Cross-dressing in film has followed a long history of female impersonation on English stage, and made its appearance in the early days of the silent films. Charlie Chaplin and Stan Laurel brought the tradition from the English music halls when they came to America with Fred Karno's comedy troupe in 1910. Both Chaplin and Laurel occasionally dressed as women in their films. Even the beefy American actor Wallace Beery appeared in a series of silent films as a Swedish woman. The Three Stooges, especially Curly (Jerry Howard), sometimes appeared in drag in their short films. The tradition has continued for many years, usually played for laughs. Only in recent decades have there been dramatic films which included cross-dressing, possibly because of strict censorship of American films until the mid-1960s. One early exception was Alfred Hitchcock's thriller Murder!, where the murderer is a transvestite who wears particularly frilly dresses and petticoats. Cross-gender acting, on the other hand, refers to actors or actresses portraying a character of the opposite gender.
Film and video
In Some Like It Hot (1959), two struggling musicians have to dress as women to escape the ire of gangsters. The film is a remake of a 1935 French movie, Fanfare of Love, from the story by Robert Thoeren and Michael Logan, which was itself remade in 1951 by German director Kurt Hoffmann as Fanfares of Love.
In Blake Edwards's 1982 musical comedy film Victor Victoria, Victoria Grant, a struggling soprano, is unable to find work but she finds success when she becomes "Count Victor Grazinski", a female impersonator. The film is a remake of Viktor und Viktoria, a German film of 1933.
David Henry Hwang's 1988 play M. Butterfly focuses on a love affair between a French diplomat and a male Beijing opera singer who plays dan, or female, roles.
Although there is some dispute as to whether the character is transgender or simply a cross-dresser, the character of Hedwig from the musical and subsequent movie Hedwig and the Angry Inch is another modern drag queen (the musical also features a male character played traditionally by a female actress, although the character's true gender is deliberately left with slight ambiguity).
Dr. Frank 'n' Furter in the Rocky Horror Picture Show wore nothing but women's clothing the entire movie/play.
In The Drew Carey Show, Drew's brother, Steve Carey, is a cross-dresser.
Robin Williams played a divorced father who dressed as a nanny to be with his children in the 1993 comedy Mrs. Doubtfire.
Dame Edna was an elderly drag queen with "wisteria-colored hair" who did international chat shows in the 1990s.
As a central plot element
Movies that feature cross-dressing as a central plot element:
- Films based on the 1599 or 1600 play As You Like It by William Shakespeare
- Films based on the 1601 or 1602 play Twelfth Night by William Shakespeare
- Several films based on the 1892 United Kingdom play Charley's Aunt by Brandon Thomas
- Les Résultats du féminisme (1906), remade as In the Year 2000 (1912); the latter believed to be lost
- The Little House in Kolomna (1913) - a Russian comedy based on the joke poem by Alexander Pushkin starring Ivan Mosjoukine
- The Masquerader (1914) - after being fired from a movie studio, Charlie Chaplin's character dresses up as a woman in order to return to the studio
- A Woman (1915) - Charlie Chaplin's character dresses up as "Nora" in order to spend more time with his new girlfriend Edna
- Yankee Doodle in Berlin (1919) - Bothwell Browne's character Captain Bob White dresses as a woman to steal a map from The Kaiser
- I Don't Want to Be a Man (Ich möchte kein Mann sein) (1920)
- The Unholy Three (1925) - Lon Chaney's character Echo poses as an elderly woman to steal a necklace
- She Goes to War (1929) - the heroine dresses as a man to fight in World War I
- The Unholy Three (1930) - sound remake
- Viktor und Viktoria (1933) - a woman impersonates a female impersonator, later remade as Victor Victoria in 1982; see below
- Queen Christina (1933) - Greta Garbo's character Christina often dresses as a boy to have greater freedom, eventually meeting Antonio, the Spanish envoy, dressed as a boy
- She Loves Me Not (1934), remade as True to the Army (1942) and How to Be Very, Very Popular (1955)
- Girls Will Be Boys (1934) - Dolly Haas disguises herself as a man
- Peter (1934) - a musical comedy by Henry Koster starring Franciska Gaal
- First a Girl (1935) - a comedy in which Jessie Matthews dresses as a man
- Sylvia Scarlett (1935) - Katharine Hepburn dresses as a man for most of the movie; this is her first movie with Cary Grant
- The Devil Doll (1936) - Lionel Barrymore plays an evil, elderly woman
- Yiddle with His Fiddle (1936) - Molly Picon plays a traveling musician who dresses as a boy for safety
- Bringing Up Baby (1938) - Cary Grant cross dresses
- The Black Sheep of Whitehall (1942) - comedian Will Hay wryly impersonates a nurse and spends the night with the hospital nurses in this wartime British comedy
- Me ha besado un hombre (1944) - Mexican comedy in which María Elena Marqués adopts her deceased brother's identity to migrate from Spain to Mexico City; remade in 1953
- La hija del regimiento (1944) - Mexican musical comedy in which Mapy Cortés, secretly raised within an all-male regiment, cross-dresses as a cadet
- Fram för lilla Märta (1945) - a Swedish film; a musician, played by Stig Järrel, cross-dresses to get a job in an all-female orchestra
- Little Giant (1946) - Bud Abbott plays the Grandmother
- The Time of Their Lives (1946) - a comedy in which Marjorie Reynolds's character Melody Allen dresses as a man
- Boy! What a Girl! (1947) - playing the part of an out of work burlesque comic named Bumpsie, Tim Moore gives a frightfully hilarious female impersonation
- Kind Hearts and Coronets (1949) - Alec Guinness plays Lady Agatha D'Ascoyne
- I Was a Male War Bride (1949) - Cary Grant is a French officer who marries a U.S. Army officer played by Ann Sheridan and cross-dresses to pass as a bride
- Yo quiero ser hombre (1950) - Mexican comedy in which Alma Rosa Aguirre cross-dresses as a boy to carry out an inheritance scheme plotted by her aunt (Sara García)
- I Am Very Macho (1953) - Mexican comedy in which Silvia Pinal cross-dresses as her pilot brother and falls in love with the fleet's captain; remake of 1944's Me ha besado un hombre (A Man Kissed Me)
- Pablo and Carolina (1957) - filmed in 1955; Mexican musical comedy in which a socialite played by Irasema Dilián pretends to be her (non-existent) brother
- Das Wirtshaus im Spessart (1958) - young countess dresses as a poor boy and joins the robbers to save her friends
- Some Like It Hot (1959) - Tony Curtis and Jack Lemmon dress as women and join an all-female band in order to hide from the mob
- Homicidal (1961) - male role played by Jean Arless was actually actress Joan Marshall
- Hussar Ballad (1962) - a Soviet musical comedy by Eldar Ryazanov based on the real life story of Nadezhda Durova, a soldier during the Napoleonic Wars
- Blonde Cobra (1963) - Jack Smith spends the whole film in drag
- Me ha gustado un hombre (1965) - Mexican comedy in which Tere Velázquez cross-dresses to get work as a hotel bellboy
- Gunn (1967) - the killer is revealed to be a cross-dresser
- Monsieur Hawarden (1968) - Mr. Hawarden is actually a woman disguised as a man to avoid prosecution for killing her lover, 15 years ago; based on a true story
- The Kremlin Letter (1969) - George Sanders plays a transvestite
- Sometimes Aunt Martha Does Dreadful Things (1971) - two criminals hide from the law, with one of them pretending to be the other's aunt
- Poszukiwany poszukiwana (1973) - by Stanis?aw Bareja
- Female Trouble (1974) - Divine plays an obese criminal woman and an obese man
- The Rocky Horror Picture Show (1975) - Tim Curry plays a self-proclaimed "sweet transvestite from Transsexual, Transylvania"
- La Cage aux Folles (1978) - features female impersonators
