History of cross dressing

Updated on Sep 25, 2024

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This article details the history of cross-dressing.

Greek

In punishment for his murder of Iphitus, Heracles/Hercules was given to Omphale as a slave. Many variants of this story say that she not only compelled him to do women's work, but compelled him to dress as a woman while her slave.

In Achilles on Skyros, Achilles was dressed in women's clothing by his mother Thetis at the court of Lycomedes, to hide him from Odysseus who wanted him to join the Trojan War.

Athena often goes to the aid of people in the guise of men in The Odyssey.

Tiresias was turned into a woman after angering the goddess Hera by killing a female snake that was coupling.

In the cult of Aphroditus, worshipers cross-dressed, men wore women's clothing and women dressed in men's clothing with false beards.

Norse

Thor dressed as Freyja to get Mjölnir back in Þrymskviða.

Odin dressed as a female healer as part of his efforts to seduce Rindr.

Hagbard in the Scandinavian legend of Hagbard and Signy (the Romeo and Juliet of the Vikings). After having slain Signy's brothers and suitors, Hagbard was no longer welcome in the hall of Signy's father Sigar. Hagbard then dressed up as one of his brother Haki's shieldmaidens to gain access to the chambers of his beloved. When the handmaidens washed his legs, they asked him why they were so furry and why his hands were so calloused. He responded with a clever verse to explain his strange appearance. Signy, however, who understood that it was Hagbard who had come to see her, explained to the maidens that his verse was truthful. Hagbard was, however, deceived by the handmaidens and he was arrested by Sigar's warriors. Hagbard was hanged and Signy committed suicide as Hagbard watched from the gallows.

Frotho I dressed as a shieldmaiden in one of his eastern campaigns.

Hervor from Hervarar saga. When Hervor learnt that her father had been the infamous Swedish berserker Angantyr, she dressed as a man, called herself Hjörvard and lived for a long time as a Viking.

Hindu

The Mahabharata: In the Agnyatbaas ("exile") period of one year imposed upon the Pandavas, in which they had to keep their identities secret to avoid detection, Arjuna cross-dressed as Brihannala and became a dance teacher.

The goddess Bahuchara Mata: In one legend, Bapiya was cursed by her and he became impotent. The curse was lifted only when he worshiped her by dressing and acting like a woman.

Devotees of the god Krishna: In the region of Brajbhoomi, some male devotees of the god Krishna, called the sakhis saints, dress in female attire to pose as his consort, the goddess Radha, as an act of devotion.

Background

Patriarchy is the social system in which men have all of the power towards women and their families in regards to the tradition, law, division of labor, and education women can take part in. Women used cross-dressing to pass as men in order to live adventurous lives outside of the home, which were unlikely to occur while living as women. Women who engaged in cross-dressing in earlier centuries were lower class women who would gain access to economic independence as well as freedom to travel risking little of what they had. Cross-dressing that consisted of women dressing as men had more positive attitudes than vice versa; Altenburger states that female to male cross-dressing depicted a movement forward in terms of social status, power, and freedom. Men who cross-dressed were looked down upon because they automatically lost status when dressed as a woman. It was also said that men would cross-dress to gain access around women for their own sexual desire.

Historical figures

Famous historical examples of cross-dressing people include:

Hua Mulan, the central figure of the Ballad of Mulan (and of the Disney film Mulan), may be a historical or fictional figure. She is said to have lived in China during the Northern Wei, and to have posed as a man to fulfill the household draft quota, thus saving her ill and aged father from serving.

Several tales of the Desert Fathers speak of monks who were disguised women, and being discovered only when their bodies were prepared for burial. One such woman, Marina the Monk, died 508, accompanied her father to a monastery and adopted a monk's habit as a disguise. When falsely accused of getting a woman pregnant, she patiently bore the accusation rather than revealing her identity to clear her name, an action praised in medieval books of saints' lives as an example of humble forbearance.

The legend of Pope Joan alleges that she was a promiscuous female pope who dressed like a man and reigned from 855 to 858. Modern historians regard her as a mythical figure who originated from 13th-century anti-papal satire.

