Johnny Depp, a gentleman rather adept at cross-dressing (see also Before Night Falls), the goofy fauxtuer cuts quite the fetching figure, be it in supple angora sweaters or full ’50s costume. Make no mistake, though: as Wood remarks, “I’m all man. I even fought in WWII. Of course, I was wearing women’s undergarments under my uniform.”

06. Victoria Grant (Julie Andrews), Victor Victoria (1982)

1982 was a banner year for movie cross-dressers: with Tootsie came this Blake Edwards’ comedy, only this time the genders were switched… and then some. Julie Andrews plays an out-of-work female soprano who lands a gig by dressing up as male female impersonator — so that’s a chick playing a dude disguised as a chick, and they’re in the opera. No wonder poor old James Garner’s stage manager succumbs to some confusion when he falls for this peculiar creature.

05. Buffalo Bill (Ted Levine), The Silence of the Lambs (1991)

All the other cross-dressers on this list are lightweights next to Buffalo Bill. Sure, you could apply some makeup, squeeze into a dress and slip on a ravishing wig to pass yourself off as a lady, but why go half-way when you can actually wear a lady instead? Moral implications aside, Bill’s really something of an artist when it comes to sewing couture, meticulously piecing together a form-hugging body suit comprised of his dead victims — and, as we later grimly discover, their nether-hair, too.

04. Joe and Jerry (Tony Curtis and Jack Lemmon), Some Like It Hot (1959)

Nobody’s perfect, as the line goes, but Tony Curtis and Jack Lemmon come pretty close in Billy Wilder’s comedy masterpiece. That is if you can overcome the central conceit that the masculine stars, who play jazzmen on the run after witnessing a mob hit, would successfully pass themselves off as female musicians in a travelling show troupe. As might be expected, touring in drag with an all-female contingent leads to a few amusing complications, not the least of which results when one of your colleagues is none other than Marilyn Monroe.

03. Divine, Pink Flamingos (1972)

John Waters called him “My Elizabeth Taylor,” and while nobody’s about to mistake the grossly obese, punk-painted Divine for any kind of “normal” lady, let alone the great screen goddess, that’s kind of the point. With his shock eye make-up, absence of eyebrows and a skin-tight dress that lavished every fold of fat, Waters’ muse was intended as both a send-up and celebration of drag queen culture, while also serving up an effectively disgusting trailer-park wife parody. Divine’s later performances in Polyester and Hairspray offer further, if distinctly more benign, pleasures.


02. Dorothy Michaels (Dustin Hoffman), Tootsie (1982)

Dustin Hoffman and drag: it bodes for something awkward to say the least, yet one of the real joys of Tootsie is just how good the star is playing Dorothy Michaels, a middle-aged soap actress who becomes an overnight star despite the fact she’s really an unemployed actor. (In movies, the only recourse for an unemployed actor is to dress in drag, it seems.) Hoffman doesn’t play it for Mrs. Doubtfire-style broad comedy, either, mining the part for pathos — even if, in that outfit, you can’t quite shake the feeling that she may be a serial killer.

01. Dr. Frank-N-Furter (Tim Curry), The Rocky Horror Picture Show (1975)

Really, could there have been any question as to who else would top this parade? Tim Curry’s lipstick-and-leather lothario is cinema’s most flamboyant monstrosity, the sweet transvestite sprung from the fevered imagination of a camp B-movie horror if it’d been set in a seedy burlesque club. Note the man’s medical credentials, too: more than simply your average cross-dresser, Dr. Furter turns the art of gender-bending glam into a precise pansexual science; so much so that he’s able to seduce male and female alike on a perverse whim. What’s more, he can assume the identity of one’s lover as the case calls for it, which proves to be a most useful form of drag indeed.

Originally published in Empire, April 2011


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