Friday's Top Five: Best cross-dressing
November 11th, 2011
10:32 AM ET

Friday's Top Five: Best cross-dressing

Adam Sandler plays both of the title characters in his movie "Jack and Jill," opening this weekend, but he's far from the first actor to experiment with cross-dressing on film. Hollywood has had a long tradition of androgynous characters.

Our list this week consists of films where men pretend to be women and women pretend to be men. Most of these stories tend to be comedies like "White Chicks" and "Bosom Buddies," but they can also be more substantive, such as Glenn Close's upcoming "Albert Nobbs."

Here's the list that tops this gender-bending genre. What are your favorites?

1. "Tootsie" (1982):  “I was a better man with you, as a woman... than I ever was with a woman, as a man. You know what I mean? I just gotta learn to do it without the dress.” – Michael Dorsey

2. "Just One of the Guys" (1985): “Of course you're confused. You're wearing my underwear.” – Buddy

3. "Mrs. Doubtfire" (1993): “Oh, as I hold this cold meat, I'm reminded of Winston.” – Mrs. Doubtfire

4. "Some Like It Hot" (1959):  “But you don’t understand, Osgood…I’m a man!” – Jerry (Osgood replies, “Nobody’s perfect!”)

5. "Victor/Victoria" (1982): “The disguise surprise comedy of the year!” – movie tagline

Honorable Mention:

"Yentl" (1983): “Sacred books are for men.” – bookseller to Yentl

"Mulan" (1998): “This time, the princess saves the prince.” – movie tagline

"The Adventures of Priscilla, Queen of the Desert" (1994):  “We dress up in women’s clothes and parade around mouthing the words to other people’s songs.” – Adam/Felicia (General Zod, Agent Smith, and Memento’s Guy Pearce drag out this Aussie import.)

soundoff (50 Responses)
  1. Dan

    What about Justine Beaver pretending to be a boy idol in "Never Say Never"?

    December 1, 2011 at 5:25 pm | Report abuse |
  2. Ben

    As Pamela wrote; Monty Python's Flying Circus frequently had cross-dressings in their movies.

    SPOILER ALERT: One of the best cross-dressing films of all time is, SPOILER ALERT: Psycho (1960).

    November 25, 2011 at 10:19 am | Report abuse |
  3. person

    What about "Shakespeare in Love?"

    November 15, 2011 at 1:03 pm | Report abuse |
  4. Mike

    If you are looking for interesting cross-dressing films, try:

    The Crying Game – A straight man falls for a cross-dresser who he thinks is a woman against the backdrop of the
    Normal – One man's journey to womanhood.
    My Breakfast on Pluto – Hardedge look a drag queen and his struggles.
    Just Like a Woman – Gets silly near the end, but a pretty realistic look at the trials and tribulations of a hetero cross-dresser.
    The World's Fastest Indian – Not about cross-dressing, but has one of the most realistic cross-dressing characters on film. This is a great movie well worth watching.

    November 14, 2011 at 1:05 pm | Report abuse |
  5. BVG

    What about "World According to Garp"? John Lithgow was nominated for an Oscar for that role.

    November 14, 2011 at 9:54 am | Report abuse |
    • Yosh

      Not positive but believe Lithgow was a transgender, so not sure if that's technically the same as simply cross-dressing.

      November 14, 2011 at 10:09 am | Report abuse |
    • Leaf on the Wind

      Even if the character wasn't cross-dressing, the actor definitely was.

      November 14, 2011 at 3:05 pm | Report abuse |
  6. MIke

    Ummm...Rocky Horror Picture Show???

    November 14, 2011 at 8:58 am | Report abuse |
  7. M

    Loved 'Priscilla' ... should have won top honors for more than only costumes.

    November 14, 2011 at 8:48 am | Report abuse |
  8. Pamela

    The Monty Python movies have them all beat!

    November 14, 2011 at 7:14 am | Report abuse |
  9. Sara

    HELLO, where is "The Birdcage"?

