Top 10 Gender-Bending Films


By Adam Sandel
Drag has been a staple of popular entertainment since the days of the Ancient Greeks. But some films feature characters that take a walk across gender lines with both comic and profound consequences. Here are ten of the best.
10. Tootsie (1982) – Dustin Hoffman stars as an out-of-work actor who disguises himself as a woman and lands a role on a hit soap opera. Romantic tensions and sex farce hijinks ensue, and the film earned 10 Oscar nods (including Best Actor and Best Picture) and a Supporting Actress win for Jessica Lange.
9. Boys Don’t Cry (1999) – Hilary Swank earned instant fame (and her first Oscar) as transgendered teen Brandon Teena who lived as a boy in a small Nebraska town. The film also put Chloe Sevigny on the map as Brandon’s love interest, but despite its compassionate tone, the film and its ultimate violence can be hard to watch.
8. Mrs. Doubtfire (1993) – Robin Williams takes his Tootsie turn as a man who disguises himself as a matronly housekeeper to spend time with his kids after a messy divorce from his ex-wife played by Sally Field. Although primarily a vehicle for Williams’ shtick, life lessons and understanding ultimately follow.
7. La Cage Aux Folles (1978) / The Birdcage (1996) – The 1978 French farce, about a gay nightclub owner and his drag diva lover who try to “play it straight” to please their son’s straight-laced in-laws, is superior to the American re-make starring Robin Williams and Nathan Lane. The film spawned a Broadway musical and is still a camp-fest with heart.
6. Transamerica (2005) – Felicity Huffman got an Oscar nod for her stunning turn as a pre-op male-to-female transsexual who discovers she once fathered a now-teenage son (Kevin Zegers) and the two embark on a road trip of personal discovery.
5. Hedwig and the Angry Inch (2001) – This film version of John Cameron Mitchell’s Off-Broadway musical follows the misadventures of a German transsexual punk rocker named Hedwig: one of the most iconic trans characters on film.
4. The Adventures of Priscilla, Queen of the Desert (1994) – This tale of two Aussie drag queens (Hugo Weaving and Guy Pearce) and their trans co-star (Terence Stamp) who cross the Australian outback to perform at a remote resort is the best drag road trip film ever made. (Skip the American knock-off To Wong Foo… which appeared the following year.)
3. Victor Victoria (1982) – Blake Edwards wrote and directed this classic sex farce starring Julie Andrews as a broke singer who hits it big in Paris disguised as a male female impersonator (a woman disguised as a man disguised as a woman). Robert Preston is delightful as her gay mentor, James Garner is perfect as the straight tycoon who’s perplexed by his attraction to “Victor,” and Lesley Ann Warren nearly steals the show as his brassy girlfriend.
2. Some Like It Hot  (1959) – The great-granddaddy of drag films is also the greatest comedy ever made, with Jack Lemmon and Tony Curtis as 1920’s musicians who dress up as women and join an all-girl band to flee Chicago after witnessing a mob hit. Marilyn Monroe gives the performance of her career as the object of their affection, and every moment in this Billy Wilder film is comic perfection.
1. The Rocky Horror Picture Show (1975) – This rock and roll sex farce horror spoof mash-up is one of the gayest, and weirdest, films ever made. Tim Curry’s Dr. Frank N. Furter, “the sweet transvestite from transsexual Transylvania,” launched a thousand Halloween costumes and the gay, bi, trans romp was a legendary midnight show institution – that caused generations of fans to come out of the closet.

About The Author

Adam Sandel is a playwright, screenwriter, lyricist, journalist and film critic living in San Francisco, California. He's the film writer for dot429 Magazine and is the host of the internet radio show "Happy Hour" on

Send this to friend