Jan 18 2010

15 Great Examples of Celebrities Cross Dressing

Published by at 10:00 am under Images,Oddly Enough

Celebrity 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

Celebrity Cross Dressing

Dennis Rodman

Celebrity Cross Dressing

Mariah Carey

Celebrity Cross Dressing

Seal

Celebrity Cross Dressing

The Hoff

Celebrity Cross Dressing

John Travolta

Celebrity Cross Dressing

Jude Law

Celebrity Cross Dressing

Brad Pitt

Celebrity Cross Dressing

Salma Hayek

Celebrity Cross Dressing

Gael Garcia Bernal

Celebrity Cross Dressing

Hilary Swank

Celebrity Cross Dressing

Eminem

Celebrity Cross Dressing

Katy Perry

Celebrity Cross Dressing

Philip Seymour Hoffman

Celebrity Cross Dressing

Dustin Hoffman

Celebrity Cross Dressing




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22 responses so far

22 Responses to “15 Great Examples of Celebrities Cross Dressing”

  1. SargentMacon 18 Jan 2010 at 11:04 am

    You forgot Ellen Degeneres.

  2. Nattybon 18 Jan 2010 at 11:21 am

    You mention one that’s missing and don’t acknowledge the other 15. Thanks.

  3. Berton 18 Jan 2010 at 11:36 am

    Probably could have found 15 pictures of Rodman alone! Thanks for not doing that though. No one wants to see that.

  4. [...] Other stuff you might like Other Columns by Ted Ursu – Standard Madness 120 Hot Girls Doing Keg Stands – COED Magazine Boba Fett’s Drink of Choice – Fork Party 29 Pictures of Babes In Star Wars Gear – Regretful Morning 15 Great Examples of Celebrities Cross Dressing – Unreality [...]

  5. Madisonon 18 Jan 2010 at 12:32 pm

    Very frightening.

    The Carey one may haunt my dreams.

  6. Nateon 18 Jan 2010 at 2:07 pm

    No Eddie Izzard? It’s hard to find pictures of him not cross-dressing.

  7. Limituson 18 Jan 2010 at 2:07 pm

    now i’m waiting for a tassi one ^^

  8. Paul Tassion 18 Jan 2010 at 2:11 pm

    ha. ha. ha.

    errrr, there was that one party in college…

  9. MacGyver1138on 18 Jan 2010 at 4:17 pm

    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!

  10. Lagrangeon 18 Jan 2010 at 4:21 pm

    Mrs. Doubtfire?

  11. bobon 18 Jan 2010 at 4:43 pm

    What about Willem Defoe in Boondock Saints

  12. VJESCIon 19 Jan 2010 at 12:37 am

    .christian slater: http://vjesci.tumblr.com/post/342021644

  13. Jokeron 19 Jan 2010 at 2:47 am

    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/

  14. [...] 15 great moments in celebrity cross dressing history <Unreality> [...]

  15. Jackie Martlingon 19 Jan 2010 at 11:13 pm

    where is that flaming Artie Lange butcher Howard Stern?

  16. [...] 15 Great Examples Of Celebrities Cross Dressing [...]

  17. [...] 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. [...]

  18. louon 01 Feb 2010 at 6:12 am

    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.

  19. Karla Jon 02 Apr 2010 at 4:00 am

    …and my nephew idolized Rodman…??

  20. Mon 17 Apr 2010 at 11:02 pm

    ohhh Oscar de la hoya’s gonna give some dark dark nightmares

  21. Mystykon 10 May 2010 at 8:43 pm

    The Hoff looks like he is about to break out singing Keep It Gay. :P

  22. ASchmalzon 28 Jan 2011 at 5:42 pm

    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

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