The Best Cross-Dressing Movies

Updated January 15, 2021 5.6k votes 1.9k voters 444.2k views87 items

List RulesMovies must feature cross-dressing and cross-dressers.

Here is a list of the best cross-dressing movies that can include a man dressed as a woman or a woman dressed as a man. 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
Released: 1975
Directed by: Jim Sharman
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Tootsie
Bill Murray, Dustin Hoffman
Released: 1982
Directed by: Sydney Pollack
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Mrs. Doubtfire
Robin Williams, Pierce Brosnan
Released: 1993
Directed by: Chris Columbus, Chuck Jones
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The Adventures of Priscilla, Queen of the Desert
Hugo Weaving, Guy Pearce
Released: 1994
Directed by: Stephan Elliott
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Some Like It Hot
Marilyn Monroe, Jack Lemmon
Released: 1959
Directed by: Billy Wilder
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Mulan
Eddie Murphy, Ming-Na Wen
Released: 1998
Directed by: Tony Bancroft, Barry Cook
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Victor Victoria
Julie Andrews, James Garner
Released: 1982
Directed by: Blake Edwards
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Just One of the Guys
Sherilyn Fenn, William Zabka
Released: 1985
Directed by: Lisa Gottlieb
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La Cage aux Folles
Ugo Tognazzi, Michel Serrault
Released: 1978
Directed by: Édouard Molinaro
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Psycho
Alfred Hitchcock, Janet Leigh
Released: 1960
Directed by: Alfred Hitchcock
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To Wong Foo, Thanks for Everything! Julie Newmar
Robin Williams, Naomi Campbell
Released: 1995
Directed by: Beeban Kidron
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Shakespeare in Love
Gwyneth Paltrow, Ben Affleck
Released: 1998
Directed by: John Madden
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The Birdcage
Robin Williams, Gene Hackman
Released: 1996
Directed by: Mike Nichols
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Kinky Boots
Chiwetel Ejiofor, Joel Edgerton
Released: 2005
Directed by: Julian Jarrold
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Dressed to Kill
Michael Caine, Angie Dickinson
Released: 1980
Directed by: Brian De Palma
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The Crying Game
Forest Whitaker, Jim Broadbent
Released: 1992
Directed by: Neil Jordan
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The New Girlfriend
Romain Duris, Anais Demoustier
Released: 2013
Directed by: François Ozon
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Just like a Woman
Julie Walters, Adrian Pasdar
Released: 1992
Directed by: Christopher Monger
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She's the Man
Amanda Bynes, Channing Tatum
Released: 2006
Directed by: Andy Fickman
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Transamerica
Felicity Huffman, Kevin Zegers
Released: 2005
Directed by: Duncan Tucker
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Ed Wood
Johnny Depp, Sarah Jessica Parker
Released: 1994
Directed by: Tim Burton
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Breakfast on Pluto
Liam Neeson, Cillian Murphy
Released: 2005
Directed by: Neil Jordan
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Cabaret
Liza Minnelli, Michael York
Released: 1972
Directed by: Bob Fosse
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Anything for Love
Alanis Morissette, Corey Haim
Released: 1993
Directed by: Michael Keusch
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Stage Beauty
Claire Danes, Alice Eve
Released: 2004
Directed by: Richard Eyre
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Breakfast on Pluto