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!
1. 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, a transgender woman in the final stages of her transition, discovers she fathered a son 17 years ago. They take a road trip, 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 encounter 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 ensue 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 includes insights from Laverne Cox, Alexandra Billings, and Candis Cayne, among other prominent trans actresses, performers, and filmmakers sharing their experiences.
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!
Love,
Lucille
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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I have seen them all. I am a woman, physiology, and physically by choice. I do not consider myself trans, because I have always been female!
I love how you put this, Jane. YES, you are a woman – period!
Great list Lucille! Of course Rocky Horror is indeed a cult classic and likely the first CD/Transvestite movie I saw… and maybe the one that que’d my interest in enhancing my own femininity. (Definitely a must see!) The Danish Girl is such a great story though with such a sad ending.. Lily was soooo courageous. I particularly enjoyed Disclosure with Laverne Cox..and I think is also a must see on the history and current status of gender transitions! Very well done! I recently enjoyed “Anything Possible” …great romantic story…of courage and a modern positive take on what should be possible. One I’m waiting to see is Dawn, her dad and the Tractor… hopefully will find a streaming service that has it this fall. I greatly enjoy an evening alone at home in some nice casual feminine attire and a bowl of popcorn to watch one of these great movies. Thanks for sharing!!
Thanks Lanna! I have not seen Anything’s Possible or Dawn, Her Dad & the Tractor either. Great suggestions. In fact, I’m going to add a running list of reader recommended movies to the post.
Movies – I want what I want , Freebie and the Bean
Some of these films are rather dated now: Some Like It Hot, Tootsie, and even The Rocky Horror Picture Show. They’re still worth seeing, but you have to go in with the understanding that they are period pieces that do not fully reflect current day understanding of the trans experience.
Shirley, that is so true. It’s interesting to see how things have evolved since the earlier movies came out. (Still a ways to go, of course, but hopefully moving in the right direction!)
The Film I saw recently was the British Film JUST LIKE A WOMAN from 1995 that featured Julie Walters as a bored single housewife and Adrian Pasdar as the CD/TV Stephanie!
Perhaps only the British Members of CdH might have seen or remember this but it was really an inspiring and heartwarming film!
Boy meets girl is a great movie and a must-see.
Yes, I agree!
My personal favorites include:
Soldier’s Girl (2003)
The heartbreaking story of romance and loss between a young soldier and a transgender performer.
https://www.imdb.com/title/tt0324013/?ref_=fn_al_tt_1
Outrageous (1977)
The story of the unlikely friendship between a schizophrenic young woman and a female impersonator, featuring amazing impersonations of actresses and singers by Craig Russell
https://www.imdb.com/title/tt0076513/?ref_=fn_al_tt_1
Dr Jekyll & Sister Hyde (1971)
Gender-bending take on the classic tale. Dr. Jekyll is searching for a formula to stave off aging, and discovers a serum using female hormones. He tests on himself (natch) and it turns him into a sensuous (though murderous) woman. Great British Hammer film B horror fare.
https://www.imdb.com/title/tt0068502/
Great list of some lesser known movies. Thanks for sharing, Stefanya!
I’ve seen 2 of the movies on the list some like it hot and rocky horror own kinky boots but haven’t watched it yet. so many movies for girls like us to take inspiration from love tina xxx