Dressing as a member of the opposite sex has a long and varied history. In the past, men and women cross-dressed to assume new roles, to enable them to do things they otherwise couldn’t, or because they just plain wanted to. Here are some individuals who for whatever reason decided to adopt the clothing of the opposite sex:
20. Mary Read, Pirate (1690 – 1721)
Raised as a boy by her mother in England, Read joined the British military at a young age. On a trip to the West Indies, the ship she was traveling on was captured by pirates, and Read decided that a pirate’s life was for her. When she later joined a new crew, a female pirate by the name of Anne Bonny took a liking to her. In a scene straight out of a movie, Bonny attempted to seduce Read, only to discover that she, too, was a female pirate. The two became lifelong companions. After being captured in 1720, Read and Bonny became the only two women to ever be convicted of piracy.
One story tells of Read winning a duel by ripping her shirt open, and then taking advantage of her opponent’s surprise to defeat him.
19. Elagabus, Emperor (204 – 222 AD)
Elagabus was made Emperor of Rome at the age of only 14, after successful political maneuvering by his maternal aunt. During his reign as Emperor, he preferred women’s dress. He had his whole body depilated, wore makeup, and referred to his chariot driver Hierocles as his husband. He even made an offer of money to any doctor who could perform surgery on him to make him biologically female.
None of this exactly made him popular in the highly traditional Rome of the time. His popularity also wasn’t helped by the fact that Elagabus married a priestess who’d been sworn to virginity, and instituted controversial sun-worshiping religious practices. He was assassinated in 222, at the age of only 18.
18. Francois De Choisy, Writer (1644 – 1724)
French author Francois De Choisy was dressed as a girl by his mother until the age of 18. Her reasons might have been political: De Choisy’s playmate, Philippe I, was also encouraged to dress as a girl, possibly so that he would not be seen as posing a threat to his older brother, King Louis XIV. As an adult, De Choisy took up male dress for a while but soon went back to his preferred female clothing. Many young women of the day visited him for fashion advice, encouraged by their mothers. He enjoyed their company: so much, in fact, that one ended up pregnant by him. Although he later wrote a number of historical and religious works, De Choisy is most famous for his tell-all book The Transvestite Memoirs, published in 1737.
17. Queen Christina of Sweden (1626-1689)
Christina’s father wanted to make sure his daughter was tough enough to rule, and so gave her a ‘masculine’ upbringing: her favorite childhood hobby was bear-hunting. Christina assumed the throne at age 18, but abdicated only ten years later under increasing pressure to marry and produce an heir. Instead, she left Sweden dressed as a man, a practice she continued on and off for the rest of her life. She converted to Catholicism and moved to Rome, where she received special permission to dress in men’s clothing. She is one of only two women ever buried in St Peter’s Church in Rome.
16. Deborah Sampson, Soldier (1760-1827)
At the age of 21, Sampson dressed in men’s clothing and enlisted to fight in the American Revolutionary War under the name of her deceased brother. Things went remarkably smoothly until she was wounded in battle: Sampson was so scared of being found out that she instructed her fellow soldiers to leave her on the field to die, but they refused. She escaped from the hospital, and removed a bullet from her own thigh. Another hospitalization in 1783 finally revealed her secret, and Sampson was given an honorary discharge. Although she later married and had children, Sampson did several speaking tours wearing her old military uniform. She was the first known American to pass as a male in war, but definitely not the last. Up to 400 women are thought to have fought in the Civil War while dressed as men.
15. Charles D’Eon, Diplomat (1728 – 1810)
A French soldier, spy and diplomat, D’Eon was sent to Russia in 1756 to reestablish diplomatic relations between the countries: he achieved this by dressing as a woman and becoming a maid of honor to the Russian Empress. Later, he worked as an ambassador in London, where at one point there was so much speculation on whether he was male or female that people actually placed bets on the London Stock Exchange. On his return to France, D’Eon demanded that he be recognized as a woman, claiming that he had in fact been born female and raised as a boy because of an inheritance dispute. The French King agreed, providing that he wear ‘appropriate’ women’s clothing. Posthumously, medical examinations revealed D’Eon to be anatomically male.
14. Marina the Ascetic, Monk (Fifth Century)
Marina was born in modern-day Lebanon. When her father wanted to join a monastery, she insisted on coming with him, dressing as a man and taking the name Marinos. After her father’s death, a girl who lived near the monastery fell pregnant and accused Marinos of seducing her. When confronted, Marinos did not deny the allegations out of a desire to not embarrass the girl. The disgraced monk was forced to live outside the monastery and raise her accuser’s child for many years. When she died at around age 40, she was finally discovered to be female. Her former accuser confessed to the lie.
