Crossdressing movies and TV shows

The list contains the best, new and most relevant crossdressing movies ordered by relevance. The recommendation service has sorted out realistic, humorous, entertaining, touching, light and captivating films and TV shows about / with crossdressing, cross dressing, storytelling, death, gender, catastrophe, dialogue, mentor, runaway and gay plots mostly in Comedy, Drama and Romance genres shot in USA, UK, Japan and other countries.
crossdressing
 68
crossdressing movies
TOP 10 movies tagged as crossdressing: The Birdcage (1996), White Chicks (2004), A Series of Unfortunate Events (2017), Monty Python's Flying Circus (1969), Honeyglue (2015), Kinky Boots (2005), Wenn die tollen Tanten kommen (1970), Man on High Heels (2014), Trade (2019), The Rocky Horror Picture Show (1975).

List of crossdressing movies

 7.1
 80K
The Birdcage (1996)
Genre: Comedy
Country: USA
Duration: 117 min.
Story: A gay cabaret owner and his drag queen companion agree to put up a false straight front so that their son can introduce them to his fiancé's right-wing moralistic parents.
Style: humorous, feel good, light, entertaining, witty ...
Audience: date night, girls' night
Plot: crossdressing, senator, gay slur, cross dressing, farce, politician, comedy of errors, disorder, gender, family values, conservative, parents and children ...
Time: 90s, 1990s
Place: florida, usa, miami, los angeles, united states ...
Is relevant ?
 5.6
 132K
White Chicks (2004)
Genre: Comedy, Crime
Country: USA
Duration: 109 min.
Story: Two FBI agent brothers, Marcus and Kevin Copeland, accidentally foil a drug bust. As punishment, they are forced to escort a pair of socialites to the Hamptons, where they're going to be used as bait for a kidnapper. But when the girls realize ...
Style: humorous, idiotic, funny, satirical, ridiculous ...
Audience: teens, date night, girls' night
Plot: cross dressing, fish out of water, working undercover, special agents, gender bending, undercover, fbi, crossdressing, gender, gender disguise, crimes, disorder ...
Time: contemporary, 21st century, 2000s
Place: usa, new york
Is relevant ?
A Series of Unfortunate Events (2017)
Genre: Adventure, Comedy, Drama, Family, Mystery
Country: USA
Duration: 50 min.
TV show
Story: The orphaned Baudelaire children face trials, tribulations and the evil Count Olaf, all in their quest to uncover the secret of their parents' death.
Style: ironic, captivating, suspense, melancholic, surreal ...
Audience: family outing, kids
Plot: orphan, crossdressing, children, danger, life is a bitch, adventure, baby, cross dressing, cynicism, storytelling, escapades, dishonesty ...
Is relevant ?
Monty Python's Flying Circus (1969)
Genre: Comedy
Country: UK
Duration: 30 min.
TV show
Story: Monty Python’s Flying Circus is a British sketch comedy series created by the comedy group Monty Python and broadcast by the BBC from 1969 to 1974. The shows were composed of surreality, risqué or innuendo-laden humour, sight gags and ...
Style: surreal, biting, not serious, suspense, witty ...
Plot: satire, crossdressing, weirdo, insanity, stupidity, monty python, cross dressing, society, artists and showbiz, goofy hero, workplace, silly humor ...
Time: 70s, 60s, 20th century, 1960s
Place: england, europe
Is relevant ?
 6.3
 507
Honeyglue (2015)
Genre: Drama, Romance
Country: USA
Duration: 107 min.
Story: After learning she only has three months to live, Morgan flips her conservative protected life upside down. That is where she meets Jordan, a purse snatching cross dresser artist, who takes her on adventure of a lifetime.
Plot: crossdressing, cancer, love, gender, death, bisexual, husband wife relationship, gender identity, cross dressing, husband and wife, brain tumor, rooftop ...
Is relevant ?
 7.1
 18K
Kinky Boots (2005)
Genre: Comedy, Drama, Music
Country: USA, UK
Duration: 107 min.
Story: Charles Price may have grown up with his father in the family shoe business in Northampton, in central England, but he never thought that he would take his father's place. Yet, the untimely death of his father places him in that position, only ...
Style: touching, humorous, inspirational, witty, sexual ...
Audience: date night, girls' night
Plot: transvestism, cabaret, factory, small town, fashion show, fashion, family business, bankruptcy, unlikely partners, fish out of water, designer, gender bending ...
Time: 21st century, contemporary
Place: england, milan italy, europe, london
Is relevant ?
Wenn die tollen Tanten kommen (1970)
Genre: Musical, Comedy
Country: West Germany
Duration: 95 min.
