Boys will be boys. But what happens when boys will be girls? With Tyler Perry again buttoning up his onscreen alter ego’s housedress for this weekend’s Madea Goes to Jail, we strip bare 10 dudes who looked like ladies.
10. Johnny Depp, Ed Wood
Once declared the worst director of all time, Edward D. Wood Jr. wasn’t just the auteur behind the mind-numbingly bad Plan B From Outer Space. As Tim Burton’s affectionate biography reminds us, Wood also employed his “talents” to squash misconceptions about cross dressing with Glen or Glenda. For Wood (an unusually sweet and sunny Depp), putting on one of his beloved Angora sweaters made him feel “comfortable,” not sexually aroused. To this end, Depp parades around looking very much at ease wearing women’s clothing rather than trying to fool anyone that he’s a she. Wood would be proud.
KEEP READING: See No. 9 …
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9. John Cameron Mitchell, Hedwig and the Angry Inch
If Dr. Frank N. Furter procreated with Twisted Sister’s Dee Snider, their “girlyboy” of a child would grow up to be the transgendered rock singer Hedwig (John Cameron Mitchell). Blessed with a wardrobe of tight, tarty costumes and blond wigs obviously pilfered from the set of Charlie’s Angels, Mitchell gets his glam on as he riffs about “The Origin of Love.” Hedwig’s bright, garish makeup, though, hides sadness and shame stemming from a botched sex-change operation. But the pain Hedwig suffers because of the angry inch between her legs is what makes her songs of love and lament so intoxicating.
KEEP READING: See No. 8 …
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8. Tim Curry, The Rocky Horror Picture Show
If anyone’s going to make a man out of you, it’s that sweet transvestite from transsexual Transylvania. Or, at the very least, Dr. Frank N. Furter will get you to jump to the left, step to the right and then do “The Time Warp” — in the name of science, of course. Tarted up in black, from his fright wig to his bustier, panties and stockings, Curry doesn’t try to pass himself off as a lady. He’s a silver-tongued, gender-bending hedonist who happily practices what he preaches. No wonder Janet and Brad fall under the spell of his pelvic thrust.
KEEP READING: See No. 7 …
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7. Tyler Perry, Diary of a Mad Black Woman, Madea’s Family Reunion, Meet the Browns and Madea Goes to Jail
As mouthy Mabel “Madea” Simmons, Perry doesn’t care whether he looks mature or motherly as the 73-year-old African American matriarch — she exists solely to dispense sage advice to troubled female family members and help Perry spread the word of God. Thankfully, she’s not much of a role model – she’s even tossed in jail in her latest romp, for goodness sake.
KEEP READING: See No. 6 …
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6. Divine, Hairspray (1988), John Travolta, Hairspray (2007)
Two Edna Turnblads, two separate but equal reactions. Hairspray didn’t just prove John Waters could downplay his gross-out antics for family audiences but that iconic drag queen Divine could make us laugh as a loving suburban wife and mother without resorting to feasting on dog poop. Not that we could ever confuse Divine for your average Baltimore homemaker. Or, for that matter, Travolta in the musical remake, all plastered in unconvincing prosthetic makeup. But he’s partying like it’s 1977, and that’s fine by us.
KEEP READING: See No. 5 …
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5. Wesley Snipes, Patrick Swayze and John Leguizamo, To Wong Foo, Thanks for Everything, Julie Newmar
“I know there are drag queens in this town!” bellows Chris Penn’s pissed-off sheriff. They’re not difficult to spot: They’re the three gym rats who look like they should be competing in the Super Bowl, not the Drag Queen of the Year contest. Snipes, Swayze and Leguizamo — hiding from Penn after he tried to rape Swayze — boast more muscles than makeup. The best of the bunch: Swayze, who conceals his dancer’s body in elegant outfits that the Golden Girls would kill to wear.
KEEP READING: See No. 4 …
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4. Robin Williams, Mrs. Doubtfire
Imagine you’re a divorced, unemployed actor desperate to see your kids. What would you do? Probably get a steady job and behave yourself so you can receive joint custody. Not Mr. Mork. He’s just so wacky that he has to pretend to be his oblivious ex-wife’s housekeeper. Shuffling around his onetime home in prosthetic make-up, a fat suit and a granny wig, he successfully hoodwinks everyone by looking and sounding like Mary Poppins a year away from retiring to Boca Raton. Really, what’s the harm in violating your former spouse’s privacy, especially if it lands you a role on TV?
KEEP READING: See No. 3 …
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3. Tony Curtis and Jack Lemmon, Some Like it Hot
Even with all the booze her scatterbrained singer guzzles, Marilyn Monroe should easily deduce that new BFF Josephine and her millionaire suitor is one and the same (Curtis). The shapeless wig sitting on Josephine’s head like a dead cat tells all. OK, we’re never convinced that Curtis and Lemmon — as musicians running from the mob — could pass themselves off as members of an all-female band. So what? We’re too busy laughing to bother about how unladylike they look. As the love-struck Joe E. Brown declares after Lemmon reveals himself to be a man, “Nobody’s perfect!” Especially men unaccustomed to high heels.
KEEP READING: See No. 2 …
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Given Hoffman’s infamous reputation as an exacting method actor, it’s not hard to imagine the finicky thespian he portrays in Tootsie as a failed version of himself. You can mentally picture him going drag to land a soap-opera role in order to fund the production of a play he wants to stage. Tootsie works not just because a bespectacled Hoffman could pass for as an older, frumpier version of Jane Fonda in 9 to 5, but because the actions of his forthright actress speak volumes about the age-old issue of sexism in the workplace. He is woman, hear him roar.
KEEP READING: See No. 1 …
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1. Jaye Davidson, The Crying Game
Admit it, the last thing you expected when IRA gunman Stephen Rea tenderly disrobed Davidson was to come eye to eye with his manhood. We were all taken in. Yes, director Neil Jordan helped matters by casting a newcomer with a unisex name, but it’s Davidson who sold us on the idea that his transvestite hairdresser was all woman, all the time. With his exotic androgynous features, slender frame, and feminine wiles, Davidson looked better as a sexy young thing than he did as a shorthaired boy dressed in cricket whites. The result: one of cinema’s biggest and best twists.