Catalina de Erauso (1592–1650), known as la monja alférez "the Nun Lieutenant", was a Spanish woman who, after being forced to enter a convent, escaped from it disguised as a man, fled to America and enrolled herself in the Spanish army under the false name of Alonso Díaz Ramírez de Guzmán. She served under several captains, including her own brother, and was never discovered. She was said to behave as an extremely bold soldier, although she had a successful career, reaching the rank of alférez (lieutenant) and becoming quite well known in the Americas. After a fight in which she killed a man, she was severely injured, and fearing her end, she confessed her true sex to a bishop. She nonetheless survived, and there was a huge scandal afterwards, specially since as a man she had become quite famous in the Americas, and because nobody had ever suspected anything about her true sex. Nevertheless, thanks to the scandal and her fame as a brave soldier, she became a celebrity. She went back to Spain, and was even granted a special dispensation by the pope to wear men's clothes. She started using the male name of Antonio de Erauso, and went back to the America, where she served in the army till her death in 1650.

Anne Bonny and Mary Read were 18th-century pirates. Bonny in particular gained significant notoriety, but both were eventually captured. Unlike the rest of the male crew, Bonny and Read were not immediately executed because Read was pregnant and Bonny stated that she was as well.

Ulrika Eleonora Stålhammar was a Swedish woman who served as a soldier during the Great Northern War and married a woman.

Charles Edward Stuart dressed as Flora MacDonald's maid servant, Betty Burke, to escape the Battle of Culloden for the island of Skye in 1746.

Mary Hamilton dressed as a man to learn medicine and later married a woman in 1746. It was also alleged that she had married and abandoned many others, for either financial gain or for sexual gratification. She was convicted of fraud for misrepresenting herself as a man to her bride.

Ann Mills fought as a dragoon in 1740.

Hannah Snell served as a man in the Royal Marines 1747–1750, being wounded 11 times, and was granted a military pension.

Charles-Geneviève-Louis-Auguste-André-Timothée Éon de Beaumont (1728–1810), usually known as the Chevalier d'Eon, was a French diplomat and soldier who lived the first half of his life as a man and the second half as a woman. In 1771 he stated that physically he was not a man, but a woman, having been brought up as a man only. From then on she lived as a woman. On her death it was discovered that her body was anatomically male.

George Sand is the pseudonym of Amandine-Aurore-Lucile Dupin, an early 19th-century French novelist who preferred to wear men's clothing exclusively. In her autobiography, she explains in length the various aspects of how she experienced cross-dressing.

Dorothy Lawrence was an English war reporter who disguised herself as a man so she could become a soldier in World War I.

Rrose Sélavy, the feminine alter-ego of the late French artist, Marcel Duchamp, remains one of the most complex and pervasive pieces in the enigmatic puzzle of the artist's oeuvre. She first emerged in portraits made by the photographer Man Ray in New York in the early 1920s, when Duchamp and Man Ray were collaborating on a number of conceptual photographic works. Rrose Sélavy lived on as the person to whom Duchamp attributed specific works of art, Readymades, puns, and writings throughout his career. By creating for himself this female persona whose attributes are beauty and eroticism, he deliberately and characteristically complicated the understanding of his ideas and motives. More contemporary artists like J. S. G. Boggs, Yasumasa Morimura, and Grayson Perry have also explored cross-dressing.

Shi Pei Pu was a male Peking Opera singer. Spying on behalf of the Chinese Government during the Cultural Revolution, he cross-dressed to gain information from Bernard Boursicot, a French diplomat. Their relationship lasted 20 years, during which they married. David Henry Hwang's 1988 play M. Butterfly is loosely based on their story.

Billy Tipton was a notable jazz pianist and saxophonist in the United States during the Great Depression. He was born Dorothy Lucille Tipton in 1914, but began living as a man in the 1930s. He was married five times to women, and adopted three boys. He led a full career as a musician and, in later life, as an entertainment agent. Other than his birth family, no one knew of his birth sex or cross-living until after his death in 1989.

Willmer "Little Ax" Broadnax was a lead singer in several important gospel quartets, most famously the Spirit of Memphis Quartet. When he died in 1994, it was discovered that he was female bodied.

Because female enlistment was barred, many women fought for both the Union and the Confederacy during the American Civil War while dressed as men.

Edward Hyde, 3rd Earl of Clarendon, colonial governor of New York and New Jersey in the early 18th century is reported to have enjoyed going out wearing his wife's clothing, but this is disputed. Hyde was an unpopular figure, and rumors of his cross-dressing may have begun as an urban legend.

In folklore

Ballads have many cross-dressing heroines. While some (The Famous Flower of Serving-Men) merely need to move about freely, many do it specifically in pursuit of a lover (Rose Red and the White Lily or Child Waters) and consequently pregnancy often complicates the disguise. In the Chinese poem the Ballad of Mulan, Hua Mulan disguised herself as a man to take her elderly father's place in the army.