- Lady Oscar (1979) - the female protagonist dresses as a man, but privately acknowledges her feminine side
- Dressed to Kill (1980) - the killer dresses as a woman
- Victor Victoria (1982) - transvestism in various forms is included in this musical comedy, remake of Viktor und Viktoria (1933); see above
- Tootsie (1982) - Dustin Hoffman becomes the female star of a television soap opera
- The Wicked Lady (1983) - Faye Dunaway plays a bored English aristocrat who disguises herself as a highwayman in order to rob carriages carrying passengers
- A Blade in the Dark (1983) - Michele Soavi plays Tony Rendina/Linda
- Sahara (1984) - Brooke Shields disguises herself as a young man so she can compete in a car race in the African desert
- Just One of the Guys (1985) - Joyce Hyser plays a boy so she can win a journalism contest
- He's My Girl (1987) - T.K. Carter plays Reggie who pretends to be Regina when his friend wins a contest trip to Los Angeles
- Mascara (1987) - a transvestite is murdered
- Delinquent in Drag (1988) - Suke Banji gets expelled from school and is forced to masquerade as a girl in his next school
- Torch Song Trilogy (1988) - Harvey Fierstein plays Arnold, a New York female impersonator
- Nobody's Perfect (1990) - Chad Lowe is kicked off his college's tennis team and dresses up as a girl to join the women's team and be closer to his crush
- Nuns on the Run (1990) - Eric Idle and Robbie Coltrane disguise as nuns
- Just Like a Woman (1992) - Adrian Pasdar is Gerald, a finance executive and transvestite, who finds himself thrown out by his wife, when she discovers women's underwear in their flat
- Ladybugs (1992) - Jonathan Brandis dresses as a girl to play on the girls' soccer team
- A Little Bit of Lippy (1992) - Chris Bernard Husband is discovered cross-dressing, wife and community must come to terms
- Little Sister (1992) - Bobby (Jonathan Silverman) becomes Roberta in order to infiltrate a sorority house and be close to Diana (Alyssa Milano)
- Mrs. Doubtfire (1993) - Robin Williams's character Daniel Hillard disguises himself as a woman so he can see his children
- Anything for Love (1993) - Chris (Corey Haim) dresses as a girl to avoid his tormentors at school
- My Summer as a Girl (1994) - Zach Braff's character Tony cross-dresses to get a job as a chambermaid
- The Adventures of Priscilla, Queen of the Desert (1994) - an offbeat comedy of two men and a trans woman traveling cross country to perform a drag show in the outback of Australia
- He's a Woman, She's a Man (1994) - Wing (Anita Yuen) is a sassy girl who enters a country-wide, males-only talent search, disguised as a male
- Color of Night (1994) - Jane March's character Rose disguises herself as her dead brother Richie
- All Men Are Liars (1995) - Mick becomes Michelle to join an all-female band in order to earn some money as a musician
- To Wong Foo, Thanks for Everything! Julie Newmar (1995) - three drag queens help people in a small town after their Cadillac breaks down on the way to Los Angeles
- Twelfth Night: Or What You Will (1996) - based on the 1623 play Twelfth Night by William Shakespeare
- My Friend Joe (1996) - Joe is a girl disguising as a boy
- The Associate (1996) - Whoopi Goldberg dresses as a white man to prove Wall Street wrong
- The Birdcage (1996) - features drag queens, including Albert Goldman (Nathan Lane), who dresses up like Val Goldman's mother to help him win the hand of his girlfriend
- Ma Vie en Rose (1997) - a young boy, Ludovic, who was born male but consistently insists that she is supposed to be a girl
- Chachi 420 (1998) - a Bollywood film reminiscent of Mrs. Doubtfire, in which a father gets divorced and also loses the custody of his daughter
- Mulan (1998) - a Chinese woman disguises herself as a soldier to fight the Huns in place of her father
- Shakespeare in Love (1998) - includes Shakespeare's use of female impersonators in his plays
- Flawless (1999) - a conservative security guard (Robert De Niro) suffers a stroke, and is assigned to a rehabilitative program that includes singing lessons with the drag queen next door
- Bruno (2000) - an eight-year-old boy who wears dresses as a source of empowerment as well as feeling the need to express himself while trying to win the spelling bee
- Big Momma's House (2000) - Martin Lawrence plays an FBI agent who goes undercover and dresses as a heavy-set woman
- Holiday Heart (2000) - Holiday Heart (Ving Rhames) is a gay drag queen who performs at a night club
- All the Queen's Men (2001) - Matt LeBlanc and Eddie Izzard head a team of Army men sent to infiltrate a German factory dressed as women
- Motocrossed (2001) - Alana Austin is a girl whose father won't let her race because she's a girl, so she goes undercover and poses as a male to race for her twin brother
- The Triumph of Love (2001) - Mira Sorvino plays the daughter of a usurper, who disguises herself as a young male scholar named Phocion to get closer to Agis, the rightful heir to the throne
- Sorority Boys (2002) - Barry Watson, Michael Rosenbaum, and Harland Williams pose as girls when they're kicked out of their dorm
- Juwanna Mann (2002) - a disgraced NBA player (Miguel A. Núñez Jr.) is fired from his job and dresses as a loud-mouthed Southern Belle in order to join the WNBA
- The Hot Chick (2002) - Rob Schneider plays a girl who turns into a man overnight, and must find a way to change back
- Girls Will Be Girls (2003) - all three of the main characters (Evie, Coco and Varla) are drag alter egos of the actors, who have existed "on their own" for several years
- Party Monster (2003) - Seth Green plays club personality James St. James
- Stage Beauty (2004) - Ned Kynaston (Billy Crudup) is an actor famed for his portrayal of female characters, particularly Desdemona in Othello
- Connie and Carla (2004) - Nia Vardalos and Toni Collette go on the run, after accidentally witnessing a mafia hit in Chicago, and wind up posing as drag queens at a gay club
- White Chicks (2004) - Shawn and Marlon Wayans play FBI agent brothers who must protect two cruise line heiresses from a kidnapping plot while in disguise of the women they are protecting
- Breakfast on Pluto (2005) - Cillian Murphy is a transgender foundling searching for love and her long-lost mother in small town Ireland and London in the 1970s
- Kinky Boots (2005) - Chiwetel Ejiofor's character Simon cross-dresses as drag queen Lola
- Tyler Perry acted as Madea in a series of comedy movies:
- She's the Man (2006) - Amanda Bynes dresses as a man to be accepted in Illyria's boys' soccer team and get revenge in Cornwall; based on the play Twelfth Night by William Shakespeare
- Butch Jamie (2007) - writer/director/actor Michelle Ehlen plays a butch lesbian actress who gets cast as a man in a film
- Jolly Fellows (2009) -- film about five drag performers
- Dil Bole Hadippa! (2009) - Bollywood actress Rani Mukerji plays a girl who dresses as a boy in order to play on the Indian cricket team
- Albert Nobbs (2011) - Albert Nobbs (Glenn Close) is a woman living as a man in order to find work in the harsh environment of 19th-century Ireland
- Cockpit (2012) - Jonas Karlsson portrays the pilot Valle who re-applies for the job as Maria and wins it through affirmative action
- Sisterakas (2012) - a film from the Philippines starring Vice Ganda as Bernice Sabroso
- The Rocky Horror Picture Show: Let's Do the Time Warp Again (2016) - Laverne Cox plays a transvestite
As a non-comedic element
Most of the above films are comedies. Films in which cross-dressing is treated in a more serious manner are relatively rare, although the list does include several dramas and biopics.
- Hotel Splendide (1932) - Features a criminal gang whose leader disguises himself as "Mrs. LeGrange"
- Young Fugitives (1938) - The heroine dresses as a man.
- Shadows on the Stairs (1941) - Tom Armitage (Miles Mander), dresses as a woman.
- The Wicked Lady (1945) - The heroine poses as a highwayman.
- She Wore a Yellow Ribbon (1949) - The heroine wears a cavalry uniform to accompany her uncle to safety.
