30 Famous Actors Dressed in Drag

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image via PacificCoastNews.com

Earlier this week, TMZ shared pictures of Jared Leto dressed in drag on the set of his new film, The Dallas Buyer’s Club (as shown in the photo above) and while dressing in drag is always a gutsy move, Jared certainly isn’t the first to step into a pair of pumps for his art. Sometimes it goes well. Sometimes, well, not so much. Sometimes actors dress in drag for comedic effect and sometimes the intent is more serious. Regardless of the reason, seeing your favorite actor, or even an actor you recognize, dressed in drag is always a memorable experience. Here are 30 famous actors dressed in drag that are sure to make an impression – for better or for worse.

image source: IMDB.com

30: Willem Defoe in Boondock Saints (1999)

I have to admit something that always gets me in trouble with most of my “film buff” friends. I really didn’t love Boondock Saints. I didn’t think it was terrible but I don’t see why so many people seem to love it as much as they do. The one thing I truly loved about this movie can be seen in the photo above. I adore Willem Defoe and I believe he was the best thing about this movie. His performance was a bit over the top but that’s what made it so enjoyable. The movie itself isn’t one of my favorites but Willem Defoe dressed in drag to kill mobsters? Definitely one of my favorite entries on this list.

image source: Showtime Networks

29: Ving Rhames as Holiday Heart in Holiday Heart (2000)

I haven’t seen Holiday Heart so I have no idea whether this film was good, bad or somewhere in between but seeing tough guy Ving Rhames dressed in drag makes me think there was at least one thing that made it worth watching. I love Ving and I love that he had the guts to take on a role like this one. From the description I read of the film, Ving plays a drag queen (Holiday Heart) who takes in a struggling drug addict (played by the incredible Alfre Woodard) and helps raise her raise her young daughter. Billed as a drama, I have to believe this one is worth checking out for the cast alone.

image source: Lionsgate Films

28: Tyler Perry as Madea

Tyler Perry has built himself quite the empire with his Madea series but I must confess, I haven’t seen a single movie in the series. It’s not for a lack of interest – the movies look good – just a lack of opportunity. Perry makes one ugly woman but I think that’s part of the appeal. It’s funnier to watch a man dressed in drag if he doesn’t pull the look off well. In all honesty though, Madea is downright gorgeous compared to a few of the other characters on this list. You’ll see what I’m talking about when we get there.

image source: Metro-Goldwyn-Mayer Studios Inc.

27: Tony Curtis and Jack Lemmon in Some Like it Hot (1959)

I have seen Some Like it Hot roughly five billion times and I love it a little more each time I see it – easily one of my favorite movies of all time. I often forget though that Tony Curtis and Jack Lemmon out on the heels and lipstick for this one. It’s not really that they make convincing women. Just look at the photo above – clearly very masculine men in drag. It’s more that I forget the men in drag are freaking Tony Curtis and Jack Lemmon. Both complete legends and I think Some Like it Hot is a great example of why that is.

image source: IMDB.com

26: Tom Hanks and Peter Scolari in Bosom Buddies (1980)

Tom Hanks has said he feels like dressing in drag as often as he did on Bosom Buddies was entirely necessary. I’m inclined to agree but I wouldn’t have changed a thing. Tom Hanks in drag? Genius and aside from the very dated hair, I have to say he didn’t look terrible as a woman. He didn’t look good, per say, but he didn’t look terrible. It’s a little weird to think Hanks went on to win several Academy Awards. I bet he didn’t expect that back in the heels and dresses days. I wasn’t yet born when Bosom Buddies was on the air but I have to imagine I wouldn’t have been able to foresee the decorated career Hanks had in front of him based on that show either.

image source: 20th Century Fox

25: Tim Curry as Doctor Frank-N-Furter in The Rocky Horror Picture Show (1975)

The Rocky Horror Picture Show is without a doubt one of my all time favorite movies. Halloween wouldn’t be Halloween without the traditional living room viewing of this classic musical. A big part of the appeal? Tim Curry’s gutsy, fearless portrayal of Doctor Frank-N-Furter. Curry’s performance of Sweet Transvestite is probably my favorite musical number from any film or television series to date and I’m quite certain it will remain that way for all time.

photo by Samuel Goldwyn

24: Stephen Dorff as Candy Darling in I Shot Andy Warhol (1996)

