best movie genres 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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The Rocky Horror Picture Show Susan Sarandon, Tim Curry, Meat Loaf Released: 1975 The Rocky Horror Picture Show is a 1975 British-American musical comedy horror film directed by Jim Sharman. The screenplay was written by Sharman and Richard O'Brien based on the 1973 musical ...more

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Mrs. Doubtfire Robin Williams, Pierce Brosnan, Sally Field Released: 1993 Mrs. Doubtfire is a 1993 American comedy film, starring Robin Williams and Sally Field and based on the novel Alias Madame Doubtfire by Anne Fine. It was directed by Chris Columbus and ...more

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Tootsie Bill Murray, Dustin Hoffman, Geena Davis Released: 1982 Tootsie is a 1982 American comedy-drama film that tells the story of a talented but volatile actor whose reputation for being difficult forces him to adopt a new identity as a woman to land a ...more

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Some Like It Hot Marilyn Monroe, Jack Lemmon, Tony Curtis Released: 1959 Some Like It Hot is a 1959 American comedy film set in 1929, directed by Billy Wilder, starring Marilyn Monroe, Tony Curtis and Jack Lemmon. The film is about two musicians who dress in drag in ...more

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crmflava added To Wong Foo, Thanks for Everything! Julie Newmar Robin Williams, Naomi Campbell, Patrick Swayze To Wong Foo, Thanks for Everything! Julie Newmar is a 1995 American comedy film, starring Wesley Snipes, Patrick Swayze, and John Leguizamo as three New York drag queens who embark on a road ...more

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The Birdcage Robin Williams, Gene Hackman, Hank Azaria Released: 1996 The Birdcage is a 1996 American comedy film, directed by Mike Nichols and stars Robin Williams, Gene Hackman, Nathan Lane, and Dianne Wiest. Dan Futterman, Calista Flockhart, Hank Azaria, and ...more

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crmflava added The Adventures of Priscilla, Queen of the Desert Hugo Weaving, Guy Pearce, Terence Stamp The Adventures of Priscilla, Queen of the Desert is a 1994 Australian comedy-drama film written and directed by Stephan Elliott. The plot follows the journey of two drag queens and a transsexual ...more

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Mulan Eddie Murphy, Ming-Na Wen, George Takei Released: 1998 Mulan is a 1998 American animated musical action-comedy-drama film produced by Walt Disney Feature Animation based on the Chinese legend of Hua Mulan. The 36th animated feature in the Walt ...more

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SilverPhoenyx added Victor Victoria Julie Andrews, James Garner, Alex Karras Victor Victoria is a 1982 film released by Metro-Goldwyn-Mayer and starring Julie Andrews, James Garner, Robert Preston, Lesley Ann Warren, Alex Karras, and John Rhys-Davies. The film was ...more

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Kinky Boots Chiwetel Ejiofor, Joel Edgerton, Nick Frost Released: 2005 Kinky Boots is a 2005 British-American comedy-drama film written by Geoff Deane and Tim Firth, and directed by Julian Jarrold. Based on a true story, the movie tells of a struggling British shoe ...more

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crmflava added The Crying Game Forest Whitaker, Jim Broadbent, Miranda Richardson The Crying Game is a 1992 British psychological thriller drama film written and directed by Neil Jordan. The film explores themes of race, gender, nationality, and sexuality against the backdrop ...more

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Just One of the Guys Sherilyn Fenn, William Zabka, Joyce Hyser Released: 1985 Just One of the Guys is a 1985 comedy film, directed by Lisa Gottlieb. The film is marketed with the tagline "Terri Griffith is about to go where no woman has gone before." It ranked ...more

8 Transgender and Cross-Dressing Cartoon Characters

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MengshaChen added Boys Don't Cry Hilary Swank, Chloë Sevigny, Natalie Zea Boys Don't Cry is a 1999 American independent romantic drama film directed by Kimberly Peirce and co-written by Andy Bienen. The film is a dramatization of the real-life story of Brandon Teena, ...more

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Psycho Julianne Moore, Viggo Mortensen, Vince Vaughn Released: 1960 Psycho is a 1998 American horror film produced and directed by Gus Van Sant for Universal Pictures, a remake of the 1960 film directed by Alfred Hitchcock. Both films are adapted from Robert ...more

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stariris99 added The New Girlfriend Romain Duris, Anaïs Demoustier, Raphaël Personnaz The New Girlfriend is a 2014 French drama film directed by François Ozon, based on the short story of the same name by Ruth Rendell. It had its world premiere at the Toronto International ...more

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MarinaFranco added Transamerica Felicity Huffman, Kevin Zegers, Carrie Preston Transamerica is a 2005 independent comedy-drama film produced by IFC Films and The Weinstein Company. The film tells the story of Bree, a transgender woman, who goes on a road trip with her ...more