Story: A young employee in a Munich travel agency takes a man friend along to Velden, a resort in which he has to settle a business matter. Through a number of misunderstandings the two men do not arrive at the resort at the expected time, nor are they ...
Plot: crossdressing, twins, drag, music, garbage, cross dressing, headache, transvestism, parody
Is relevant ?
Man on High Heels (2014)
Genre: Action, Comedy
Country: South Korea
Duration: 125 min.
Story: Ji-wook is a cold-blooded detective who would brutally assault and stop at nothing to catch criminals. However, despite her perfectly masculine appearance, Ji-wook struggles with a secret desire to be a woman. At last, Ji-wook decides to transition. ...
Style: exciting, psychological, tense, captivating
Plot: police officer, transsexual, transvestism, police, gang, crossdressing, cross dressing, car accident, hostage, revenge, flashback, danger ...
Time: 21st century, contemporary
Place: seoul, south korea
Is relevant ?
 5.6
 54
Trade (2019)
Genre: Drama
Country: USA
Duration: 113 min.
Story: Trade tells the story of two men, one a streetwise hustler, the other a straight-laced lawyer, who meet and form a relationship that brings to light who they really are. Inspired by the book "Boulevard Girls" by David Kaye.
Plot: crossdressing, attorney, truth, love, human, transsexual, married, blow job, cross dressing, deception, train, sex scene ...
Is relevant ?
The Rocky Horror Picture Show (1975)
Genre: Comedy, Musical
Country: UK, USA
Duration: 100 min.
Story: Sweethearts Brad and Janet, stuck with a flat tire during a storm, discover the eerie mansion of Dr. Frank-N-Furter, a transvestite scientist. As their innocence is lost, Brad and Janet meet a houseful of wild characters, including a rocking biker ...
Style: cult film, humorous, sexy, sexual, offbeat ...
Plot: transvestism, lgbt, cult, mad scientist, cannibalism, dancer, butler, castle, dark and stormy night, audience participation, gender bending, crossdressing ...
Time: 70s, 20th century
Place: transylvania, ohio
Is relevant ?
Laurence Anyways (2012)
Genre: Drama, Romance
Country: Canada, France
Duration: 168 min.
Story: The story of an impossible love between a woman named Fred and a transgender woman named Laurence who reveals her inner desire to become her true self: a woman.
Style: sincere, emotional, romantic, social, uplifting ...
Plot: transsexual, gender identity, impossible love, lgbt, couple relations, love and romance, follow your dream, poetry, coming out, gender bending, showdown, reject ...
Time: 80s, 90s, 1990s, 20th century
Place: montreal, quebec, montreal quebec
Is relevant ?
 7.0
 857
Mayo Chiki! (2011)
Genre: Animation, Comedy, Romance
Country: Japan
Duration: 25 min.
TV show
Story: When you've got acute gynophobia, even a pretty girl can be like a malady, and as the sparring partner for his family of female wrestlers, Sakamachi Kinjiro has the worst case ever! Just one touch makes his nose bleed, so school's a bloody ...
Style: humorous, captivating, light, entertaining, semi serious ...
Plot: romance, master and servant, nudity (full frontal - brief), school, power relations, wrestling, butler, youth, social awkwardness, cross dressing, love, friendship ...
Time: 21st century, contemporary
Place: japan, asia
Is relevant ?
Related movie lists
Is This a Zombie? (2011)
Genre: Animation, Action, Comedy, Fantasy, Romance
Country: Japan
Duration: 25 min.
TV show
Story: Some guys have no luck; he’s got no pulse. That’s life for poor unfortunate, undead Ayumu. First, he was murdered by a serial killer. Total bummer. Then he was resurrected as a zombie by a cute little Necromancer. That seemed pretty cool until ...
Style: ecchi, humorous, exciting, entertaining, captivating ...
Plot: harem, zombie, supernatural, vampire, magic, serial killer, curses spells and rituals, reincarnation, rivalry, imaginary, heroes, danger ...
Place: japan
Is relevant ?
 7.0
 226
Sarazanmai (2019)
Genre: Animation, Comedy, Fantasy, Music
Country: Japan
TV show
Story: The stage is Asakusa. One day, three second-year middle school students — Kazuki Yasaka, Toi Kuji, and Enta Jinai — meet a kappa-like creature named Keppi, who is the self-proclaimed heir to the throne of Kappa Kingdom. Keppi forcibly takes the ...
Style: surreal, touching, captivating, yaoi
Plot: male bonding, teenage love, teenage sexuality, love, teenage crush, gay love, male friendship, love triangle, secret love, friendship between men, zombie, cross dressing ...
Is relevant ?
Princess Jellyfish (2010)
Genre: Animation, Comedy, Romance
Country: Japan
Duration: 22 min.
