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The use of "drag" in this sense appeared in print as early as 1870 but its origin is uncertain. One suggested etymological root is 19th-century theatre slang, from the sensation of long skirts trailing on the floor.
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There is a long history of drag in the performing arts, spanning a wide range of cultural as well as artistic traditions.
Drag in the theatre arts manifests two kinds of phenomenon. One is cross-dressing in the performance, which is part of the social history of theatre. The other is cross-dressing within the theatrical fiction (i.e. the character is a cross-dresser), which is part of literary history.
Drag is often played for comic effect. Examples include the female characters (at times caricatures) played by male members of Monty Python, and Tony Curtis and Jack Lemmon in Some Like It Hot. In other cases the comedy may be primarily in the material being performed, and not necessarily in the fact that the women characters are portrayed by men, such as in many Kids in the Hall sketches.
Baden-Powell, founder of the Scout Movement, was keen on amateur theatricals from Charterhouse public school where, among other roles, he played female operatic roles. In the army he made a speciality of female roles and would often make his own dresses. His stage speciality was what he called his skirt dance.
Cross-dressing elements of performance traditions are widespread cultural phenomena. In England, actors in Shakespearean plays, and all Elizabethan theatre, were all male; female parts were played by young men in drag. Shakespeare used the conventions to enrich the gender confusions of As You Like It, and Ben Jonson manipulated the same conventions in Epicœne, or The Silent Woman, (1609). The plot device of the film Shakespeare in Love (1998) turns upon this Elizabethan convention. During the reign of Charles II the rules were relaxed to allow women to play female roles on the London stage, reflecting the French fashion, and the convention of men routinely playing female roles consequently disappeared. However, in current-day British pantomime, the Pantomime dame is a traditional role played by a man in drag, while the Principal boy, such as Prince Charming or Dick Whittington, is played by a girl.
Within the dramatic fiction, a double standard historically affected the uses of drag. In male-dominated societies where active roles were reserved to men, a woman might dress as a man under the pressures of her dramatic predicament. In these societies a man's position was above a woman's, causing a rising action that suited itself to tragedy, sentimental melodrama and comedies of manners that involved confused identities. A man dressed as a woman was thought to be a falling action only suited to broad low comedy and burlesque. Les Ballets Trockadero de Monte Carlo are an all male ballet troupe where much of the humor is in seeing male dancers en travesti; performing roles usually reserved to females, wearing tutus and dancing en pointe with considerable technical skill.
These conventions of male-dominated societies were largely unbroken before the 20th century, when rigid gender roles were undermined and began to dissolve. This evolution changed drag in the last decades of the 20th century. Among contemporary drag performers, the theatrical drag queen or street queen may at times be seen less as a "female impersonator" per se, but simply as a drag queen, and the role of the queen existing as an identity based in neither mainstream male nor mainstream female conventions. Examples include The Cockettes, Danny La Rue or RuPaul.
Men dressed or disguised as women have featured in traditional customs and rituals for centuries. For example, the characters of some regional variants of the traditional mummers play, which were traditionally always performed by men, include Besom Bet(ty); numerous variations on Bessy or Betsy; Bucksome Nell; Mrs Clagdarse; Dame Dolly; Dame Dorothy; Mrs Finney; Mrs Frail and many others. The variant performed around Plough Monday in Eastern England is known as the Plough Play (also Wooing Play or Bridal Play) and usually involves two female characters, the young "Lady Bright and Gay" and "Old Dame Jane" and a dispute about a bastard child.
A character called Bessy also accompanied the Plough Jags (aka Plough Jacks, Plough Stots, Plough Bullocks, etc.) even in places where no play was performed: "she" was a man dressed in women's clothes, who carried a collecting box for money and other largesse.
"Maid Marian" of the Abbots Bromley Horn Dance is played by a man, and the Maid Marians referred to in old documents as having taken part in May Games and other festivals with Morris dancers would most probably also have been men. The "consort" of the Castleton Garland King was traditionally a man (until 1956, when a woman took over the role) and was originally simply referred to as "The Woman".
In Baroque opera, where soprano roles for men were sung by castrati, Handel's heroine Bradamante, in the opera Alcina, disguises herself as a man to save her lover, played by a male soprano; contemporary audiences were not the least confused. In Romantic opera, certain roles of young boys were written for alto and soprano voices and acted by women en travestie (in English, in "trouser roles"). The most familiar trouser role in pre-Romantic opera is Cherubino in Mozart's Marriage of Figaro (1786). Romantic opera continued the convention: there are trouser roles for women in drag in Rossini's Semiramide (Arsace), Donizetti's Rosamonda d'Inghilterra and Anna Bolena, Berlioz's Benvenuto Cellini, and even a page in Verdi's Don Carlo. The convention was beginning to die out with Siebel, the ingenuous youth in Charles Gounod's Faust (1859) and the gypsy boy Beppe in Mascagni's L'Amico Fritz, so that Offenbach gave the role of Cupid to a real boy in Orphée aux Enfers. But Sarah Bernhardt played Hamlet in tights, giving French audiences a glimpse of Leg (the other in fact being a prosthesis) and Prince Orlovsky, who gives the ball in Die Fledermaus, is a mezzo-soprano, to somewhat androgynous effect. The use of travesti in Richard Strauss's Rosenkavalier (1912) is a special case, unusually subtle and evocative of its 18th-century setting, and should be discussed in detail at Der Rosenkavalier.
