films The Best Cross-Dressing Movies  

All Genre Movies Lists
4.9k votes 1.2k voters 348.4k views 78 items Embed

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!
list ordered by

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

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2
225 83
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Mrs. Doubtfire Robin Williams, Pierce Brosnan, Sally Field Released: 1993

3
175 63
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Tootsie Bill Murray, Dustin Hoffman, Geena Davis Released: 1982

4
144 55
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Some Like It Hot Marilyn Monroe, Jack Lemmon, Tony Curtis Released: 1959

5
141 54
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The Birdcage Robin Williams, Gene Hackman, Hank Azaria Released: 1996

6
113 32
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crmflava added To Wong Foo, Thanks for Everything! Julie Newmar Robin Williams, Naomi Campbell, Patrick Swayze

7
102 42
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crmflava added The Adventures of Priscilla, Queen of the Desert Hugo Weaving, Guy Pearce, Terence Stamp

8
133 58
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Mulan Eddie Murphy, Ming-Na Wen, George Takei Released: 1998

9
67 29
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SilverPhoenyx added Victor Victoria Julie Andrews, James Garner, Alex Karras

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102 39
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Kinky Boots Chiwetel Ejiofor, Joel Edgerton, Nick Frost Released: 2005

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

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76 47
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Just One of the Guys Sherilyn Fenn, William Zabka, Joyce Hyser Released: 1985

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76 48
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MengshaChen added Boys Don't Cry Hilary Swank, Chloë Sevigny, Natalie Zea

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

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MarinaFranco added Transamerica Felicity Huffman, Kevin Zegers, Carrie Preston

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

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63 33
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Just like a Woman Julie Walters, Adrian Pasdar, Paul Freeman Released: 1992

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stariris99 added The New Girlfriend Romain Duris, Anaïs Demoustier, Raphaël Personnaz

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43 36
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Stage Beauty Claire Danes, Alice Eve, Billy Crudup Released: 2004

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28 15
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JesscaWalker added Breakfast on Pluto Liam Neeson, Cillian Murphy, Brendan Gleeson

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

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

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

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

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DarleeneTucker added Peacock Susan Sarandon, Ellen Page, Cillian Murphy

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

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but chickens double d added Ed Wood Johnny Depp, Sarah Jessica Parker, Bill Murray

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

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Tom Islava added The Producers Gene Wilder, Kenneth Mars, Zero Mostel

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

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CatherineSchulze added Orlando Tilda Swinton, Billy Zane, Toby Jones

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Anything for Love Alanis Morissette, Corey Haim, Nicole Eggert

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38 28
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Sorority Boys Brian Posehn, Michael Rosenbaum, Heather Matarazzo Released: 2002

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

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

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

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

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

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

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

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CecilSeaside added Yentl Barbra Streisand, Mandy Patinkin, Amy Irving

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TamaraWilson added Albert Nobbs Glenn Close, Jonathan Rhys Meyers, Mia Wasikowska

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

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NipperCSeaturtle added The Brandon Teena Story

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ZoeKrygiel added First a Girl Anna Lee, Martita Hunt, Cameron Hall

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punksnotdead added Crimes of Passion Kathleen Turner, Anthony Perkins, Annie Potts

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NipperCSeaturtle added I Shot Andy Warhol Justin Theroux, Jill Hennessy, Stephen Dorff

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