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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!

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…

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