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!
list ordered by

1
256 107
Mrs. Doubtfire is listed (or ranked) 1 on the list The Best Cross-Dressing Movies
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

2
289 111
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 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

3
206 84
Tootsie is listed (or ranked) 3 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

4
178 69
Some Like It Hot is listed (or ranked) 4 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

5
136 42
To Wong Foo, Thanks for Everyt... is listed (or ranked) 5 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

6
155 66
The Birdcage is listed (or ranked) 6 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 stars Robin Williams, Gene Hackman, Nathan Lane, and Dianne Wiest. Dan Futterman, Calista Flockhart, Hank Azaria, and ...more

7
129 54
The Adventures of Priscilla, Q... is listed (or ranked) 7 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

8
152 71
Mulan is listed (or ranked) 8 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

9
76 38
Victor Victoria is listed (or ranked) 9 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

10
123 47
Kinky Boots is listed (or ranked) 10 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

11
89 44
The Crying Game is listed (or ranked) 11 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

12
88 54
Just One of the Guys is listed (or ranked) 12 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

13
54 20
The New Girlfriend is listed (or ranked) 13 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

14
82 57
Boys Don't Cry is listed (or ranked) 14 on the list The Best Cross-Dressing Movies
MengshaChen added 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

15
83 39
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
41 18
Breakfast on Pluto is listed (or ranked) 16 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

17
82 72
Psycho is listed (or ranked) 17 on the list The Best Cross-Dressing Movies
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

18
38 17
Transamerica is listed (or ranked) 18 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

19
108 66
She's the Man is listed (or ranked) 19 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

20
48 40
Stage Beauty is listed (or ranked) 20 on the list The Best Cross-Dressing Movies
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

21
26 12
My Life in Pink is listed (or ranked) 21 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

22
25 13
La Cage aux Folles is listed (or ranked) 22 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

23
22 10
Ed Wood is listed (or ranked) 23 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

24
100 107
White Chicks is listed (or ranked) 24 on the list The Best Cross-Dressing Movies
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

25
55 57
Shakespeare in Love is listed (or ranked) 25 on the list The Best Cross-Dressing Movies
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

26
14 5
Cabaret is listed (or ranked) 26 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

27
26 18
Peacock is listed (or ranked) 27 on the list The Best Cross-Dressing Movies
DarleeneTucker added 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

28
46 31
Anything for Love is listed (or ranked) 28 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

29
22 15
Orlando is listed (or ranked) 29 on the list The Best Cross-Dressing Movies
CatherineSchulze added 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.

30
11 3
The Producers is listed (or ranked) 30 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

31
29 25
Midnight in the Garden of Good... is listed (or ranked) 31 on the list The Best Cross-Dressing Movies
Countermoon added 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

32
44 32
Sorority Boys is listed (or ranked) 32 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

33
33 37
Nuns on the Run is listed (or ranked) 33 on the list The Best Cross-Dressing Movies
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

34
45 35
Ladybugs is listed (or ranked) 34 on the list The Best Cross-Dressing Movies
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

35
14 10
Robin Hood: Men in Tights is listed (or ranked) 35 on the list The Best Cross-Dressing Movies
Tom Islava added 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

36
15 12
Monty Python and the Holy Grai... is listed (or ranked) 36 on the list The Best Cross-Dressing Movies
Tom Islava added 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

37
36 37
Dressed to Kill is listed (or ranked) 37 on the list The Best Cross-Dressing Movies
Michael Caine, Angie Dickinson, Dennis Franz Released: 1981 This film is a 1980 American thriller film written and directed by Brian De Palma and starring Michael Caine, Angie Dickinson, Nancy Allen and Keith Gordon. It centers on an event involving a ...more

38
9 5
The World According to Garp is listed (or ranked) 38 on the list The Best Cross-Dressing Movies
CecilSeaside added 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

39
13 10
Monty Python's Life of Brian is listed (or ranked) 39 on the list The Best Cross-Dressing Movies
Tom Islava added 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

40
14 12
Albert Nobbs is listed (or ranked) 40 on the list The Best Cross-Dressing Movies
TamaraWilson added 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

41
13 3
Hurricane Bianca is listed (or ranked) 41 on the list The Best Cross-Dressing Movies
xxxxx added Hurricane Bianca Alan Cumming, Rachel Dratch, Willam Belli

42
10 7
The Adventures of Sebastian Co... is listed (or ranked) 42 on the list The Best Cross-Dressing Movies
NipperCSeaturtle added 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.

43
9 6
First a Girl is listed (or ranked) 43 on the list The Best Cross-Dressing Movies
ZoeKrygiel added 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

44
11 9
A Funny Thing Happened on the ... is listed (or ranked) 44 on the list The Best Cross-Dressing Movies
Tom Islava added 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

45
31 26
Connie and Carla is listed (or ranked) 45 on the list The Best Cross-Dressing Movies
David Duchovny, Debbie Reynolds, Toni Collette Released: 2004 Connie and Carla is a 2004 American comedy film directed by Michael Lembeck and starring Nia Vardalos, Toni Collette, and David Duchovny. The screenplay was written by Vardalos. The film was ...more

46
7 8
Before Night Falls is listed (or ranked) 46 on the list The Best Cross-Dressing Movies
NipperCSeaturtle added 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

47
9 11
Robin Hood is listed (or ranked) 47 on the list The Best Cross-Dressing Movies
Tom Islava added 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

48
8 10
I Shot Andy Warhol is listed (or ranked) 48 on the list The Best Cross-Dressing Movies
NipperCSeaturtle added 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

49
30 29
Flawless is listed (or ranked) 49 on the list The Best Cross-Dressing Movies
Robert De Niro, Philip Seymour Hoffman, Chris Bauer Released: 1999 Flawless is a 1999 crime comedy-drama film that stars Robert De Niro and Philip Seymour Hoffman. It was directed by Joel Schumacher, who also wrote the screenplay. Other cast members include ...more

50
22 29
Twelfth Night: Or What You Wil... is listed (or ranked) 50 on the list The Best Cross-Dressing Movies
Helena Bonham Carter, Ben Kingsley, Kyra Sedgwick Released: 1996 Twelfth Night or What You Will is a 1996 British film adaptation of William Shakespeare's play, directed by Trevor Nunn and featuring an all-star cast. The adaptation is given a northern Central ...more