Willy/Milly (1986): A drama where Willy/Milly has to choose if they want to be a girl or a boy.
Boys Don't Cry (1999): A drama film based on the real-life story of Brandon Teena, a transgender man who was raped and murdered by his male friends after they discovered he was female assigned at birth (FAAB). The movie received lots of media attention when its star Hilary Swank, who played Brandon, won the Academy Award for Best Actress.
Flying with One Wing (2003): Revolutionary Sri Lankan movie – a transgender man, Manju, is discovered after being taken to a clinic after a car accident. Film contains themes about sexism, homophobia.
Funny Kinda Guy (2005): A documentary following the singer Simon de Voil's transition to manhood, encountering the sacrifice of his female singing voice and his discovery of true love. Directed by Travis Reeves, a man who has also transitioned.
Strange Circus (2005): Yuji, the novelist's assistant, is a transgender man.
Boy I Am (2006): A documentary that explores antagonism in the lesbian community as a result of the increased visibility of transgender men.
Itty Bitty Titty Committee (2007): A comedy about young feminists who spread their message through public art and vandalism. Aggie (played by Lauren Mollica) is transgender, and the only man allowed in the group. He bonds with the main character, Anna, and develops an apparent crush on her.
Sleepaway Camp series (1983, 1988, 1989, 2008): Angela Baker (portrayed by Felissa Rose in the first and fourth installments and Pamela Springsteen in the second and third), the killer and main character of the series, is a trans woman.
Kiss of the Spider Woman (1985): Luis Molina and Valentin Arregui are cell mates in a South American prison. Luis is found guilty of immoral behaviour and Valentin is a political prisoner. To escape reality Luis invents romantic movies, while Valentin tries to keep his mind on the situation he is in. During the time they spend together, the two come to understand and respect one another. Molina is more accurately transgender, if not transsexual.
Just Like a Woman (1992): British comedy-drama film directed by Christopher Monger starring Julie Walters, Adrian Pasdar, and Paul Freeman. The film is based on the novel Geraldine, For the Love of a Transvestite by Monica Jay, and is one of the few "cross-dressing" films in which the hero is actually a transvestite. Gerald Tilson, a finance executive, finds himself thrown out by his wife when she discovers women's underwear in their flat; in fact the clothes belong to him. He takes lodgings with Monica, who gradually discovers his alter ego, "Geraldine".
Orlando (1992): Tilda Swinton portrays Orlando, a character whose sex changes after 2/3 of the film.
Tales of the City (1993): In the miniseries, based on Armistead Maupin's series of novels, Anna Madrigal (played by Olympia Dukakis), the landlady of the San Francisco apartment building in which the story is centered is revealed, in the concluding episode, to be a trans woman.
Better Than Chocolate (1999): Features a sub-plot involving the transsexual character named Judy (Peter Outerbridge), who struggles with family rejection throughout the film and who has a crush on, and ultimately begins a romantic relationship with, lesbian separatist Frances (Ann-Marie MacDonald), who owns the gay & lesbian bookstore in which the film's central character Maggie (Karyn Dwyer) works. Judy also becomes friends with Maggie's somewhat sexually repressed mother, Lila (Wendy Crewson)
Creature (1999): Documentary by Parris Patton about trans woman Stacey Hollywood; a four year chronicle of Stacey's transformation into womanhood, life in the West Hollywood LGBT nightclub scene, and her journey from Los Angeles back home to visit her conservative Christian family in North Carolina.
Todo sobre mi madre (1999): A movie by Pedro Almodóvar focused on Manuela, a nurse whose son is struck by a car and killed. The son's father is a transvestite. Agrado, a friend of Manuela, is a prostitute.
En Soap (English: A Soap, 2006): A Danish film about the love between a (pre-operative) trans woman and a lesbian.