TV show
Story: Amamizukan is an apartment complex where no boys are allowed. Tsukimi, a girl who adores jellyfish, lives there happily with her friends who all have nerdy obsessions of their own. Their peaceful lives gradually start to change when a beautiful ...
Plot: cross dressing, crossdressing, jellyfish, afro, boarding house, politician, women, nerd
Place: japan
Is relevant ?
 5.4
 13K
Psycho III (1986)
Genre: Horror, Mystery, Thriller
Country: USA
Duration: 93 min.
Story: Norman Bates is still running his little motel, and he has kept the dressed skeleton he calls mother. One of his guests is a young girl who has left the convent where she lived. To get some help he employs a young man. One day a nosey journalist ...
Style: twists and turns, scary, serious, realistic, atmospheric ...
Audience: teens
Plot: murder, mental illness, psychopath, slasher, serial killer, split personality, voyeurism, hotel, woman in danger, blood, gore, nun ...
Time: 80s, 20th century
Place: usa
Is relevant ?
 6.7
 15K
Dragonslayer (1981)
Genre: Action, Adventure, Fantasy
Country: USA, UK
Duration: 108 min.
Story: The sorcerer and his apprentice Galen are on a mission to kill an evil dragon in order to save the King’s daughter from being sacrificed in accordance to a pact that the King himself made with the dragon to protect his kingdom. A fantasy film from ...
Style: suspenseful, serious, captivating, atmospheric, stylized ...
Plot: dragon, sword and sorcery, dark fantasy, magic, rescue, beast, apprentice, human sacrifice, adventure, sacrifice, supernatural, daring rescue ...
Time: middle ages, 80s
Is relevant ?
 6.8
 769
Blend S (2017)
Genre: Animation, Comedy, Drama
Country: Japan
Duration: 23 min.
TV show
Story: High school girl Maika Sakuranomiya has trouble finding a part-time job because of how scary she looks when smiling. However, she is scouted one day by an Italian man who is also the manager of Stile, a café where its waitresses are given unique ...
Style: unusual plot structure, entertaining, humorous, captivating, touching
Plot: waitress, slice of life, cafeteria, workplace situations, strong female lead, friendship, rich and poor, ambition, family relations, sexual content, romance, coworker relationship ...
Is relevant ?
Related movie lists
The Best Way to Walk (1976)
Genre: Drama, Romance
Country: France
Duration: 82 min.
Story: In a vacation camp somewhere in the French country, 1960. Marc et Philippe are two of the counsellors. Marc is very virile, while Philippe is more reserved. A night, Marc surprises Philippe dressed and made-up like a woman. From now on, he will keep ...
Style: semi serious, realistic, touching, psychological, humorous ...
Plot: friendship, racism, summer camp, youth, gays and lesbians, coming of age, buddies, teaching the ways of the world, teenage love, coming out, sexual relations, innocence lost ...
Time: 80s, 60s, 1960s
Place: paris france, france
Is relevant ?
 3.8
 175
Delivery Boys (1985)
Genre: Comedy, Sport
Country: USA
Duration: 91 min.
Story: A gang of boys under the Brooklyn Bridge are united by their common interest in break dancing. Some work as pizza delivery boys, hence they call themselves the "Delivery Boys". They form a dance team and enter a local break dance contest, ...
Plot: pizza delivery boy, prayer, erection, clique, sculptor, meditation, pizza delivery, pizzeria, pizza, contest, older woman younger man relationship, adultery ...
Place: new york
Is relevant ?
 6.5
 1K
Absolution (1978)
Genre: Drama, Mystery, Thriller
Country: UK
Duration: 95 min.
Story: At a Catholic public school, Benjamin Stanfield is tired of being the teacher's pet and decides to play a practical joke on his form master Father Goddard. In confession, Stanfield tells Goddard that he has accidentally murdered his friend ...
Style: bleak, psychological, suspenseful, realistic, serious ...
Plot: boarding school, prank, murder, deadly, clergy, crimes, hopes, investigation, rebellion, mind game, teachers and students, crime ...
Time: 70s
Is relevant ?
Wild Tigers I Have Known (2006)
Genre: Drama
Country: USA
Duration: 81 min.
Story: A lyrical telling of the coming of age of a 13-year-old boy who learns to cope with his new found sexuality and his unrequited love for the cool kid in school.
Style: surreal, serious, sentimental, sincere, touching ...
Plot: gay teenager, coming of age, friendship, teenage love, gays and lesbians, youth, gender, teenage life, pretense, make believe, family relations, lifestyle ...
Time: contemporary
Is relevant ?
 7.4
 19K
Tomboy (2011)
Genre: Drama
Country: France
Duration: 82 min.