- Glen or Glenda (1953) - Inspired by his own experiences, Ed Wood wrote, directed, and starred in the movie as a troubled cross-dresser, in a sort of plea for acceptance. Originally an exploitation film about Christine Jorgensen.
- Psycho (1960) - Norman Bates (Anthony Perkins), is a killer who wears his dead mother's clothes.
- Monsieur Hawarden (1968) - Title character Mr. Hawarden is actually a woman who disguises herself as a man to avoid prosecution for a murder she committed fifteen years ago.
- Dog Day Afternoon (1975) - Sonny robs a bank to finance his wife Leon's sex change operation. Chris Sarandon plays Leon.
- The Tenant (1976) - The main character suffers from a split personality.
- The World According to Garp (1982) - John Lithgow plays a former pro football player who identifies as a woman.
- Yentl (1983) - Barbra Streisand plays a Polish Jewish woman who disguises herself as a man so she can study the Talmud in early 20th-century Europe.
- Last Exit to Brooklyn (1989) Alexis Arquette plays Georgette, a transvestite, thrown out of the family home who falls in love with a local criminal.
- The Silence of the Lambs (1991) - Ted Levine plays serial killer Jame Gumb, better known as Buffalo Bill who makes the skins of his female victims into a woman suit for him to wear.
- The Crying Game (1992) - An IRA member develops an unexpected relationship with a pre-op transgender woman.
- The Ballad of Little Jo (1993) - A lone woman in the Old West takes on a male role in order to survive.
- M. Butterfly (1993) - a French diplomat (Jeremy Irons) becomes infatuated with a performer in a Chinese opera, where all roles are performed by men.
- The Adventures of Priscilla, Queen of the Desert (1994) -- a drag queen takes his act on the road.
- The King of Masks (1996) - A Chinese girl poses as a boy in order to get adopted by an elderly man.
- Liang Po Po: The Movie (1999) - Jack Neo cross-dressed as an elderly woman.
- Boys Don't Cry (1999) - The true story of Brandon Teena (Hilary Swank), a transgender man who pursued a relationship with a young woman (Chloë Sevigny), and was beaten, raped and murdered by his male acquaintances.
- Baran (2001) - An Iranian boy falls in love with a young Afghan refugee, who must dress as a boy to keep her job at a construction site.
- Osama (2003) - A 12-year-old Afghan girl dresses like a boy in order to get a job during the regime of the Taliban.
- The Heart is Deceitful Above All Things (2004) - While on the run, Sarah disguises her son, Jeremiah, as a girl and passes him off as her "sister" until he is raped by her current boyfriend and is found out. (Note: In the movie adaption, Jeremiah is played by both Cole and Dylan Sprouse in different scenes, both of whom have had several other roles that involved cross-dressing.)
- Peacock (2010) - Cillian Murphy plays John Skillpa, a man who as a result of severe child abuse has formed the alternate personality of Emma Skillpa and dresses as a woman to become Emma.
- Les Miserables (2012) - Éponine changes her clothes from feminine to masculine in order to join the June Rebellion.
- Dallas Buyers Club (2013) - Jared Leto plays Rayon, an HIV-positive transgender woman involved in a business smuggling unapproved pharmaceutical drugs into the United States.
- The Boxtrolls (2014) - Archibald Snatcher is disguised as Madame Frou-Frou.
- Rudhramadevi (2015) - A young princess is disguised as a boy to keep the succession of her royal family line intact.
- The Danish Girl (2015) - Fictionalized story of artist Einar Wegener who first dresses as a woman to become Lili Elbe, and subsequently has sex reassignment surgery.
- Teen Titans Go! To the Movies (2018) - Slade is disguised as a female movie director named Jade Wilson.
As a minor plot element
Many other comedy films include instances of humorous cross-dressing, but do not feature it as a central plot element. Movies in which cross-dressing plays a minor but important role include:
- Morocco (1930) - Marlene Dietrich wears a tuxedo.
- Sherlock Holmes (1932) - Clive Brook poses as a woman.
- Babes in Toyland (1934) - Stan Laurel poses as a bride.
- The Scarlet Pimpernel (1934) - Leslie Howard poses as a woman.
- The Bold Caballero (1936) - Robert Livingston poses as a woman.
- Professor Beware (1938) - Harold Lloyd poses as a woman.
- Tower of London (1939) - Nan Grey poses as a chimney sweep.
- Honolulu Lu (1941) - Lupe Vélez dresses up as Adolf Hitler in this wartime comedy.
- National Velvet (1944) - Elizabeth Taylor as Velvet Brown, who disguises herself as a male jockey, and trains a horse for the Grand National steeplechase.
- Sunset Boulevard (1950) - Gloria Swanson dresses up as Charlie Chaplin.
- Houdini (1953) - Janet Leigh dresses up as Harry Houdini.
- Calamity Jane (1953) - Dick Wesson poses as an actress.
- Casanova's Big Night (1954) - Bob Hope appears in drag.
- Abbott and Costello Meet the Keystone Kops (1955) - Lou Costello appears in drag.
- Man of a Thousand Faces (1957) - James Cagney dresses as a woman for a few scenes.
- Swiss Family Robinson (1960) - Janet Munro dresses as a boy to appear less vulnerable to pirates.
- Thunderball (1965) - A former enemy of Bond fakes his death and poses as his own widow in the prologue segment.
- The Producers (1968) - Roger De Bris (Christopher Hewett) appears in a women's evening gown and tiara.
- The Damned (1969) - Directed by Luchino Visconti. Martin's (a character played by Helmut Berger) drag performance as Marlene Dietrich in The Blue Angel at his grandfather's birthday celebration, notorious at the time of the film's release, has since become an iconic image in cinema history.
- Freebie and The Bean (1973) - Mystery hit man turns out to be a convincing transvestite.
- Arabian Nights (1974) - Zumurrud disguises as a man, comes to a far-away kingdom where she becomes king
- Thunderbolt and Lightfoot (1974) - Jeff Bridges cross-dresses to distract bank guards in a robbery.
- 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.
- Gable and Lombard (1976) - Carole Lombard (Jill Clayburgh) disguises herself as an extra to see Clark Gable (James Brolin) act.
- Perfect Gentlemen (1978)
- Monty Python's Life Of Brian (1979) - Several "women" (actually portrayed by the all-male Python ensemble) disguise themselves as men in order to attend a stoning.
- Dragonslayer (1981) - Caitlin Clarke plays a young woman whose father disguised her as a boy from birth in order to protect her from an annual lottery in which young women are selected to be fed to the dragon.
- Deathstalker (1983) - The sorcerer Munkar, turns his henchman Gargit into the image of Princess Codille (Barbi Benton), in order to seduce the hero Deathstalker.
- Yellowbeard (1983) - Captain Hughes sneaks a woman on board ship by having her dress as a man.
- Angel (1984) - Dick Shawn plays street-smart transvestite, who is like a den-mother to the main character, child prostitute, Angel.
- Ronia, the Robber's Daughter (1984) - A robber dresses as a female to con other robbers.
- Pee-wee's Big Adventure (1985) - To disguise themselves from the police, Pee-wee Herman and an escaped convict dress as husband and wife, with Pee-wee as the wife.
- Armed and Dangerous (1986) - John Candy dresses as a Divine-type drag queen to track down criminals.
- Betty Blue (1986) - Zorg dresses (and passes) as a woman ("Josephine") in two crucial scenes.
- Outrageous Fortune (1987) - Bette Midler and Shelley Long disguise themselves as pre-pubescent boys to gain entry into a remote brothel in New Mexico.
- Willow (1988) - Madmartigan (portrayed by Val Kilmer) disguises himself (unsuccessfully) as a woman to hide an apparent infidelity from a jealous husband.
- Hairspray (1988) - While not exactly a plot element, the role of Edna Turnblad has always been played by a man in drag, and was indeed written with that intention, most recently portrayed by John Travolta in the 2007 remake.
- Tango & Cash (1989) - Kurt Russell cross-dresses to escape from the police.