Occasionally, men in ballads also disguise themselves as women, but not only is it rarer, the men dress so for less time, because they are merely trying to elude an enemy by the disguise, as in Brown Robin, The Duke of Athole's Nurse, or Robin Hood and the Bishop. According to Gude Wallace, William Wallace disguised himself as a woman to escape capture, which may have been based on historical information.

Fairy tales seldom feature cross-dressing, but an occasional heroine needs to move freely as a man, as in the German The Twelve Huntsmen, the Scottish The Tale of the Hoodie, or the Russian The Lute Player. Madame d'Aulnoy included such a woman in her literary fairy tale, Belle-Belle ou Le Chevalier Fortuné.

In the cities Techiman and Wenchi (both Ghana) men dress as women – and vice versa – during the annual Apoo festival (April/May).

In literature

In the myth of the Trojan War, Achilles' mother Thetis wanted to keep him from joining the Greek forces (and thus dying in battle as was prophesied), so she dresses him in women's clothes and hides him among a cloister of women. When the Greek envoy arrives to fetch him for battle, Odysseus is suspicious of Achilles' absence and concocts a scheme to reveal the deception: he offers gifts to all the women, including among them a sword and shield. Then he has an alarm sounded, and when Achilles instinctively grabs the weapons to defend himself, the ruse is revealed and he must join the Greek army and fight at Troy.

In Ludovico Ariosto's Orlando Furioso, Bradamante, being a knight, wears full-plate armor; similarly, Britomart wears full-plate armor in Edmund Spenser's The Faerie Queene. Intentionally or not, this disguises them as men, and they are taken as such by other characters. In Orlando Furioso, Fiordespina falls in love with Bradamante; her brother Ricciardetto disguises himself as his sister, dressing as a woman, persuades Fiordespina that he is Bradamante, magically changed into a man to make their love possible, and in his female attire is able to conduct a love affair with her.

In Giannina Braschi's mock diary, "Intimate Diary of Solitude/el diario intimo de la soledad" (the finale of the Latin American trilogy "Empire of Dreams/el imperio de los suenos") the heroine Mariquita Samper is a cross-dressing Macy's makeup artist who plots a literary revolution to kill the narrator.

In Arcadia, Sir Philip Sidney has one of the heroes, Pyrocles, disguise himself as an Amazon called Zelmane in order to approach his beloved Philoclea.

Lord Byron in his Don Juan, had Don Juan disguised as a woman in a harem.

Mark Twain's Huckleberry Finn disguises himself as a girl at one point in the novel, not very successfully.

In Anthony Powell's From a View to a Death, Major Fosdick's penchant for going to his room and donning a black sequin evening dress and a large picture-hat ultimately leads to his unraveling.

In Terry Pratchett's novel Monstrous Regiment, he has an entire regiment of females (of assorted species) dressing as males to join the army, satirizing the phenomenon of crossdressing during wartime.

In Tolkien's The Lord of the Rings, Éowyn disguises herself as man under the name Dernhelm to fight in the Battle of the Pelennor Fields outside the city Minas Tirith.

In Tamora Pierce's Song of the Lioness series, the main character, Alanna, disguises herself as a boy for eight years in order to become a knight.

In Religion

Cross dressing in Modern England was against their religion do to Biblical prohibitions against it. Cross-dressing went against the Law of God, therefore those that performed such disobedient actions would be looked down upon by society. The Law of God claimed that men could not put on women's clothing. This was because by wearing garments of the opposite sex, would create confusion and society would have trouble differentiating men from women. Also, it was stated that by cross-dressing you would be falsifying your true sex.

Cross-dressing characters

William Shakespeare made substantial use of cross-dressing for female characters who took on masculine clothing to carry out actions difficult for women. In Shakespeare's play The Merchant of Venice, Portia and her maid dress as men to plead in court on the merchant's behalf, and are quite successful in their ruse; in the same play, Shylock's daughter Jessica dresses as a man to elope with her Christian lover. Twelfth Night, or What You Will deals extensively with cross-dressing through the female protagonist Viola. She disguises herself as Cesario and immediately finds herself caught up in a love triangle. She loves Duke Orsino who loves Countess Olivia who loves Cesario. Luckily, all is resolved when Viola's presumed dead twin brother Sebastian comes along. We only see Viola as Viola in one scene; for the rest of the play she is dressed as Cesario. When Rosalind and Celia flee court in As You Like It, Rosalind dresses, for their protection, as a man. However, as a way to further complicate the situation for comedic affect, Shakespeare has Rosalind's male character "Ganymede" dress as a woman to help a male friend, Orlando de Boys, practice wooing Rosalind, with whom he is smitten, while at the same time fending off the affections Phoebe has for "Ganymede". In other words, it is a man, (the actor), dressing as a woman, dressing as a man, dressing as a woman.

