The Best Cross-Dressing Movies

Originally By 4k votes 993 voters 311k views 78 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
    + 200
    - 67
    Mrs. Doubtfire is listed (or ranked) 1 on the list The Best Cross-Dressing Movies

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

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  2. 2
    + 209
    - 64
    The Rocky Horror Picture Show is listed (or ranked) 2 on the list The Best Cross-Dressing Movies


    Susan Sarandon, Tim Curry, Meat Loaf Released: 1975

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  3. 3
    + 150
    - 50
    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
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    Some Like It Hot is listed (or ranked) 4 on the list The Best Cross-Dressing Movies


    Marilyn Monroe, Jack Lemmon, Tony Curtis Released: 1959

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  5. 5
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    The Birdcage is listed (or ranked) 5 on the list The Best Cross-Dressing Movies


    Robin Williams, Gene Hackman, Hank Azaria Released: 1996

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  6. 6
    + 93
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    To Wong Foo, Thanks for Everyt... is listed (or ranked) 6 on the list The Best Cross-Dressing Movies

    added by crmflava
    Robin Williams, Naomi Campbell, Patrick Swayze

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  7. 7
    + 79
    - 26
    The Adventures of Priscilla, Q... is listed (or ranked) 7 on the list The Best Cross-Dressing Movies

    added by crmflava
    Hugo Weaving, Guy Pearce, Terence Stamp

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  8. 8
    + 115
    - 45
    Mulan is listed (or ranked) 8 on the list The Best Cross-Dressing Movies


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

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  9. 9
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    - 23
    Victor Victoria is listed (or ranked) 9 on the list The Best Cross-Dressing Movies

    added by SilverPhoenyx
    Julie Andrews, James Garner, Alex Karras

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  10. 10
    + 79
    - 29
    Kinky Boots is listed (or ranked) 10 on the list The Best Cross-Dressing Movies


    Chiwetel Ejiofor, Joel Edgerton, Nick Frost Released: 2005

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  11. 11
    + 70
    - 40
    Just One of the Guys is listed (or ranked) 11 on the list The Best Cross-Dressing Movies


    Sherilyn Fenn, William Zabka, Joyce Hyser Released: 1985

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  12. 12
    + 58
    - 24
    The Crying Game is listed (or ranked) 12 on the list The Best Cross-Dressing Movies

    added by crmflava
    Forest Whitaker, Jim Broadbent, Miranda Richardson

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  13. 13
    + 68
    - 46
    Psycho is listed (or ranked) 13 on the list The Best Cross-Dressing Movies


    Julianne Moore, Viggo Mortensen, Vince Vaughn Released: 1960

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  14. 14
    + 60
    - 41
    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

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  15. 15
    + 83
    - 46
    She's the Man is listed (or ranked) 15 on the list The Best Cross-Dressing Movies


    Amanda Bynes, Channing Tatum, Jessica Lucas Released: 2006

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  16. 16
    + 56
    - 26
    Just like a Woman is listed (or ranked) 16 on the list The Best Cross-Dressing Movies


    Julie Walters, Adrian Pasdar, Paul Freeman Released: 1992

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  17. 17
    + 23
    - 9
    The New Girlfriend is listed (or ranked) 17 on the list The Best Cross-Dressing Movies

    added by stariris99
    The New Girlfriend Romain Duris, Anaïs Demoustier, Raphaël Personnaz

  18. 18
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    - 31
    Stage Beauty is listed (or ranked) 18 on the list The Best Cross-Dressing Movies


    Claire Danes, Alice Eve, Billy Crudup Released: 2004

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  19. 19
    + 23
    - 10
    Breakfast on Pluto is listed (or ranked) 19 on the list The Best Cross-Dressing Movies

    added by JesscaWalker
    Liam Neeson, Cillian Murphy, Brendan Gleeson

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  20. 20
    + 17
    - 5
    Monty Python's The Meaning of ... is listed (or ranked) 20 on the list The Best Cross-Dressing Movies

    added by RileyJo81
    John Cleese, Terry Gilliam, Eric Idle

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  21. 21
    + 17
    - 5
    Transamerica is listed (or ranked) 21 on the list The Best Cross-Dressing Movies

    added by MarinaFranco
    Felicity Huffman, Kevin Zegers, Carrie Preston

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  22. 22
    + 75
    - 75
    White Chicks is listed (or ranked) 22 on the list The Best Cross-Dressing Movies


    Evangeline Lilly, Jaime King, Jennifer Carpenter Released: 2004

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  23. 23
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    - 42
    Shakespeare in Love is listed (or ranked) 23 on the list The Best Cross-Dressing Movies


    Gwyneth Paltrow, Ben Affleck, Judi Dench Released: 1998

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  24. 24
    + 11
    - 2
    La Cage aux Folles is listed (or ranked) 24 on the list The Best Cross-Dressing Movies

    added by RileyJo81
    Ugo Tognazzi, Michel Serrault, Michel Galabru

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  25. 25
    + 15
    - 7
    Orlando is listed (or ranked) 25 on the list The Best Cross-Dressing Movies

    added by CatherineSchulze
    Tilda Swinton, Billy Zane, Toby Jones

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  26. 26
    + 12
    - 4
    My Life in Pink is listed (or ranked) 26 on the list The Best Cross-Dressing Movies