- Total Recall (1990) - Arnold Schwarzenegger disguises himself as a lady in an attempt to avoid Michael Ironside, who wants to capture him on his return to Mars.
- Sleeping with the Enemy (1991) - Julia Roberts disguises herself as a young man in order to visit her elderly mother and avoid her possessive husband.
- Robin Hood (1991) - Uma Thurman's character Marion disguises as Martin to join the band of Robin Hood.
- Hook (1991) - Glenn Close plays a pirate who is part of Captain Hook's crew.
- Robin Hood: Men In Tights (1993) - Little John, Ahchoo, Will Scarlet O'Hara and Blinkin disguise themselves as women to go see the archery contest that Robin of Loxley is competing in.
- Ace Ventura: Pet Detective (1994) - Sean Young plays Lt. Lois Einhorn, who is really a football player named Ray Finkle in disguise.
- Ed Wood (1994) - Directed by Tim Burton, the biopic stars Johnny Depp as the famous low-budget transvestite filmmaker.
- Junior (1994) - Arnold Schwarzenegger disguises himself to hide in a women's shelter during the last few months of an experimental male pregnancy.
- The Brady Bunch Movie (1995) - RuPaul Charles appears in drag as high school guidance counselor, Mrs. Cummings.
- Brain Candy (1996) - Several female characters played by The Kids in the Hall, a Canadian comedy troupe.
- Con Air (1997) - Renoly Santiago appears as Ramon 'Sally-Can't Dance' Martinez - an effeminate, transvestite inmate who appears sexually subservient to his fellow detainees.
- The Fifth Element (1997) - Chris Tucker appears as Ruby Rhod, a "RuPaul/Dennis Rodman"-inspired media sensation who tags along with Korben Dallas on his mission to save the earth.
- Entre las piernas (Between Your Legs) (1998) - Victor Rueda passes as a woman in this Spanish drama.
- Wild Wild West (1999) - U.S. Marshal Artemus Gordon (Kevin Kline) disguises himself as a prostitute. Jim West (Will Smith) also appears as a belly dancer to rescue U.S. Marshal Artemus Gordon from antagonist Arliss Loveless (Kenneth Branagh).
- The Boondock Saints (1999) - FBI Agent Paul Smecker (Willem Dafoe) disguises himself as a prostitute in order to infiltrate the Yakavetta headquarters.
- 100 Girls (2000) - Jonathan Tucker's character Matthew dresses in drag.
- The Last of the Blonde Bombshells (2000) - Ian Holm plays Patrick, who attempted to avoid enlistment during World War II by dressing as a woman.
- Wonder Boys (2000) - Michael Cavadias's character Tony/Antonia is a part-time transvestite.
- Sweet November (2001) - Sara's two confidantes, Chaz and Brandon, are gay transvestites.
- Camp (2003) - One of the main characters, Michael, gets beaten up for wearing a dress, fishnet stockings, and high heels to his high school prom. Later on in the film, in his birthday party at camp, all his friends dress in drag as part of the celebration. Because of this, the camp director is on a crusade to be more like a normal summer camp.
- The Mudge Boy (2003) - Duncan Mudge (Emile Hirsch) wears his deceased mother's wedding dress.
- L'île de Black Mor (The Island of Black Mor) (2004) - In Jean-François Laguionie's motion picture, Petit Moine (Little Monk), captured by the pirates in a monastery, reveals to be a girl disguised as a boy, which leads to many arguments, since women on board are forbidden by pirate law.
- The Lord of the Rings: The Return of the King (2003) - Éowyn dresses as a soldier to be allowed to fight with the men.
- Rent (2005) - One of the main characters, Angel, is a drag queen.
- Robots (2005) - Fender, voiced by Robin Williams, slowly unleashes his cross-dressing tendencies.
- The Producers (2005) - The gay director, Roger De Bris, wears a dress when he is supposed to be the Grand Duchess Anastasia.
- Offside (2006) - An Iranian girl disguises herself as a boy to go attend the 2006 World Cup qualifying match between Iran and Bahrain.
- Pirates of the Caribbean: Dead Man's Chest (2006) - Elizabeth Swann disguises as a cabin boy aboard a Scottish merchant vessel.
- Stardust (2007) - Captain Shakespeare is a closeted cross-dresser.
- The Gamers: Dorkness Rising (2008) - Director Matt Vancil A male gamer rather unsuccessfully plays a female character.
- Rage (2009) - Jude Law plays Minx, a transvestite supermodel.
- The Disappearance of Haruhi Suzumiya (2010) - During the alternate universe sequence, Haruhi, who in this universe is a Kouyouen student, wears Kyon's tracksuit when disguising herself as a North High student.
- Denizen (2010) - The lead character (J.A. Steel) is a lesbian with a cross-dressing father, who is a general in the US Army.
- J. Edgar (2011) - after his mother dies, Hoover is shown donning her dress and necklace
- A Star is Born (2018) - The lead character, Ally, works as a performer at a drag club where she is discovered by Jackson Maine.
- The Beach Bum (2019) - The lead character, Moondog, disguises himself in women's clothing to escape discovery from the police.
Comedic element in documentary
- In the documentary, Giuliani Time, there are excerpts from Rudy Giuliani's appearance in a video, which was shown for the occasion of an Inner Circle press dinner.
Milton Berle was one of the most famous early cross-dressing comedians in skits and such on his NBC shows from 1948 to 1956. Harvey Korman played a hefty Jewish mother character on The Carol Burnett Show. Flip Wilson created the memorable recurring character Geraldine Jones on The Flip Wilson Show. The first episode of the Blackadder II series ends with Blackadder's servant, Baldrick, acting as bridesmaid, and Lord Flashheart swapping clothes and running off with Blackadder's bride. Some other comedy sketch shows, such as Monty Python's Flying Circus, Little Britain, The League of Gentlemen, Saturday Night Live and The Kids in the Hall routinely feature visual cross-dressing, with men dressing as women and sometimes speaking in falsetto. Not to be outdone in this regard, the (female) British team of French and Saunders have produced many sketches in which one or both of the actresses portray men. Rudy Giuliani appeared on Saturday Night Live dressed as a woman. Doing some of his best routines, Jonathan Winters played the character, Maude Fricket.
Kenan Thompson currently plays a range of women on Saturday Night Live.
Australian male comedian Barry Humphries has appeared as Dame Edna in several shows.
British stand-up comedian and actor Eddie Izzard, who describes himself as an 'executive' or 'action' transvestite and regularly cross-dresses both on and off stage, has acted in several films (including most recently Valkyrie), as well as releasing his stand-up work on video and DVD (Live at the Ambassadors (1993), Unrepeatable (1994), Definite Article (1996), Glorious (1997), Dress to Kill (1999), Circle (2002), and Sexie (2003)).
The Monty Python troupe have been known to cross dress for comedic purposes in their TV series and films. The troupe usually dress up as older, more unarousing women referred to by the troupe as "pepperpots". Although member Terry Jones was most famous for his female characters, all the members have been seen in drag in one sketch or another; members Michael Palin and Eric Idle have been said to look the most feminine, Graham Chapman specialized in screeching, annoying housewives and John Cleese, whom the troupe has said is the most hilarious in drag, appears so extremely unfeminine, with his square chin and six-foot, five-inch frame that it is funny. Cleese also wore female clothes while appearing as himself in a magazine advertisement for American Express. Monty Python's Flying Circus also did a sketch called "The Lumberjack Song," about a lumberjack who likes to "put on women's clothing and hang around in bars."
In Clue: The Musical, Mrs. White is usually played by a man.
In all versions of Hairspray--the original film, the stage musical, and the film adapted from the musical--Edna Turnblad is played by a man.
On some plays and films by Tyler Perry, he dresses up as a woman to play as Madea.
Meryl Streep played a male rabbi in an episode of Angels in America.
Michelle Ehlen plays a butch lesbian actress who gets cast as a man in a film in the comedic feature Butch Jamie.