Marina is only one of dozens of women throughout history thought to have entered religious life posing as men. There is even a story of an undercover female Pope, Pope Joan, although that one at least has no historical basis.
13. Isabelle Eberhardt, Explorer (1877 – 1904)
Born in Switzerland, Eberhardt moved to North African in 1897, where she became an explorer under the assumed name of Si Mahmoud Essadi. Male clothing allowed her to move freely in Arab society, and she eventually joined the Sufi sect Qadiriyya, impressing them so much with her piety that she was initiated as a faqir, a male member of the order. During her short life, she also acted as a spy and briefly took up arms in an Algerian revolt against France.
12. Shi Pei-Pu, Spy (1938 – 2009)
Male opera singer Shi Pei-Pu met Bernard Boursicot, an employee at the French Embassy in Beijing, when Shi was 26. After convincing Boursicot that he was actually a woman dressed as a man, they began an affair. Amazingly, the charade continued for 20 years, with Shi at one stage claiming to have borne him a son. Boursicot even began handing over secret documents to the Chinese in order to help Shi’s position in the Communist party. In 1982, Boursicot brought Shi and his son to Paris, where they were eventually arrested for espionage. When Shi’s identity was revealed, Boursicot physically attacked him, slashing his throat. Shi survived. A successful play and then movie, M. Butterfly, was loosely based on Shi’s life.
11. Joan of Arc, Soldier (1412 – 1431)
During the Hundred Years War, when large areas of France were occupied by the English, this young peasant girl heard heavenly voices commanding her to cut her hair, dress as a man, and go lead an army. Joan convinced Charles VII, the French claimant to the throne, that she was for real, and was given an army and supplies. She led a series of military successes that ended with Charles being crowned King.
At the age of 19, Joan was captured and handed over to a pro-English Bishop, who subjected her to an illegal trial. In Europe at the time, cross-dressing was actually condoned, providing that a woman did it for safety or protection. Nevertheless, Joan was convicted of ‘relapsed heresy’ when she took up male dress again in prison, probably after a rape attempt. She was burned at the stake. Later, the unjust decision was overturned in court, and Joan is now considered a saint by the Catholic Church and a heroine of France.
10. Milton Berle, Actor (1908-2002)
Having lived until the ripe old age of 94, Berle clearly saw a lot of changes in his lifetime from 1908-2002. He had the distinction of being one of the America's first television stars on Texaco Star Theater in the 40's. How did he make such a name for himself? By dressing in drag, of course!
His cross-dressing shtick came from earlier vaudeville sensibilities, which were by no means edgy, but by introducing the concept to television, it reached many middle-American households that otherwise wouldn't know what fun it was to dress up in women's clothes!
9. Dorthy Lawrence , Writer (1896-1964)
In a conventionally more noble pursuit, Dorothy Lawrence was an English reporter who was tired of getting denied access to the English troops on the front lines of WWI. She would circumvent this by enlisting in the English Army to gain the access she desired. However, the anxiety living this lie proved too much and she turned herself in after 10 days of service. She was arrested as a spy, but not charged, however, she was forbidden from writing on her experience, however brief. Her notes and thoughts were finally made public years later, though that defeated the purpose of her pursuit.
8. George Sand, Novelist (1804-1876)
Born Amantine Lucile Aurore Dupin, Sand kept company with men (including Frederic Chopin) throughout her whole life, but took to wearing men's clothing and adopting the clearly masculine name George Sand. Sand's claim to fame was not only as a baroness, but as a novelist and memoir writer.
She also took to smoking tobacco in public, which, in Victorian France, was considered just as manly as wearing men's clothes. Charles Beaudelaire was a particularly harsh detractor of not only her social habits, but her work as well, claiming, “She is stupid, heavy and garrulous. Her ideas on morals have the same depth of judgment and delicacy of feeling as those of manageresses and kept women…. The fact that there are men who could become enamoured of this slut is indeed a proof of the abasement of the men of this generation.”
7. Hua Mulan (1368-1644)
Legendary figure from ancient China who was originally described in a Chinese poem known as the Ballad of Mulan . In the poem, Hua Mulan takes her aged father's place in the army. She fought for 12 years and gained high merit, but she refused any reward and retired to her hometown instead.
