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

February 28, 2012 ‐ By

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…

MadameNoire Video

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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! 


    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…



  • 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

    • Kimwantgold234111

      My friend just met a chocolate man on Blackwhitehub.COMit’s where for men and women looking for interracial’ship for a fabulous lifestyle
      It’s a nice place for black white sing’les, to interact with each other…no bounds or extremes in front of true love.