Story: A French family with two daughters, 10-year-old Laure and 6-year-old Jeanne, moves to a new neighborhood during the summer holidays. With her tomboy ways, Laure is immediately mistaken for a boy by the local kids and passes herself off as Mickaël.
Style: serious, captivating, touching, sincere, emotional ...
Plot: transsexual, child protagonist, sexual identity, gender, friendship, gender bending, family relations, youth, self discovery, dishonesty, society, cross dressing ...
Time: contemporary, 21st century, 2010s
Place: europe, france, paris france
Is relevant ?
 5.6
 73K
Body Hunt (2012)
Genre: Drama, Horror, Thriller
Country: USA, Canada
Duration: 101 min.
Story: A mother and daughter move to a new town and find themselves living next door to a house where a young girl murdered her parents. When the daughter befriends the surviving son, she learns the story is far from over.
Style: suspenseful, twists and turns, scary, surprise ending, suspense ...
Audience: teens, girls' night, chick flick
Plot: teenage life, haunted by the past, youth, cross dressing, danger, small town, parents and children, friendship, family relations, insanity, mother daughter relationship, female protagonist ...
Time: contemporary, 21st century
Place: usa
Is relevant ?
 7.0
 247K
Mrs. Doubtfire (1993)
Genre: Comedy, Drama, Family
Country: USA
Duration: 125 min.
Story: Loving but irresponsible dad Daniel Hillard, estranged from his exasperated spouse, is crushed by a court order allowing only weekly visits with his kids. When Daniel learns his ex needs a housekeeper, he gets the job -- disguised as an English ...
Style: feel good, touching, humorous, light, sentimental ...
Audience: family outing, date night, kids, girls' night
Plot: family, comedy of errors, cross dressing, nanny, divorce, family relations, kids and family, hidden identity, custody battle, gender bending, parenthood, actor playing female role ...
Time: 90s, 20th century, 1990s
Place: san francisco, usa
Is relevant ?
 6.7
 86K
Sweet November (2001)
Genre: Drama, Romance
Country: USA
Duration: 119 min.
Story: Nelson is a man devoted to his advertising career in San Francisco. One day, while taking a driving test at the DMV, he meets Sara. She is very different from the other women in his life. Nelson causes her to miss out on taking the test and later ...
Style: romantic, touching, sentimental, emotional, realistic ...
Audience: girls' night, chick flick
Plot: romance, love story, terminal illness, tragic love, fall in love, love and romance, self discovery, couples, leukemia, love, workaholic, unfulfillment ...
Time: 21st century, contemporary
Place: san francisco, usa, new jersey
Is relevant ?
 6.6
 5K
Motocrossed (2001)
Genre: Action, Adventure, Family
Country: USA
Duration: 110 min.
Story: Motocrossed! is a 2001 Disney Channel Original Movie (based on the Shakespeare play Twelfth Night), about a girl named Andrea Carson who loves motocross, despite the fact that her father finds her unsuited for the sport, being that she is "just ...
Style: humorous, feel good, semi serious, captivating, realistic
Audience: family outing
Plot: motorcycle race, motocross, gender bending, extreme sport, teenage life, against the odds, ambition, family life, contests and competitions, rivalry, sport, underdog ...
Time: contemporary, 21st century
Is relevant ?
 6.2
 3K
Breakout (1975)
Genre: Action, Adventure, Drama
Country: USA
Duration: 96 min.
Story: A bush pilot is hired for $250,000 to go to Mexico to free an innocent prisoner.
Style: suspenseful, light, exciting, entertaining, rough ...
Audience: boys' night
Plot: false accusation, prison, escape, fugitives, chase, manhunt, danger, rescue, adventure, prison life, captivity, warden ...
Time: 70s
Place: mexico, latin america, ireland, boston
Is relevant ?
 4.9
 30K
Boat Trip (2002)
Genre: Comedy
Country: USA, Germany
Duration: 94 min.
Story: Two straight men mistakenly end up on a "gays only" cruise.
Style: humorous, not serious, realistic, entertaining, sexy ...
Audience: teens, girls' night
Plot: homosexuality, pretending to be gay, bikini, cruise ship, fish out of water, farce, lifestyle, fall in love, comedy of errors, singleness, goofy hero, buddies ...
Time: contemporary, 21st century
Place: sweden, cuba
Is relevant ?
 7.8
 334
Playback (2010)
Genre: Drama, Thriller
Country: USA
Duration: 84 min.
Story: A detective must uncover the truth behind the death of his daughter. But the truth hits close to home.
Style: suspenseful, disturbing, realistic, serious, tense ...
Plot: sex addict, riddles and clues, investigation, parents and children, danger, deadly, estrangement, family relations, murder, death in the family, police detective, murder investigation ...
Time: contemporary, 21st century
Place: usa
Is relevant ?