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Just like a Woman Julie Walters, Adrian Pasdar, Paul Freeman Released: 1992 Just Like a Woman is a 1992 British comedy-drama film directed by Christopher Monger starring Julie Walters, Adrian Pasdar, and Paul Freeman. The film is based on the novel Geraldine, For the ...more

The Best Fantasy Movies

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She's the Man Amanda Bynes, Channing Tatum, Jessica Lucas Released: 2006 She's the Man is a 2006 American romantic comedy film directed by Andy Fickman, inspired by William Shakespeare's play Twelfth Night. The film stars Amanda Bynes, Channing Tatum, Laura Ramsey, ...more

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JesscaWalker added Breakfast on Pluto Liam Neeson, Cillian Murphy, Brendan Gleeson Breakfast on Pluto is a 2005 comedy-drama film written and directed by Neil Jordan and based on the novel of the same name by Patrick McCabe, as adapted by Jordan and McCabe. This dark comedy ...more

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Stage Beauty Claire Danes, Alice Eve, Billy Crudup Released: 2004 Stage Beauty is a 2004 British-American-German romantic period drama directed by Richard Eyre. The screenplay by Jeffrey Hatcher is based on his play Compleat Female Stage Beauty, which was ...more

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RileyJo81 added La Cage aux Folles Ugo Tognazzi, Michel Serrault, Michel Galabru La Cage aux Folles is a 1978 French-Italian film adaptation of the 1973 play La Cage aux Folles by Jean Poiret. It is co-written and directed by Édouard Molinaro and stars Ugo Tognazzi ...more

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White Chicks Evangeline Lilly, Jaime King, Jennifer Carpenter Released: 2004 White Chicks is a 2004 American buddy cop comedy film written, produced and directed by Keenen Ivory Wayans, and also written and produced by Wayans brothers Shawn and Marlon Wayans, who also ...more

The Best War Movies Ever

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NipperCSeaturtle added My Life in Pink Michèle Laroque, Vincent Grass, Jean-Philippe Écoffey Ma vie en rose is a 1997 Belgian drama film directed by Alain Berliner. It tells the story of Ludovic, a child who is seen by family and community as a boy, but consistently communicates being a ...more

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Shakespeare in Love Gwyneth Paltrow, Ben Affleck, Judi Dench Released: 1998 Shakespeare in Love is a 1998 British-American romantic comedy-drama film directed by John Madden, written by Marc Norman and playwright Tom Stoppard. The film depicts an imaginary love affair ...more

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DarleeneTucker added Peacock Susan Sarandon, Ellen Page, Cillian Murphy Peacock is a 2010 American psychological thriller directed by Michael Lander, written by Lander and Ryan Roy, and starring Cillian Murphy, Ellen Page and Susan Sarandon. It was editor Sally ...more

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RileyJo81 added Monty Python's The Meaning of Life John Cleese, Terry Gilliam, Eric Idle Monty Python's The Meaning of Life, also known as The Meaning of Life, is a 1983 British musical sketch comedy film written and performed by the Monty Python troupe, and directed by one of its ...more

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Countermoon added Midnight in the Garden of Good and Evil Kevin Spacey, Jude Law, John Cusack Midnight in the Garden of Good and Evil is a 1997 American crime drama film directed by Clint Eastwood, and an adaptation of the book of the same name by John Berendt, which was based on ...more

The Dumbest Movie Sequel Titles

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Anything for Love Alanis Morissette, Corey Haim, Nicole Eggert Anything for Love is a 1993 direct-to-video teen comedy film, starring Corey Haim and Nicole Eggert. It was aired on television in the United States as Just One of the Girls, and as He's My Girl ...more

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but chickens double d added Ed Wood Johnny Depp, Sarah Jessica Parker, Bill Murray Ed Wood is a 1994 American period comedy-drama biopic directed and produced by Tim Burton, and starring Johnny Depp as cult filmmaker Ed Wood. The film concerns the period in Wood's life when he ...more

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CatherineSchulze added Orlando Tilda Swinton, Billy Zane, Toby Jones Orlando is a 1992 drama romance film written by Sally Potter and Virginia Woolf and directed by Sally Potter.

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Tom Islava added Robin Hood: Men in Tights Patrick Stewart, Mel Brooks, Dave Chappelle Robin Hood: Men in Tights is a 1993 French-American musical adventure comedy film and a parody of the Robin Hood story. Produced and directed by Mel Brooks, the film stars Cary Elwes, Richard ...more

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Nuns on the Run Eric Idle, Robbie Coltrane, Janet Suzman Released: 1990 Nuns on the Run is a 1990 British comedy film starring Eric Idle and Robbie Coltrane, also featuring Camille Coduri and Janet Suzman. It was written and directed by Jonathan Lynn and produced by ...more

36 Rare Photos From World War II

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Tom Islava added Monty Python and the Holy Grail John Cleese, Terry Gilliam, Eric Idle Monty Python and the Holy Grail is a 1975 British comedy film written and performed by the comedy group of Monty Python, and directed by Gilliam and Jones. It was conceived during the hiatus ...more

