The Best Cross-Dressing Movies Films
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The Best Cross-Dressing Movies By   [161 more lists]

A list of the best cross-dressing movies. If you believe we've missed on, please feel free to add it to the list yourself. Genre-wise, this list includes both dramas and comedies (and even a few thrillers). Cross-dressing has been a staple of storytelling since ancient Greece. At times, it was even required by law as women were sometimes prohibited from working as actors. While some may consider crossdressing (and transvestites) as something that only belongs in comedy, that is far from the truth. Many of these films are dramas, and movies like "Psycho" are all out horrors. That said, many of them are indeed uplifting comedies. Enjoy!

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Rank     Name Release Directed by Genre(s)
  1. 1
    1961
    William Castle
    Horror, Slasher
    Released: 1961
  2. 2
    2002
    Wallace Wolodarsky
    Comedy, LGBT, Sex comedy
    Released: 2002
  3. 3
    2006
    Andy Fickman
    Comedy, Romance Film, Romantic comedy
    Released: 2006
  4. 4
    2006
    Kenneth Branagh
    Drama, Comedy, Costume drama, Period piece, Romance Film, Romantic comedy, Television movie, Romantic drama, Film adaptation More
    Released: 1936
  5. 5
    2000
    Raja Gosnell
    Comedy, Crime, Action
    Released: 2000
  6. 6
    1947
    Arthur H. Leonard
    Comedy, Black-and-white, Musical
    Released: 1947
  7. 7
    1980
    Brian De Palma
    Psychological thriller, Mystery, Thriller, Horror, Slasher, Crime Thriller, Indie, Suspense, Erotica, Erotic thriller More
    Released: 1981
  8. 8
    1974
    John Waters
    Drama, Comedy, LGBT, Crime Fiction, Black comedy, Indie, Cult
    Released: 1974
  9. 9
    1993
    Chris Columbus
    Drama, Comedy, Family, LGBT
    Released: 1993
  10. 10
    1990
    Jonathan Lynn
    Comedy, Slapstick, Crime Fiction, Indie
    Released: 1990
  11. 11
    2004
    Richard Eyre
    Drama, Comedy, Period piece, LGBT, Romance Film, Romantic comedy, Romantic drama More
    Released: 2004
  12. 12
    1996
    Donald Petrie
    Comedy
    Released: 1996
  13. 13
    1996
    Trevor Nunn
    Drama, Comedy, Romance Film, Romantic comedy, Film adaptation
    Released: 1996
  14. 14
    1998
    Barry Cook, Tony Bancroft
    Family, Animation, Musical, Adventure, Music, Children's, Drama Film
    Released: 1998
  15. 15
    2001
    Stefan Ruzowitzky
    Drama, Comedy, Period piece, Action, Action/Adventure
    Released: 2001
  16. 16
    1994
    Richard Rush
    Psychological thriller, Mystery, Thriller, Crime Thriller, Indie, Erotica, Erotic thriller More
    Released: 1994
  17. 17
    2003
    Richard Day
    Comedy, LGBT, Romantic comedy, Parody
    Released: 2003
  18. 18
    2002
    Jesse Vaughan
    Comedy, Sports, Romance Film, Romantic comedy, Sports
    Released: 2002
  19. 19
    2003
    Fenton Bailey, Randy Barbato
    Drama, Period piece, Biography, LGBT, Crime Fiction, Crime Thriller, Black comedy, Indie More
    Released: 2003
  20. 20
    1996
    Mike Nichols
    Comedy, LGBT
    Released: 1996
  21. 21
    2001
    Steve Boyum
    Family, Action
    Released: 2001
  22. 22
    1983
    Lamberto Bava
    Mystery, Thriller, Horror, Music, Slasher, World cinema, Giallo
    Released: 1983
  23. 23
    1993
    Michael Keusch
    Comedy, Teen
    Released: 1993
  24. 24
    2004
    Michael Lembeck
    Comedy, LGBT, Buddy film
    Released: 2004
  25. 25
    Released: 1988
  26. 26
    1999
    Joel Schumacher
    Drama, Comedy, LGBT, Indie
    Released: 1999
  27. 27
    1992
    Christopher Monger
    Drama, Comedy, LGBT
    Released: 1992
  28. 28
    1985
    Lisa Gottlieb
    Comedy, Sports, Romance Film, Romantic comedy, Teen, Coming of age
    Released: 1985
  29. 29
    1992
    Sidney J. Furie
    Comedy, Family, Sports
    Released: 1992
  30. 30
    1992
    Jimmy Zeilinger
    Released: 1992
  31. 31
    1998
    Gus Van Sant
    Psychological thriller, Mystery, Thriller, Horror, Slasher
    Released: 1960
  32. 32
    1959
    Billy Wilder
    Comedy, Black-and-white, Romance Film, Romantic comedy, Screwball comedy, Sex comedy More
    Released: 1959
  33. 33
    2002
    Tom Brady
    Comedy, Fantasy
    Released: 2003
  34. 34
    1970
    John Huston
    Drama, Thriller, Film adaptation, Political thriller, Spy
    Released: 1969
  35. 35
    1975
    Jim Sharman
    Comedy, Musical, Horror, Parody, Cult, Sex comedy
    Released: 1975
  36. 36
    2004
    Keenen Ivory Wayans
    Comedy, Action, Action/Adventure, LGBT, Slapstick, Buddy film
    Released: 2004
  37. 37
    2005
    Julian Jarrold
    Comedy, Indie
    Released: 2005
  38. 38
    2001
    Francis Girod
    Drama, Psychological thriller, Thriller, LGBT, World cinema
    added by: ChrisRCman
  39. 39
    1998
    John Madden
    Drama, Comedy, Costume drama, Period piece, Romance Film, Romantic comedy, Romantic drama More
    Released: 1998
  40. 40
    1982
    Sydney Pollack
    Comedy, Romance Film, Romantic comedy, Drama Film
    Released: 1982
  41. 41
    Paul Bogart
    Released: 1988
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