Joe and Jerry in Billy Wilder's 1959 Some Like It Hot, two struggling musicians, have to dress up as women to escape the ire of gangsters. The film is a remake by Wilder and I. A. L. Diamond of a 1935 French movie, Fanfare d'amour, from the story by Robert Thoeren and Michael Logan, which was itself remade in 1951 by German director Kurt Hoffmann as Fanfaren der Liebe.

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 (旦), 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 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.

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.

Cross-dressing actors and actresses

In Renaissance England it was illegal for women to perform in theatres, so female roles in the plays of Shakespeare and his contemporary playwrights were originally played by cross-dressing men or boys. (See also Stage Beauty.) Therefore, the original productions of the above-mentioned Shakespeare plays actually involved double-cross-dressing: male actors playing female characters disguising themselves as males. Academic research into the contemporary attitudes towards the practise have yielded a variety of interpretations. Laura Levine argues that "an all-male acting troupe was the natural and unremarkable product of a culture whose conception of gender was "teleologically male""; she also suggests that contemporary protests against the practise (believing it made young actors "effeminate") reflected "deepseated fears that the self was not stable and fixed but unstable and monstrous and infinitely malleable unless strictly controlled.

Cross-dressed female actors are referred to as playing "trouser roles," a historical example of an actress famous for trouser roles is Julie d'Aubigny, aka "La Maupin" (1670–1707).

In the late 19th century, one of the most famous actresses was the cross-dressing woman Vesta Tilley. She grew up working in a music hall from age 5 well into her fifties. In the late 1890s, she was the highest paid woman in Britain. What made her so famous was her tendency to dress as a man and act out "masculine" scenes and roles.

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.

All roles in Japanese Noh dramas are traditionally played by male actors. Actors playing female roles wear feminine costumes and female-featured masks.

Japanese Kabuki theatre began in the 17th century with all-female troupes performing both male and female roles. In 1629 the disrepute of kabuki performances (or of their audiences) led to the banning of women from the stage, but kabuki's great popularity inspired the formation of all-male troupes to carry on the theatrical form. In Kabuki, the portrayal of female characters by men is known as onnagata. The practice is detailed in a story of the same name by the Japanese writer, Yukio Mishima.

In ancient China, nearly all the characters in Chinese Opera were performed by men, so that all the male actors, who played the role of a female were crossdressing. A famous cross-dressing opera singer is Mei Lanfang. From early 20th century, Shanghai yue opera (or Shaoxin opera) is developed from all male to all female genre. Although male performers were introduced into this opera in 1950s and 1960s, today, Shanghai yueju (yue opera) is still associated as the only all female opera and the second most popular opera in China.

Meryl Streep played a male rabbi in Angels of America once.

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. For more information about cross-dressing in movies and television, see the article Cross-dressing in film and television. 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."

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.

The British writer, presenter and actor Richard O'Brien sometimes cross-dresses and ran a "Transfandango" ball aimed at transgender people of all kinds in aid of charity for several years in the early 2000s (decade).

The Takarazuka Revue is a contemporary all-female Japanese acting company, known for their elaborate productions of stage musicals. Takarazuka actresses specialize in either male or female roles, with male role actresses receiving top billing.

In pantomime plays that are traditionally adaptations of fairy tales and performed around Christmastide, the role of lead male was once commonly played by a principal boy—a young, attractive, female. This practise has fallen out of favour recently, with popular male television and pop stars taking these roles. Conversely, the role of a pantomime dame, a middle aged woman played by a man for comic relief, is still one of the mainstays of the Pantomime.

In Star Wars Episode IV: A New Hope, the male alien bounty hunter Greedo was portrayed by both a male and a female, each acting in different shots.

Michelle Ehlen plays a butch lesbian actress who gets cast as a man in a film in the comedic feature Butch Jamie.

Eddie Izzard, a British stand-up comedian and actor, states that he has cross-dressed his entire life. He often performs his act in feminine clothing, and has discussed his cross dressing as part of his act. He calls himself an "executive transvestite".

