1. Robin Williams as “Mrs. Euphegenia Doubtfire” in “Mrs. Doubtfire” (1993)
The most notable cross-dressing role on this list goes to none other than Robbin Williams. Williams not only won America’s heart as favorite cross-dressing male star of all time, but also the entire world’s.
2. Cillian Murphy as “Kitten” in “Breakfast On Pluto” (2005)
To prepare for the role of Kitten, Cillian Murphy studied women’s body language and for a few weeks met with a drag queen who instructed him while out clubbing with friends. Source
3. Chris Lilley as “Jen Okazaki” in “Angry Boys” (2011)
No one can play a manipulative Japanese mother quite like comedian Chris Lilley. Out of the 6 characters Lilley plays in the hilarious new show, Angry Boys, his character of Jen Okazaki definitely takes the cake.
4. Johnny Depp as “Bon Bon” in “Before Night Falls” (2000)
Johnny Depp is one actor who deserves two spots on this list since he has played drag in not one, but two films. In this film, Depp plays two roles — a sadistic prison warden and a transvestite.
5. Jude Law as “Minx” in “Rage” (2009)
Jude Law got in touch with his feminine side when he played the role of the transvestite supermodel, “Minx,” in the film, Rage.
6. John Travolta as “Edna Turnblad” in “Hairspray” (2007)
Travolta had big shoes to fill in the role of Edna Turnblad, made legendary by Divine. For this role, Travolta strapped on a fat suit and insisted on using realistically feminine cosmetics.
7. John Mitchell Cameron as “Hedwig” in “Hedwig And The Angry Inch” (2001)
John Cameron Mitchell wins the award for the sexiest film queen.
8. Tim Curry as “Dr. Frank-N-Furter” in “The Rocky Horror Picture Show” (1975)
Cross dressing for a role takes a lot of time, work and dedication. And in his role as Dr. Frank-N-Furter, Tim Curry managed to take this character and make it a cult legend.
9. Nathan Lane as “Williams’ Wife” in “The Birdcage”
Nathan Lane + Drag = one of the most hilarious dinner party scenes ever filmed.
10. Dustin Hoffman as “Dorothy Michaels” in “Tootsie” (1982)
Desperate times call for desperate measures. And when Dustin Hoffman’s character, Michael Dorsey is strapped for a job, he does the only thing left to do – cross-dresses for a gig. You’ve got to admit, Hoffman makes one convincing lady.