What a week for drag this has been ...

First there was the debut trailer for 'Jack and Jill,' where Adam Sandler plays his own twin sister by throwing a wig on and talking like the Long Island version of the Herlihy Boy. Then there was the debut trailer for 'Sherlock Holmes: A Game of Shadows,' where Robert Downey Jr. disguises himself in a bonnet and hooker makeup for a bunch of scenes. Nothing against drag, and more power to RDJ for dolling himself up for our entertainment, but let's not kid ourselves -- Stevie Wonder wouldn't hesitate to call these guys out as a dudes with those get-ups on.

That got us thinking: Of all the men in Hollywood who have rocked a bra and lipstick for the camera, which of them still ended up looking like dudes? We'll save the Mrs. Doubtfires and Edna Turnblads for another day -- this one's for the guys who look like ladies who still just look like guys.

Hit the jump to see the rest of this fabulous bunch.
The Wayans Brothers in 'White Chicks'

Fellas, if you want to look like a woman, Jocelyn Wildenstein probably isn't the best source of inspiration to start with. If you walked up the Wilson sisters in real life, chances are you wouldn't be able to peg either one as Shawn or Marlon Wayans, but that doesn't mean you wouldn't think twice about putting a lighter to their faces just to see if they melt. No, they don't look like men, but since they barely look human, we think it's safe to say that they missed the mark.

Eddie Murphy in 'Norbit'

Somehow, some way, we managed to find what is far and away the most flattering picture of Eddie Murphy fat-suit-ing it up yet again as Rasputia in the Razzie favorite 'Norbit.' If there's anything positive we can say about the movie and Rasputia, it's that the makeup crew deserved the Oscar nomination they got. So in that regard, Murphy pulls it off, but by the same token, Rasputia is far too repulsive not to include here.

Kevin Kline in 'Wild Wild West'
(Clip starts at the 1:57 mark. And, sorry, the only clip we could find was in German.)

Good thing he had Will Smith to give him some pointers on the best thing to make fake breasts with, because Kevin Kline needed all the help he could get as Artemis Gordon in 'Wild Wild West.' At least he gets points for those high-class duds and what looks to be a terribly expensive wig, but who knew Kline had such a manly face? That guy with the ear horn must have had some seriously low standards going for him.

Tyler Perry as Madea

Eddie Murphy made it work in 'The Nutty Professor,' Martin Lawrence kinda got some mileage out of it in 'Big Momma's House,' but no many how many times he straps on those big fake boobs, zips up his muumuu, and starts saying "Halleluyer!" in a high-pitched voice behind grandma glasses, it's still Tyler Perry, Adam's apple and all. Maybe we're just tired of the schtick, but what can we say, Madea looks like a man.

Johnny Depp in 'Ed Wood'

At least his character made an effort in 'Before Night Falls,' but as much as we love Johnny Depp as Ed Wood, he and his mustache make for a pretty sad drag queen. He didn't make much of an effort outside of raiding his wife's closet, although that never bothered Ed any, and as long as he was happy, we were happy. Just a bit of a shame considering what a handsome devil Depp is -- he had so much potential to be one of the greats.

The 'Sorority Boys'

All right, maybe Barry Watson could get away with it, but as for Harland Williams and Michael Rosenbaum, there's no mistaking those two as fraternity boys. It wasn't exactly a Swiss watch of a plan trying to break into a sorority with this crew in tow, yet another horribly flawed scenario that no human being in their right mind would buy. Why? Because some boys just can't look like girls, like, for example, Harland Williams.

Willem Dafoe in 'The Boondock Saints'
(Clip is NSFW for F-bombs, assassinations and a dude getting his groin kicked in.)

For a guy who looks more like Denis Leary's creepy uncle than his hot sister and is arguably known for his distinctive mug as much as he is for his acting chops, we've never really understood how Willem Dafoe got stuck playing a woman, let alone a convincing one in 'The Boondock Saints.' Props to him for going all-out, rolling around spread eagle with his panties out and even sucking a dude's face like a vacuum, but how he ever managed to seduce that guy instead of getting pistol-whipped the second he showed his face is beyond us. Come on, it's Willem Dafoe, there's no way you can miss that.

Michael Jeter in 'The Fisher King'
Let's get one thing straight: Michael Jeter was awesome in 'The Fisher King' and had one of the best scenes of the whole darn movie. But then again, like we need to say it more than once, if you're looking to duck into the little girl's room to powder up, shaving your damn mustache should be priority number one. Hard not to look at the guy and think, That's Mr. Noodle in a dress, but even if he's not the most convincing member of the finer sex out there, he sure was quite the queen.

Oh yes, the history of men in drag on film is quite expansive and has given us as many lookers as it has failures, so now we want to hear from you: Which other actors should probably stick to shopping in the men's section?
Jack and Jill
PG 2011
Based on 26 critics

An ad man (Adam Sandler) dreads his passive-aggressive twin sister's annual Thanksgiving visit. Read More

Sherlock Holmes: A Game of Shadows
PG-13 2011
Based on 38 critics

The famous detective and his astute associate face their archenemy, evil genius Moriarty. Read More

categories Features