Classic trouser parts (male characters intended to be played by women) include the title character in Peter Pan (J.M. Barrie) and Cherubino in The Marriage of Figaro (Beaumarchais).

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.

In opera

An entire cross-dressing genre of operatic roles, called "pants roles", "trouser roles", or "travesty roles". These are male roles performed by women, typically mezzo-sopranos but occasionally by sopranos. Some female opera singers specialize in these types of roles.

A major artistic reason for "pants roles" was that some storylines required young boy characters, but the actual performance required an adult's vocal strength and stage experience in addition to a high, boyish voice. Women were thus better suited to these boy roles than actual boys. Some examples of these boyish pants roles are Cherubino in "The Marriage of Figaro," Siebel in "Faust," and Hansel in "Hansel and Gretel". Other pants roles were created due to the need for an adult male character to seem other-worldly (Orpheus in "Orfeo ed Euridice") or unmanly (Prince Idamante in "Idomeneo"). In some cases, the casting of a woman in a "pants role" may have been just an excuse to have an attractive actress appear in tight-fitting trousers. During the Grand Opera era, women typically worn voluminous dresses onstage. Some male operatic roles originally written to be sung in the voice range of castrati (men castrated in boyhood, whose voices never descended into the normal male register) are now usually cast with female singers in male costume.

Beethovens' only opera, Fidelio, is unusual in that it features a female character who cross-dresses as part of the plot. Fidelio involves a woman who disguises herself as a young man as part of a plan to rescue her husband from prison. In "The Marriage of Figaro" Cherubino dresses as a girl to avoid army duty. The part of Cherubino is thus played by a woman, who plays a man who dresses as a woman.

In the early 20th century, German composer Richard Strauss included a major trouser role in two operas: the Composer in "Ariadne auf Naxos" and Octavian in "Der Rosenkavalier."

In modern music

Boy George

"Arnold Layne", the first released single by British psychedelic rock group Pink Floyd, is about a transvestite who steals women's clothes from washing lines. (The song was written by Syd Barrett who supposedly cross-dressed at a later point in his life when going through a mental breakdown.)

Nicky Wire, bassist of the Manic Street Preachers, has cross dressed throughout his career.

The Kinks' 1970 hit "Lola" is a song about an encounter with a transvestite.

Pete Burns, the lead singer of the new wave band Dead or Alive, cross-dressed in the band's music videos, performances, and in his appearances on TV. However, Burns is dismissive of the term "cross-dressing" to describe his style, as said in numerous television interviews and in his autobiography.

The late actor and singer Harris Glenn Milstead became known for his drag persona, Divine.

Prince, in his early career made androgynous fashion choices; he wore high-heeled shoes.

Marilyn Manson often wear androgynous costumes in their performances, music videos and public appearances.

Maynard James Keenan of the band Tool cross-dressed during performances in the late 1990s as part of his stage act.

Kurt Cobain, the lead singer of the American grunge band Nirvana, often cross-dressed at home and on stage.

Billie Joe Armstrong of Green Day wrote a song about cross-dressing called "King for a Day", which was featured in the band's 1997 album nimrod..

Brian Viglione, member of the punk cabaret group The Dresden Dolls, has cross-dressed since he was 12 years old.

The Who's song "I'm a Boy" is about a young boy dressed as a girl.

The Bitch and Animal song "Drag King Bar" is about cross-dressing.

"Be My Human Tonight" by Norman Iceberg also talks about the concept.

Queen cross-dressed in their video for the song, "I Want to Break Free".

Annie Lennox is seen dressed in a suit, tie, gloves, and cane in the music video for "Sweet Dreams (Are Made of This)".

The rock band Twisted Sister often dresses cross dressed on stages and photo shoots.

Red Hot Chili Peppers frontman Anthony Kiedis has been known to crossdress on stage and, occasionally, in videos.

AC/DC's former singer Bon Scott dressed once to a school girl (as an opposite to Angus Young)

Placebo's frontman Brian Molko is androgynous and bisexual, often cross-dressing on and offstage.

Placebo's song Nancy Boy is about a sensitive boy who "Does his makeup in his room" and dresses like a girl.

IAMX (also Chris Corner) cross-dresses in his video for My Secret Friend along with Imogen Heap.

Verka Serduchka, Ukrainian male singer who always performs as a female.

Jeffree Star, male singer and Myspace celebrity, is almost always wearing women's clothes.