The self-consciously risqué bourgeois high jinks of Brandon Thomas' Charley's Aunt (London, 1892) were still viable theatre material in La Cage aux Folles 1978, which was remade, as The Birdcage, as late as 1996. In the 1890s the slapstick drag traditions of undergraduate productions (notably Hasty Pudding Theatricals at Harvard College, annually since 1891 and at other Ivy League schools like Princeton University's Triangle Club or the University of Pennsylvania's Mask and Wig Club) were permissible fare to the same middle-class American audiences that were scandalized to hear that in New York City, rouged young men in skirts were standing on tables to dance the Can-Can in Bowery dives like The Slide. Drag shows were popular night club entertainment in New York in the 20s, then were forced underground, until the "Jewel Box Revue" played Harlem's Apollo Theater in the 1950s: "49 men and a girl." The girl received a roar of applause, when she was revealed as the same smart young man in dinner clothes who had been introducing each of the evening's acts. Drag as a last-resort tactic in situational farce (its only permissible format at the time) made a big Hollywood splash in Some Like It Hot (1959).
For the San Francisco drag troupe, The Cockettes (1970–72), who performed with glitter eyeshadow and gilded mustaches and beards, the term "genderfuck" was coined. Drag broke out from underground theatre in the persona of Divine in John Waters's Pink Flamingos (1972): see also Charles Pierce. The crowd surrounding Andy Warhol's Factory scene of the 1960s–1980s also included some drag queens who achieved a certain amount of fame, such as Candy Darling and Holly Woodlawn, both immortalized in the Lou Reed song "Walk on the Wild Side." The cult hit movie musical The Rocky Horror Picture Show has inspired several generations of young people to attend performances in drag, although many of these fans would deny that they are actually transvestites.
On American network television, only the broadest slapstick drag tradition was generally represented. Few American TV comedians consistently used drag as a comedy device, among them Milton Berle, Flip Wilson and Martin Lawrence, although drag characters have occasionally been popular on sketch TV shows like In Living Color (with Jim Carrey's grotesque female bodybuilder) and Saturday Night Live (with the Gap Girls, among others). On the popular 1960s military sitcom, McHale's Navy, Ensign Parker (Tim Conway) sometimes had to dress in drag (often with hilarious results) whenever McHale and/or his crew had to disguise themselves in order to carry out their elaborate schemes. Gilligan's Island occasionally features men dressing in women's clothes, though this was not considered drag since it was not for a performance. The popular Canadian comedy group The Kids in the Hall also used drag in many of their skits. Dame Edna, the drag persona of Australian actor Barry Humphries, is the host of several specials, including The Dame Edna Experience. Dame Edna also tours internationally, playing to sell-out crowds, and has appeared on TV's Ally McBeal.
Dame Edna represents an anomalous example of the drag concept. Her earliest incarnation was unmistakably a man dressed (badly) as a suburban housewife. Edna's manner and appearance became so feminised and glamorised that even some of her TV show guests appear not to see that the Edna character is played by a man. The furor surrounding Dame Edna's "advice" column in Vanity Fair magazine suggests that one of her harshest critics, actress Salma Hayek, was unaware Dame Edna was a female character played by a man.
On stage and screen, the actor-playwright-screenwriter-producer Tyler Perry has included his drag character of Madea in some of his most noted productions, such as the stage play Diary of a Mad Black Woman and the feature film he based upon it.
Maximilliana and RuPaul co-star together in the TV show Nash Bridges starring Don Johnson and Cheech Marin during the two-part episode "'Cuda Grace." Maximilliana, looking passable, leads one of the investigators to believe she is "real" and sexually advances only to learn there is something extra down there, greatly to his dismay.
In the United Kingdom, drag has been more common in comedy, on both film and television. Alastair Sim plays the headmistress Miss Millicent Fritton in The Belles of St Trinian's (1954) and Blue Murder at St Trinian's (1957). He played the role straight; no direct joke about the actor's true gender is made. However, Miss Fritton is quite non-feminine in her pursuits of betting, drinking and smoking. The gag is that whilst her school sends out girls into a merciless world, it is the world that need beware. Despite this, or perhaps because of Sim's portrayal, subsequent films in the series went on to use actresses in the headmistress role (Dora Bryan and Sheila Hancock respectively). The 21st century re-boot of the series however reverted to drag, with Rupert Everett in the role.
