Actors who were more interesting playing a person of the opposite sex.

[Baitball Blogger]

Top on my list is Amanda Bynes in "She's the man."

Second is Dustin Hoffman in Tootsie.

[HopeHoops]

1. Robin Williams in "Mr. Doubtfire"

[Baitball Blogger]

2. +1

[Honeycombe8]

6. Cute movie. But I never thought for a second that he looked like a woman...

in that movie. He portrayed what men think of as women, some sort of caricature. He looked odd, but not like a woman, to me. Like Dustin Hoffman in Tootsie. Also a cute movie. But I had to use my imagination to believe that all those people couldn't tell he was a guy after one look at Tootsie. He didn't look like a woman at all. He looked like a man with male hips, a male face, big hands, and a wig. But it was make believe and a comedy, so it was okay.

[Doc_Technical]

3. Linda Hunt

The Year of living Dangerously

http://www.imdb.com/title/tt0086617/

[progressoid]

13. +1

[gratuitous]

19. That's who first occurred to me

An overlooked gem, "The Year of Living Dangerously" was a very good film, exploring a lot of different themes and issues against the upheaval of a popular uprising against a benevolent despot who had turned ruthless dictator. Linda Hunt's Billy Kwan has to come to terms with his prior support of Sukarno in the face of what he has personally witnessed.

When the movie premiered, nobody knew that a woman was playing Kwan (this was released in the days before the internet), and when the closing credits ran, crowds were heard to gasp when Linda Hunt's name rolled by.

[undeterred]

4. Jaye Davidson

Dil in The Crying Game

[Honeycombe8]

7. He really looked like a woman in that movie. nt

[undeterred]

8. Never saw that surprise coming.

Movie is 20 years old this year.

[Lydia Leftcoast]

12. He still looked like a woman after the secret was revealed

Even with the short haircut and the sailor outfit.

[LynneSin]

23. I have a hilarious story about "The Crying Game"

I went with this guy I was seeing for years. I liked the guy alot but he could be a bit of a dickweed at times.

He almost starting drooling immediately over Dil when we saw 'The Crying Game'. Mind you neither of us knew what the big to-do was about the movie but I suspected something wasn't right about Dil whereas my date couldn't get enough of Dil.

Mind you I about pissed my pants laughing when they finally did the big reveal on Dil. My date claims 'he knew' and I was like 'BULLSHIT' - I was wipng the damn drool off your face during the movie.

[Honeycombe8]

5. I wouldn't say MORE interesting, but Vanessa Redgrave as tennis pro Richard Radley...

who becomes Renee Richards is at least as interesting as she is in all her movies, which is pretty darn interesting.

The movie was a made for TV movie called "Second Serve." It's a true story. I tell you, if you didn't know who she was, you'd think she's a man when she's playing Richard Radley in the first half. And she somehow LOOKS like a man dressing to be like a woman in the second half, rather than the real woman she is. How does she do it? I just don't know. She's a remarkable actress.

[SOteric]

9. Glenn Close, "Albert Nobbs"

[GoCubsGo]

10. Patrick Swayze, John Leguizamo and Wesley Snipes.

They were in "Too Wong Foo, Thanks for Everything. Julie Newmar". It's one of my favorite movies. They played drag queens, and while not technically the opposite sex, they spent the entire film dressed as women. And, disgustingly, they all look better in a dress than I do. I guess shouldn't be surprised at that. I swear that designers of women's clothing design them for prepubescent males. They certainly don't design them for a figure that has curves, at least not the kind of curves I have.

[AnneD]

29. One of my ...

all time fav's.....

I should look so good. I don't want to look like a drag queen, just a drag princess.

[KamaAina]

11. Tyler Perry as Madea

the only redeeming feature of his entire oeuvre.

[Baitball Blogger]

14. Madea! How could I have forgotten Madea!

[pink-o]

15. John Travolta as Edna Turnblatt

In Hairspray. I love the whole soundtrack, anyway!

[Tom_Foolery]

16. Tom Hanks and Peter Scolari in "Bosom Buddies". n/t

[Tabasco_Dave]

17. Tim Curry

[XemaSab]

18. Hillary Swank

In the Brandon Teena Story.

[RiffRandell]

22. Yes.

Plus she won the Oscar, well deserved. Such a sad story.

[BlueIris]

36. That's my pick, too.

Amazing work in that one.

[LeftinOH]

20. Divine as, well.. Divine.

He was way more interesting (and interesting looking) as a woman.

[Ineeda]

21. Dame Edna Everage

http://www.dame-edna.com/gallery.htm

Fabulous!

[Baitball Blogger]

28. I haven't heard from her in a while.

What is she up to these days?

[LynneSin]

24. I can't believe we've gone this far without Terrance Stamp, Guy Pearce and Hugo Weaving....

You have 3 guys that played some serious badasses in the movie (Weaving was Agent Smith in the Matrix Triology) and they played some of the most memorable women in the movies with "Pricilla Queen of the Desert"

[Baitball Blogger]

26. I was waiting for someone to bring them up.

Guy Pearce in that little bunny-like outfit was just AH-dorable.

[FloridaJudy]

25. Steve Martin in "All of Me"

Played different genders with each half of his body simultaneously. It was a bravura performance, though Martin rarely turns in a poor one.

[Baitball Blogger]

27. He is truly amazing.

[AnneD]

30. No Victor...

Victoria yet?

[Baitball Blogger]

31. Give it up for Julie Andrews!

[Graybeard]

32. Flip Wilson's "Geraldine".

Flip Wilson was a really funny comic who had his own primetime weekly variety show (Golden Globe and two Emmys) at a time when blacks were scarce on the tube.

But his act really perked up when he came on stage every week in full drag and make-up as Geraldine Jones.

[Baitball Blogger]

33. "What you see is what you get."

[riderinthestorm]

34. Wilson Jermaine Heredia who played Angel in Rent

Many years on Broadway and in the movie version, won a Tony Award for his performance. Then did a drag stint again in La Cage Aux Folles.

[kwassa]

35. Tilda Swinton as Bob Dylan