I’ve always thought Stephen Dorff is an attractive guy. Little did I know he’d also be attractive as a woman. There are precious few examples of actors who look good in drag but I feel pretty comfortable saying most would agree with me when I say Stephen is one of those men. He does look better as a man but the female version of him isn’t half bad. It’s also worth mentioning, I Shot Andy Warhol was a brilliant movie that has been among my favorites since the first time I saw it right after its release in ’96.

photo by Joe Lederer for Revolution Studios

23: Shawn Wayans and Marlon Wayans in White Chicks (2004)

Nope. All wrong. Nearly everything about this movie was bad. No, bad isn’t strong enough. Terrible. Atrocious. Horrific. I don’t often watch movies I don’t think I’ll enjoy and as a result, I haven’t seen many movies I can honestly say I didn’t like. That is probably why I consider White Chicks the single worst movie I’ve ever seen in my life. It probably isn’t the worst movie ever made and I know a lot of people did enjoy it. I just don’t have a whole lot to compare it with in the “movies I don’t like” category and for that reason, it takes the cake. No, that’s not fair. I saw All About Steve because Sandra Bullock and Bradley Cooper are always awesome. They weren’t. Terrible movie – either worse or, at the very least, just as bad as White Chicks. No one dressed in drag for that one though – perhaps surprisingly.

image source: news.de

22: Robin Williams as Mrs. Euphegenia Doubtfire in Mrs. Doubtfire (1993)

I know a lot of people dislike Mrs. Doubtfire but I’m not one of those people. I thought this movie was fantastic. I laughed out loud more times than I can count and I enjoy it just as much now as I did the first time I saw it. Robin Williams made a very homely woman, yes, but he also made a hilarious one. I thought this movie was absolutely great from start to finish – a true classic and a great example of how to properly use a man dressed in drag for the greatest comedic effect.

image source: Universal City Studios Inc.

21: Patrick Swayze, Wesley Snipes and John Leguizamo To Wong Foo Thanks for Everything, Julie Newmar (1995)

This movie is another great example of men dressed in drag for comedy that works beautifully. Patrick Swayze, Wesley Snipes and John Leguizamo were fabulous in this film. I know it gets a whole lot of hate but I honestly can’t see why. I thought it succeeded when it was meant to be funny but handled more serious scenes well also. On top of that, I think John Leguizamo looked surprisingly hot as a lady. Not so sure about Swayze and Snipes but they still pulled it off well.

image source: Metro-Goldwyn-Mayer Studios Inc.

20: Nathan Lane in The Birdcage (1996)

For a long time, The Birdcage was one of my favorite comedic films. I thought it was funny, smart and a little over the top which pretty much made it ideal for me. Nathan Lane and Gene Hackman were a big part of the films’ appeal for me though. Their performances were excellent and I loved Nathan’s drag scenes. I thought they were done very well. It can be easy to go way too far over the top with such things but The Birdcage pulled it back just enough to make those scenes enjoyable and entertaining without going too far.

image source: rottentomatoes.com

19: Miguel Bose in High Heels (1991)

I must confess, I really wasn’t familiar with Miguel Boss at all until I was doing research for this article but I have to say, he makes a very good looking woman and apparently, he’s also a very good looking man. I’m going to have to look into this film, and this actor, a little bit more.

image source: Atlantic Streamline

18: Matt Leblanc in All the Queen’s Men (2001)

This was another research time surprise. I’m familiar with Matt Leblac, of course, but I had no idea he’s done drag. I wasn’t familiar with the movie so I decided to check it out and I have to say, it isn’t terrible. It’s not the greatest but it’s worth a watch. Matt pulls off drag very well. He looks better dressed as a man but he doesn’t make an exceptionally unattractive female so I’d say that’s a win for him, especially considering the man that takes the next spot on our list.

image source: Fox Home Video

17: Martin Lawrence in Big Momma’s House (2000)

Martin Lawrence. Yup. That is just a flat out frightening sight but I can’t deny the comedic value. I enjoyed the first Big Momma’s House movie but didn’t get around to checking out the rest. That’s not really a comment on the movie but rather a comment on my laughably short attention span. I think when it comes to men dressing in drag for comedy, Martin definitely got it right. He was funny, silly and over the top and that’s really what it takes to make a movie like this one work.

image source: TriStar Pictures

16: Liev Schreiber in Mixed Nuts (1994) and as Vilma in Taking Woodstock (2009)

I love Liev Schreiber as an actor. I think he’s incredibly versatile and talented. I also have never found him especially attractive. For that reason, I was a little surprised to see how good he looks in drag. He has very hard, masculine features but somehow, the drag makeup an wigs softened those features. He wasn’t exactly a knockout in drag, but he didn’t look all that bad and maybe even a bit more attractive as a woman.