In Japan, visual kei musicians often appear crossdressing such as Hizaki and Jasmine You (both from Versailles), Kaya (vocalist of Schwarz Stein), Bou (ex-guitarist of An Cafe), Yumehito (guitarist of Ayabie), Tatsuhi (bassist of Zoro) and Aya (Guitarist of Psycho le Cému). In addition to his musical career, Mana, from the bands Malice Mizer and Moi dix Mois, is a fashion designer who often cross-dresses.

Lou Reed wrote songs about / including "T.V.'s", with the earliest example being "Sister Ray" from the Velvet Underground's 1968 album White Light/White Heat, and followed by Reed's solo album hit, the infamous "Walk on the Wild Side" from the Bowie-produced 1972 album Transformer. This song was in reference to the T.V.'s who were a part of the Andy Warhol entourage: "Sugar Plum Fairy", "Candy Darling", and "Jackie 'O'".

U2 wore dresses on the Achtung Baby sleeve notes.

Led Zeppelin also dressed in drag in one of the pics on Physical Graffiti, they also hung out with drag queens.

Steven Tyler of Aerosmith is a known crossdresser.

New York Dolls donned an androgynous wardrobe, wearing disheveled wigs, smudged lipstick, stilted platforms, painfully tight lurex/satin pants and crimpoline dresses.

France

As the Hundred Years War developed in the late Middle Ages, cross dressing in France was a way for women to join the cause against England.

In the seventeenth century, France underwent a period where there was a financially driven social conflict in what has been named the Fronde. Throughout the duration of the Fronde, French women often utilized cross dressing to enlist in the army as a male soldier to join the opposition with their male family members against the parliament and its affiliates. Cross dressing also became a more common strategy for women to conceal their gender as they traveled, granting a safer and more efficient route. The practice of cross dressing was present more so in literary works than in real life situations despite its effective concealing properties.

England

In England, during the medieval times, Cross dressing was used as a way to practice theater. Cross-dressing was used was by men and young boys dressing and playing both roles of male and female. During early modern London, religious authorities were against cross-dressing in theater due to it disregarding social conduct and causing gender confusion. Later, during the eighteenth century in London, crossdressing became a part of the club culture. Crossdressing took a part in men’s only clubs where men would meet at these clubs dressed as women and drink. One of the most well known clubs for men to do this was known as the Molly Club or Molly House.

Japan

Japan has a centuries-old tradition of male kabuki theatre actors cross-dressing onstage. Transgender men (and more rarely, women) were also "conspicuous" in Tokyo's gei (gay) bar and club subculture in the pre- and post-World War II period. By the 1950s, publications concerning MTF cross-dressing were in circulation, advertising themselves as aimed at the "study" of the phenomenon. Fully-fledged "commercial" magazines aimed at cross-dressing 'hobbyists' began publishing after the launch of the first such magazine, Queen, in 1980. It was affiliated with the Elizabeth Club, which opened branch clubs in several Tokyo suburbs and other cities.

Thailand

Through the pre-modern age, cross-dressing and Transgendered appearance in Thailand was apparent in many contexts including same-sex theater performance. The term Kathoey came to describe anyone from cross-dressers to Transgender men (and women) as the practice became more prevalent in everyday life. Lack of colonization by Western civilizations in Thailand have led to different ways of thinking about gender and self-identity. In turn, Thailand has fostered one of the most open and tolerant traditions towards Kathoeys and cross-dressers in the world. In contrast to many Western civilizations, where homosexuality and cross-dressing have been historically criminal offenses, Thai legal codes have not explicitly criminalized these behaviors. It was not until the 20th century that a public majority, whether on stage or in public, came to assume cross-dressing a sign of transgenderism and homosexuality.

China

Since the Yuan dynasty, cross-dressing has had a unique significance in Chinese opera. Period scholars cite it as the time in Chinese theatre as the “golden age.” The rise of dan, though characterized as female characters, was a prominent feature of the Peking Opera and many males took the roles of females. There were schools dedicated to the specific dan training as well. Female crossdressers in the Chinese opera were also valued immensely and prospered far more better than male crossdressers did.

Cross-dressers from other fields

The British writer and doctor Vernon Coleman cross-dresses and has written several articles defending men who cross-dress, stressing they are often heterosexual and usually do not want to change sex.

Bruce Jenner cross-dressed before undergoing a sex change operation and renaming herself Caitlyn Jenner.

British artist and Turner Prize winner, Grayson Perry often appears as his alter-ego, Clare.

References

History of cross-dressing Wikipedia

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