Male Actors Who Cross-dress for Success
Jeff Bridges in Thunderbolt and Lightfoot as John Doherty
John Leguizamo in To Wong Foo Thanks for Everything, Julie Newmar as Chi-Chi Rodriguez
Johnny Depp in Before Night Falls as Bon Bon / Lieutenant Victor
John Travolta in Hairspray as Edna Turnblad
Jude Law in Rage as Minx
Kurt Russell in Tango & Cash as Gabriel Cash
Martin Lawrence in Big Momma's House as Malcolm Turner / Big Momma
Nathan Lane in The Birdcage as Albert Goldman
Patrick Swayze in To Wong Foo Thanks for Everything, Julie Newmar as Vida Boheme
Robin Williams in Mrs. Doubtfire as Daniel Hillard / Mrs. Euphegenia Doubtfire
love this show! can't wait for the new season. 
always nice to see people care about their health 
Nice post! I was wondering, as I usually read most of the entries here is there any way I can ...
If you go to any city in the world there are guys who make a great living out of cross dressing!
That’s not Hugo Weaving. That’s Terence Stamp in the same movie and the same costume :-)
Bernardette… or Ralph! Haha… hilarious movie.
I love the picture of Tim Curry in Rocky Horror Picture Show. A favourite cross-dresser of mine is Eddie Izzard!♥
I’m missing Jamie Farr (Maxwell Q. Klinger from M*A*S*H) in that that list.
I missed Johnny Depp in “Ed Wood”.
And what about “Life of Brian”? Most of the women there are also played by men.