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The Best Cross-Dressing Movies

Updated January 15, 2021 5.6k votes 1.9k voters 444.2k views87 items

List RulesMovies must feature cross-dressing and cross-dressers.

Here is a list of the best cross-dressing movies that can include a man dressed as a woman or a woman dressed as a man. 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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  • The Rocky Horror Picture Show1
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    The Rocky Horror Picture Show

    Susan Sarandon, Tim Curry

    Released1975

    Directed byJim Sharman

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  • Tootsie2
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    Tootsie

    Bill Murray, Dustin Hoffman

    Released1982

    Directed bySydney Pollack

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  • Mrs. Doubtfire3
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    Mrs. Doubtfire

    Robin Williams, Pierce Brosnan

    Released1993

    Directed byChris Columbus, Chuck Jones

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  • The Adventures of Priscilla, Queen of the Desert4

    Released1994

    Directed byStephan Elliott

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  • Some Like It Hot5
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    Some Like It Hot

    Marilyn Monroe, Jack Lemmon

    Released1959

    Directed byBilly Wilder

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  • Mulan6
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    Mulan

    Eddie Murphy, Ming-Na Wen

    Released1998

    Directed byTony Bancroft, Barry Cook

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  • Victor Victoria7
    78
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    Victor Victoria

    Julie Andrews, James Garner

    Released1982

    Directed byBlake Edwards

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  • Just One of the Guys8
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    Just One of the Guys

    Sherilyn Fenn, William Zabka

    Released1985

    Directed byLisa Gottlieb

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    #57 of 116 The Funniest Movies About High School#5 of 23 Movies You Never Expected To Show Skin

  • La Cage aux Folles9
    36
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    La Cage aux Folles

    Ugo Tognazzi, Michel Serrault

    Released1978

    Directed byÉdouard Molinaro

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  • Psycho10
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    Psycho

    Alfred Hitchcock, Janet Leigh

    Released1960

    Directed byAlfred Hitchcock

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    #7 of 230 The Best Psychological Thrillers of All Time#6 of 722 The Best Horror Movies Of All Time

  • To Wong Foo, Thanks for Everything! Julie Newmar11
    175
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    Released1995

    Directed byBeeban Kidron

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  • Shakespeare in Love12
    47
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    Shakespeare in Love

    Gwyneth Paltrow, Ben Affleck

    Released1998

    Directed byJohn Madden

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  • The Birdcage13
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    The Birdcage

    Robin Williams, Gene Hackman

    Released1996

    Directed byMike Nichols

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  • Kinky Boots14
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    Kinky Boots

    Chiwetel Ejiofor, Joel Edgerton

    Released2005

    Directed byJulian Jarrold

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  • Dressed to Kill15
    35
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    Dressed to Kill

    Michael Caine, Angie Dickinson

    Released1980

    Directed byBrian De Palma

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  • The Crying Game16
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    The Crying Game

    Forest Whitaker, Jim Broadbent

    Released1992

    Directed byNeil Jordan

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  • The New Girlfriend17
    80
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    The New Girlfriend

    Romain Duris, Anais Demoustier

    Released2013

    Directed byFrançois Ozon

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  • Just like a Woman18
    87
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    Just like a Woman

    Julie Walters, Adrian Pasdar

    Released1992

    Directed byChristopher Monger

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  • She's the Man19
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    She's the Man

    Amanda Bynes, Channing Tatum

    Released2006

    Directed byAndy Fickman

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  • Transamerica20
    53
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    Transamerica

    Felicity Huffman, Kevin Zegers

    Released2005

    Directed byDuncan Tucker

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  • Ed Wood21
    45
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    Ed Wood

    Johnny Depp, Sarah Jessica Parker

    Released1994

    Directed byTim Burton

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  • Breakfast on Pluto22
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    Breakfast on Pluto

    Liam Neeson, Cillian Murphy

    Released2005

    Directed byNeil Jordan

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  • Cabaret23
    36
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    Cabaret

    Liza Minnelli, Michael York

    Released1972

    Directed byBob Fosse

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  • Anything for Love24
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    Anything for Love

    Alanis Morissette, Corey Haim

    Released1993

    Directed byMichael Keusch

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  • Stage Beauty25
    44
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    Stage Beauty

    Claire Danes, Alice Eve

    Released2004

    Directed byRichard Eyre

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