Top 10 Movies Involving Cross Dressing

I'm just like everybody else, I put on my skirt 1 leg at a time.
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1.
Tootsie (1982)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Michael Dorsey, an unsuccessful actor, disguises himself as a woman in order to get a role on a trashy hospital soap. (116 mins.)
Director: Sydney Pollack
“ Dustin Hoffman gets dolled up for most of the movie ” - TalkinPikchorBox
 
2.
Mrs. Doubtfire (1993)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
After a bitter divorce, an actor disguises himself as a female housekeeper to spend time with his children held in custody by his former wife. (125 mins.)
Director: Chris Columbus
“ Robin Williams probably one of the hairiest persons to ever put on a skirt ” - TalkinPikchorBox
 
3.
The Crying Game (1992)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
A British soldier is kidnapped by IRA terrorists. He befriends one of his captors, who is drawn into the soldier's world. (112 mins.)
Director: Neil Jordan
“ Is this a spoiler? ” - TalkinPikchorBox
 
4.
Boys Don't Cry (1999)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Female-born Teena Brandon adopts his male identity of Brandon Teena and attempts to find himself and love in Nebraska. (118 mins.)
Director: Kimberly Peirce
“ Attaboy ! ” - TalkinPikchorBox
 
5.
Some Like It Hot (1959)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
When two male musicians witness a mob hit, they flee the state in an all-female band disguised as women, but further complications set in. (121 mins.)
Director: Billy Wilder
“ Tony Curtis and Jack Lemmon dress as women and join an all-girl band, in order to hide from the mob ” - TalkinPikchorBox
 
6.
White Chicks (2004)
    1 2 3 4 5 6 7 8 9 10 5.5/10 X  
Two disgraced FBI agents go way undercover in an effort to protect hotel heiresses the Wilson Sisters from a kidnapping plot. (109 mins.)
“ Scary stuff ” - TalkinPikchorBox
 
7.
Just One of the Guys (1985)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
Terry Griffith has got it all -- looks, popularity, the perfect college boyfriend, and an article that's... (90 mins.)
Director: Lisa Gottlieb
“ Joyce Hyser plays a boy so she can win a journalism contest ” - TalkinPikchorBox
 
8.
The Birdcage (1996)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
A gay cabaret owner and his drag queen companion agree to put up a false straight front so that their son can introduce them to his fiancée's right-wing moralistic parents. (117 mins.)
Director: Mike Nichols
“ Yes, Mam. I mean, Man...Mama. Just yes. ” - TalkinPikchorBox
 
9.
Big Momma's House (2000)
    1 2 3 4 5 6 7 8 9 10 5.1/10 X  
In order to protect a beautiful woman and her son from a robber, a male FBI agent disguises himself as a large grandmother. (99 mins.)
Director: Raja Gosnell
“ Cross dressing at a whole other level ” - TalkinPikchorBox
 
10.
The Dark Knight (2008)
    1 2 3 4 5 6 7 8 9 10 9.0/10 X  
When the menace known as the Joker emerges from his mysterious past, he wreaks havoc and chaos on the people of Gotham, the Dark Knight must accept one of the greatest psychological and physical tests of his ability to fight injustice. (152 mins.)
“ The Joker in a nurses uniform. ” - TalkinPikchorBox