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

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  27. 27
    + 9
    - 1
    Monty Python and the Holy Grai... is listed (or ranked) 27 on the list The Best Cross-Dressing Movies

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

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  28. 28
    + 24
    - 19
    Midnight in the Garden of Good... is listed (or ranked) 28 on the list The Best Cross-Dressing Movies

    added by Countermoon
    Kevin Spacey, Jude Law, John Cusack

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  29. 29
    + 36
    - 24
    Anything for Love is listed (or ranked) 29 on the list The Best Cross-Dressing Movies


    Alanis Morissette, Corey Haim, Nicole Eggert

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  30. 30
    + 17
    - 13
    Peacock is listed (or ranked) 30 on the list The Best Cross-Dressing Movies

    added by DarleeneTucker
    Susan Sarandon, Ellen Page, Cillian Murphy

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  31. 31
    + 7
    - 2
    Monty Python's Life of Brian is listed (or ranked) 31 on the list The Best Cross-Dressing Movies

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

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  32. 32
    + 7
    - 2
    Robin Hood: Men in Tights is listed (or ranked) 32 on the list The Best Cross-Dressing Movies

    added by Tom Islava
    Patrick Stewart, Mel Brooks, Dave Chappelle

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  33. 33
    + 9
    - 5
    Ed Wood is listed (or ranked) 33 on the list The Best Cross-Dressing Movies

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

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  34. 34
    + 25
    - 31
    Nuns on the Run is listed (or ranked) 34 on the list The Best Cross-Dressing Movies


    Eric Idle, Robbie Coltrane, Janet Suzman Released: 1990

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  35. 35
    + 5
    - 2
    The Adventures of Sebastian Co... is listed (or ranked) 35 on the list The Best Cross-Dressing Movies

    added by NipperCSeaturtle
    Famke Janssen, Gabriel Macht, Adrian Grenier

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  36. 36
    + 4
    - 1
    A Funny Thing Happened on the ... is listed (or ranked) 36 on the list The Best Cross-Dressing Movies

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

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  37. 37
    + 22
    - 23
    Diary of a Mad Black Woman is listed (or ranked) 37 on the list The Best Cross-Dressing Movies

    added by MarySSpiegel
    Tyler Perry, Shemar Moore, Tamara Taylor

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  38. 38
    + 7
    - 6
    Albert Nobbs is listed (or ranked) 38 on the list The Best Cross-Dressing Movies

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

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  39. 39
    + 28
    - 32
    Dressed to Kill is listed (or ranked) 39 on the list The Best Cross-Dressing Movies


    Michael Caine, Angie Dickinson, Dennis Franz Released: 1981

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  40. 40
    + 3
    - 1
    Cabaret is listed (or ranked) 40 on the list The Best Cross-Dressing Movies

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

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  41. 41
    + 2
    - 0
    The Producers is listed (or ranked) 41 on the list The Best Cross-Dressing Movies

    added by Tom Islava
    Gene Wilder, Kenneth Mars, Zero Mostel

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  42. 42
    + 2
    - 0
    The World According to Garp is listed (or ranked) 42 on the list The Best Cross-Dressing Movies

    added by CecilSeaside
    Robin Williams, Glenn Close, John Lithgow

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  43. 43
    + 31
    - 29
    Ladybugs is listed (or ranked) 43 on the list The Best Cross-Dressing Movies


    Rodney Dangerfield, Tommy Lasorda, Jonathan Brandis Released: 1992

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  44. 44
    + 1
    - 0
    Yentl is listed (or ranked) 44 on the list The Best Cross-Dressing Movies

    added by CecilSeaside
    Barbra Streisand, Mandy Patinkin, Amy Irving

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  45. 45
    + 2
    - 2
    The Lion King is listed (or ranked) 45 on the list The Best Cross-Dressing Movies

    added by Tom Islava
    Whoopi Goldberg, Jeremy Irons, Matthew Broderick

    ;
  46. 46
    + 2
    - 2
    Robin Hood is listed (or ranked) 46 on the list The Best Cross-Dressing Movies

    added by Tom Islava
    Brian Bedford, Peter Ustinov, Phil Harris

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  47. 47
    + 2
    - 2
    Before Night Falls is listed (or ranked) 47 on the list The Best Cross-Dressing Movies

    added by NipperCSeaturtle
    Johnny Depp, Sean Penn, Javier Bardem

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  48. 48
    + 1
    - 1
    First a Girl is listed (or ranked) 48 on the list The Best Cross-Dressing Movies

    added by ZoeKrygiel
    Anna Lee, Martita Hunt, Cameron Hall

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  49. 49
    + 27
    - 26
    Sorority Boys is listed (or ranked) 49 on the list The Best Cross-Dressing Movies


    Brian Posehn, Michael Rosenbaum, Heather Matarazzo Released: 2002

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  50. 50
    + 4
    - 5
    I Shot Andy Warhol is listed (or ranked) 50 on the list The Best Cross-Dressing Movies

    added by NipperCSeaturtle
    Justin Theroux, Jill Hennessy, Stephen Dorff

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