On television, Benny Hill portrayed several female characters, the Monty Python troupe and The League of Gentlemen often played female parts in their skits. The League of Gentlemen are also credited with the first ever portrayal of "nude drag," where a man playing a female character is shown naked but still with the appropriate female anatomy, like fake breasts and a merkin.Within the conceit of the sketch/film, they are actually women: it is the audience who are in on the joke.
Monty Python women, whom the troupe called pepperpots, are random middle-aged working/lower middle class typically wearing long brown coats that were common in the 1960s. Save for a few characters played by Eric Idle, they looked and sounded very little like actual women with their caricatural outfits and shrill falsettos. However, when a sketch called for a "real" woman, the Pythons almost always called on Carol Cleveland. The joke is reversed in the Python film Life of Brian where "they" are pretending to be men, including obviously false beards, so that they can go to the stoning. When someone throws the first stone too early the Pharisee asks "who threw that," and they answer "she did, she did,..." in high voices. "Are there any women here today?" he says, "No no no" they say in gruff voices.
In the 1970s the most familiar drag artist on British television was Danny La Rue. La Rue's act was essentially a music hall one, following on from a much older, and less sexualised tradition of drag. His appearances were often in variety shows such as The Good Old Days (itself a pastiche of music hall) and Sunday Night at the London Palladium. Such was his popularity that he made a film, Our Miss Fred (1972). Unlike the "St Trinians" films, the plot involved a man having to dress as a woman.
Kenny Everett dragged up in his TV show as an OTT screen star called Cupid Stunt. Kenny was particularly unconvincing as a woman because he had a beard to which a lot of flesh-tone makeup was applied. However she says "all in the best possible taste" as she exposed her knickers as she re-crossed her legs. She is in more of the Dame Edna genre. David Walliams and (especially) Matt Lucas often play female roles in the British television comedy Little Britain. Walliams also notably plays the part of Emily Howard – a "rubbish transvestite," who makes an unconvincing woman.
In the UK, non-comedic representations of drag acts are less common, and usually a subsidiary feature of another story. A rare exception is the television play (1968) and film (1973), The Best Pair of Legs in the Business. In the film version Reg Varney plays a holiday camp comedian and drag artist whose marriage is failing.
The world of popular music has a venerable history of drag. Marlene Dietrich was a popular actress and singer who sometimes performed dressed as a man, such as in the films Blue Angel and Morocco. In the glam rock era many male performers (such as David Bowie and The New York Dolls) donned partial or full drag. This tradition waned somewhat in the late 1970s but was revived in the new wave era of the 1980s, as pop singers Boy George (of Culture Club), Pete Burns (of Dead or Alive), and Philip Oakey (of The Human League), frequently appeared in a sort of semi-drag, while female musicians of the era dabbled in their own form of androgyny, with performers like Annie Lennox, Phranc and The Bloods sometimes performing as drag kings. The male grunge musicians of the 1990s sometimes performed wearing deliberately ugly drag – that is, wearing dresses but making no attempt to look feminine, not wearing makeup and often not even shaving their beards. (Nirvana did this several times, notably in the In Bloom video.) However, possibly the most famous drag artist in music in the 1990s was RuPaul. In Japan there are several musicians in the visual kei scene, such as Mana (Moi dix Mois and Malice Mizer), Kaya (Schwarz Stein), Hizaki and Jasmine You (both Versailles), who always or usually appear in full or semi-drag. Maximilliana worked with RuPual in the Nash Bridges episode "Cuda Grace" and was a regular at the now defunct Queen Mary Show Lounge in Studio City, California until the very end. Max (short for Maximilliana) is most well known for her performance as Charlie/Claire in Ringmaster: the Jerry Springer Movie. Max has also appeared in other movies including Shoot or Be Shot and 10 Attitudes as well as on television shows including Nash Bridges as mentioned above, Clueless, Gilmore Girls, The Tonight Show with Jay Leno, Mas Vale Tarde with Alex Cambert, MadTV, The Tyra Banks Show, The Tom Joyner Show, America's Got Talent, and many others. As of November 11, 2011, Maximilliana had released her first album of all original, fun, dance music for the LGBT community and made it available on iTunes, Amazon.com and CdBaby.
In gay slang, a "queen" is an effeminate gay man, or a gay man with a specialized quality. Along with "drag," the term "drag queen" has entered the general lexicon.
Drag queens (first use in print, 1941) are stereotypically viewed to be gay men that dress in drag, either as part of a performance or for personal fulfillment. Though a good portion who wear women's clothing are straight men, the term drag queen distinguishes them from transvestites, transsexuals or transgender people. Doing drag here often includes wearing dramatically heavy makeup, wigs and prosthetic devices as part of the costume. Females are called drag kings; however, drag king also has a much wider range of meanings. It is currently most often used to describe entertainment (singing or lip-synching) in which there is no necessarily firm correlation between a performer's deliberately macho onstage persona and offstage gender identity or sexual orientation, just as cis males who do female drag for the stage may or may not identify as being either gay or female in personal identity. A faux queen is usually a woman doing traditional female drag in the same spirit as men have done.