image source: tumblr.com

15: Kurt Russell in Tango & Cash (1989)

I must’ve seen Tango & Cash ten times or more. I’m not a huge fan of the movie but I am a huge fan of traditionally tough guy actors dressed in drag and Kurt may have been one of my favorites to ever give it a shot. He’s a homely woman, sure, but not as bad as one may expect and far from the worst. The movie itself would probably get five out of ten stars from me but Kurt Russell in drag? Definitely ten out of ten.

image source: mediaanarchist.com

14: Jude Law as Minx in Rage (2009)

I watched Rage three times before I realized Jude Law was in it. I saw it twice more before I gave up trying to figure out what role he played and looked it up on IMDB. Imagine my surprise when I realized the dark haired beauty, Minx, I’d been admiring was actually Jude Law. Now, I love Jude. I’ve loved Jude since The Talented Mr. Ripley. I’ve always found him incredibly attractive but I can’t lie. I think he’s even more attractive in drag. He pulls it off better than most although I am a little bit jealous Jude makes a more attractive woman than I do.

image source: New Line Cinema

13: Johnny Depp in Ed Wood (1994) and as Bon Bon in Before Night Falls (2000)

I’m quite sure Johnny has dressed in drag for three movies but I couldn’t find confirmation that he dressed in drag for Don Juan as well so I decided to leave it off the list. Besides, I’m only using one picture (how could I not use the picture above?) so I suppose it honestly doesn’t matter all that much. Here’s the thing about Johnny Depp in drag. He doesn’t necessarily look more attractive but, aside from the facial hair, he doesn’t look bad either. It really should come as no surprise that Johnny has done drag twice (or three times) on film. He’s an eccentric actor who chooses diverse, interesting roles so it seems only natural that he’s put on lipstick a few times. He still looks far more normal than he did in Charlie and the Chocolate Factory or Alice in Wonderland.

image source: IMDB.com

12: John Travolta as Edna Turnblad in Hairspray (2007)

I’m sorry but that is a terribly frightening image. John Travolta just does not make a good looking woman although that may have been a result of the wig and the wardrobe. Looks aside, he definitely sold the role. His performance in Hairspray was fantastic. It was about as far over the top as a performance can be but that’s the whole point. This is an over the top movie and I think, when keeping that in mind, he did an exceptional job.

image source: theanticipator.blogspot.com

11: John Cameron Mitchell as Hedwig in Hedwig and the Angry Inch (2001)

John Cameron Mitchell is a genius. I have watched Hedwig and the Angry Inch far too many times to count. I checked it out for Michael Pitt (whom I adore) but it’s John’s performance as Hansel/Hedwig that keeps me coming back for more and more. John developed the character himself and not only stared in the film adaptation (it began as a stage show) but directed as well. He’s since had a hand in some of my favorite films including Rabbit Hole which is, without question, one of the best movies I’ve ever seen.

image source: collider.com

10: Jamie Foxx as Wanda Wayne in In Living Color (1991)

I honestly never thought the whole Wanda Wayne thing was all that funny. She was more annoying than she was funny but that doesn’t change the fact that she is one of Jamie Foxx’s most memorable characters. It’s easy to say Foxx makes one ugly female but I don’t think that’s necessarily true. Take away the duck lips, the crossed eyes and the facial hair and add a less dated wardrobe and Foxx’s Wanda may have been almost attractive. Well, maybe not but it’s fun to imagine all the same.

image source: mlive.com

09: Jamie Farr as Corporal Maxwell Q. Klinger in M*A*S*H (1972)

There was no way I could do this list without including Jamie Farr. As Klinger on M*A*S*H Farr was everything one can hope for in a man dressed in drag for the purpose of comedy. His outfits were always over the top and his personality even more so and that’s what made Klinger such an endearing character. Jamie Farr is most definitely missed as are television shows as compelling and entertaining as M*A*S*H.

image by Terry Richardson

08: James Franco in Candy Magazine (2011)

I wasn’t sure whether or not I should put James Franco in this list because his turn in drag wasn’t for a movie but was instead for a magazine spread but I decided it counts. I mainly decided that because it’s my list, I love Franco and I love these photos. Not only is James Franco dressed in drag in these photos but they were shot by my all time favorite photographer, Terry Richardson. Everything about this spread works. They’re dramatic, over the top and somehow – and I can’t possibly explain how – incredibly sexy. James Franco’s Candy magazine spread definitely deserves a place on this list.

