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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Some Like It Hot, The Rocky Horror Picture Show and All About My Mother are all personal favourites.
I also recommend: La Cage aux Folles (1978), The Crying Game (1992) and The Adventures of Priscilla, Queen of the Desert (1994)… no doubt I will think of more!
Priscilla, Queen of the Desert: 1994- Guy Pierce
Switch. – Elli Barkin, Jimmy Smitts
The first movie that shook my grounds being a young boy was – of course- “Rocky Horror Picture Show”. But following that there hasn’t been anything serious to me, not “Tootsie” and alikes. The one movie that makes me see and believe being trans is all possible was “The Crying Game” by Neil Jordan in 1992. Oh god, how I longed to be Dil back then. Unfortunately, it took me another 30 years to step out into the light but that is a different story.
Chris
All of the listed movies are great except one of my favorites, Mrs. Doubtfire.
I suppose it’s not all that current but Mrs. Doubtfire is one.
To Wang Foo Thanks for Everything, Julie Newmar.
These were all good movies. Freebie and the bean and Rocky Horror Picture Show were my favorites. I don’t remember the actors name who played in Freebie And The Bean but she was awesome and beautiful. I would like to be in a movie someday very close to it. The ducumentary “DEVINE” is an excellent must see as well. Paris is Burning was an excellent watch as well. Jackie*
I want what I want – way ahead of its time – movie from the 1960s
The New Girlfriend – great story – very special
The Christine Jorgensen Story – older movie – with good intentions to tell Christine’s story
Zerophilia – Fantasy and adolescent film about some people who change sex during intercourse!