film The Best Cross-Dressing Movies

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List Rules 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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Mrs. Doubtfire Robin Williams, Pierce Brosnan Sally Field - Released: 1993

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

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

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

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

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

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

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

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Victor Victoria Julie Andrews, James Garner Alex Karras

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Kinky Boots Chiwetel Ejiofor, Joel Edgerton Nick Frost - Released: 2005

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The Crying Game Forest Whitaker, Jim Broadbent Miranda Richardson

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

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Psycho Julianne Moore, Viggo Mortensen Vince Vaughn - Released: 1960

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

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

The Best Dressed Oscar Winning Ladies of the Millennium 15 Amazing Roles Almost Played by Nicolas Cage

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Just like a Woman Julie Walters, Adrian Pasdar Paul Freeman - Released: 1992

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Stage Beauty Claire Danes, Alice Eve Billy Crudup - Released: 2004

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The New Girlfriend Romain Duris, Anaïs Demoustier Raphaël Personnaz

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

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Breakfast on Pluto Liam Neeson, Cillian Murphy Brendan Gleeson

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Transamerica Felicity Huffman, Kevin Zegers Carrie Preston

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

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

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Orlando Tilda Swinton, Billy Zane Toby Jones

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La Cage aux Folles Ugo Tognazzi, Michel Serrault Michel Galabru

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Monty Python and the Holy Grail John Cleese, Terry Gilliam Eric Idle

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My Life in Pink Michèle Laroque, Vincent Grass Jean-Philippe Écoffey

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Anything for Love Alanis Morissette, Corey Haim Nicole Eggert

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Peacock Susan Sarandon, Ellen Page Cillian Murphy

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Ed Wood Johnny Depp, Sarah Jessica Parker Bill Murray

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

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Monty Python's Life of Brian Michael Palin, Terry Jones Eric Idle

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Nuns on the Run Eric Idle, Robbie Coltrane Janet Suzman - Released: 1990

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Robin Hood: Men in Tights Patrick Stewart, Mel Brooks Dave Chappelle

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Albert Nobbs Glenn Close, Jonathan Rhys Meyers Mia Wasikowska

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Cabaret Liza Minnelli, Michael York Joel Grey

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The Adventures of Sebastian Cole Famke Janssen, Gabriel Macht Adrian Grenier

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A Funny Thing Happened on the Way to the Forum Buster Keaton, Jon Pertwee Michael Crawford

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

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The World According to Garp Robin Williams, Glenn Close John Lithgow

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The Producers Gene Wilder, Kenneth Mars Zero Mostel

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Diary of a Mad Black Woman Tyler Perry, Shemar Moore Tamara Taylor

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Yentl Barbra Streisand, Mandy Patinkin Amy Irving

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

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

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Before Night Falls Johnny Depp, Sean Penn Javier Bardem

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I Shot Andy Warhol Justin Theroux, Jill Hennessy Stephen Dorff

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

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The Lion King Whoopi Goldberg, Jeremy Irons Matthew Broderick