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!

  • 6 ReRanks
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  1. 1
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    most listed
    Harvey Fierstein, Polly Holliday, Robert Prosky Released: 1993

    ) open buy at  
  2. 2
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    - 34

    Lynne Thigpen, Murray Schisgal, Sydney Pollack Released: 1982

    ) open buy at  
  3. 3
    + 148
    - 35

    ranked low on reranks
    Barry Bostwick, Richard O'Brien, Tim Curry Released: 1975

    ) open buy at  
  4. 4
    + 78
    - 27

    Jack Lemmon, Marilyn Monroe, Tony Curtis Released: 1959

    ) open buy at  
  5. 5
    + 93
    - 31

    Nathan Lane, Christine Baranski, Dianne Wiest Released: 1996

    ) open buy at  
  6. 6
    + 38
    - 15

    added by SilverPhoenyx
    James Garner, John Rhys-Davies, Robert Preston

    ) open buy at  
  7. 7
    + 56
    - 35

    Gus Van Sant, Julianne Moore, Viggo Mortensen Released: 1960

    ) open buy at  
  8. 8
    + 51
    - 32

    Katy Boyer, Clayton Rohner, Billy Jayne Released: 1985

    ) open buy at  
  9. 9
    + 46
    - 16

    added by crmflava
    Hugo Weaving, Terence Stamp, Julia Cortez

    ) open buy at  
  10. 10
    + 28
    - 28

    often listed & ranked high on reranks
    Claire Danes, Rupert Everett, Edward Fox Released: 2004

    ) open buy at  
  11. 11
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    - 26

    ranked low on reranks
    June Foray, Harvey Fierstein, Donny Osmond Released: 1998

    ) open buy at  
  12. 12
    + 49
    - 16

    added by crmflava
    Blythe Danner, RuPaul, Naomi Campbell

    ) open buy at  
  13. 13
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    - 22

    Chiwetel Ejiofor, Geoffrey Streatfeild, Sarah-Jane Potts Released: 2005

    ) open buy at  
  14. 14
    + 37
    - 28

    Ben Affleck, Simon Callow, Imelda Staunton Released: 1998

    ) open buy at  
  15. 15
    + 22
    - 26

    often listed
    Robbie Coltrane, Eric Idle, Colin Campbell Released: 1990

    ) open buy at  
  16. 16
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    - 49

    Marlon Wayans, Jaime King, Evangeline Lilly Released: 2004

    ) open buy at  
  17. 17
    + 39
    - 17

    ranked low on reranks & added by crmflava
    Stephen Rea, Jim Broadbent, Forest Whitaker

    ) open buy at  
  18. 18
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    - 28

    added by MengshaChen
    Peter Sarsgaard, Lecy Goranson, Jeannetta Arnette

    ) open buy at  
  19. 19
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    Released: 1988

    ) open buy at  
  20. 20
    + 20
    - 18

    Philip Seymour Hoffman, Rory Cochrane, Daphne Rubin-Vega Released: 1999

    ) open buy at  
  21. 21
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    - 27

    David Margulies, Angie Dickinson, Dennis Franz Released: 1981

    ) open buy at  
  22. 22
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    added by Countermoon
    Kim Hunter, John Cusack, Jack Thompson

    ) open buy at  
  23. 23
    + 14
    - 22

    Ben Kingsley, Richard E. Grant, Imelda Staunton Released: 1996

    ) open buy at  
  24. 24
    + 4
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    added by RileyJo81
    Matt Frewer, Jane Leeves, John Cleese

    ) open buy at  
  25. 25
    + 7
    - 18

    Raf Vallone, George Sanders, Dean Jagger Released: 1969

    ) open buy at  
  26. 26
    + 9
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    Cookie Mueller, Susan Walsh, Mink Stole Released: 1974

    ) open buy at  
  27. 27
    + 2
    - 2

    added by TamaraWilson
    Jonathan Rhys Meyers, Maria Doyle Kennedy, Aaron Taylor-Johnson

    ) open buy at  
  28. 28
    + 3
    - 1

    Leslie Phillips, Sid James, Shirley Eaton

    ) open buy at  
  29. 29
    + 1
    - 1

    added by RileyJo81
    Michel Serrault, Michel Galabru, Walter Lucchini

    ) open buy at  
  30. 30
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    - 33

    ranked low on reranks
    Vinnie Jones, Channing Tatum, Robert Hoffman Released: 2006

    ) open buy at  
  31. 31
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    - 20

    Julie Walters, Adrian Pasdar, Paul Freeman Released: 1992

    ) open buy at  
  32. 32
    + 26
    - 22

    Molly Parker, Alanis Morissette, Kevin McNulty

    ) open buy at  
  33. 33
    + 20
    - 17

    added by MarySSpiegel
    Tamela Mann, Steve Harris, Shemar Moore

    ) open buy at  
  34. 34
    + 11
    - 7

    added by JesscaWalker
    Stephen Rea, Kathryn Pogson, Brendan Gleeson

    ) open buy at  
  35. 35
    + 6
    - 2

    added by CatherineSchulze
    Billy Zane, Tilda Swinton, Ned Sherrin

    ) open buy at  
  36. 36
    + 3
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    added by NipperCSeaturtle
    Hélène Vincent, Cristina Barget, Jean-François ...

    ) open buy at  
  37. 37
    + 2
    - 1

    added by NipperCSeaturtle
    The Brandon Teena Story

    buy at  
  38. 38
    + 20
    - 25

    Rodney Dangerfield, Jackée Harry, Jeannetta Arnette Released: 1992

    ) open buy at  
  39. 39
    + 2
    - 2

    added by but chickens double d
    Vincent D'Onofrio, Martin Landau, Patricia Arquette

    ) open buy at  
  40. 40
    + 2
    - 2

    added by MarinaFranco
    Felicity Huffman, Elizabeth Peña, Stella Maeve

    ) open buy at  
  41. 41
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    added by stariris99
    The New Girlfriend Romain Duris, Anaïs Demoustier, Raphaël Personnaz

    buy at  
  42. 42
    + 1
    - 1

    added by NipperCSeaturtle
    Javier Bardem, John Ortiz, Diego Luna

    ) open buy at  
  43. 43
    + 1
    - 1

    added by NipperCSeaturtle
    Nicole Ari Parker, Gabriel Macht, Clark Gregg

    ) open buy at  
  44. 44
    + 1
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    added by NipperCSeaturtle
    Stephen Dorff, Peter Friedman, Reg Rogers

    ) open buy at  
  45. 45
    + 17
    - 22

    Toni Collette, Dash Mihok, Debbie Reynolds Released: 2004

    ) open buy at  
  46. 46
    + 1
    - 2

    new! & added by NipperCSeaturtle
    Will Smith, Renée Zellweger, Jack Black

    ) open buy at  
  47. 47
    + 7
    - 10

    added by DarleeneTucker
    Graham Beckel, Ellen Page, Josh Lucas

    ) open buy at  
  48. 48
    + 15
    - 24

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

    ) open buy at  
  49. 49
    + 10
    - 18

    Dylan McDermott, Natasha Lyonne, Marilyn Manson Released: 2003

    ) open buy at  
  50. 50
    + 15
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    about to drop off
    Martin Lawrence, Cedric the Entertainer, Nia Long Released: 2000

    ) open buy at  
55 +

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