Dressing up boys and girls dating

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[edit]

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 musicalcomedy filmVictor 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[edit]

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
• Sysmäläinen (1938) – Finnish film set in the 17th century where the main female character disguises herself as a man who pretends to be a woman.
• 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
• Op med lille Martha (1946) - a Danish remake of Fram för lilla Märta
• 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 Stanisław 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
• Yentl (1983) - Barbra Streisand poses as a boy in order to study at a yeshiva
• 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 man
• 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
• 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 under the name of Ping to fight the Huns in place of her father^[1]
• Shakespeare in Love (1998) – includes Shakespeare's use of female impersonators in his plays
• Adolescence of Utena (1999) – Utena Tenjou, a tomboyish girl, cross-dresses to be a male student at Ohtori Academy where she is drawn into a series of swordsmen's duels to win the hand of Anthy Himemiya, the mysterious "Rose Bride"
• 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 racer 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 portrayed as Madea in a series of comedy films:
• 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[edit]

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.

• The Female Highwayman (1906) – Features a female criminal who dresses as a man while committing thefts and an armed robbery
• 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 Afghanrefugee, 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[edit]

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) – 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)^[2]
• 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 (Paul Reubens) and an escaped convict (Judd Omen) 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.^[3]
• 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.
• Lilo & Stitch (2002) - Pleakley, a male alien who formerly served as an agent of the Galactic Federation, disguises himself as a woman when visiting Earth with his partner Dr. Jumba Jookiba.
• Boat Trip (2002) – Two straight men (Cuba Gooding Jr. and Horatio Sanz) mistakenly end up on gay cruise together and encounter the flamboyantly gay Hector (Maurice Godin) who introduces himself in drag as well as Tom (Ken Campbell) who cross-dresses regularly. There are also other instances of drag throughout the film.
• 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.
• The Lord of the Rings: The Return of the King (2003) – Éowyn dresses as a soldier to be allowed to fight with the men.
• 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.
• 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 DuchessAnastasia.
• 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^[4]
• 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[edit]

• 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.

Television[edit]

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 actorEddie 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.^{[citation needed]}

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[edit]

• 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.