Jan 18 2010
15 Great Examples of Celebrities Cross Dressing

Amidst the whole Kiefer Sutherland wearing a dress on Letterman because of a football bet he lost last week, our man Paul decided to email me a request. That request was to find more examples of celebrities doing the whole cross dressing thing.
Now I’m not sure what kind of kinky stuff you’re into Paul but I must admit your query was somewhat innovative. I decided to put on my detective hat to find some shining examples of this kind of behavior.
I managed to find 15 pictures that might just disturb the hell out of most of you.
Examples of celebrities cross dressing after the jump
Oscar De La Hoya

Dennis Rodman

Mariah Carey

Seal

The Hoff

John Travolta

Jude Law

Brad Pitt

Salma Hayek

Gael Garcia Bernal

Hilary Swank

Eminem

Katy Perry

Philip Seymour Hoffman

Dustin Hoffman

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You forgot Ellen Degeneres.
You mention one that’s missing and don’t acknowledge the other 15. Thanks.
Probably could have found 15 pictures of Rodman alone! Thanks for not doing that though. No one wants to see that.
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Very frightening.
The Carey one may haunt my dreams.
No Eddie Izzard? It’s hard to find pictures of him not cross-dressing.
now i’m waiting for a tassi one ^^
ha. ha. ha.
errrr, there was that one party in college…
Yikes. Some of these are quite disturbing.
I was thinking about To Wong Foo: Thanks for Everything the whole time. Swayze, you were awesome, but you made a hideous woman!
Mrs. Doubtfire?
What about Willem Defoe in Boondock Saints
.christian slater: http://vjesci.tumblr.com/post/342021644
What about the three amigos that played in “To wong foo, thanks for everything, julie newmar”
Snipes, Swayze RIP and Leguizamo…
Which i must say Leguizamo did a AMAZING job.
http://www.imdb.com/title/tt0114682/
[...] 15 great moments in celebrity cross dressing history <Unreality> [...]
where is that flaming Artie Lange butcher Howard Stern?
[...] 15 Great Examples Of Celebrities Cross Dressing [...]
[...] because of a football bet he lost last week you had to figure someone would put together a list of celebrities who cross dressed. Similar Posts:None Found You can follow any responses to this entry through the RSS 2.0 feed. [...]
keifer, love the name, that was the green shit i smoked 30 yrs ago brought into canada in gas tanks where all six of us passed out on the football field.
…and my nephew idolized Rodman…??
ohhh Oscar de la hoya’s gonna give some dark dark nightmares
The Hoff looks like he is about to break out singing Keep It Gay.
Totally missed an opportunity for three at once: To Wong Foo Thanks for Everything, Julie Newmar. Snipes, Swayze, and Leguizamo. Gotta love it!
And of course, Rocky Horror! Tim Curry rocks some pumps in that one