The Best Cross-Dressing Movies Films

The Best Cross-Dressing Movies

Originally By 3.6k votes 840 voters 286k views 71 items tags f p @

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
    + 193
    - 52
    The Rocky Horror Picture Show is listed (or ranked) 1 on the list The Best Cross-Dressing Movies


    Susan Sarandon, Tim Curry, Meat Loaf Released: 1975

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  2. 2
    + 182
    - 61
    Mrs. Doubtfire is listed (or ranked) 2 on the list The Best Cross-Dressing Movies

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

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  3. 3
    + 133
    - 44
    Tootsie is listed (or ranked) 3 on the list The Best Cross-Dressing Movies


    Bill Murray, Dustin Hoffman, Geena Davis Released: 1982

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  4. 4
    + 113
    - 40
    The Birdcage is listed (or ranked) 4 on the list The Best Cross-Dressing Movies


    Robin Williams, Gene Hackman, Hank Azaria Released: 1996

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  5. 5
    + 100
    - 34
    Some Like It Hot is listed (or ranked) 5 on the list The Best Cross-Dressing Movies


    Marilyn Monroe, Jack Lemmon, Tony Curtis Released: 1959

    ;
  6. 6
    + 73
    - 19
    The Adventures of Priscilla, Q... is listed (or ranked) 6 on the list The Best Cross-Dressing Movies

    added by crmflava
    Hugo Weaving, Guy Pearce, Terence Stamp

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  7. 7
    + 101
    - 40
    Mulan is listed (or ranked) 7 on the list The Best Cross-Dressing Movies


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

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  8. 8
    + 80
    - 17
    To Wong Foo, Thanks for Everyt... is listed (or ranked) 8 on the list The Best Cross-Dressing Movies

    added by crmflava
    Robin Williams, Naomi Campbell, Patrick Swayze

    ;
  9. 9
    + 66
    - 38
    Just One of the Guys is listed (or ranked) 9 on the list The Best Cross-Dressing Movies


    Sherilyn Fenn, William Zabka, Joyce Hyser Released: 1985

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  10. 10
    + 45
    - 20
    Victor Victoria is listed (or ranked) 10 on the list The Best Cross-Dressing Movies

    added by SilverPhoenyx
    Julie Andrews, James Garner, Alex Karras

    ;
  11. 11
    + 71
    - 25
    Kinky Boots is listed (or ranked) 11 on the list The Best Cross-Dressing Movies

    ranked low on reranks
    Chiwetel Ejiofor, Joel Edgerton, Nick Frost Released: 2005

    ;
  12. 12
    + 64
    - 43
    Psycho is listed (or ranked) 12 on the list The Best Cross-Dressing Movies


    Julianne Moore, Viggo Mortensen, Vince Vaughn Released: 1960

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  13. 13
    + 53
    - 21
    The Crying Game is listed (or ranked) 13 on the list The Best Cross-Dressing Movies

    added by crmflava
    Forest Whitaker, Jim Broadbent, Miranda Richardson

    ;
  14. 14
    + 54
    - 39
    Boys Don't Cry is listed (or ranked) 14 on the list The Best Cross-Dressing Movies

    added by MengshaChen
    Hilary Swank, Chloë Sevigny, Natalie Zea

    ;
  15. 15
    + 38
    - 29
    Stage Beauty is listed (or ranked) 15 on the list The Best Cross-Dressing Movies


    Claire Danes, Alice Eve, Billy Crudup Released: 2004

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  16. 16
    + 74
    - 42
    She's the Man is listed (or ranked) 16 on the list The Best Cross-Dressing Movies


    Amanda Bynes, Channing Tatum, Jessica Lucas Released: 2006

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  17. 17
    + 46
    - 21
    Just like a Woman is listed (or ranked) 17 on the list The Best Cross-Dressing Movies


