Dude Looks Like a Lady: The Best and Worst Attempts at Men Playing Women in Movies

February 28, 2012  |  

Men have been dressing up as women on camera for years. Check out Tony Curtis and Jack Lemmon in Some Like it Hot, or even watch Martin Lawrence do Sheneneh Jenkins on his classic show Martin. And while most attempts are funny, they rarely come close to the essence of a true lady. The men on this list, well, some of them did actually come close, while others looked and sounded nothing like women (maybe linebackers in a dress), but all of them were pretty entertaining if I must say so myself. Check ’em out!

Source: EW.com

Ving Rhames as “Holiday Heart”

I know Rhames was really trying to be taken seriously in this role with his long nails and long hair, but everytime I look at that man I can’t help but look at him as crazy Marcellus Wallace from Pulp Fiction, or even Melvin in Baby Boy, a role he played just a year after doing the TV movie, Holiday Heart. Playing a colorful and popular drag queen with a big heart, Rhames can be pretty touching in the movie, but something about his big ‘ol self in all that makeup just seems too unreal. Sorry, he’s just better off as a crazy man in his film roles. But I can’t lie, everytime this movie comes on, I have to watch…

Source: bert-trashboi.blogspot.com

All the Fellas From To Wong Foo, Thanks for Everything, Julie Newmar

OMG, I love this movie like no other! Probably because these guys did such a transformation to play these characters, but also because it’s just adorable. And now, everytime I see Wesley Snipes I can’t help but think of him in a shiny brown wig and in a form-fitting dress with a high voice. Not your ordinary road trip movie, when the three drag queens hit a small, dusty town, they rearrange everything about it in no time flat. I must say, John Leguizamo was probably the most realistic looking woman out of the three (Patrick Swayze and Snipes come off more bulky and buff, especially in the face), so I’ll say his attempt to be a woman was good, while Snipes and Swayze weren’t fooling anybody! However, they still did an awesome job.

Source: fearlessfathers.wordpress.com

Robin Williams as “Mrs. Doubtfire”

Williams wasn’t a drag queen in this film, but just a frustrated father trying to find a way to have more time with his children in any way possible. Somehow he thought dressing up and pretending to be their nanny was the best option. Nope! But it sure was the most entertaining option! With the right mask and makeup, you can’t deny that Williams definitely could fool you if he was walking down the street in the opposite direction. He definitely had that grandma look down pat. And I loved his little accent. Great movie, good attempt!

Source: articles.nydailynews.com

Tyler Perry as “Madea”

Whether he wanted it this way or not, these days, when you think of Tyler Perry, you probably are somewhat thinking about the controversial character Madea he plays in many of his films. You know, the gun-toting, slick talking lady with the breast that hang like elephant ears? I don’t think anyone would truly think he looks like a woman as Madea, but I’m sure we’ve all seen a woman (whether it was an aunt or a friend’s mother) who had the same play-n0-games mentality as her. She was funny on stage and in the first couple of movies, but at this point, Madea is kind of a no thanks for me.

Source: listal.com

Nathan Lane in The Birdcage

I love how adamant Nathan Lane’s character of Albert is about the fact that he’s a woman. He’s definitely dramatic enough to pass as a woman with his high shrill shrieks, his up and down emotions and the fact that he does everything with his pinky up. Add that to the fact the he was the queen bee drag star, Starina, at The Birdcage. But when he’s asked to play it straight for the sake of his lover’s son, he can’t and goes off the script by showing up as his mother instead. Crazy wig, high pitched voice and all. Lane can do no wrong to me, especially in this hilarious film, so I have to say that it was a good showing on his part!

Source: acidemic.com

Martin as “Big Momma”

Man, Big Momma’s House was like the movie series that went on way too long. They were going to milk Martin Lawrence in a dress for all it was worth. And while he was entertaining, it wasn’t the second coming of Sheneneh Jenkins or anything like that. But with enough dancing and a few hilarious lines, I could forget his random attempt at being an old woman since he still looked exactly like himself: “You know Big Momma could never forget that a**. I mean, asthma…” lol He wasn’t much worse than a Madea though…

Source: altfg.com

Chiwetel Ejiofor in “Kinky Boots”

Ha! Bet you never knew this beautiful brother was somewhere dressing up in short dresses and sashaying all over the place. But that’s exactly what Ejiofor did as Lola in the film Kinky Boots. In his thigh high boots he definitely was switching and looking uber-feminine, but that deep voice they couldn’t really conceal hid homeboy back a little. But with the right wig and makeup…yeah, I’ve definitely seen women who looked worse and he was GETTING IT. Just saying. Loved it!