    November 13, 2011 at 10:44 pm | Report abuse |
  10. bellestarrr

    from a primo xdresser I liked the CRYING GAME..guy/girl was very convincing..but it wasnt a comedy..very serious subject..from the beginning of recorded history men have been crossdressing so its really nothing new under the sun its just a twist on the old ying and yang....its the puritans(america) who cannot seem to understand its roots

    November 13, 2011 at 9:58 pm | Report abuse |
  11. corntrader19

    "Some Like It Hot" is one of my all time favorite movies and I am sick and tired of reviewers trying to read more into it than what is there: It's just a movie! Get off the STUPID analyzations! Cross dressing has nothing to do with this movie. Tony Curtis once said "It's a 30 minute burlesque routine made into a two hour movie."

    November 13, 2011 at 8:08 pm | Report abuse |
  12. RS

    I do like all of these. But what about Jason Isaacs in Sweet November ? I am glad to see The Adventures of Priscilla Queen of the Desert. That was my first intro to Hugo Weaving. Funny because while watching the Matrix, I kept saying "That kinda looks like my boy in Priscilla" sure enough that was him going from a drag queen to an evil computer agent. And yes Birdcage and To Wong Foo should've been in there. I loved those movies.

    November 13, 2011 at 3:50 pm | Report abuse |
    • Leaf on the Wind

      If you like Hugo Weaving, you should see an Australian film from the early nineties call "Proof" in which he plays a blind man who takes photographs. Bonus treat: Russell Crowe in a delightful supporting role, before any of us in the U.S. ever heard of him.

      November 14, 2011 at 3:03 pm | Report abuse |
  13. Levi

    Hello? The Birdcage?? That drag queen was so cute! I wanted to kiss his bottom 😀

    November 13, 2011 at 12:17 pm | Report abuse |
    • Leaf on the Wind

      Which one? "Birdcage" was about a night club full of drag queens.

      November 14, 2011 at 3:00 pm | Report abuse |
  14. Guest

    What about Pat? Or the church lady?
    And theres Jethrine Bodine.

    November 12, 2011 at 4:42 pm | Report abuse |
  15. Mike

    Harry Crumb

    November 12, 2011 at 1:07 pm | Report abuse |
    • yosh

      Nice reference, while thinking about John Candy, might as well add Armed and Dangerous to the list

      November 13, 2011 at 9:02 am | Report abuse |
  16. cobweb

    My fav is a guilty pleasure, "She's the Man," a 2006 film starring Amanda Bynes. It was based on Shakespeare's "Twelfth Night," and I love the connections to the play that are woven into the film's story.

    November 12, 2011 at 1:01 pm | Report abuse |
  17. Randyb

    Charly's Aunt with Jack Benny Cross Dressing. Hilarious.

    November 12, 2011 at 12:40 pm | Report abuse |
  18. jillmarie

    "The Birdcage" should have been included, but great list. I love the shout out to "Just One Of The GHuys"- great 80's flick.

    November 12, 2011 at 11:44 am | Report abuse |
    • Yosh

      It was a toss-up between Birdcage and Doubtfire, can't have Robin Williams dominating the entire list

      November 13, 2011 at 9:01 am | Report abuse |
    • Josh

      Gee, for "Birdcage", I would put Gene Hackman ahead of Robin Williams for _best_ cross dressing.

      November 14, 2011 at 12:41 pm | Report abuse |
    • Leaf on the Wind

      So many who need to see "Birdcage" again . . . Robin Williams did no cross-dressing in that movie. Nathan Lane did, Hank Azaria (brilliant performance!!!) did, sort-of, but seeing Gene Hackman in a platinum blond wig and a gigantic white dress was one of the funniest scenes ever!

      November 14, 2011 at 2:58 pm | Report abuse |
  19. dj riz

    'kink boots', 'la cage aux folles' ( the original , and better, 'birdcage', ) and no john waters films – his entire 40 + year output features cross dressing as a subtext.. hell ..divine made a better drag queen than anybody on this list

    November 12, 2011 at 11:32 am | Report abuse |
  20. Roger Jollie

    Michael J. Fox was missed for his minor role in Back to the Future II.