The Kids in the Hall comedy troupe often dress up as female characters. In contrast to Monty Python, who dressed as women in an exaggerated fashion for comedic purposes, The Kids in the Hall usually played women straight, their reasoning for cross-dressing being that there are few if any women involved in their projects. This has gone on to be one of the group's defining characteristics.
Matt Lucas and David Walliams regularly cross-dress in the Little Britain television comedy show, with Lucas in particular often somewhat more feminine and convincing in his appearance and performances than cross-dressing comedians of the past. The two also sometimes play a pair of unconvincing transvestites as a parody of some cross-dressers who try to act in a stereotypically feminine way while not succeeding in "passing" as women.
In the 1992 Kannada movie Bombat Hendthi, a well-known male actor and dancer named Sridar crossdresses. His character and the character's friends want to rent a house, but the owners are not willing to rent to bachelors. So Sridhar crossdresses to become his friend's wife, while the rest of the actors (Sihi-kahi Chandru, Tennis Krishna, Ramesh Bhatt, Malashri and Anjali) are in supporting roles.
Programs that feature cross-dressing
- All in the Family featured female impersonator character "Beverley Lasalle" in later episodes
- 'Allo 'Allo! featuring cross-dressing in most episodes.
- The 1st Shop of Coffee Prince (2007) - The main character pretends to be a boy in order to obtain a job at a coffee shop that only hires men.
- Angry Boys (2011) - Chris Lilley cross-dresses as two characters, Ruth (Gran) Sims and Jen Okazaki in this Australian comedy show.
- Are You Being Served? often features John Inman taking on female roles. Some of the other cast members such as Frank Thornton occasionally appear in drag as well.
- Arrested Development - Tobias Fünke (played by David Cross) disguises himself as a British nanny named Mrs. Featherbottom in order to maintain a relationship with his estranged family. (This is a direct reference to the film Mrs. Doubtfire). This development is an outcropping of the fact that, throughout the series, Tobias exhibits signs of being a latent homosexual.
- Baskets - Louie Anderson portrays Christine Baskets, the matriarch of a quirky family in Bakersfield, California.
- In Axis Powers: Hetalia, Poland cross-dresses as a hobby and has a "valley girl" accent.
- The Big Bang Theory - In the first two episodes of the series a cross-dresser is described as having occupied Apartment 4B prior to Penny. The character was not named or seen until a flashback scene in Season 3, Episode 22 when Leonard Hofstadter knocks on her apartment door and Louie/Louise, portrayed by Ajgie Kirkland en femme, directs Leonard to the "crazy guy across the hall" (Sheldon Cooper). Sheldon also dresses up as a french maid after losing a bet with Howard Wolowitz. The whole gang dress as female DC superheroes after losing a bet.
- Blackadder has several cross-dressing incidences.
- In "Bells", Kate (Gabrielle Glaister) dresses up as "Bob" in order to earn money working as a valet for Lord Blackadder, who finds himself attracted to this young "boy", eventually discovering Kate's identity and arranging a marriage, in which Baldrick takes the role of a bridesmaid. Lord Flashheart interrupts and steals away "Bob", but not before exchanging clothing with her.
- In "Chains", Prince Ludwig the Indestructible (Hugh Laurie) impersonates Queenie with a perfect disguise (really Laurie overdubbing Miranda Richardson).
- In "Amy and Amiability" from Blackadder the Third, Amy Hardwood (Miranda Richardson) assumes the role of a highwayman in order to get money for her bankrupt father.
- Kate returns in "Major Star" from Blackadder Goes Forth as Bob Parkhurst, driver for General Melchett. Also, Lieutenant George (Hugh Laurie in a different role) dresses in drag as "Georgina" for a music-hall show, put on to entertain the troops. He inadvertently draws the amorous attentions of Melchett. "Georgina" is only able to escape Melchett's efforts at marriage through a report from Captain Blackadder, that she wandered into no-man's land and trod on a cluster of landmines.
- Black Butler (2010) - In one episode Ciel dresses as a woman.
- Bosom Buddies - Tom Hanks and Peter Scolari star as two single men who must regularly disguise themselves as women, in order to live in a ladies-only hotel, the only apartment they can afford.
- Boston Legal character Clarence Bell is a transvestite client who came for legal help after being fired from his job. He later joined the firm as a legal assistant and eventually as a lawyer.
- Boy Meets World - Different characters cross-dress in later episodes.
- Briefgeheim - French teacher Ms. Tijnman is actually a man dressed as a woman.
- Bucket & Skinner's Epic Adventures (2011) in the episode "Epic Girls" Bucket and Skinner disguise themselves as girls in order to sneak into a party. They are also shown trying on different dresses.
- In season 4 of Criminal Minds Jackson Rathbone plays a janitor at a hotel with split-personality disorder. The character, Adam, is a shy, abused, withdrawn young man. His alter-personality, is a strong, confident, southern women named Amanda. Adam/Amanda tries to kill his/her father because of all of the abuse suffered. Afterwards 'Amanda' becomes the dominant personality. At the end of the episode 'Amanda' is shown to have undergone a transformation, complete with make-up, a long curled wig, and pink clothing.
- Crusoe (2008) - A recurring character Oliver is revealed to actually be a woman named Olivia (played by Mía Maestro). Crusoe discovered her one-day when she was bathing for the first time on the island after being aboard the ship for so long. She pretends to be Oliver and helps the doctor for her personal safety from the male crew.
- In Cyberchase, Delete impersonates Motherboard with a wig and some makeup.
- Cybersix (TV series) from the 1999 serial and the comic, dresses as a male teacher named Adrian Seidelman, in order to escape Von Richter (her creator).
- Chihiro Fujisaki from Danganronpa cross-dresses as a female because of his deep insecurity about his weak physique, resorting to cross-dressing to hide his gender identity.
- Dårfinkar & dönickar - The main character Simone is mistaken for a boy on her first day at a new school when she does not correct her teacher for mispronouncing her name as Simon.
- Deal or No Deal - On the episode that aired on February 14, 2008, contestant Edward Tommasi wore heels and a dress to win a $10 bet.
- Degrassi: The Next Generation (renamed Degrassi from the tenth season) features a transgender student in season 10, Adam Torres (portrayed by Jordan Todosey). Adam is biologically female, but he identifies as male and dresses as a boy. Adam wants to keep the fact that he's transgender a secret, and hopes that the people he meets will see him as male.
- Dexter's Laboratory - Many episodes feature Dexter in drag. Examples being Dimwit Dexter, Remember Me?, and Tribe Called Girl.
- Doctor Who
- In the 1966 story "The Highlanders" the second Doctor (Patrick Troughton) dresses as an old washerwoman as a ruse to try to find his companions in a crowded tavern in the aftermath of the Battle of Culloden.
- In 1973 in "The Green Death" the third Doctor (Jon Pertwee) disguises himself as a cleaning lady to infiltrate Global Chemicals, where he engages in banter with the UNIT operative Mike Yates and refers to his plastic bucket as his 'handbag'. Both these interludes of 'cross-dressing' are played mainly for their comic value amid serious story-lines.
- Dragon Ball
- In the episode "Oolong the Terrible" (in a scene adapted from the Dragon Ball manga's fifth chapter "Oo! Oo! Oolong, Bulma and Goku learn that a shapeshifter named Oolong has been kidnapping village girls to marry him. Bulma comes up with a plan to rescue the girls by tricking Oolong into taking Goku crossdressing as Pochawompa the next girl Oolong has his sights on. When Oolong first appears he is in the form of a red devil and tries to flirt with Goku who unfortunately has to take a leak though Oolong mistakenly assumes "she" is being shy and transforms into a handsome man causing Bulma leave her hiding place to woo him, while Goku takes the opportunity to relieve himself unfortunately Oolong notices and enraged turns into a bull though Goku responds by removing the dress and challenging Oolong to a fight.
