Entertainment

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!
list ordered by
1
To Wong Foo, Thanks for Everyt... is listed (or ranked) 1 on the list The Best Cross-Dressing Movies
crmflava added 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
2
The Rocky Horror Picture Show is listed (or ranked) 2 on the list The Best Cross-Dressing Movies
Susan Sarandon, Tim Curry, Meat Loaf
Released: 1975 The Rocky Horror Picture Show is a 1975 musical horror comedy film directed by Jim Sharman, based on the 1973 musical stage play by Richard O'Brien. A newly engaged couple have a breakdown in an ...more
3
Mrs. Doubtfire is listed (or ranked) 3 on the list The Best Cross-Dressing Movies
Robin Williams, Pierce Brosnan, Sally Field
Released: 1993 Mrs. Doubtfire is a 1993 American comedy-drama film directed by Chris Columbus, based on the novel Alias Madame Doubtfire by Anne Fine. A recently divorced actor (Robin Williams) decides to ...more
4
Tootsie is listed (or ranked) 4 on the list The Best Cross-Dressing Movies
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
5
Some Like It Hot is listed (or ranked) 5 on the list The Best Cross-Dressing Movies
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
6
The Adventures of Priscilla, Q... is listed (or ranked) 6 on the list The Best Cross-Dressing Movies
crmflava added 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
7
The Birdcage is listed (or ranked) 7 on the list The Best Cross-Dressing Movies
Robin Williams, Gene Hackman, Hank Azaria
Released: 1996 The Birdcage is a 1996 American comedy film directed by Mike Nichols, and a remake of the 1978 Franco-Italian film La Cage aux Folles by Édouard Molinaro. A gay cabaret owner (Robin ...more
8
Kinky Boots is listed (or ranked) 8 on the list The Best Cross-Dressing Movies
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
9
Mulan is listed (or ranked) 9 on the list The Best Cross-Dressing Movies
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
10
The Crying Game is listed (or ranked) 10 on the list The Best Cross-Dressing Movies
crmflava added 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
11
Victor Victoria is listed (or ranked) 11 on the list The Best Cross-Dressing Movies
SilverPhoenyx added 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
12
The New Girlfriend is listed (or ranked) 12 on the list The Best Cross-Dressing Movies
stariris99 added 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
13
Just One of the Guys is listed (or ranked) 13 on the list The Best Cross-Dressing Movies
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
14
She's the Man is listed (or ranked) 14 on the list The Best Cross-Dressing Movies
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
15
Just like a Woman is listed (or ranked) 15 on the list The Best Cross-Dressing Movies
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
16
Transamerica is listed (or ranked) 16 on the list The Best Cross-Dressing Movies
MarinaFranco added 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
17
Breakfast on Pluto is listed (or ranked) 17 on the list The Best Cross-Dressing Movies
JesscaWalker added 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
18
Ed Wood is listed (or ranked) 18 on the list The Best Cross-Dressing Movies
but chickens double d added 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
19
Psycho is listed (or ranked) 19 on the list The Best Cross-Dressing Movies
Alfred Hitchcock, Janet Leigh, Anthony Perkins
Released: 1960 Psycho is a 1960 American horror film directed by Alfred Hitchcock. The film centers on an encounter between a secretary, Marion Crane, who ends up at a secluded motel after taking money from ...more
20
The Producers is listed (or ranked) 20 on the list The Best Cross-Dressing Movies
Tom Islava added 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
21
Cabaret is listed (or ranked) 21 on the list The Best Cross-Dressing Movies
Tom Islava added 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
22
Anything for Love is listed (or ranked) 22 on the list The Best Cross-Dressing Movies
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
23
La Cage aux Folles is listed (or ranked) 23 on the list The Best Cross-Dressing Movies
RileyJo81 added 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
24
My Life in Pink is listed (or ranked) 24 on the list The Best Cross-Dressing Movies
NipperCSeaturtle added 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
25
Sorority Boys is listed (or ranked) 25 on the list The Best Cross-Dressing Movies
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 incident they did not