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!

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

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  1. 1
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    most listed
    Robin Williams, Pierce Brosnan, Sally Field Released: 1993

    ) open
  2. 2
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    - 31


    Bill Murray, Dustin Hoffman, Geena Davis Released: 1982

    ) open
  3. 3
    + 140
    - 32

    ranked low on reranks
    Susan Sarandon, Meat Loaf, Tim Curry Released: 1975

    ) open
  4. 4
    + 91
    - 29


    Robin Williams, Gene Hackman, Calista Flockhart Released: 1996

    ) open
  5. 5
    + 75
    - 27


    Marilyn Monroe, Jack Lemmon, Tony Curtis Released: 1959

    ) open
  6. 6
    + 36
    - 13

    added by SilverPhoenyx
    Julie Andrews, James Garner, Alex Karras

    ) open
  7. 7
    + 54
    - 33


    Julianne Moore, Vince Vaughn, Viggo Mortensen Released: 1960

    ) open
  8. 8
    + 49
    - 30


    Sherilyn Fenn, William Zabka, Arye Gross Released: 1985

    ) open
  9. 9
    + 45
    - 15

    added by crmflava
    Hugo Weaving, Guy Pearce, Terence Stamp

    ) open
  10. 10
    + 27
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    often listed & ranked high on reranks
    Claire Danes, Alice Eve, Tom Wilkinson Released: 2004

    ) open
  11. 11
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    - 25

    ranked low on reranks
    Eddie Murphy, George Takei, Donny Osmond Released: 1998

    ) open
  12. 12
    + 46
    - 15

    added by crmflava
    Robin Williams, Naomi Campbell, RuPaul

    ) open
  13. 13
    + 52
    - 21


    Chiwetel Ejiofor, Joel Edgerton, Nick Frost Released: 2005

    ) open
  14. 14
    + 35
    - 28


    Gwyneth Paltrow, Ben Affleck, Judi Dench Released: 1998

    ) open
  15. 15
    + 22
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    Eric Idle, Robbie Coltrane, Janet Suzman Released: 1990

    ) open
  16. 16
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    Evangeline Lilly, Jaime King, Jennifer Carpenter Released: 2004

    ) open
  17. 17
    + 37
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    ranked low on reranks & added by crmflava
    Forest Whitaker, Jim Broadbent, Miranda Richardson

    ) open
  18. 18
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    - 27

    added by MengshaChen
    Hilary Swank, Chloë Sevigny, Natalie Zea

    ) open
  19. 19
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    Released: 1988

    ) open
  20. 20
    + 20
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    Robert De Niro, Philip Seymour Hoffman, Chris Bauer Released: 1999

    ) open
  21. 21
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    - 26


    Michael Caine, Angie Dickinson, Dennis Franz Released: 1981

    ) open
  22. 22
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    added by Countermoon
    Jude Law, Kevin Spacey, John Cusack

    ) open
  23. 23
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    Helena Bonham Carter, Ben Kingsley, Kyra Sedgwick Released: 1996

    ) open
  24. 24
    + 6
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    Orson Welles, Max von Sydow, George Sanders Released: 1969

    ) open
  25. 25
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    added by RileyJo81
    John Cleese, Eric Idle, Terry Gilliam

    ) open
  26. 26
    + 9
    - 17


    Divine, Mink Stole, Edith Massey Released: 1974

    ) open
  27. 27
    + 1
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    added by TamaraWilson
    Glenn Close, Jonathan Rhys Meyers, Brendan Gleeson

    ) open
  28. 28
    + 1
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    added by RileyJo81
    Ugo Tognazzi, Michel Galabru, Michel Serrault

    ) open
  29. 29
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    Kenneth Williams, Sid James, Leslie Phillips

    ) open
  30. 30
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    ranked low on reranks
    Amanda Bynes, Channing Tatum, Jessica Lucas Released: 2006

    ) open
  31. 31
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    Julie Walters, Adrian Pasdar, Paul Freeman Released: 1992

    ) open
  32. 32
    + 20
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    added by MarySSpiegel
    Tyler Perry, Shemar Moore, Tamara Taylor

    ) open
  33. 33
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    Alanis Morissette, Corey Haim, Nicole Eggert

    ) open
  34. 34
    + 10
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    added by JesscaWalker
    Liam Neeson, Cillian Murphy, Brendan Gleeson

    ) open
  35. 35
    + 4
    - 2

    added by CatherineSchulze
    Tilda Swinton, Billy Zane, Toby Jones

    ) open
  36. 36
    + 2
    - 1

    added by MarinaFranco
    Felicity Huffman, Kevin Zegers, Carrie Preston

    ) open
  37. 37
    + 1
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    added by NipperCSeaturtle
    Johnny Depp, Sean Penn, Javier Bardem

    ) open
  38. 38
    + 1
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    new! & added by NipperCSeaturtle

    ) open
  39. 39
    + 1
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    added by NipperCSeaturtle
    Famke Janssen, Adrian Grenier, Gabriel Macht

    ) open
  40. 40
    + 1
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    new! & added by NipperCSeaturtle
    Michèle Laroque, Jean-Philippe Écoffey, Vincent Grass

    ) open
  41. 41
    + 1
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    added by NipperCSeaturtle
    Justin Theroux, Jill Hennessy, Stephen Dorff

    ) open
  42. 42
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    new! & added by NipperCSeaturtle
    Angelina Jolie, Christina Aguilera, Will Smith

    ) open
  43. 43
    + 17
    - 21


    David Duchovny, Toni Collette, Debbie Reynolds Released: 2004

    ) open
  44. 44
    + 19
    - 24


    Rodney Dangerfield, Tommy Lasorda, Jonathan Brandis Released: 1992

    ) open
  45. 45
    + 1
    - 1

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

    ) open
  46. 46
    + 4
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    added by stariris99
    Romain Duris, Anaïs Demoustier, Raphaël Personnaz

    ) open
  47. 47
    + 7
    - 9

    added by DarleeneTucker
    Susan Sarandon, Ellen Page, Cillian Murphy

    ) open
  48. 48
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    added by JesscaWalker
    Jason Mewes, Kate del Castillo, Tommy Lister

    ) open
  49. 49
    + 14
    - 22


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

    ) open
  50. 50
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    Macaulay Culkin, Seth Green, Chloë Sevigny Released: 2003

    ) open
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