Nothing beats unwinding with a good movie. It just so happens that some of the best movies ever made feature transgender, crossdressing, or drag themes.
In this post, I’ve compiled a list of ten must-see transgender and gender bending films that should be on your watch list.
I’ve also included a list of reader-recommended favorites for your viewing pleasure!
The Danish Girl (2015)
The Danish Girl is based on the life of painter Lili Elbe, who transitioned to female in 1930s Denmark. Lili undergoes the world’s first gender reassignment surgery with the support of her wife, Gerda, in this beautiful story of unconditional love.
2. Ma Vie En Rose (1997)
This Golden Globe-winning Belgian film offers a rare look at a child’s transgender experience. Ma Vie en Rose tells the story of Ludovic, a young boy who identifies as a girl and wishes to live as one despite the disapproval of his family and community.
3. Transamerica (2005)
Despite the controversy of a cisgender woman (Felicity Huffman) playing a transgender character, Transamerica helped bring attention to trans issues back in 2005. Bree is a transgender woman in the final stages of her transition who discovers that she fathered a son 17 years ago. They go on a road trip together, and Bree must confront him with the truth about who she truly is.
4. The Rocky Horror Picture Show (1975)
This cult classic musical comedy features Brad and Jane, whose car breaks down during a thunderstorm. They wander into the mansion of Dr. Frank-N-Furter, a crossdressing scientist, and meet a house full of eccentric characters. The Rocky Horror Picture Show is three hours of campy fun and one of those movies everybody should see.
5. Some Like It Hot (1959)
Some Like It Hot was groundbreaking for defying the gender norms of its time. In this 1959 film starring Marilyn Monroe, two male musicians witness a mob murder. To avoid being killed themselves, they disguise themselves as women and join an all-female band. All sorts of hilarious complications ensure in this classic comedy.
6. Tootsie (1982)
Tootsie is another gender bending classic comedy to add to your list. Michael Dorsey, a failed actor, disguises himself as a woman to land a role on a soap opera. He gets the part and becomes a celebrity. This leads to issues when he falls for the leading actress.
7. Kinky Boots (2005)
2005 was a banner year for transgender films and Kinky Boots is a must-see. Charlie Price inherits his father’s shoe factory, which is about to go bankrupt. To save the family business, Charlie is inspired to change the product to drag footwear after meeting the performer, Lola.
8. All About My Mother (1999)
Pablo Almodóvar, a Spanish director, is well-known for his inclusion of trans characters and performers. In All About My Mother, Manuela’s son Esteban is killed in an accident. She goes to Barcelona to share the news with Esteban’s father, who is now living as a transgender woman.
9. Disclosure (2020)
Disclosure is a documentary that examines how transgender people are portrayed in the media. It features Laverne Cox, Alexandra Billings, and Candis Cayne, among other prominent trans actresses, performers, and filmmakers.
10. Paris is Burning (1990)
Paris is Burning is the original documentary that inspired the hit TV show, POSE. It examines the drag ballroom culture of Harlem, NYC in the 1980s and shows the community’s experiences with transphobia, homophobia, and racism during that time period.
What are YOUR favorite transgender / crossdressing movies?
Needless to say, it was hard to narrow down this list to just 10 movies! Have you seen any of these films? If so, what did you think of them?
I’d love to know which transgender / crossdressing movies YOU recommend. Please share in the comments below!
Reader Recommended Movies
P.S. Thank you ladies for the excellent movie recommendations that have been pouring in! I’m going to keep a running list here for your viewing pleasure.
- To Wong Foo, Thanks for Everything! Julie Newmar (1995)
- Freebie and the Bean (1974)
- I Am Divine (2013)
- I Want What I Want (1972)
- The New Girlfriend (2014)
- The Christine Jorgensen Story (1970)
- Anything Possible (2022)
- Dawn, Her Dad and the Tractor (2021)
- Just like a Woman (1992)
- Boy Meets Girl (2014)
- Soldier’s Girl (2003)
- Outrageous (1977)
- Dr Jekyll & Sister Hyde (1971)
- Hedwig and the Angry Inch (2001)
- Victor/Victoria (1982)
- Normal (2003)
- Myra Breckinridge (1970)
- The Celluloid Closet (1995)
- Everybody’s Talking About Jamie (2021)
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