Grilled (2006): A comedy film in which Sofía Vergara plays character of Loridonna, a sultry trans woman who seduces unsuspecting Maurice (Ray Romano) when he and Dave (Kevin James), two desperate meat salesmen, knock on her door. A call from a suicidal friend interrupts signing the contract, so Maurice and Dave offer to drive her to her friend's house, hoping to close the deal. There, troubles multiply as they meet an arms dealer (Kim Coates) - who outs Lori to Maurice just before they got intimate, then hit-men working for a gregarious mob boss (Burt Reynolds).
Red without Blue (2007): A documentary featuring identical twins, one of which transitions to female during the film.
Citulja za Eskobara (2008): Serbian movie includes trans woman named Borko becoming girl named Lela in the meanwhile, as the story goes, with not so much focus on her transition...
Der Spalt (2014): The first movie about the core-misunderstanding of transsexual women. It's about a girl named "Alex", who is born with body-parts that do not fit to her gender. The people around her do not believe that she exists.
Zerophilia (2006): A boy is discovered to be a Zerophiliac, a fictitious genetic disorder, which switches the sex of the protagonist whenever they orgasm.
Wandering Son (2011): An 11-episode anime adaptation produced by AIC Classic based on the manga by Takako Shimura. The story depicts a transgender girl named Shūichi Nitori, and her friend Yoshino Takatsuki, a transgender boy. The series deals with issues such as transsgenderism, gender identity, and the beginning of puberty.
Lyubov-Morkov (2007): A Russian film, Любовь-Морковь Andrei and Marina are married for 7 years and they feel there is no more love. They ask a famous doctor to help them, and he helps... by putting their minds into the bodies of each other. Now Andrei is in his wife's head, so he lives the life of his own wife, who runs an art gallery, and Marina in the body of Andrei becomes a lawyer...
Hit & Miss: Chloë Sevigny plays a transgender woman, Mia. Mia is a contract killer who finds out that her ex-girlfriend, from before transitioning, is dead and that she was pregnant and had their child.
Hollyoaks: In 2010, the character Jason Costello was introduced as the British soap opera's first character to have gender dysphoria.
The L Word: Moira becomes Max, a transsexual man. He becomes aggressive and unpredictable during his transition due to the hormones he is taking, and Jenny then dumps him because she does not want to be in a relationship with a man.
One Piece: Mr. 2 Bon Kurei (better known as Bon Clay in English adaptations) is an okama, or transgender agent, of the criminal organization Baroque Works. Another character, Emporio Ivankov (aka Iva) is the "Queen" of Kamabakka Queendom (Kamabakka literally means "full of transvestites") and possess the powers of the "Horu Horu no Mi" devil's fruit, which grants the user the ability to create and control special hormones that can affect anyone they strike by however the user desires. One of his techniques is Emporio Onna Hormone (エンポリオ･女ホルモン, literally translated as Emporio Female Hormone) which are special female hormones that when injected into a male, causes said male (including Iva himself) to be transformed complete into a female (Iva uses it to change the sex of male opponents and even himself to female)
Orphan Black: Tony Sawicki (formerly Antoinette) is a clone and criminal. He is introduced in season two and is suspected to return in later seasons. Every other known clone in his "batch" is female.
Queer as Folk: Later seasons featured a minor transgender character named Kiki (usually described by other characters as "Kiki the waitress, formerly known as Kenny the Waiter").
The Riches: Sam Malloy, the youngest child of the family on whom the series focuses, is a possibly non-binary pre-teen who usually prefers feminine gender expression, in spite of being assigned male at birth. Sam's parents and siblings respect and accept Sam's gender expression.
Waterloo Road: In 2011, British School-based Drama Waterloo Road introduced fictional transgender character, 'Martin Dunbar' played by Matt Greenwood in Series 7, Episode 2 of the BBC Drama Series. The episode features around the 'coming out' and coming-to-terms story line of the pupil. Kacey Barry, played by Brogan Ellis, is forced to come to terms with her gender issues in series 8 (episode 18, man of the match") when Barry outs Kacey as a girl on the football pitch after Zoe kisses her/him.