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!
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  1. 1
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    Susan Sarandon, Meat Loaf, Tim Curry Released: 1975

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    Robin Williams, Pierce Brosnan, Sally Field Released: 1993

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    Bill Murray, Dustin Hoffman, Geena Davis Released: 1982

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    Robin Williams, Gene Hackman, Calista Flockhart Released: 1996

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    Marilyn Monroe, Jack Lemmon, Tony Curtis Released: 1959

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    Eddie Murphy, George Takei, Donny Osmond Released: 1998

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    Julianne Moore, Vince Vaughn, Viggo Mortensen Released: 1960

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    Chiwetel Ejiofor, Joel Edgerton, Nick Frost Released: 2005

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    added by crmflava Robin Williams, Naomi Campbell, RuPaul

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    added by crmflava Hugo Weaving, Guy Pearce, Terence Stamp

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    added by SilverPhoenyx Julie Andrews, James Garner, Alex Karras

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    Sherilyn Fenn, William Zabka, Arye Gross Released: 1985

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    added by MengshaChen Hilary Swank, Chloë Sevigny, Natalie Zea

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    added by crmflava Forest Whitaker, Jim Broadbent, Miranda Richardson

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    Amanda Bynes, Channing Tatum, Jessica Lucas Released: 2006

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    Gwyneth Paltrow, Ben Affleck, Judi Dench Released: 1998

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    added by MarySSpiegel Tyler Perry, Shemar Moore, Tamara Taylor

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    Evangeline Lilly, Jaime King, Jennifer Carpenter Released: 2004

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    Claire Danes, Alice Eve, Tom Wilkinson Released: 2004

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

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    Julie Walters, Adrian Pasdar, Paul Freeman Released: 1992

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    Eric Idle, Robbie Coltrane, Janet Suzman Released: 1990

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    added by JesscaWalker Liam Neeson, Cillian Murphy, Brendan Gleeson

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

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    added by DarleeneTucker Susan Sarandon, Ellen Page, Cillian Murphy

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    David Duchovny, Toni Collette, Debbie Reynolds Released: 2004

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    Alanis Morissette, Corey Haim, Nicole Eggert

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    added by JesscaWalker Jason Mewes, Kate del Castillo, Tommy Lister

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    added by Countermoon Jude Law, Kevin Spacey, John Cusack

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    added by JesscaWalker

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    Bruce Willis, Brad Dourif, Lesley Ann Warren Released: 1994

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    Adam Sandler, Rachel McAdams, Anna Faris Released: 2003

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    Released: 1988

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    Michael Caine, Angie Dickinson, Dennis Franz Released: 1981

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    Helena Bonham Carter, Ben Kingsley, Kyra Sedgwick Released: 1996

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    Eddie Izzard, Matt LeBlanc, Edward Fox Released: 2001

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    Divine, Mink Stole, Edith Massey Released: 1974

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    Macaulay Culkin, Seth Green, Chloë Sevigny Released: 2003

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    Rodney Dangerfield, Tommy Lasorda, Jonathan Brandis Released: 1992

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    Orson Welles, Max von Sydow, George Sanders Released: 1969

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    Paul Giamatti, Martin Lawrence, Terrence Howard Released: 2000

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    Michael Rosenbaum, Brian Posehn, Harland Williams Released: 2002

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

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    Snub Pollard, James Westerfield, Glenn Corbett Released: 1961

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    Kappei Yamaguchi, Yasunori Matsumoto, Michie Tomizawa Released: 1988

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    Marco Vivio, Michele Soavi, Andrea Occhipinti Released: 1983

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    Alyssa Milano, Tia Carrere, Jonathan Silverman Released: 1992

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    Miss Coco Peru, Eric Stonestreet, Jack Plotnick Released: 2003

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    Bryce Dallas Howard, Kevin Kline, Alfred Molina Released: 1936

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    Riley Smith, Alana Austin, Mary-Margaret Humes Released: 2001

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