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Tom Islava added Cabaret Liza Minnelli, Michael York, Joel Grey Cabaret is a 1972 musical film directed by Bob Fosse and starring Liza Minnelli, Michael York and Joel Grey. The film is set in Berlin during the Weimar Republic in 1931, under the ominous ...more

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Sorority Boys Brian Posehn, Michael Rosenbaum, Heather Matarazzo Released: 2002 Sorority Boys is a 2002 American comedy film directed by Wallace Wolodarsky, about a group of college guys who dress up as women in order to prove their innocence for a crime they did not

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Tom Islava added The Producers Gene Wilder, Kenneth Mars, Zero Mostel The Producers is a 1968 American satirical dark comedy film written and directed by Mel Brooks. The film is set in the late 1960s and it tells the story of a theatrical producer and an ...more

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Dressed to Kill Michael Caine, Angie Dickinson, Dennis Franz Released: 1981 Dressed to Kill is a 1980 American erotic crime thriller film written and directed by Brian De Palma and starring Michael Caine, Angie Dickinson, Nancy Allen and Keith Gordon. It centers on the ...more

30 Realizations That Will Change Your Life in Some Small Way

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Tom Islava added Monty Python's Life of Brian Michael Palin, Terry Jones, Eric Idle Monty Python's Life of Brian is an album released by Monty Python in conjunction with the 1979 film Monty Python's Life of Brian. It mostly contains scenes from the movie with only brief linking ...more

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Ladybugs Rodney Dangerfield, Tommy Lasorda, Jonathan Brandis Released: 1992 Ladybugs is a sports-comedy family film released in 1992 starring Rodney Dangerfield and directed by Sidney J. Furie. Dangerfield plays a businessman who takes over a girls soccer team which the ...more

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CecilSeaside added The World According to Garp Robin Williams, Glenn Close, John Lithgow The World According to Garp is 1982 American comedy-drama film directed by George Roy Hill and starring Robin Williams in the title role. It is based on the novel of the same title by John ...more

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NipperCSeaturtle added The Adventures of Sebastian Cole Famke Janssen, Gabriel Macht, Adrian Grenier The Adventures of Sebastian Cole is a 1998 American comedy-drama film written and directed by Tod Williams and starring Adrian Grenier as the title character.

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Tom Islava added A Funny Thing Happened on the Way to the Forum Buster Keaton, Jon Pertwee, Michael Crawford A Funny Thing Happened on the Way to the Forum is a 1966 farce musical comedy film, based on the stage musical of the same name. It was inspired by the farces of the ancient Roman playwright ...more

15 Amazing Roles Almost Played by Nicolas Cage

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ZoeKrygiel added First a Girl Anna Lee, Martita Hunt, Cameron Hall First a Girl is a 1935 British comedy film directed by Victor Saville and starring Jessie Matthews. First a Girl was adapted from the 1933 German film Viktor und Viktoria written and directed by ...more

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NipperCSeaturtle added Before Night Falls Johnny Depp, Sean Penn, Javier Bardem Before Night Falls is a 2000 American drama film directed by Julian Schnabel. The screenplay is based on the autobiography of the same name of Reinaldo Arenas, which was published in English in ...more

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TamaraWilson added Albert Nobbs Glenn Close, Jonathan Rhys Meyers, Mia Wasikowska Albert Nobbs is a 2011 drama film directed by Rodrigo García and starring Glenn Close. The screenplay is based on a novella by Irish novelist George Moore. The film received mixed ...more

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CecilSeaside added Yentl Barbra Streisand, Mandy Patinkin, Amy Irving Yentl is a 1983 romantic musical drama film from United Artists, and directed, co-written, co-produced, and starring Barbra Streisand based on the play of the same name by Leah Napolin and Isaac ...more

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NipperCSeaturtle added I Shot Andy Warhol Justin Theroux, Jill Hennessy, Stephen Dorff I Shot Andy Warhol is a 1996 independent film about the life of Valerie Solanas and her relationship with the artist Andy Warhol. The movie marked the debut of Canadian director Mary Harron. The ...more

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punksnotdead added Crimes of Passion Kathleen Turner, Anthony Perkins, Annie Potts Crimes of Passion is a 1984 film directed by Ken Russell starring Kathleen Turner, Anthony Perkins, John Laughlin and Annie Potts. The film explores themes of human relationships and mental ...more

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Hurricane Bianca is listed (or ranked) 49 on the list The Best Cross-Dressing Movies
xxxxx added Hurricane Bianca Alan Cumming, Rachel Dratch, Willam Belli

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Tom Islava added Robin Hood Brian Bedford, Peter Ustinov, Phil Harris Robin Hood is a 1973 American animated film produced by Walt Disney Productions which was first released in the United States on November 8, 1973. The 21st animated feature in the Walt Disney ...more