The Best Cross-Dressing Movies Films

The Best Cross-Dressing Movies

Originally By 3.5k votes 823 voters 282k views 70 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
    + 191
    - 50
    The Rocky Horror Picture Show is listed (or ranked) 1 on the list The Best Cross-Dressing Movies


    The Rocky Horror Picture Show Susan Sarandon, Tim Curry, Meat Loaf Released: 1975

  2. 2
    + 179
    - 60
    Mrs. Doubtfire is listed (or ranked) 2 on the list The Best Cross-Dressing Movies

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

  3. 3
    + 130
    - 44
    Tootsie is listed (or ranked) 3 on the list The Best Cross-Dressing Movies


    Tootsie Bill Murray, Dustin Hoffman, Geena Davis Released: 1982

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


    The Birdcage Robin Williams, Gene Hackman, Hank Azaria Released: 1996

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


    Some Like It Hot Marilyn Monroe, Jack Lemmon, Tony Curtis Released: 1959

  6. 6
    + 71
    - 19
    The Adventures of Priscilla, Q... is listed (or ranked) 6 on the list The Best Cross-Dressing Movies

    added by crmflava
    The Adventures of Priscilla, Queen of the Desert Hugo Weaving, Guy Pearce, Terence Stamp

  7. 7
    + 100
    - 40
    Mulan is listed (or ranked) 7 on the list The Best Cross-Dressing Movies


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

  8. 8
    + 79
    - 17
    To Wong Foo, Thanks for Everyt... is listed (or ranked) 8 on the list The Best Cross-Dressing Movies

    added by crmflava
    To Wong Foo, Thanks for Everything! Julie Newmar Robin Williams, Naomi Campbell, Patrick Swayze

  9. 9
    + 45
    - 20
    Victor Victoria is listed (or ranked) 9 on the list The Best Cross-Dressing Movies

    added by SilverPhoenyx
    Victor Victoria Julie Andrews, James Garner, Alex Karras

  10. 10
    + 65
    - 38
    Just One of the Guys is listed (or ranked) 10 on the list The Best Cross-Dressing Movies


    Just One of the Guys Sherilyn Fenn, William Zabka, Joyce Hyser Released: 1985

  11. 11
    + 70
    - 25
    Kinky Boots is listed (or ranked) 11 on the list The Best Cross-Dressing Movies

    ranked low on reranks
    Kinky Boots 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

    ;
  13. 13
    + 54
    - 38
    Boys Don't Cry is listed (or ranked) 13 on the list The Best Cross-Dressing Movies

    added by MengshaChen
    Boys Don't Cry Hilary Swank, Chloë Sevigny, Natalie Zea

  14. 14
    + 52
    - 21
    The Crying Game is listed (or ranked) 14 on the list The Best Cross-Dressing Movies

    added by crmflava
    The Crying Game Forest Whitaker, Jim Broadbent, Miranda Richardson

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

    often listed & ranked high on reranks
    Claire Danes, Alice Eve, Billy Crudup Released: 2004

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


    She's the Man Amanda Bynes, Channing Tatum, Jessica Lucas Released: 2006

  17. 17
    + 68
    - 63
    White Chicks is listed (or ranked) 17 on the list The Best Cross-Dressing Movies


    White Chicks Evangeline Lilly, Jaime King, Jennifer Carpenter Released: 2004

  18. 18
    + 45
    - 21
    Just like a Woman is listed (or ranked) 18 on the list The Best Cross-Dressing Movies

    ranked low on reranks
    Julie Walters, Adrian Pasdar, Paul Freeman Released: 1992

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


    Shakespeare in Love Gwyneth Paltrow, Ben Affleck, Judi Dench Released: 1998

  20. 20
    + 10
    - 4
    Monty Python's The Meaning of ... is listed (or ranked) 20 on the list The Best Cross-Dressing Movies

    added by RileyJo81
    Monty Python's The Meaning of Life John Cleese, Terry Gilliam, Eric Idle

  21. 21
    + 8
    - 1
    La Cage aux Folles is listed (or ranked) 21 on the list The Best Cross-Dressing Movies

    added by RileyJo81
    La Cage aux Folles Ugo Tognazzi, Michel Serrault, Michel Galabru

  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

    ;
  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

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


    Dressed to Kill Michael Caine, Angie Dickinson, Dennis Franz Released: 1981

  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


    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
    + 16
    - 24
    Twelfth Night: Or What You Wil... is listed (or ranked) 29 on the list The Best Cross-Dressing Movies

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

    ;
  30. 30
    + 9
    - 3
    Transamerica is listed (or ranked) 30 on the list The Best Cross-Dressing Movies

    added by MarinaFranco
    Transamerica Felicity Huffman, Kevin Zegers, Carrie Preston

  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
    Midnight in the Garden of Good and Evil Kevin Spacey, Jude Law, John Cusack

  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

    ;
  36. 36
    + 26
    - 28
    Ladybugs is listed (or ranked) 36 on the list The Best Cross-Dressing Movies


    Ladybugs Rodney Dangerfield, Tommy Lasorda, Jonathan Brandis Released: 1992

  37. 37
    + 4
    - 1
    Monty Python's Life of Brian is listed (or ranked) 37 on the list The Best Cross-Dressing Movies

    added by Tom Islava
    Monty Python's Life of Brian Michael Palin, Terry Jones, Eric Idle

  38. 38
    + 4
    - 1
    Monty Python and the Holy Grai... is listed (or ranked) 38 on the list The Best Cross-Dressing Movies

    added by Tom Islava
    Monty Python and the Holy Grail John Cleese, Terry Gilliam, 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
    Ed Wood 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
    Diary of a Mad Black Woman 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


    Connie and Carla David Duchovny, Debbie Reynolds, Toni Collette Released: 2004

  45. 45
    + 21
    - 26
    Sorority Boys is listed (or ranked) 45 on the list The Best Cross-Dressing Movies


    Sorority Boys Brian Posehn, Michael Rosenbaum, Heather Matarazzo Released: 2002

  46. 46
    + 3
    - 3
    The Brandon Teena Story is listed (or ranked) 46 on the list The Best Cross-Dressing Movies

    added by NipperCSeaturtle
    The Brandon Teena Story

  47. 47
    + 2
    - 2
    Crimes of Passion is listed (or ranked) 47 on the list The Best Cross-Dressing Movies

    added by punksnotdead
    Kathleen Turner, Anthony Perkins, Annie Potts

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

    added by NipperCSeaturtle
    Before Night Falls Johnny Depp, Sean Penn, Javier Bardem

  49. 49
    + 1
    - 1
    Cabaret is listed (or ranked) 49 on the list The Best Cross-Dressing Movies

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

  50. 50
    + 13
    - 20
    Torch Song Trilogy is listed (or ranked) 50 on the list The Best Cross-Dressing Movies


    Released: 1988

    ;
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