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Hollywood's Most Convincing Men in Drag

Brandon T. Jackson and Martin Lawrence in "Big Momma's: Like Father, Like Son"
Fox

Really, who doesn't love a man in drag?

From Tyler Perry and Robin Williams to those kooky kids at Harvard who put on the annual Hasty Pudding silliness, a dude in dainty duds is often the cause of a good laugh, an occasional heartfelt moment and even some family-oriented warm fuzzies.

With "Big Momma's: Like Father, Like Son" hitting theaters this week – and "Tyler Perry's Madea's Big Happy Family" arriving in April – we're counting down the most convincing male movie cross-dressers from the utterly ridiculous sight gags to the jaw-droppingly feminine.

Shawn & Marlon Wayans, "White Chicks" (2004)

The Wayans Brothers in "White Chicks"
Sony

Quite simply, "White Chicks" fails in every possible sense to depict Shawn and Marlon Wayans as women. Instead of trust-fund, valley-girl debutantes, they appear to have some sort disease causing albino skin and a hair condition. Some viewers even find them offensive. Sure, the film offers a few one-liners -- "You're so stupid you went to Dr. Dre for a boob job," anyone? – but we still wind up completely bewildered that anyone, even a fictional movie character, would ever believe the Wayans as white chicks.

Ted Levine, "The Silence of the Lambs" (1991)

Ted Levine in "The Silence of the Lambs"
MGM

When people think of this film, they immediately refer to the visionary direction from Jonathan Demme or the incredible performances by Jodie Foster and Anthony Hopkins. Rarely do they think of the guy Hopkins and Foster were chasing the whole time, the transsexual, maniacal serial killer Jame "Buffalo Bill" Gumb. While he was a skillful and proficient murderer, if Buffalo Bill ever actually wore one of his transgendered, skin-stitched outfits in public, he'd certainly scare off the observers. One of the greatest film villains ever? Sure. One of the best cross- dressers? Not a chance.

Nathan Lane, "The Birdcage" (1996)

Nathan Lane in "The Birdcage"
United Artists

"The Birdcage" is considered one of the funniest films of the 1990s, but, when it comes to Nathan Lane as a woman, it just doesn't fly. Of course, the humor comes from the actor's inability to convince anyone that he's a lady. With his lack of makeup, manly strut and decibel piercing laugh at his son’s engagement dinner, neither the characters or audience can buy him as a broad.

Arnold Schwarzenegger, "Junior" (1994)

Arnold Schwarzenegger in "Junior"
Universal

One word comes to mind when thinking of the female Arnold Schwarzenegger  in "Junior:" Ew. With very little exception ("Kindergarten Cop"), moviegoers tend to want to see Schwarzenegger in kicking villainous ass as a gun wielding, action machine. But watching him get injected with an experimental fertility serum in "Junior" to become a pregnant man is just creepy. The movie isn't without its funny moments -- especially when Schwarzenegger describes his sensitive nipples or his bouts with morning sickness. Still, stick to what you know Arnold:  dressing in drag really isn't your bag.

Martin Lawrence, "Big Momma's House" (2000)

Martin Lawrence in "Big Momma's House"
Fox

Funnyman Martin Lawrence brings drag into the millennium as FBI agent Malcolm Turner, who dons a serious fat suit as well as girly garb in order to track down a murderous bank robber. If this were a list of convincing fat suits, Momma may rank higher. And, while we love the character enough to see a third movie, no one's really buying that yellow-haired wig.

Tyler Perry, "Madea's Family Reunion" (2002)

Tyler Perry as Madea
Lions Gate Films

Tyler Perry is a well-built, finely-featured and easily recognizable figure, but it's his character Madea who really put him on the map. Still, why anyone would ever really believe that his burly-built, soulful grandma creation is dumbfounding. The facts can’t be ignored though: moviegoers simply loved seeing him slip into an older woman’s dressings, and his gregarious and hilarious turn as Madea cemented him as one of the most prominent and influential filmmakers and multi-media moguls in the world. While we never really believed that Madea was a female underneath those XXL gowns, that didn’t stop her from making us laugh our asses off while pushing Perry to superstardom.

Tim Curry, "The Rocky Horror Picture Show" (1975)

Tim Curry in "The Rocky Horror Picture Show"
Twentieth Century Fox

Curry may be one of the flashiest and most beloved cinematic cross-dressers ever as the fearful and menacing Dr. Frank-N-Furter in this cult classic. While the devilish doc wasn't trying to give the impression that his hairy-ape physique belonged to a woman, his powerful credo of individualism and love for the simple right for a man to proudly wear lingerie certainly endears him to us.