    November 12, 2011 at 11:00 am | Report abuse |
  21. Grog Says

    Milton Berle, the king.......
    I mean queen (chukle)

    November 12, 2011 at 9:02 am | Report abuse |
  22. Ronald H. Witt

    I, Ronald H. Witt, am telling not even compare this Sandler movie to Tootsie.

    November 12, 2011 at 4:24 am | Report abuse |
  23. Gianna

    Perhaps the truest and most heartfelt of all films about cross dressing : NORMAL with Tom Wilkerson and Jessica Lange.
    They produced a list of the money-making movies with mass appeal (for the morons on board that means: the least offensive to the conservatives from East Bumfcuk).

    November 12, 2011 at 3:31 am | Report abuse |
  24. MissyLynne

    TO WONG FOO, THANKS FOR EVERYTHING, JULIE NEWMAR!!! Best cross-dressing movie ever you guys! How could you skip over that one!?

    November 12, 2011 at 12:18 am | Report abuse |
  25. Akira

    What about Bugs Bunny? You can't forget Bugs Bunny!

    November 11, 2011 at 11:18 pm | Report abuse |
  26. Miriam

    Remember "Bosom Buddies"? Ha!

    November 11, 2011 at 9:46 pm | Report abuse |
  27. Autumn Sandeen

    Not exactly crossdressing films, but Transamerica, Different For Girls, Boys Don't Cry, and The Crying Game are no doubt among the best dramas with either transgender themes, or transgender major characters, that have been produced.

    November 11, 2011 at 4:46 pm | Report abuse |
  28. Philygirl

    Diamond Rick and I agree that Some Like it Hot was the best and maybe the first of it's kind...

    November 11, 2011 at 4:34 pm | Report abuse |
    • Duane

      I agree. Some Like It Hot is definitely the best. Amazing performances by Marilyn Monroe, Jack Lemmon, and Tony Curtis–as well as the many supporting characters. I would place Tootsie second.

      November 12, 2011 at 2:25 pm | Report abuse |
  29. GirlCrush

    "Boys Don't Cry"
    "The Birdcage"
    "Rocky Horror Picture Show"

    November 11, 2011 at 12:44 pm | Report abuse |
    • Leaf on the Wind

      Birdcage is great! Even Gene Hackman wore a dress and a wig! Hilarious!

      November 14, 2011 at 2:54 pm | Report abuse |
    • coliee1289

      Rocky Horror Picture Show should have been number 1!

      November 15, 2011 at 9:52 am | Report abuse |

    – White Chicks (2004)
    – Juwanna Mann (2002)
    – Holiday Heart (2000)

    November 11, 2011 at 11:51 am | Report abuse |
  31. Hello...How-Are-Ya...I'm-Arnold-Horeshack

    -To Wong Foo, Thanks for Everything! Julie Newmar (1994)
    – Big Momma's House (2000)

    November 11, 2011 at 11:45 am | Report abuse |
    • Yosh

      Agreed that Wong Foo is missing from the official list

      November 11, 2011 at 11:54 am | Report abuse |
    • RayJacksonMS

      Too Wong Foo was a second rate rip off of Priscilla Queen of the Desert. I"m sure that's why it didn't make the list.

      November 11, 2011 at 7:19 pm | Report abuse |
  32. Yosh

    I can tell by the amount of comments so far, this topic is too scary!

    November 11, 2011 at 11:24 am | Report abuse |
  33. HP

    What About: "The Associate" & "To Wong Foo Thanks For Everything Julie Newmar"

    November 11, 2011 at 11:09 am | Report abuse |
    • Max

      To Wong Foo is an american rip off of Priscilla Queen of the Desert. Priscilla is 10 times better.

      November 12, 2011 at 12:59 pm | Report abuse |

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