    Julie Walters, Adrian Pasdar, Paul Freeman Released: 1992

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  18. 18
    + 68
    - 63
    White Chicks is listed (or ranked) 18 on the list The Best Cross-Dressing Movies


    Evangeline Lilly, Jaime King, Jennifer Carpenter Released: 2004

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  19. 19
    + 40
    - 38
    Shakespeare in Love is listed (or ranked) 19 on the list The Best Cross-Dressing Movies


    Gwyneth Paltrow, Ben Affleck, Judi Dench Released: 1998

    ;
  20. 20
    + 9
    - 1
    La Cage aux Folles is listed (or ranked) 20 on the list The Best Cross-Dressing Movies

    added by RileyJo81
    Ugo Tognazzi, Michel Serrault, Michel Galabru

    ;
  21. 21
    + 10
    - 4
    Monty Python's The Meaning of ... is listed (or ranked) 21 on the list The Best Cross-Dressing Movies

    added by RileyJo81
    John Cleese, Terry Gilliam, Eric Idle

    ;
  22. 22
    + 19
    - 8
    Breakfast on Pluto is listed (or ranked) 22 on the list The Best Cross-Dressing Movies

    added by JesscaWalker
    Liam Neeson, Cillian Murphy, Brendan Gleeson

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  23. 23
    + 32
    - 23
    Anything for Love is listed (or ranked) 23 on the list The Best Cross-Dressing Movies


    Alanis Morissette, Corey Haim, Nicole Eggert

    ;
  24. 24
    + 6
    - 5
    Albert Nobbs is listed (or ranked) 24 on the list The Best Cross-Dressing Movies

    added by TamaraWilson
    Glenn Close, Jonathan Rhys Meyers, Mia Wasikowska

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  25. 25
    + 24
    - 31
    Dressed to Kill is listed (or ranked) 25 on the list The Best Cross-Dressing Movies


    Michael Caine, Angie Dickinson, Dennis Franz Released: 1981

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  26. 26
    + 16
    - 7
    The New Girlfriend is listed (or ranked) 26 on the list The Best Cross-Dressing Movies

    ranked low on reranks & added by stariris99
    The New Girlfriend Romain Duris, Anaïs Demoustier, Raphaël Personnaz

  27. 27
    + 23
    - 31
    Nuns on the Run is listed (or ranked) 27 on the list The Best Cross-Dressing Movies

    often listed & ranked high on reranks
    Eric Idle, Robbie Coltrane, Janet Suzman Released: 1990

    ;
  28. 28
    + 10
    - 3
    My Life in Pink is listed (or ranked) 28 on the list The Best Cross-Dressing Movies

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

    ;
  29. 29
    + 10
    - 3
    Transamerica is listed (or ranked) 29 on the list The Best Cross-Dressing Movies

    added by MarinaFranco
    Felicity Huffman, Kevin Zegers, Carrie Preston

    ;
  30. 30
    + 16
    - 24
    Twelfth Night: Or What You Wil... is listed (or ranked) 30 on the list The Best Cross-Dressing Movies

    often listed & ranked high on reranks
    Helena Bonham Carter, Ben Kingsley, Kyra Sedgwick Released: 1996

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  31. 31
    + 10
    - 5
    Orlando is listed (or ranked) 31 on the list The Best Cross-Dressing Movies

    added by CatherineSchulze
    Tilda Swinton, Billy Zane, Toby Jones

    ;
  32. 32
    + 15
    - 11
    Peacock is listed (or ranked) 32 on the list The Best Cross-Dressing Movies

    added by DarleeneTucker
    Susan Sarandon, Ellen Page, Cillian Murphy

    ;
  33. 33
    + 23
    - 21
    Flawless is listed (or ranked) 33 on the list The Best Cross-Dressing Movies


