This curated list of Western films explores the intriguing theme of cross-dressing, where characters often disguise themselves for various reasons, adding layers of humor, drama, and unexpected plot twists to the classic Western genre. These films not only entertain but also challenge traditional gender roles, providing a fresh perspective on the rugged landscapes of the Wild West.

Calamity Jane (1953)
Description: This musical Western features Doris Day as the legendary Calamity Jane, who dresses as a man to win the heart of Wild Bill Hickok, showcasing the comedic and romantic elements of cross-dressing in the Old West.
Fact: The film's title song, "Secret Love," won the Academy Award for Best Original Song in


The Man Who Shot Liberty Valance (1962)
Description: While not central to the plot, there's a humorous scene where John Wayne's character, Tom Doniphon, briefly dresses as a woman to avoid recognition.
Fact: The film is often cited for its exploration of the myth versus reality in the American West.


The Life and Times of Judge Roy Bean (1972)
Description: Paul Newman's character, Judge Roy Bean, at one point dresses as a woman to escape from a group of outlaws, adding a comedic element to his otherwise stern persona.
Fact: The film was directed by John Huston, who also had a cameo as Grizzly Adams.


The Outlaw Josey Wales (1976)
Description: While not primarily about cross-dressing, the film features a scene where Josey Wales disguises himself as a woman to infiltrate an enemy camp, adding a humorous twist to his character's cunning.
Fact: Clint Eastwood directed and starred in this film, which was a significant departure from his typical Western roles.


The Frisco Kid (1979)
Description: Gene Wilder plays a Polish rabbi who, in one scene, dresses as a woman to escape danger, providing a light-hearted moment in this Western comedy.
Fact: The film was originally intended for Mel Brooks to direct, but he passed it on to Gene Wilder.


The Quick and the Dead (1995)
Description: Sharon Stone's character, Ellen, adopts a male persona to enter a deadly quick-draw competition, showcasing the theme of gender disguise in a high-stakes environment.
Fact: The film was directed by Sam Raimi, known for his work on the "Evil Dead" series.


The Legend of Zorro (2005)
Description: While not a traditional Western, it includes scenes where Zorro disguises himself as a woman to infiltrate a party, blending action with comedic elements of cross-dressing.
Fact: This sequel to "The Mask of Zorro" was the last film to feature Antonio Banderas and Catherine Zeta-Jones as Zorro and Elena.


The Great Train Robbery (1903)
Description: This silent film includes a scene where a character disguises himself as a woman to evade capture, one of the earliest uses of cross-dressing in cinema.
Fact: It is considered one of the first narrative films and was directed by Edwin S. Porter.


The Ballad of Little Jo (1993)
Description: Suzy Amis stars as Josephine Monaghan, who adopts a male identity to survive in the harsh environment of the American West, highlighting the lengths one might go to for survival and independence.
Fact: The film was inspired by the real-life story of Josephine Monaghan, though many details were fictionalized.


The Villain (1979)
Description: Kirk Douglas plays Cactus Jack Slade, who disguises himself as a woman to trick his nemesis, providing a comedic twist to this parody of Western films.
Fact: The film was intended as a spoof of the Western genre, with Douglas playing against type as the villain.
