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The Best Cross-Dressing Movies 

Ranker Film
Originally by
Updated March 21, 2019 6.9k votes 1.8k voters 436.4k views 73 items

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!

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1
The Rocky Horror Picture... is listed (or ranked) 1 on the list The Best Cross-Dressing Movies
Susan Sarandon, Tim Curry, Meat Loaf

Released: 1975

Directed by: Jim Sharman

Released: 1975 The Rocky Horror Picture Show is a 1975 musical horror comedy film by 20th Century Fox produced by Lou Adler and Michael White and directed by Jim Sharman. The screenplay was written by Sharman ...more

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2
Mrs. Doubtfire is listed (or ranked) 2 on the list The Best Cross-Dressing Movies
Robin Williams, Pierce Brosnan, Sally Field

Released: 1993

Directed by: Chris Columbus, Chuck Jones

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

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3
Tootsie is listed (or ranked) 3 on the list The Best Cross-Dressing Movies
Bill Murray, Dustin Hoffman, Geena Davis

Released: 1982

Directed by: Sydney Pollack

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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4
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

Directed by: Billy Wilder

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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5
The Adventures of Prisci... is listed (or ranked) 5 on the list The Best Cross-Dressing Movies
crmflava added Hugo Weaving, Guy Pearce, Terence Stamp

Released: 1994

Directed by: Stephan Elliott

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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6
Mulan is listed (or ranked) 6 on the list The Best Cross-Dressing Movies
Eddie Murphy, Ming-Na Wen, George Takei

Released: 1998

Directed by: Tony Bancroft, Barry Cook

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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7
Victor Victoria is listed (or ranked) 7 on the list The Best Cross-Dressing Movies
SilverPhoenyx added Julie Andrews, James Garner, Alex Karras

Released: 1982

Directed by: Blake Edwards

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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8
Just One of the Guys is listed (or ranked) 8 on the list The Best Cross-Dressing Movies
Sherilyn Fenn, William Zabka, Joyce Hyser

Released: 1985

Directed by: Lisa Gottlieb

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

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9
Psycho is listed (or ranked) 9 on the list The Best Cross-Dressing Movies
Alfred Hitchcock, Janet Leigh, Anthony Perkins

Released: 1960

Directed by: Alfred Hitchcock

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

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10
La Cage aux Folles is listed (or ranked) 10 on the list The Best Cross-Dressing Movies
RileyJo81 added Ugo Tognazzi, Michel Serrault, Michel Galabru

Released: 1978

Directed by: Édouard Molinaro

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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11
To Wong Foo, Thanks for ... is listed (or ranked) 11 on the list The Best Cross-Dressing Movies
crmflava added Robin Williams, Naomi Campbell, Patrick Swayze

Released: 1995

Directed by: Beeban Kidron

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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12
The Birdcage is listed (or ranked) 12 on the list The Best Cross-Dressing Movies
Robin Williams, Gene Hackman, Hank Azaria

Released: 1996

Directed by: Mike Nichols

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

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13
Shakespeare in Love is listed (or ranked) 13 on the list The Best Cross-Dressing Movies
Gwyneth Paltrow, Ben Affleck, Judi Dench

Released: 1998

Directed by: John Madden

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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14
Kinky Boots is listed (or ranked) 14 on the list The Best Cross-Dressing Movies
Chiwetel Ejiofor, Joel Edgerton, Nick Frost

Released: 2005

Directed by: Julian Jarrold

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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15
Dressed to Kill is listed (or ranked) 15 on the list The Best Cross-Dressing Movies
Michael Caine, Angie Dickinson, Dennis Franz

Released: 1980

Directed by: Brian De Palma

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

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16
The Crying Game is listed (or ranked) 16 on the list The Best Cross-Dressing Movies
crmflava added Forest Whitaker, Jim Broadbent, Miranda Richardson

Released: 1992

Directed by: Neil Jordan

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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17
She's the Man is listed (or ranked) 17 on the list The Best Cross-Dressing Movies
Amanda Bynes, Channing Tatum, Jessica Lucas

Released: 2006

Directed by: Andy Fickman

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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18
Just like a Woman is listed (or ranked) 18 on the list The Best Cross-Dressing Movies
Julie Walters, Adrian Pasdar, Paul Freeman

Released: 1992

Directed by: Christopher Monger

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
19
The New Girlfriend is listed (or ranked) 19 on the list The Best Cross-Dressing Movies
stariris99 added Romain Duris, Anaïs Demoustier, Raphaël Personnaz

Released: 2014

Directed by: François Ozon

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
20
Transamerica is listed (or ranked) 20 on the list The Best Cross-Dressing Movies
MarinaFranco added Felicity Huffman, Kevin Zegers, Carrie Preston

Released: 2005

Directed by: Duncan Tucker

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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21
Breakfast on Pluto is listed (or ranked) 21 on the list The Best Cross-Dressing Movies
JesscaWalker added Breakfast on Pluto Liam Neeson, Cillian Murphy, Brendan Gleeson

Released: 2005

Directed by: Neil Jordan

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22
White Chicks is listed (or ranked) 22 on the list The Best Cross-Dressing Movies
Shawn Wayans, Marlon Wayans, Jaime King

Released: 2004

Directed by: Keenen Ivory Wayans

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23
Anything for Love is listed (or ranked) 23 on the list The Best Cross-Dressing Movies
Alanis Morissette, Corey Haim, Nicole Eggert

Released: 1993

Directed by: Michael Keusch

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24
Ed Wood is listed (or ranked) 24 on the list The Best Cross-Dressing Movies
but chickens double d added Johnny Depp, Sarah Jessica Parker, Bill Murray

Released: 1994

Directed by: Tim Burton

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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25
Sorority Boys is listed (or ranked) 25 on the list The Best Cross-Dressing Movies
Brian Posehn, Michael Rosenbaum, Heather Matarazzo

Released: 2002

Directed by: Wallace Wolodarsky

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