The historical setting of Hua Mulan is uncertain. The earliest accounts of the legend state that she lived during the Northern Wei dynasty (386–534).The Hua Mulan crater on Venus is named after her.
6. J. Edgar Hoover, FBI (1895-1972)
This hard-nosed FBI chief was known for maintaining files on virtually every person that had a semblance of interest about them. Turns out that J. Edgar was a pretty interesting guy himself, known for cross-dressing under the name Murielâ in the late 50's according to some socialites. It has never been definitively proven that he was a cross dresser or even gay, though he did attack anyone who made the mistake of any insinuations. It's also been intimated that organized crime blackmailed Hoover with this info so as to escape his zealous prosecution.
5. Billy Tipton, Musician (1914-1989)
Billy Lee was a bandleader and jazz musician in America, having lived from 1914 to 1989. Born Dorothy Tipton, he lived his entire adult life as a man until his death. In fact, it wasnt discovered until after his death that he had been a woman living as a man. Tipton took company with women throughout his life, identifying himself as straight.
4.Norah Vincent, Author
Vincent was a senior fellow at the Foundation for the Defense of Democracies from its 2001 inception to 2003. She has also had columns at Salon.com, The Advocate,the Los Angeles Times, and the Village Voice.Vincent's book Self-Made Man retells an eighteen-month experiment in which she disguised herself as a man.This follows in the tradition of undercover journalism such as Black Like Me. Vincent talked about the experience in HARDtalk extra on BBC on April 21, 2006 and described her experiences in male-male and male-female relationships. She joined an all-male bowling club, joined a men's therapy group, went to a strip club, visited Catholic monks in a cloister, and dated women. Vincent writes about how the only time she has ever been considered excessively feminine was during her stint as a man: her alter ego, Ned, was assumed to be gay on several occasions, and features which in her as a woman had been seen as “butch” became oddly effeminate when seen in a man. (She is a lesbian.) Vincent asserts that, since the experiment, she has never been more glad to be female.
3. Divine, Performer (1945-1988)
also known as Harris Glenn Milstead, was an American actor, singer and drag queen. A character actor who often performed female roles in both cinema and theater, Divine also adopted a female drag persona in his musical performances, leading People magazine to describe him as the "Drag Queen of the Century".He was often associated with independent filmmaker John Waters and starred in ten of Waters's films, usually in a leading role. Concurrent with his acting career, he also had a successful career as a disco singer during the 1980s, at one point being described as "the most successful and in-demand disco performer in the world.
2. Dame Edna Everage, Entertainer
Dame Edna is a character created and played by Australian dadaist performer and comedian, Barry Humphries, famous for her lilac-coloured or "wisteria hue" hair and cat eye glasses or "face furniture," her favourite flower, the gladiola ("gladdies") and her boisterous greeting: "Hello Possums!" As Dame Edna, Humphries has written several books including an autobiography, My Gorgeous Life, appeared in several films and hosted several television shows (on which Humphries has also appeared as himself and other alter-egos).
Humphries has regularly updated Edna, originally a drab Melbourne housewife satirising Australian suburbia. The character adopted an increasingly outlandish wardrobe after being performed in London in the 1960s, and grew in stature and popularity. Following film appearances and an elevation todamehood in the 1970s, the character evolved to "Housewife and Superstar", then "Megastar" and finally "Gigastar". Throughout the 1980s and 1990s Dame Edna became increasingly known and popular in North America after multiple stage and television appearances.
1. RuPaul , Entreprenuer
is an American actor, drag queen, model, author, and recording artist, who first became widely known in the 1990s when he appeared in a wide variety of television programs, films, and musical albums. Previously, he was a fixture on the Atlanta and New York City club scenes during the 1980s and early 90s. RuPaul has on occasion performed as a man in a number of roles, usually billed as RuPaul Charles. RuPaul is noted among famous drag queens for his indifference towards the gender-specific pronouns used to address him—both "he" and "she" have been deemed acceptable. "You can call me he. You can call me she. You can call meRegis and Kathie Lee; I don't care! Just as long as you call me."She hosted a short-running talk show on VH1, and currently hosts reality television shows RuPaul's Drag Race and RuPaul's Drag U. Rupaul is also known for his hit song "Supermodel (You Better Work)".
“An eccentric, transgender singer is one of the show’s hopefuls this year -- advancing past the show’s famous boot camp, Hollywood Week, last week...”