- In the episode "Look Out for Launch" (in a scene adapted from the Dragon Ball manga's twenty-seventh chapter "Nothing to Sneeze At" ), in order to trick Good Launch into wearing pink frilled black lingerie leotard with matching leggings, Master Roshi convinces her and Goku (who is young & naive) that it is a training uniform with Master Roshi, Krillin, and Goku wearing identical lingerie as "training uniforms" so Launch won't suspect Roshi's real reason which is to see Launch in lingerie as he is an old lecher in addition to being a legendary martial artist. Unfortunately for Roshi, Launch's personality changes when she sneezing going from her good and innocent persona to her tough gun-toting Bad Launch persona, who unlike her good persona quickly realizes what she's wearing and angrily pulls out an IMI Uzi to shot at them in a comical fashion before sneezing again and returning to her Good Launch persona with neither Goku nor Good Launch realizing Master Roshi's deception due to their pure-hearted personalities.
- Dragon Ball GT
- In the episode ?Trunks the Bride? Trunks was forced to dress up as a bride to save a girl and planet's village after it was attacked by a monster named Zoonama who can create earthquakes. It was supposed to be Goku as the fake bride, but because he was too short to wear the dress he and Pan agreed on making him the fake bride.
- In ?Whiskers of Power? Trunks as Trunksette becomes the ?bride? for Zoonama as he is taken to Soonama's lair while there Goku, Pan, and Doma, the bride's fi?acee, try to cut Zoonama's whiskers as he drinks a potion to knock him out, they only cut one and he wakes up! With Pan finding out that Zoonama can only predict earthquakes and not make them, Zoonama's lair, really a volcano, burst in to flames as Goku blast it with his Kamehameha destroying it as the episode ends with Goku, Pan, and a happy-to-be-out-that-dress Trunks is given a dragon ball though someone steals it.
- El Hazard - Makoto Mizuhara impersonates Princess Fatora of Roshtaria who is kidnapped by the Phantom Tribe because of his uncanny resemblance to the princess.
- The Drew Carey Show - Drew's brother, Steve Carey, is a cross-dresser.
- The Famous Five TV series
- Fetch! with Ruff Ruffman - A Children's game show on PBS Kids Go!. Some episodes have boys dressing up in female outfits. Jay in Season 3 wore a cheerleading outfit (but it had shorts) in the episode "The Ol' Switcheroo", and in the episode of Season 4 called "Is it a Bird? Is it a Plane? It's...Ruffmanman!", Brian was with Bethany as part of the "Indestructible Butterflies"
- Firefly - Mal Reynolds (played by Nathan Fillion) wears a dress and a bonnet as a disguise while saving a town from bandits. He is later asked about this, and his response indicates that he has cross-dressed in the past.
- The Flip Wilson Show (1970) - Flip Wilson plays Geraldine Jones as a recurring character in this sketch variety series.
- Friends - Chandler's father (played by Kathleen Turner) is a cross-dresser.
- Fruits Basket - Ritsu Sohma dresses as female, because it makes him feel more confident, and comfortable. His cousins Ayame Sohma and his younger brother, Yuki occasionally cross-dress because they look good in female clothing. With the former it's voluntary, the latter less so.
- Fushigi Yuugi - Nuriko, one of the Suzaku Seven Celestial Warriors, dresses as a woman in memory of his dead sister. In the middle of the manga series, the Suzaku Warriors had had to dress up as women to avoid being killed in the island of Nyousei, where barbaric, cannibalistic, anti-masculinist women lived. This idea is excluded from the anime series, but revived in the omake.
- In Game of Thrones, Arya Stark is a tomboy who prefers more masculine activities such as sword fighting instead of the more feminine activities like embroidery. After her father is arrested and executed she assumes the identity of a boy named "Arry" and tries to return to her family.
- In the anime Genesis Climber Mospeada (also known as the New Generation segment of Robotech) the character of Yellow Belmont/Lancer cross-dresses as a means of disguise, as well as to perform in his rock singer identity (known as Yellow Dancer in Robotech).
- Gintama - In Episode 24 Gintoki and Katsura are wearing female kimono as Piko and Zuka.
- Glee - In Season 3, episode 16 ("Saturday Night Glee-ver"), actor Alex Newell portrays Wade Adams, a member of rival glee club Vocal Adrenaline, who performs as his transgender alter ego "Unique". In Season 4, Wade/Unique becomes a recurrent character.
- Golden Girls - Dorothy Zbronak's (Beatrice Arthur) brother Phil Petrillo, who was never seen on air, is a cross-dresser. When he died in the episode Ebbtide's Revenge, Phil's widow Angela had him buried in a teddy, to which Dorothy said to her roommates "it looks like he died in a Benny Hill sketch!".
- Gravitation - The main character, Shuichi Shindou, wears his sister's schoolgirl uniform and dons a maid outfit to try to get the attention of Eiri Yuki.
- H2O: Footprints in the Sand (2008) - Hamaji Yakumo is a boy who cross-dresses as a girl.
- Hana-Kimi (1997-2004) - The manga series centers on Mizuki Ashiya, a Japanese girl who lives in the United States. One day, she sees a track and field competition on TV, and becomes attracted to one of the high jump competitors, Izumi Sano. She begins to idolize the young athlete and eventually transfers to Japan to attend the same school that Sano attends. There is a catch, however: Sano attends an all-boys high school, named Osaka Gakuen and Mizuki must disguise herself as a boy to enter. It has been adapted into four drama shows: Hanazakarino Kimitachihe (Taiwan), Hanazakari no Kimitachi e (Japan), Hanazakari no Kimitachi e (Japan) and To the Beautiful You (Korea).
- Happiness! (2006) - A secondary character of the series, Jun Watarase, is a boy who dresses as a girl.
- HeartCatch PreCure - For the first half of the series, Itsuki Myoudouin cross-dresses as a boy because her brother is too ill to be heir of their dojo.
- Heaven's Lost Property - In episode 11, Sugata dresses like a long-haired woman while Mikako dresses like a man. Also, Tomoki is transformed into a girl called "Tomoko".
- He's a Lady - The 2004 reality television series involves male contestants competing with each other to act as effeminately as possible, including cross-dressing.
- Himegoto (2014) - The protagonist, Hime Arikawa, dresses as a girl.
- Hollyoaks character Kris Fisher is a cross-dresser.
- iCarly - In the episode "iWant My Website Back", Spencer dressed as an old lady to fool Nevel into giving iCarly their URL back, but instead, he attracted an old man.
- InuYasha - Jakotsu of the Band of seven always wears women's clothes and repeatedly flirts with InuYasha.
- Invader Zim - In the episode "Walk for your Lives", Zim uses a fat lady disguise to get rid of an explosion that is exploding really really slowly.
- I My Me! Strawberry Eggs - Main character Hibiki Amawa disguises himself as a woman to obtain a job as a teacher at school that will only hire women.
- In the British TV sitcom Keeping Up Appearances Hyacinth's brother-in-law Bruce is a cross-dresser which Hyacinth tries not to let people find out about. In several episodes one can see Bruce in his outfits.
- Goretti from Killinaskully was played by actor Pat Shortt.
- Various characters from Kuroshitsuji including main character Ciel Phantomhive and Grell Sutcliff crosdress in some episodes and the OVAs.
- Leonardo - Lisa disguises herself as a boy (Tomaso) so she may study art under Andrea del Verrocchio.
- Love in the Moonlight (2016) - A 19th-century Korean girl dressed as a boy and eventually becomes a eunuch.
- The Loud House - Lincoln dresses up as a girl like in episodes like Overnight Success, A Novel Idea and Cover Girls.
- Maid Sama! - Aoi Hyoudou, an internet celebrity, cross-dresses so he won't be made fun of for liking cute, girl things.
- Maria Holic (2009) - Mariya Shid? is a boy who cross-dresses as a girl.
- M*A*S*H - Klinger regularly cross-dresses as part of a futile attempt to be dismissed from the military.
- McHale's Navy - Whenever McHale and/or his crew have to disguise themselves in order to carry out one of their elaborate schemes, it's usually Tinker (Billy Sands) or Ensign Parker (Tim Conway) who has to dress up as a woman.
