Several movies feature transgender as a central plot element, or well known movies in which a transgender/transsexual character plays a minor but important role:
Milly/Willy (1986): A drama where Milly/Milly has to chose if she/he wants 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 transsexual 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.
Romeos (2011): A drama and tragicomedy which revolves around the romantic relationship between Lukas, a 20 year old gaytrans man who is transitioning from female to male, and a cisgender gay man named Fabio.
The Christine Jorgensen Story (1970): Former Army private from the Bronx undergoes surgery and hormone treatments in Denmark in 1952 to transition from male to female.
Dr. Jekyll and Sister Hyde (1971): A different take on the Dr. Jekyll and Mr. Hyde story in which the main character's transformation also involves a sex change.
Dog Day Afternoon (1975): Al Pacino's lover, played by Chris Sarandon, was a pre-operative transgender woman. Pacino's character was robbing a bank to pay for the operation.
Salò, or the 120 Days of Sodom (1975) – Directed by Pier Paolo Pasolini: The four masters dress in women's clothes and coerce their male victims, clothed in wedding dresses, into same-sex marriage.
The World According to Garp (1982): In this film, the character Roberta Muldoon (played by John Lithgow in an Oscar-nominated role) is a transgender former football player.
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.
Soapdish (1991): In this soap opera parody, Montana Morehead (Cathy Moriarty), the show's star and scheming antagonist, is revealed, on live television, as a transgender woman.
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.
A Transgender Path (1995): A documentary short about the experiences of Jo Ryan, a transgender student at the University of New Hampshire who came out in the early 1990s.
Different for Girls (1996): A British comedy film about two childhood friends who are reunited, after one of them has undergone sex reassignment surgery.
Ma vie en rose (1997): A Belgian film about a young child, Ludovic, who believes that he was born in the wrong body and should have been a girl.
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.
Hedwig and the Angry Inch (2001): An off-Broadway cult musical adapted for cinema about a transgender German glam rocker (John Cameron Mitchell) recounting the story of her betrayal by her former boyfriend.
Beautiful Boxer (2003): A Thai film based on the real life story of Nong Thoom/Parinya Charoenphol, a Muaythai boxer who underwent a sex change operation to become a woman.
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...
Mora The Explorer (2010): A children's series animated shorts, based on the children's book series of the same name, spanning, 3 episodes, film short (in discussion with PIXAR/ DreamWorks and Sony pictures). The plot revolves around a cat named, Mora The Explorer a Male to Female Trans woman becomes a young girl again when they discover a magical world to fight against Anti-Violence in their kitchen. Starred, Voice-over-Narrated by International OUT! celebrity (Author, Actress, Activist, Model, Producer, Director, Recording Artist) trans woman Jenna Fox (played by the Out-nominated Jenna Fox).
Ticked-Off Trannies With Knives (2010): A rape/revenge "transploitation" film about a trio of trans women who avenge themselves on three men who brutally attack them and kill two of their friends.
"Gun Hill Road" (2011): A drama about a recently released ex-convict coping with his estranged wife and son, who is going through transition from male to female.
The Forgotten DJ/ Model (2011): A drama/Bio film. The plot revolves around an International celebrity trans woman named Jenna Fox (played by the Oscar-nominated Jenna Fox).
Jane Friday (2011): A supernatural film series, spanning, 13 episodes, three feature films. The plot revolves around an trans woman detective, named Jane Friday, with a talking black cat as a partner. Starred International OUT! celebrity (Author, Actress, Activist, Model, Producer, Director, Recording Artist) trans woman Jenna Fox (played by the Out-nominated Jenna Fox).
The Skin I Live In (2011) [Spanish: La piel que habito]: A Pedro Almodóvar film in which a young man named Vicente, portrayed Jan Cornet, is kidnapped by Antonio Banderas' character, undergoes forced sex reassignment surgery and becomes a woman named Vera, portrayed by Elena Anaya.
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 transsexuality, gender identity, and the beginning of puberty.
CSI: Crime Scene Investigation: The fifth season episode "Ch-ch-changes" focuses on illegal sex reassignment operations in the female transsexual community, and features several transsexual characters.
Dirty Sexy Money: Candis Cayne, actress and transsexual performer plays Carmelita, a transsexual woman who has an affair with married New York attorney General Patrick Darling, played by William Baldwin.
Family Guy: In the episode "Quagmire's Dad", Glenn Quagmire's father, Lieutenant Commander Dan Quagmire, has gender reassignment surgery and changes her name to Ida Quagmire.
Glee: Alex Newell plays Wade Adams (aka Unique), who is transgender.
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 identity disphoria.
Just Shoot Me: Jenny McCarthy plays Brandi, formerly Burt, an old college friend of Finch's, in the episode "There's Something About Allison."
Law & Order: Special Victims Unit: Transgender characters are featured in episodes "Fallacy" (Season 4) and "Transitions" (Season 10).
The Love Boat: In a 1980s episode, MacKenzie Phillips portrays a trans woman who is eventually accepted as a friend by her old high school classmate, series regular Fred Grandy.
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.
My Family: Diana Weston plays Charlie Briggs, an old college friend of Ben's who is transsexual.
NCIS: In the Season 1 episode "Dead Man Talking," the female person of interest in a stakeout turns out to be the male murder suspect.
Nip/Tuck: Famke Janssen played Ava Moore in the American plastic surgery based television drama series. Jonathan Del Arco plays Sophia Lopez, whose botched surgery leads the doctors to a doctor who routinely botches surgery on transgender patients in season 1. Cherry Peck (Willam Belli) figures prominently in season 3.
Number 96: In 1973, Carlotta played a showgirl revealed as transgender.
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)
Orange is the New Black: Sophia Burset (portrayed by Laverne Cox) is an inmate who serves time for credit card theft. Before transitioning, she was known as Marcus.
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").
Second Serve: A TV film based on the autobiography of tennis pro Renée Richards (played by Vanessa Redgrave), whose player status was challenged in 1976 when it was revealed that she was transsexual.
Tales of the City (1993): Based on Armistead Maupin's novel of the same name, this miniseries is set in a San Francisco apartment building run by an Anna Madrigal (Olympia Dukakis), an oversolicitous transsexual landlady.
"TransGeneration" (2005): An eight episode documentary series of four transgender college students.
Twin Peaks (1990): David Duchovny portrays an FBI agent cross dresser who purportedly picked it up while working undercover.
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.