Popular Crossdressing Films

Men in Dresses: A Celebration of Cross-Dressing Men in Popular Movies

Grab some popcorn and bunge watch some of the best movies featuring cross-dressing as a central plot line! For decades, cross-dressing roles in film have been both captivating and controversial, pushing boundaries and sparking conversations about gender, identity, and performance. Beyond simple comedy, these roles can offer insightful portrayals of societal norms, self-discovery, and the fluidity of expression. While the topic has evolved significantly over time, with some films falling short of modern sensitivities, these movies offer a glimpse into the history of cross-dressing representation in cinema.

Here's a list of the top movies featuring men in dresses, and why they're worth watching:

1. Some Like It Hot (1959): A Classic Comedy Gem

Two musicians witness a mob hit and escape by disguising themselves as women in an all-female band. A bombshell Marilyn Monroe is their sweet foil and she alone makes this film a must see for a class in crossdressing and passing!

Why it's worth watching: A timeless classic. The film is hilarious and offers a lighthearted yet surprisingly progressive commentary on gender roles for its time thanks to the performance of Jack Lemmon and Tony Curtis.

2. Tootsie (1982): A Masterclass in Acting and Social Commentary

Synopsis: An out-of-work actor adopts a female persona to land a role in a soap opera, leading to unexpected professional success and personal growth. A crossdressing 

Why it's worth watching: Dustin Hoffman's performance is nothing short of brilliant. Beyond the comedic elements, the film explores sexism in the workplace and the actor's evolving understanding of the female experience.

3. Victor/Victoria (1982): A Musical Extravaganza with a Twist

Synopsis: A starving singer in 1930s Paris finds success by pretending to be a male female impersonator.

Why it's worth watching: Julie Andrews shines in this stylish and witty musical. It plays with gender expectations and explores the freedom and challenges that come with defying societal norms. The costumes and choreography are stunning, and the film offers a sophisticated take on identity and performance.

4. Mrs. Doubtfire (1993): A Heartwarming Family Comedy

Synopsis: A divorced father disguises himself as an elderly female housekeeper to spend more time with his children.

Why it's worth watching: Robin Williams' comedic genius is on full display. While the film relies on comedic tropes related to physical comedy and mistaken identity, it ultimately explores the themes of family, love, and the lengths a parent will go to for their children.

5. The Adventures of Priscilla, Queen of the Desert (1994): A Vibrant Celebration of Identity

Synopsis: Two drag queens and a transgender woman travel across the Australian Outback in a bus named Priscilla, encountering prejudice and acceptance along the way.

Why it's worth watching: A groundbreaking film that helped bring drag culture and transgender themes to a wider audience. It's a visually stunning and emotionally resonant road trip movie that celebrates individuality, friendship, and self-acceptance.

6. Hedwig and the Angry Inch (2001): A Rock Musical with a Powerful Message

Synopsis: An East German singer, who underwent a botched sex reassignment surgery, tours the U.S. with her band while grappling with her identity and past. 

Why it's worth watching: A cult classic and a phenomenal rock musical. It is a profound exploration of gender identity, self-discovery, and the search for wholeness. The music is incredible, and the story is both heartbreaking and inspiring.

7. Connie and Carla (2004): A Silly and Sweet Musical Romp

Synopsis: Two women witness a murder and go into hiding by masquerading as drag queens performing in a gay bar.

Why it's worth watching: Offers a lighthearted and humorous take on the world of drag performance. The film features catchy musical numbers and emphasizes the importance of friendship and finding inner confidence.