- Megaman NT Warrior (Rockman EXE) - Villain Magnus Gauss (Gauss Magnets) cross-dresses as a woman and is obsessed with Dr. Wily. In one episode (unaired in the dub), three of the main characters cross-dress as idol singer Aki-chan to rescue a group of kidnapped girls.
- In Merlin's Apprentice a young girl Brianna disguises herself as a boy squire in order to avenge her family's loss of land.
- "Written in Blood", the second episode of crime drama Midsomer Murders, features a cross-dressing victim.
- Rich Fulcher plays a woman named Eleanor in the season 3 episode "Eels" of the British comedy show The Mighty Boosh. He continues to dress as Eleanor for stand-up comedy gigs, and refers to her as a separate person from himself. In the season 2 episode "Nanageddon", main characters Howard Moon (Julian Barratt) and Vince Noir (Noel Fielding) dress as nanas in order to sneak into a bingo game and find the elusive demon, Nanatoo.
- Mobile Suit Gundam 00, Gundam pilot Tieria Erde cross-dresses in the second season in order to gain entrance to a party.
- Mobile Suit Gundam ZZ, Gundam pilot Judau Ashta cross-dresses in the second season to free his female companions from a harem
- Along with the members of Monty Python's Flying Circus dressing up as women for comedic purposes, Monty Python featured a sketch called "The Lumberjack Song", about a lumberjack who likes to "put on women's clothing and hang around in bars."
- Minami-ke - Makoto regularly cross-dresses as Mako-chan to get close a girl he likes. Another character, T?ma is a tomboy with three older brothers that regularly wears male clothing.
- Mr. Headmistress (1998) - TV movie - Ex-con Harland Williams disguises himself as the new Headmistress of an all-girl school to avoid some thugs.
- Murder, She Wrote - The episode "Birds of a Feather" features two drag queens. Also in "Amsterdam Kill", there is a woman disguised as a man and there is another in one of the episodes set in Ireland.
- My Little Pony - In the episode called "Brotherhooves Social", Big MacIntosh is disguised as a mare named Orchard Blossom with a blond wig and a blue dress complete with pink makeup and fake eyelashes.
- Nail Shop Paris (2013) - An author tries to break out of her writer's block by disguising herself as a boy so she can base her next novel on a nail salon staffed only by men.
- In The Nick Cannon Show Nick dresses like a woman in 6 episodes.
- Otoboku - Mizuho Miyanokoji cross-dresses to attend a girls' school as per his grandfather's wishes.
- On Our Own the oldest brother of an orphaned family cross dresses, pretending to be an older aunt, to keep his family together until he is legally of age. Features the Smollett family.
- One Piece - A Japanese anime and a manga about pirates includes a number of cross-dressing characters, the okamas. The most notable of them are Mr. 2 (a.k.a.Bon Clay) who can change his physical appearance and Emporio Ivankov, a queen of a drag queen kingdom, who can change his sex by controlling the hormones (and strongly resembles Tim Curry's Dr. Frank-N-Furter from the Rocky Horror Picture Show).
- One Well-Raised Daughter - In this South Korean serial drama, the main protagonist, a female has to dress like a boy in order to inherit her family's Soy Sauce business in order to keep it out of the hands of a scheming woman and a competing company. Although she is outed after she succeeds, she exacts revenge on them upon learning their plans to take over the business.
- Opposite Sex (2000) - In the pilot episode, the first three boys (Milo Ventimiglia, Kyle Howard and Chris Evans) in a formerly all-girls school do a drag routine in the schools annual talent show.
- Otome wa Boku ni Koishiteru (2006) - The main character of the series, Mizuho Miyanokouji, is a boy who cross-dresses as a girl.
- Ouran High School Host Club - Main character Haruhi Fujioka cross-dresses regularly and is initially mistaken as male by the members of the Host Club. Also, various Host Club members cross-dress on occasion, including manga episodes 10 (Hikaru, Kaoru, and Hunny as part of a plan to keep Haruhi away from Saint Lobelia's Zuka Club, and in the anime adaptation, Tamaki and Kyoya also cross-dress for the same reason), 11 (Hikaru and Kaoru take turns dressing as the witch of the central wing), 15 (Hikaru, Kaoru, Tamaki, and Mori all dress in Alice costumes, and Kyoya portrays the Black Queen as well as Alice's mother in this chapter), and 20 (Hunny while going undercover with the Host Club to monitor Haruhi and Hikaru's date).
- Perfect Strangers Larry dresses up as a woman in the episode Just a Gigolo.
- Pokémon - James from Team Rocket, often appears in a dress or skirt, and in one of the banned episodes, he is even seen in a bikini complete with inflatable breasts. A partial list of characters including Ash Ketchum (three times), and Jessie and Meowth of Team Rocket, have also been known to cross-dress, although not as often as James. One of Misty's older sisters dress up as a prince and Gastly also once disguised as a beautiful maiden and an old woman at a summer festival.
- The Powerpuff Girls (1998) - Bubbles disguises herself as one of the Rowdyruff Boys, Boomer, to go undercover and track down his brothers, Brick and Butch. Professor Utonium also disguises himself as a woman in another episode.
- Pretty Cure (2004) - In one episode, Nagisa Misumi disguises herself as a man twice in an attempt to reclaim Mepple, who had been confiscated. In a later episode, Nagisa plays the part of Romeo in Verone Academy's school play of Romeo and Juliet.
- Princess Knight - Princess Sapphire disguises herself like a man to fight in her adventures.
- Princess Princess - Three students in an all-male school dress as girls to raise the spirits of the other students.
- Robin Hood (2006) - Djaq (played by Anjali Jay) is a Saracen who true name is Saffiya, but she disguises herself as a boy by adopting her dead twin brother's name and appearance.
- Ramen Fighter Miki - Episode 10 Part 1 includes a scene where Kankuro is wearing Miki's outfit while trying to beat her at her own game (that being ramen delivery). Then at the end of Episode 12 Part 1, he dons the disguise of an aristocratic lady to try to get Miki to challenge him.
- Ranma 1/2 - A Japanese Anime about a martial artist called Ranma who can transform into a girl. His gender is easily changed through means not under his control, so a costume which works on one gender often suddenly and comically becomes inappropriate cross-dressing. Also appearing in the anime and manga are Tsubasa Kurenai and Konatsu, who are male cross-dressers, and Ukyo Kuonji, a female cross-dresser and potential love interest of the gender-changing Ranma.
- The Riches (2007) - Sam Malloy (Aidan Mitchell), the youngest son of an Irish-American Traveller family, prefers cross-dressing. Even though under certain circumstances Sam can wear boys' clothes, he occasionally reverts to girls' clothing, much to the embarrassment of his family. (The Riches also features Eddie Izzard portraying Sam's non-transvestite dad, Wayne Malloy.)
- The Rose of Versailles (1979-1980) - Oscar François de Jarjayes, the main character of the series, is a woman who was raised as a boy and who cross-dresses as a man.
- RuPaul's Drag Race (2009-present) a competition reality show premised around Drag Queens, men who cross-dress professionally as a means of entertainment. The show gives a deeper side to the art of female impersonation, as well as insight into the world of a gay drag artist.
- Sailor Moon - In one episode of the first season, Zoisite (one of the villains) disguises himself as Sailor Moon. In the "Sailor Moon Super S" season, Fish-Eye always dresses like a woman. In both "Sailor Moon S" and "Sailor Stars" seasons, Haruka Tenoh (Sailor Uranus) wears masculine clothes most of the time, and even chooses to wear the masculine version of her school uniform, to the point of being mistaken for a boy by other characters. In "Sailor Stars", Seiya, Taiki, and Yaten, became Sailor Starlights.
- Samantha oups! (2004-2007) - French comedy series starring two men who portray themselves as women--Samantha (played by David Strajmayster) and Chantal (Guillaume Carcaud).