Source: criminalminds.wikia.com

Tim Curry as “Dr. Frank D. Furter”

The self-proclaimed sweet Transvestite from Transsexual, Transylvania, Tim Curry’s Dr. Frank-N-Furter was one hell of a man and woman in The Rocky Horror Picture Show. In his platform shoes and lingerie, he could definitely both scare the living daylights out of you, as well as be pretty enchanting. With a body that’s not too big and bulky but more lean and light, Curry and his wide, mischievous smile, face full of makeup and hardcore switch definitely gave off a feminine air. Not bad…but I can’t look at him right anyway since he once played the object of my childhood nightmares: the clown in Stephen King’s It.

Source: Bossip

Miguel A. Nunez, Jr. in Juwanna Mann

Child please. In what seemed to be the basketball version of Tootsie, Juwanna Mann wasn’t as cute, but it definitely was silly as hell. I know some female basketball players can have a somewhat hard appearance from time to time, but with his tall self and that wig, Miguel A. Nunez, Jr. wasn’t fooling anybody. But just like Holiday Heart, this is another one of those ratchet movies I find myself glued to whenever it comes on. Country got you crazy!

Source: everydayhealth.com

Dustin Hoffman in Tootsie

You know times had to be really hard for Hoffman’s character of Michael Dorsey to feel the need to go the womanly route and dress up like an actress named Dorothy, but he did, and the Oscar-winning film Tootsie definitely created a new revolution in dudes looking like ladies on-screen. Clearly, he looked nothing like an actual woman, and that fake Southern accent still sounded like a guy doing his best impression of the girl from The Beverly Hillbillies (and her wardrobe was so blah), but it’s still an awesome movie and who doesn’t love Dustin Hoffman?

Source: montrealfilmjournal.com

Eddie Murphy as “Rasputia” in Norbit

I actually thought this was one of the worst movies I’ve ever seen, but whoever does Murphy’s makeup in these films sure whips his face right. And I’m not mad at the wigs they had on him because they were on point at time. The crazy Rasputia character was definitely the best part of the movie, what with her feminine mannerisms, too tiny clothes and obsessive personality. Sadly, I’ve seen women like this character in real life–maybe not at that size–so Murphy wasn’t too off…You know you’ve come across a few Rasputias yourself!

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  • Tamenolin

    Í can´t  believe you didn´t mention Cillian Murphy as “Kitten” in “Breakfast on Pluto”- definitely the most convincing man as a woman I´ve ever seen! 

  • TIMEWARP

    I love Rocky Horror Picture Show…almost sh*t my pants when I saw  Dr. Frank-N-Furter. He’s not believable as a woman but he was very feminine

  • Wonka

    What about Jaye Davidson from The Crying Game. Had me fooled all the way to the end…

  • MESHA_BANKS

    ALL OF THE ABOVE LMFAO

  • As you make your bed, so you must lie upon it

  • i think the point of them not pulling it off was for comedic purposes.

  • Pingback: Lady Luck Productions » The Best and Worst Attempts at Men Playing Women in Movies …()

  • The article was hilarious…but what’s with all the Madea hate?

  • IllyPhilly

    Juwanna Mann, Eddie Murphy, and Martin looked like terrible women. Kinky Boots was the 1st movie I saw that guy in. When I seen 4 brothers I couldn’t help, but laugh. Men love dressing like women. How many movies has there been where it was vice versa?

  • Vic

    And the emasculation continues!

  • Oletta

    Miguel Nunez (Juwanna Mann), could play as Whitney Houston…..he looks kinda like her from the Bodyguard movie…..but my preference would be Kelly Rowland!

    • Hughesw88

      Wow! I didnt even think about kelly playing the role
      of whitney…….PERFECT!

  • Abc

    Resputia looks like Aretha franklin

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