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21 Trans Films Spanning Nearly Four Decades. While there are many excellent documentaries out there, I’ve restricted this list to films.
I also omitted films that emphasized cross-dressing or centered around drag queens, as they deserve their own category.
13 Months (1978)
It’s a dark and unforgiving film about a man who goes to Casablanca to undergo sex reassignment surgery in the hope that the man he loves will care about him, too.
The film has been labeled “difficult to categorize,” being brutal and graphic, but also beautiful and nonsensical at times, and featuring some memorable monologues.
Just Like a Woman (1992)

A comedy-drama about a financial executive yuppie (and closeted transvestite) who is kicked out of his home and divorced because his wife thinks he’s having an affair.
He moved into his new home and slowly revealed his other identity to his recently divorced landlord. The changes were accompanied by humor and warmth, while love and tolerance gradually unfolded.
The Crying Game (1992)

IRA member Fergus forms an unexpected bond with a kidnapped British soldier (Jody) in his charge. After a hostage escape goes terribly wrong, Fergus flees to London to fulfill a promise and visit Jody’s girlfriend.
Amid a conflict with his hunting IRA colleagues, Fergus finds himself caught up in his own emotional struggles, while his romantic feelings for Geordie’s girlfriend emerge.
Mr. Butterfly (1993)

Based on the play of the same name, the series tells the story of a French diplomat who is sent to Beijing during the Cultural Revolution. While adjusting to life in China, he meets a Chinese Peking Opera actress and quickly falls in love with her. However, as their relationship develops and secrets are revealed, he discovers that she is actually a man.
This is a powerful, well-acted, and unforgettable film that should be watched by everyone.
Priscilla Queen of the Desert (1994)

When drag queen Anthony agrees to hit the road, he invites other cross-dressers and transgender friends to join him. The three performers travel across the Australian desert in a colorful bus named Priscilla, performing for enthusiastic audiences and homophobic locals.
But when the other two performers learn the truth about why Anthony took the job, their performances and friendships are threatened.
My Pink Life (1997) Belgian

The film tells the story of Ludovic, who is considered a boy by his family and community but continues to behave like a girl, and follows his family’s struggle to accept this gender expression while fighting the community’s need to “cure” him.
A powerful film that tells everything from suicide to community violence through a child’s eyes.
Boys Don’t Cry (1999)

An Oscar-winning film (based on true events), it tells the story of Brandon Teena, a teenager whose family is forced to relocate due to his gender transition, only to find that the next town over is just as unwelcoming.
Fair warning – some scenes can be difficult to watch and won’t leave you with any warm feelings or sense of closure at the end, but Hilary Swank’s performance is incredible.
Hedwig and the Angry Inch (2001)

A rock musical with a cult following, it tells the story of an East German transgender man who survives a botched sex-change operation and travels with his band, The Angry Inch.
They perform to enthusiastic crowds and homophobic small towns while following an ex-boyfriend on tour as he breaks her heart and takes away the musical soul she has left. NOTE: There are multiple movie/Broadway versions available.
Soldier’s Girl (2003)

After a new soldier (Barry) is sent to Tennessee, he and his cranky, drug-addicted friend go to a drag show. Barry finds himself obsessed with one of the transgender drag queens.
However, as their relationship deepens, Barry’s friend grows resentful and begins spreading rumors… and recruiting his fellow soldiers for deadly revenge. Based on a true story.
Normal (2003)

After 25 years of marriage and being a model citizen in his community, a Midwestern husband/father announced his plans to undergo sex reassignment surgery.
Despite the disapproval of his co-workers, boss, friends, church and family, he has the support of his daughter, his last friend and his loving, steadfast wife. This is a story of devotion and love – most stories would end in divorce and misery.
The Wild Side (2004)

Stephanie is a transgender woman who makes a living as a prostitute in Paris and returns home to care for her ailing mother (who still doesn’t approve of Stephanie’s lifestyle).
She brings in two roommates (one is a Russian soldier who went AWOL, the other an Armenian con man)—but the friendship quickly turns into a romance, and she decides to keep both of them rather than choose.
The Beautiful Boxer (2004) Embassy in Thailand

A biopic about Parinya Charoenphol, a famous transgender woman, Thai boxer, actress and model from Singapore.
The film begins when she is a little girl who loves red lipstick and flowers, and follows her journey to self-acceptance and practicing Taekwondo to pay for surgery.
Pretty Woman(2005)

Bree, a transgender woman preparing to undergo surgery, experiences an unexpected journey when she learns she has a son, who is now a teenage runaway living on the streets of New York City. However, Bree’s social worker will not allow her to proceed with surgery unless she faces and processes this new aspect of her life.
Some scenes are weird, some are crude, but many are touching.
Breakfast on Pluto (2005)

Abandoned as an infant by his mother on the steps of their small Irish town vicarage, Patrick was later found and placed in an abusive foster home.
As a teenager, Patrick admitted that he was transgender, changed his name to “Kitten”, and went to London with a rock band to find his mother. Along the way, he worked as a magician’s assistant, a prostitute and a dancer.
Albert Nobbs (2011)

Albert Nobbs struggles to survive in late 19th century Ireland, where female independence is discouraged. Disguised as a man in order to work as a housekeeper at Dublin’s most elegant hotel, Albert meets a handsome painter and hopes to escape the lie she has been living. Glenn Close gives a stunning performance.
If you plan to watch this film, don’t forget to bring tissues.
Romeo (2011)

The show revolves around the relationship between two young men, one of whom deals with the difficulties of life as a transgender man, while the other supports him along the way.
Many have commented that it is one of the few films that actually focuses on gay transgender issues. And, while the plot may be simple, the characters are not.
Tomboy (2011) French

The play tells the story of a 10-year-old girl who moves to a new town during the summer vacation. She is mistaken for a boy and when asked her name again she says her name is Mickäel and continues to call herself a boy.
Even though the gender transition is more hinted at than stated outright, the conflicts and emotions are still real and sometimes heartbreaking.
Lawrence Anyway (2012) French Canadians

A drama-comedy that follows the decade-long relationship between Laurence (a French teacher, soon-to-be-published author, and transgender woman living as a man) and his fiancée/lover.
We follow them and see their once passionate, loving relationship disintegrate into one filled with anger, pain, on-and-offs, lies, and endless hookups.
Boy Meets Girl (2014)

21-year-old Ricky is a transgender woman who lives in a small town but dreams of moving to New York City to become a designer. She spends most of her time working or hanging out with her only friend, Robby, who has been with her for the past 15 years.
One day, a woman walks into her coffee shop and a friendship unexpectedly blossoms, which then develops into a relationship.
Orange (2015)

The story follows a transgender sex worker who discovers her boyfriend/pimp has been cheating on her while she’s been locked up and tracks her down on Christmas Eve.
The film is unique not only because of its extremely low budget, but also because it was shot entirely on iPhones (a secret that remained secret until the premiere).
The Danish Girl (2015)

Set in Copenhagen in the early 1920s, artist Einer Wgenre is in a relationship with his artist wife. However, after dressing her in a dress (as a body double), he soon discovers that it has inspired him to want to be a woman.
After both psychotherapy and “treatment” failed, Einar decided to undergo the first sex-reassignment surgery in history.
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Also, if you want more interesting, must-read articles, you might like these:
Are there any other great trans films you’ve discovered that aren’t included in this collection? If so, please share them in the comments!