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

    ;
  34. 34
    + 21
    - 19
    Midnight in the Garden of Good... is listed (or ranked) 34 on the list The Best Cross-Dressing Movies

    added by Countermoon
    Kevin Spacey, Jude Law, John Cusack

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  35. 35
    + 27
    - 28
    Ladybugs is listed (or ranked) 35 on the list The Best Cross-Dressing Movies


    Rodney Dangerfield, Tommy Lasorda, Jonathan Brandis Released: 1992

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  36. 36
    + 5
    - 2
    The Adventures of Sebastian Co... is listed (or ranked) 36 on the list The Best Cross-Dressing Movies

    added by NipperCSeaturtle
    Famke Janssen, Gabriel Macht, Adrian Grenier

    ;
  37. 37
    + 4
    - 1
    Monty Python and the Holy Grai... is listed (or ranked) 37 on the list The Best Cross-Dressing Movies

    added by Tom Islava
    John Cleese, Terry Gilliam, Eric Idle

    ;
  38. 38
    + 4
    - 1
    Monty Python's Life of Brian is listed (or ranked) 38 on the list The Best Cross-Dressing Movies

    added by Tom Islava
    Michael Palin, Terry Jones, Eric Idle

    ;
  39. 39
    + 3
    - 1
    A Funny Thing Happened on the ... is listed (or ranked) 39 on the list The Best Cross-Dressing Movies

    added by Tom Islava
    Buster Keaton, Jon Pertwee, Michael Crawford

    ;
  40. 40
    + 6
    - 5
    Ed Wood is listed (or ranked) 40 on the list The Best Cross-Dressing Movies

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

    ;
  41. 41
    + 20
    - 23
    Diary of a Mad Black Woman is listed (or ranked) 41 on the list The Best Cross-Dressing Movies

    added by MarySSpiegel
    Tyler Perry, Shemar Moore, Tamara Taylor

    ;
  42. 42
    + 7
    - 20
    The Kremlin Letter is listed (or ranked) 42 on the list The Best Cross-Dressing Movies

    often listed & ranked high on reranks
    Orson Welles, Max von Sydow, George Sanders Released: 1969

    ;
  43. 43
    + 4
    - 3
    I Shot Andy Warhol is listed (or ranked) 43 on the list The Best Cross-Dressing Movies

    added by NipperCSeaturtle
    Justin Theroux, Jill Hennessy, Stephen Dorff

    ;
  44. 44
    + 20
    - 24
    Connie and Carla is listed (or ranked) 44 on the list The Best Cross-Dressing Movies


    David Duchovny, Debbie Reynolds, Toni Collette Released: 2004

    ;
  45. 45
    + 1
    - 0
    First a Girl is listed (or ranked) 45 on the list The Best Cross-Dressing Movies

    new! & added by ZoeKrygiel
    Anna Lee, Martita Hunt, Cameron Hall

    ;
  46. 46
    + 21
    - 26
    Sorority Boys is listed (or ranked) 46 on the list The Best Cross-Dressing Movies


    Brian Posehn, Michael Rosenbaum, Heather Matarazzo Released: 2002

    ;
  47. 47
    + 3
    - 3
    The Brandon Teena Story is listed (or ranked) 47 on the list The Best Cross-Dressing Movies

    added by NipperCSeaturtle
    The Brandon Teena Story

  48. 48
    + 2
    - 2
    Before Night Falls is listed (or ranked) 48 on the list The Best Cross-Dressing Movies

    added by NipperCSeaturtle
    Johnny Depp, Sean Penn, Javier Bardem

    ;
  49. 49
    + 2
    - 2
    Crimes of Passion is listed (or ranked) 49 on the list The Best Cross-Dressing Movies

    added by punksnotdead
    Kathleen Turner, Anthony Perkins, Annie Potts

    ;
  50. 50
    + 1
    - 1
    Cabaret is listed (or ranked) 50 on the list The Best Cross-Dressing Movies

    added by Tom Islava
    Liza Minnelli, Michael York, Joel Grey

    ;
72 +

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