- Sasameki Koto (2009) - Masaki Akemiya is a boy who cross-dresses as a girl.
- Saved by the Bell - Zach and Screech occasionally dress as women either to disguise themselves or for comic effect.
- SheZow -- A cartoon about a preteen boy who gains a magical ring that grants him superpowers, but since the ring is intended only for a girl, his superhero form is cross-dressed.
- In the Silver Spoons episode "The Most Beautiful Girl in the World", Ricky (Ricky Schroeder) is convinced to dress up in drag and be a friend's date for a dance because his friend saved Ricky from an almost fatal accident previously.
- In The Simpsons episode "Girls Just Want to Have Sums", Lisa Simpson disguises herself as a boy named Jake Boyman in order to learn math when the school is segregated by gender. Bart has also worn girls' clothes on several occasions, sometimes by choice, and sometimes against his will.
- Something in the Air (2000-2002) - Features a cross-dressing politician, Doug Rutherford (played by Roger Oakley).
- SpongeBob SquarePants - SpongeBob has dressed like a woman in several episodes. His best friend Patrick Star cross-dresses in order to protect himself from an assassin in the episode "That's No Lady".
- Star Trek: Deep Space Nine has on several occasions featured characters cross-dressing. In "Profit and Lace", the character Quark dresses as a woman to prevent an enemy of his to ascend to the power of Grand Nagus. In another Ferengi-related episode, "Rules of Acquisition", a female Ferengi cross-dresses because females are not permitted to earn profit in the Ferengi culture. "Rules of Acquisition" is also one of the few episodes that references how the Federation views homosexuality when the character Dax discusses that it's a normal thing for a man to be in love with another man (She doesn't know that the man she is chatting with at the time is really a woman, cross-dressed).
- On The Suite Life on Deck, Bailey pretended to be a boy so she could attend Seven Seas High on the SS Tipton because all of the girls rooms were taken. She becomes Zack's roommate and he agrees to keep it a secret. It is quickly found that Bailey is actually a girl and she ends up rooming with London.
- The Suite Life of Zack & Cody - Both Zack and Cody (played by real life twins Cole and Dylan Sprouse) cross-dress in several episodes for numerous reasons; one most notably being Cody entering a beauty pageant for young girls while Zack approves of it because the first prize is a new bike.
- Summer Heights High (2007) - Chris Lilley cross-dresses for the character of Ja'mie King in this Australian comedy; she is often seen wearing a green school dress.
- Sungkyunkwan Scandal - In 18th century Korea, a young girl dresses as a boy so she can attend a prestigious school and earn money to support her impoverished family.
- The Jeffersons (1975-1985) - George's navy buddy Eddie (Edie) Stokes and employee Leroy cross-dress to fool Louise when George can't find the real Eddie .
- Three's Company (1977-1984) - Jack Tripper, played by John Ritter, dresses up as a woman in two episodes
- Three's Company (1977-1984) - Larry Dallas played by Richard Kline dresses up as a woman in one episode.
- Tipping the Velvet (2002) - A coming of age story about a young woman named Nan (Rachael Stirling) who falls in love with a male impersonator.
- Together (2009) - Singaporean drama which in episode 10, Yao Wuji (Zhang Zhen Huan) was asked to cross-dress as part of his job of being an Ah Gua (a man who acts like a woman) which made his father (Wang Yuqing) to nearly kill him by constantly beating him. He was also seen cross-dressing in episode 9.
- Twin Peaks (1990-1991) - The character Catherine Martell (Piper Laurie) disguises as Japanese investor Mr. Tojamura, Denise/Dennis Bryson (David Duchovny) is a male character who wear women's clothes because it relaxes him, and at one point Windom Earle (Kenneth Welsh) impersonates the Log Lady.
- The Ugliest Girl in Town (1968) - sitcom about a male American actor who accepts a female modeling job in London to be with his girlfriend.
- Uh Oh! - During episode 74 of the first season, a part of the Slime Tour obstacle course race that took place in Victoria, British Columbia included an obstacle where the three participants had to first put on ball gowns à la Queen Victoria before moving on to the next obstacle; one of the children in the race was a boy named "Rad" Rhys.
- We Can Be Heroes (2005) - Chris Lilley cross-dresses for two characters, Pat Mullins and Ja'mie King in this Australian mockumentary, the first show that Lilley created.
- Work It (2012) - American television sitcom about two men who must dress as women in order to keep a job in a bad economy.
- World Wrestling Entertainment wrestler Dustin Rhodes portrayed "Goldust", a gimmick that involved cross-dressing as well as former wrestler Vito LoGrasso, who later gained the nickname "The Toughest Man To Ever Wear A Dress". Tyler Breeze's "Fashion Police" gimmick alongside Fandango also involved cross-dressing. Numerous other male wrestlers in various promotions have also donned women's clothing as a punishment for losing a match over the years such as Brian Pillman and Perry Saturn.
- Young Americans (2000) TV series in which one of the female characters poses as a boy.
- You Can't Do That On Television - Several comedy sketches, particularly in the early years, featured boys in the cast wearing dresses for various reasons.
- You Rang, M'Lord? - Cissy is a lesbian cross-dresser, complete with monocle, cravat and short hair.
- You're Beautiful (2009) - A young nun cross-dresses as a boy to impersonate her brother in a boy band. You're Beautiful was remade into the 2013 Taiwanese series Fabulous Boys.
- Yu Yu Hakusho - In The Deadly Triad episode (first season of the series), when Yusuke Urameshi fights against the Three Devils, he finds that Miyuki, one of Three Demons, is biologically a man, but in Miyuki's heart (s)he is a woman. However, this "discovery" was edited out of the English version of this series.
- Zoey 101 In one episode of this show Lola disguises herself as a boy to prove boys can still act the same if a girl is around.
- In Zoids: Chaotic Century episode 28 "Run, Wolf!" Prince Rudolph Zeppelin III is disguised as a girl in order to hide his identity.
Animation, cartoons and anime
Bugs Bunny frequently cross-dresses in his cartoons for either comedic effect, or to confound a male opponent. Notable examples include "Rabbit of Seville", "What's Opera Doc" and "Rabbit Seasoning", all in attempts to deceive Elmer Fudd.
Birdo from the Super Mario series is an interdeterminate, though highly suspected, cross-dressing male dinosaur.
Doctor N. Gin from the Crash Bandicoot series wears a ballerina dancer outfit in Crash Tag Team Racing. The tutu, obtained through one of Crash's missions, is an alternative costume that made N. Gin feel "pretty" and boosted his self-esteem.
Him from the Powerpuff Girls series is shown every time, wearing a typical skirt, fishnet stockings, and high-heeled boots.
In the Disney film Mulan, derived from a Chinese ballad-poem, the character Fa Mulan disguises herself as a man, to take her elderly father's place in the army.
Jessie and James from Pokémon cross-dress as ballet performers and wedding couples.
In the manga and anime Ouran High School Host Club, the main character of Haruhi Fujioka cross-dresses as a boy so that she can work in a host club to pay off a debt she owes to the other members. Haruhi's father is also a cross-dresser.
In the manga and live action series of Hana-Kimi (Hanazakari no Kimitachi e), the main character, Mizuki Ashiya, cross-dresses as a boy to attend an all-boys boarding school to meet her idol, Izumi Sano.
In the manga and anime Shugo Chara, Nagihiko Fujisaki cross-dresses as his "twin" Nadeshiko out of family tradition. He also crossdresses in his transformation Yamato Maihime.
In the manga and anime Mermaid Melody Pichi Pichi Pitch Pure, one of Michel's servants, named Lady Bat, cross-dresses as a female, actually a male.
In the anime Himegoto, the main character, Hime Arikawa, cross-dresses to join the Student Council who promises to pay off the debt created by Hime's parents. There are also four other characters who cross dress, including Hime's brother, Kaguya, HIro Toyotomi, No. 1, and Mitsunaga Oda, all of whom are against the Student Council.