Cross-dressing in films often serves as a comedic or dramatic device, allowing characters to explore identity, challenge societal norms, or simply hide in plain sight. This collection of movies showcases the diverse ways filmmakers have used this theme to entertain, enlighten, and sometimes provoke thought. From classic comedies to heartfelt dramas, these films offer a unique lens through which to view gender roles and personal transformation.
Some Like It Hot (1959)
Description: Two musicians witness a mob hit and flee disguised as women in an all-female band, leading to comedic and romantic entanglements.
Fact: The film was groundbreaking for its time, featuring cross-dressing in a mainstream comedy. It was also the last film Marilyn Monroe completed.
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Tootsie (1982)
Description: Dustin Hoffman plays a struggling actor who dresses as a woman to land a role on a soap opera, leading to hilarious and insightful situations about gender roles.
Fact: Dustin Hoffman's character was inspired by real-life experiences of actors who had to cross-dress for roles. The film won an Academy Award for Best Supporting Actress for Jessica Lange.
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Victor/Victoria (1982)
Description: A struggling female singer in 1930s Paris pretends to be a male female impersonator, leading to a series of mistaken identities and romantic complications.
Fact: Julie Andrews won a Golden Globe for her role, and the film was nominated for several Academy Awards.
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The Crying Game (1992)
Description: A twist involving cross-dressing is central to this thriller about an IRA member and his unexpected relationship with a woman.
Fact: The film won the Best Original Screenplay Oscar and was nominated for Best Picture.
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Mrs. Doubtfire (1993)
Description: Robin Williams stars as a father who disguises himself as a British nanny to spend time with his children after losing custody in a divorce.
Fact: The film was inspired by the book "Madame Doubtfire" by Anne Fine. Robin Williams improvised much of his dialogue, leading to numerous outtakes.
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To Wong Foo, Thanks for Everything! Julie Newmar (1995)
Description: Three drag queens travel across America, spreading joy and facing challenges, all while dressed in drag.
Fact: The film features cameos by RuPaul and Quentin Crisp, adding to its cultural significance.
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The Birdcage (1996)
Description: A gay couple, one of whom is a drag queen, must pretend to be straight to meet the conservative parents of their son's fiancée.
Fact: The film is a remake of the French film "La Cage aux Folles." Robin Williams and Nathan Lane's performances were critically acclaimed.
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Big Momma's House (2000)
Description: An FBI agent goes undercover as an elderly woman to catch a criminal, leading to comedic situations.
Fact: Martin Lawrence's performance in drag was both a commercial and critical success, spawning sequels.
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Hairspray (2007)
Description: While not strictly about cross-dressing, the film features characters embracing different gender expressions, notably Edna Turnblad, played by John Travolta in drag.
Fact: John Travolta was not the first choice for Edna; the role was originally played by Divine in the 1988 version.
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Kinky Boots (2005)
Description: A struggling shoe factory owner teams up with a drag queen to produce a line of high-heeled boots for men, leading to personal and professional transformation.
Fact: The film was inspired by a true story and later adapted into a successful Broadway musical.
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