The Best Cross-Dressing Movies Films
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The Best Cross-Dressing Movies

List Criteria: Movies must feature cross-dressing and cross-dressers.

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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  1. 1
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    Susan Sarandon, Meat Loaf, Tim Curry Released: 1975

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  2. 2
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    Robin Williams, Pierce Brosnan, Sally Field Released: 1993

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  3. 3
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    Bill Murray, Dustin Hoffman, Geena Davis Released: 1982

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  4. 4
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    Robin Williams, Gene Hackman, Calista Flockhart Released: 1996

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  5. 5
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    Marilyn Monroe, Jack Lemmon, Tony Curtis Released: 1959

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  6. 6
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    Julianne Moore, Vince Vaughn, Viggo Mortensen Released: 1960

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  7. 7
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    Eddie Murphy, George Takei, Donny Osmond Released: 1998

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  8. 8
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    added by SilverPhoenyx Julie Andrews, James Garner, Alex Karras

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  9. 9
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    added by crmflava Hugo Weaving, Guy Pearce, Terence Stamp

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  10. 10
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    added by crmflava Robin Williams, Naomi Campbell, RuPaul

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  11. 11
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    Chiwetel Ejiofor, Joel Edgerton, Nick Frost Released: 2005

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  12. 12
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    Sherilyn Fenn, William Zabka, Arye Gross Released: 1985

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  13. 13
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    added by crmflava Forest Whitaker, Jim Broadbent, Miranda Richardson

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  14. 14
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    added by MengshaChen Hilary Swank, Chloë Sevigny, Natalie Zea

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  15. 15
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    added by MarySSpiegel Tyler Perry, Shemar Moore, Tamara Taylor

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  16. 16
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    Gwyneth Paltrow, Ben Affleck, Judi Dench Released: 1998

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  17. 17
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    Evangeline Lilly, Jaime King, Jennifer Carpenter Released: 2004

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  18. 18
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    Amanda Bynes, Channing Tatum, Jessica Lucas Released: 2006

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  19. 19
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    Claire Danes, Alice Eve, Tom Wilkinson Released: 2004

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  20. 20
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    Eric Idle, Robbie Coltrane, Janet Suzman Released: 1990

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  21. 21
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    Robert De Niro, Philip Seymour Hoffman, Chris Bauer Released: 1999

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  22. 22
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    new! & added by JesscaWalker Liam Neeson, Cillian Murphy, Brendan Gleeson

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  23. 23
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    added by DarleeneTucker Susan Sarandon, Ellen Page, Cillian Murphy

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  24. 24
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    Alanis Morissette, Corey Haim, Nicole Eggert

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  25. 25
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    Julie Walters, Adrian Pasdar, Paul Freeman Released: 1992

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  26. 26
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    new! & added by JesscaWalker

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  27. 27
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    new! & added by JesscaWalker Jason Mewes, Kate del Castillo, Tommy Lister

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  28. 28
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    David Duchovny, Toni Collette, Debbie Reynolds Released: 2004

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  29. 29
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    Adam Sandler, Rachel McAdams, Anna Faris Released: 2003

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  30. 30
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    Bruce Willis, Brad Dourif, Lesley Ann Warren Released: 1994

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  31. 31
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    added by Countermoon Jude Law, Kevin Spacey, John Cusack

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  32. 32
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    Released: 1988

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  33. 33
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    Michael Caine, Angie Dickinson, Dennis Franz Released: 1981

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  34. 34
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    Rodney Dangerfield, Tommy Lasorda, Jonathan Brandis Released: 1992

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  35. 35
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    Helena Bonham Carter, Ben Kingsley, Kyra Sedgwick Released: 1996

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    Eddie Izzard, Matt LeBlanc, Edward Fox Released: 2001

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    Michael Rosenbaum, Brian Posehn, Harland Williams Released: 2002

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  38. 38
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    Lil' Kim, Vivica A. Fox, Vlade Divac Released: 2002

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    Paul Giamatti, Martin Lawrence, Terrence Howard Released: 2000

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  40. 40
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    Divine, Mink Stole, Edith Massey Released: 1974

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  41. 41
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    Orson Welles, Max von Sydow, George Sanders Released: 1969

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  42. 42
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    Marco Vivio, Michele Soavi, Andrea Occhipinti Released: 1983

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  43. 43
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    Snub Pollard, James Westerfield, Glenn Corbett Released: 1961

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  44. 44
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    Kappei Yamaguchi, Yasunori Matsumoto, Michie Tomizawa Released: 1988

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    Alyssa Milano, Tia Carrere, Jonathan Silverman Released: 1992

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    Macaulay Culkin, Seth Green, Chloë Sevigny Released: 2003

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  47. 47
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    Bryce Dallas Howard, Kevin Kline, Alfred Molina Released: 1936

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    Miss Coco Peru, Eric Stonestreet, Jack Plotnick Released: 2003

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  49. 49
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    added by ChrisRCman Micheline Presle, Richard Bohringer, Stéphane Metzger

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  50. 50
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    Gene Krupa, Tim Moore, Slam Stewart Released: 1947

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