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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!

Vote for your favorite crossdresser movies, or movies about crossdressers, or movies with crossdressing right this second!

The Best Cross-Dressing Movies Films
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  1. 1
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    Susan Sarandon, Tim Curry, Meat Loaf Released: 1975

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    most listed
    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, Hank Azaria Released: 1996

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  5. 5
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    Eddie Murphy, Ming-Na Wen, George Takei Released: 1998

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  6. 6
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    Marilyn Monroe, Jack Lemmon, Tony Curtis Released: 1959

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  7. 7
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    added by crmflava
    Hugo Weaving, Guy Pearce, Terence Stamp

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  8. 8
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    added by crmflava
    Robin Williams, Naomi Campbell, Patrick Swayze

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  9. 9
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    added by SilverPhoenyx
    Julie Andrews, James Garner, Alex Karras

    ; buy at  
  10. 10
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    Sherilyn Fenn, William Zabka, Joyce Hyser Released: 1985

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  11. 11
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    Julianne Moore, Viggo Mortensen, Vince Vaughn Released: 1960

    ; watch now
  12. 12
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    Chiwetel Ejiofor, Joel Edgerton, Nick Frost Released: 2005

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  13. 13
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    added by MengshaChen
    Hilary Swank, Chloë Sevigny, Natalie Zea

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  14. 14
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    - 18

    added by crmflava
    Forest Whitaker, Jim Broadbent, Miranda Richardson Watch for Free with Amazon Prime Free Trial

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  15. 15
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    - 34


    Amanda Bynes, Channing Tatum, Jessica Lucas Released: 2006

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  16. 16
    + 39
    - 31


    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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    Claire Danes, Alice Eve, Billy Crudup Released: 2004

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  19. 19
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    Julie Walters, Adrian Pasdar, Paul Freeman Released: 1992

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  20. 20
    + 6
    - 1

    added by RileyJo81
    John Cleese, Terry Gilliam, Eric Idle

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  21. 21
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    Eric Idle, Robbie Coltrane, Janet Suzman Released: 1990

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  22. 22
    + 22
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    Michael Caine, Angie Dickinson, Dennis Franz Released: 1981

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  23. 23
    + 3
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    added by TamaraWilson
    Glenn Close, Jonathan Rhys Meyers, Mia Wasikowska

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  24. 24
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    added by JesscaWalker
    Liam Neeson, Cillian Murphy, Brendan Gleeson

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  25. 25
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    Alanis Morissette, Corey Haim, Nicole Eggert

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  26. 26
    + 9
    - 2

    added by CatherineSchulze
    Tilda Swinton, Billy Zane, Toby Jones

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  27. 27
    + 1
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    added by RileyJo81
    Ugo Tognazzi, Michel Serrault, Michel Galabru

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  28. 28
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    Helena Bonham Carter, Ben Kingsley, Kyra Sedgwick Released: 1996

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  29. 29
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    Robert De Niro, Philip Seymour Hoffman, Chris Bauer Released: 1999

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  30. 30
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    added by MarySSpiegel
    Tyler Perry, Shemar Moore, Tamara Taylor

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  31. 31
    + 9
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    added by stariris99
    The New Girlfriend Romain Duris, Anaïs Demoustier, Raphaël Personnaz

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  32. 32
    + 5
    - 2

    added by MarinaFranco
    Felicity Huffman, Kevin Zegers, Carrie Preston

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  33. 33
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    added by Countermoon
    Kevin Spacey, Jude Law, John Cusack Watch for Free with Amazon Prime Free Trial

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

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  35. 35
    + 4
    - 2

    added by NipperCSeaturtle
    Michèle Laroque, Vincent Grass, Jean-Philippe Écoffey

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  36. 36
    + 7
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    often listed & Ranked High on Reranks
    Orson Welles, Max von Sydow, George Sanders Released: 1969

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  37. 37
    + 3
    - 1

    added by NipperCSeaturtle
    Famke Janssen, Gabriel Macht, Adrian Grenier

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  38. 38
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    added by DarleeneTucker
    Susan Sarandon, Ellen Page, Cillian Murphy

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    added by but chickens double d
    Johnny Depp, Sarah Jessica Parker, Bill Murray

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  40. 40
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    added by NipperCSeaturtle
    Justin Theroux, Jill Hennessy, Stephen Dorff

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  41. 41
    + 1
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    new! & added by punksnotdead
    Kathleen Turner, Anthony Perkins, Annie Potts

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  42. 42
    + 18
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    David Duchovny, Debbie Reynolds, Toni Collette Released: 2004

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  43. 43
    + 2
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    added by NipperCSeaturtle
    The Brandon Teena Story

  44. 44
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    added by NipperCSeaturtle
    Johnny Depp, Sean Penn, Javier Bardem

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  45. 45
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    Released: 1988

    ; buy at  
  46. 46
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    Matt LeBlanc, Eddie Izzard, Edward Fox Released: 2001

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  47. 47
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    added by NipperCSeaturtle
    Angelina Jolie, Christina Aguilera, Will Smith

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  48. 48
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    added by JesscaWalker

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  49. 49
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    Brian Posehn, Michael Rosenbaum, Heather Matarazzo Released: 2002

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  50. 50
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    added by JesscaWalker
    Jason Mewes, Kate del Castillo, Tiffany Mulheron

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67 +

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