Tony Curtis & Jack Lemmon, "Some Like it Hot" (1959)

Tony Curtis and Jack Lemmon in "Some Like It Hot"
United Artists

Attempting to flee from Chicago mobsters, Tony Curtis and Jack Lemmon disguise themselves as two female performers in a traveling circus where they fall in love with the production's biggest star, Sugar (played with delightful quirkiness by Marilyn Monroe).  Classic film hilarity ensues, and, even though they didn't pass for the prettiest ladies, we become so enamored with Curtis and Lemmon's antics that we couldn't care less.

Wesley Snipes & Patrick Swayze, "To Wong Foo: Thanks for Everything, Julie Newmar" (1995)

Wesley Snipes and Patrick Swayze in Too Wong Foo Thanks for Everything, Julie Newmar"
Universal

Sure, Patrick Swayze could be a light on his feet – the "Dirty Dancing" star was a killer dancer, after all – but the guy was all man. Ditto for his co-star, Wesley Snipes, so, needless to say, when the pair of them traded fists and muscle-baring shirts for lipstick and sequins, fans couldn't help but raise their eyebrows. Despite their sculpted face and chiseled physiques, every once in awhile, we catch ourselves thinking, "Actually, Patrick Swayze is kinda pretty."

Hugo Weaving , "The Adventures of Priscilla, Queen of the Desert" (1994)

Hugo Weaving in "The Adventures of Priscilla, Queen of the Desert"
Gramercy Pictures

Hugo Weaving may be most recognizable for his roles as the sinister Agent Smith in the “Matrix” trilogy or the wise, silver-tongued elf leader Elron in “The Lord of the Rings" trilogy, but he made a drag-tastic splash in "The Adventures of Priscilla, Queen of the Desert." As Tick, who, along with two others, he dresses himself outrageous sequined outfits and performs classic '70s and '80s diva ballads. Weaving takes his newfound feminism to a whole new level when he declares, "you can make a fine living in a pair of heels."

Johnathan Brandis, "Ladybugs" (1992)

Johnathan Brandis in "Ladybugs"
Paramount

Rodney Dangerfield may not get any respect, but we have to give some props to Johnathan Brandis' transformation into Martha so he can play soccer on the girls' team. It's downright debatable whether or not he looks more lovely than the player, Kimberly, who inspires him to join the team in the first place. As all the girls accept Martha as one of their own, and, well, we do too.

Jaye Davidson, "The Crying Game" (1992)

Jaye Davison in "The Crying Game"
Miramax

Every once in a while, a man dressed as a woman is not the source of comedy, but, rather, the source of tragedy. This dark thriller represents the latter. Jaye Davidson plays Dil, who appears to be a pretty and eloquent woman. Only later (spoiler alert!) do we discover that she is really a he. Said twist shocks both the characters and viewers alike.

Divine, "Pink Flamingos" (1972)

Divine in "Pink Flamingos"
Fine Line Features

John Waters is a prime example of a director who isn't afraid to have his films deemed morally taboo, socially inappropriate or downright sexually blasphemous. So for those who enjoy a little Waters every now and again, "Pink Flamingos" isn't all that different from his usual fare… that is, until you realize that fat, loud-mouthed woman whom you’ve been watching through rambunctious cursing and crazy sexual depravity was actually a guy. The curvaceous Divine has us going the entire time.

Dustin Hoffman in "Tootsie" (1982)

Dustin Hoffman in "Tootsie"
Columbia

In what is considered to be one of the funniest movies of all time, Dustin Hoffman plays Michael Dorsey, an actor with a reputation for being difficult to work with and thus unhireable. In order to get back in the game, Dorsey dresses up as a lady to become soap opera star and overnight celebrity Dorothy Michaels. With a glossy orange perm, oversized bifocals and teal-green dress, Hoffman proves that if his career ever goes sour (not likely!), he can safely drag himself up for a few extra gigs.

Cillian Murphy, "Breakfast on Pluto" (2005)

Sony

Before he was having his mind incepted and  psycho-terrorizing Gotham City with hydro-hallucinogenics in a Scarecrow mask, Cillian Murphy was loving life in the streets of London as transsexual Patrick Braden in the wildly imaginative "Breakfast on Pluto." As he drapes on that powdered blonde wig and highlights his rosy red cheeks, Cillian elegantly shines with feminine sensuality.  Between his wistful voice and light features, well, we'll just say it – the guy sure is pretty.

Robin Williams, "Mrs. Doubtfire" (1993)

Robin Williams in "Mrs. Doubtfire"
Twentieth Century Fox

Robin Williams is like Michael Phelps of Tinseltown's men in drag: he just can't be beat. Williams thoroughly convinced his clueless family that Mrs. Doubtfire was an elderly, uptight yet warmhearted and loveable British nanny. In the process, viewers just as easily forget they're watching a divorced father go to extremes to spend time with his kids. Williams was so convincing that during the film's production, he reportedly strolled the streets of San Francisco in full makeup and costume without a single stranger recognizing him.

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