image source: IMDB.com

07: Guy Pearce and Hugo Weaving in The Adventures of Priscilla, Queen of the Desert (1994)

There were actually many famous actors dressed in drag in this film, but I had to choose a picture to go with the caption and I could say no to this shot of Guy Pearce and Hugo Weaving. Guy doesn’t look half bad as a lady. Hugo … well, um, boy that guy can act, am I right?

image source: mediaanarchist.com

06: Gael Garcia Bernal as Angel in Bad Education (2004)

It’s almost a shame I decided to put this list in alphabetical order because it means following up this shot of a surprisingly lovely Gael Garcia Bernal dressed in drag with … well, you’ll see. I’ve only seen Bad Education once but don’t remember it all that well. I do, however, recall thinking that Gael looks pretty good in drag – masculine, but still good. He’s definitely hotter as a man (smoking hot, I’d say) but he’s no where near as bad as what we’re about to talk about.

image source: IMDB.com

05: Eddie Murphy as Mama and Grandma Klump in The Nutty Professor (1996) and as Rasputina in Norbit (2007)

Dear Heavens! My eyes! I can’t even deal with that wretched sight. I’ve scrolled down so I can type this without having to look at the photo but it isn’t helping. That image is burned on my brain and will haunt me as I sleep. Eddie Murphy isn’t the most traditionally attractive man in the world but dress him and drag and it’s all so much worse. I like Eddie Murphy. I liked The Nutty Professor movies and thought he did a great job in them. I have not seen Norbit, mainly to save myself the traumatic experience of seeing a whole movie featuring images like the one above.

image source: mediaanarchist.com

04: Dustin Hoffman as Dorothy Michaels in Tootsie (1982)

When one things of actors dressed in drag  for a movie role, Dustin Hoffman as Dorothy Michaels in Tootsie almost certainly comes to mind. There’s a good reason for that. He didn’t make the most attractive looking woman but he played the role perfectly all the same. It was a great performance in a great movie. Although Tootsie was released the year I was born, I’ve watched in time and time again because like everything good in life, it is absolutely ageless.

image source: mediaanarchist.com

03: Cillian Murphy as Patrick ‘Kitten’ Brayden in Breakfast on Pluto (2005)

Cillian Murphy is one of my favorite actors so when I heard about Breakfast on Pluto, I knew I had to see it. I wasn’t disappointed. Cillian gives Jude Law a run for his “looks hot in drag” money but beyond that, his performance as Kitten was absolutely flawless. I recognize the fact that this movie isn’t for everyone but it was definitely for me.

image source: imdb.com

02:  Barry Watson as Daisy in Sorority Boys (2002)

I always liked Barry Watson on 7th Heaven but when I heard about Sorority Boys I wasn’t exactly sold on the idea. In the film, Barry stars as a rowdy frat boy who is kicked out of his dorm along with his two friends (played by Harland Williams and Michael Rosenbaum). The three boys decide to dress in drag so they can live in “DOG House” which is, hilariously, where the “unattractive girls” are resigned to live. What can I even say about this movie? Well … Barry Watson looks pretty hot in drag. Beyond that, I’ll only say I used ‘hilariously’ in the most sarcastic possible way. This one was White Chicks bad, friends. It really was. I have to admit though, there were a few genuinely funny moments which puts it just ahead of the Wayans disaster.

image source: FlynetPictures.com

01: Adam Sandler as Jill Sadelstein in Jack and Jill (2011)

In the intro, I mentioned some actors have pulled off dressing in drag more than others and so far, we’ve talked about some of the people that didn’t do it so well. I’d have to say though that Adam Sandler is probably the best example of dressing in drag gone wrong. That isn’t a comment on how Adam looked in drag or even how he portrayed Jill Sadelstein. In the movie hadn’t been so atrociously terrible, I might have a different opinion. As it stands though, the movie was awful and Adam’s attempt at playing a woman will forever be linked with that.

This the cross dressing doesn’t go both ways? You’re wrong! Over the years, many actresses have dressed in drag for various film roles. Want to see them? Make sure you come back next week to see the list dedicated to actresses dressed in drag.

 

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2 Responses

  1. AnnaBeth

    03/29/2013, 02:10 pm

    I think that even though it isn’t a movie, David Tennant as “Davina” is great. He makes a strangely good woman and the sketch is great. I love this list it totally made my day.

    Reply
  2. Dave

    12/08/2013, 04:37 am

    I wanted to point out that the photo for item 21 is of Gael Garcia Bernal in an earlier section of the film “Bad Education”. You also have him for item 06. Good list though.

    Reply

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