1. Moll Cutpurse
Mary Frith, nicknamed Moll Cutpurse, was an English criminal of the turn of the 17th century. She was a thief, street performer, and pimp, who scandalized society not only through her crimes, but because she adopted male clothing, smoked a pipe, and liberally used foul language. Moll Cutpurse was also nicknamed “The Roaring Girl,” as rowdy young men of the time were colloquially known as roaring boys.
Around the age of 30, Mary Frith married Lewknor Markham, probably for reasons of convenience. She allegedly claimed to be personally uninterested in sex, though she worked as a pimp, setting both men and women up with lovers. Moll Cutpurse became something of a legend in her time, with plays and biographies taking her as their subject. She lived into her seventies, dying of dropsy in 1659.
2. Abbé de Choisy
The story of François Timoléon, Abbé de Choisy is best known from his Memoirs. A member of the court of Louis XIV, the Abbé de Choisy was dressed in women’s clothing by his mother until the age of 18. After a few years of dressing as a man, he reverted to his childhood habits, dressing in extravagant female costume for various court and society events.
According to his Memoirs, de Choisy was quite the ladies’ man, using his feminine disguise as a tool to seduce young women at court under their mother’s eyes. His favorite companion was an actress named Roselie, also a cross dresser, and the two enjoyed appearing in public together wearing clothing of the opposite gender. In his thirties, the Abbé de Choisy gave up cross dressing and the court life for the monastery and the pen, becoming ordained priest in 1685 at the age of 41. He wrote many historical and religious works in addition to his infamous Memoirs.
3. Chevalier d’Eon
The Chevalier d’Eon, later Mademoiselle d’Eon, lived the first half of life as a man and the second as a woman. His biological sex was a matter of speculation until a post-mortem examination. D’Eon worked as a spy in the service of Louis XV during the 1650s, possibly using a female disguise in this line of work. He also served as a captain of the French Army during the Seven Years’ War, receiving the prestigious Order of Saint Louis. He became a temporary ambassador in London, and when replaced by the new ambassador, published government secrets in retaliation. D’Eon remained in exile in London, but received an annuity from Louis XV.
After his career as a spy was effectively over, rumors began to circulate that the Chavalier d’Eon was actually a woman. After Louis XV’s death, d’Eon was allowed to return to France. He began claiming that he was born a woman, and received official recognition as a woman by Louis XVI. However, the king demanded that d’Eon dress as a woman as well and granted him funds for a new, appropriate wardrobe. Mademoiselle d’Eon published an autobiography, ghostwritten by a friend, in 1779. D’eon spent his last years in London with a widow, Mrs. Cole, and died in 1810 at the age of 82.
4. George Sand
George Sand was the pen name of French author Amandine Dupin. She became Baronness Dudevant through marriage in 1822, at the age of 19. After having two children, George Sand left her husband in 1831, embarking on a more Bohemian lifestyle. She was formally separated from her husband in 1835, and took the children to live with her.
George Sand scandalized society by wearing men’s clothes, taking on a man’s name, smoking tobacco in public, and having frequent affairs. She also gained access to men’s society. Many of Sand’s lovers were noted artists, writers, and musicians of the era, including author Alfred de Musset and composer Frederic Chopin. The 1833 erotic novel Gamiani is rumored to have been written by de Musset about Sand’s exploits. She lived to the age of 76.
5. Annie Hindle
Annie Hindle was a drag performer of the American variety stage in the 19th century. Born in England, she moved to America in 1868, in her early 20s. Annie Hindle had been performing on stage since she was a young child, and she continued to do so in America, developing a male onstage persona and gaining some fame for her performances in the 1870s.
Annie Hindle was briefly married twice, but in 1858, she became a groom. She married her dresser, Annie Ryan, giving her own first name as Charles. The witness was another male impersonator. The ruse was soon discovered, and Hindle’s career was over. Oddly, newspapers reported that she was actually a man, thereby invalidating her male impersonation, but not her marriage. Annie Hindle returned to wearing women’s clothing after the wedding, and Hindle and Ryan lived together in Jersey City until the latter’s death.
6. Gladys Bentley
Gladys Bentley was a blues singer and pianist of the Harlem Renaissance of the 1920s. She usually performed wearing a white coat and top hat, sang sexually explicit songs, and lived openly as a lesbian, even publicly marrying her female lover. In the 1930s, she performed at the Ubangi Club with a backup chorus of female impersonators.
When the Harlem Renaissance started to decline after the repeal of Prohibition, Gladys moved to Los Angeles. She continued to perform at gay clubs, but found the culture of 1940s Los Angeles much less permissive than that of 1920s Harlem. In the McCarthy era, Gladys Bentley began dressing as a woman, married a man, and claimed in an Ebony magazine article that she had been “cured” of her lesbianism by female hormones and a man’s love. She died in 1960, at the age of 52.
7. Virginia Charles Prince
A pioneer in transgender rights, Virginia Charles Prince was born Arnold Lowman in 1913 in Los Angeles, California and began cross dressing as a teenager. Like many male cross dressers, Prince considered himself a heterosexual who felt more comfortable wearing women’s clothing. His first wife left him because of his cross dressing, believing he was homosexual. The breakup of his marriage was somewhat of a blessing in disguise, however, since it increased his visibility and led other transvestites to contact him.
Virginia started the first support group for male-to-female cross dressers, published the magazine Transvestia, and wrote many books on the subject. He may have coined the term “transgender.” Prince married and divorced a second time, and afterwards began living as a woman. Beginning in the 1960s, Prince dressed as a woman at all times, and even underwent surgery and hormone therapy to become more feminine. However, Prince stressed that such measures were not necessary or desirable for every transvestite. Virginia Charles Prince passed away in Los Angeles at the age of 96.
8. Billy Tipton
Born Dorothy Lucille Tipton, Billy Tipton first took on a male identity in order to further his career as a jazz musician and bandleader. Though Billy’s male identity began as an onstage persona, he was living as a man by the age of 26, and continued to do so for the rest of his life. Billy had a lesbian relationship before living as a man in private, but none of the women he was subsequently involved with, let alone his colleagues, were aware of his real sex.
With the exception of a prostitute with whom he had an affair, Billy had a sexless relationship with most of the women in his life, telling them that he was unable to have sex because of a serious injury. He claimed that the injury had also broken his ribs, requiring him to keep his chest bandaged – though actually, it was to hide his breasts. He lived for nearly 30 years with stripper Kitty Kelly, and they adopted three sons together. When Billy Tipton was revealed to be a biological female upon his death from an untreated ulcer in 1989, Kitty Kelly tried to keep it a secret, though one of their sons leaked the story. Kitty claimed to have had no idea throughout their relationship that Billy had been born a woman.
9. Ed Wood
American filmmaker Ed Wood began his career with an autobiographical film entitled Glen or Glenda. He not only wrote and directed the film, but starred in the title role as a man who enjoyed cross dressing, particularly in angora sweaters, a predilection Wood shared. Ed Wood’s interest in film and in wearing women’s clothing started at a young age. He received his first camera as a gift for his 12th birthday. He served in the marines from 1942 to 1946, and claimed to have worn women’s undergarments under his uniform. After leaving the marines, Ed Wood worked in a carnival, playing many different parts in the freak show, including the bearded lady.
Wood went on to film and direct horror, sci-fi, and exploitation movies, including what he considered his masterpiece, Plan 9 from Outer Space. Later in his career, he turned to pornography, with films including The Photographer and The Undergraduate. He also wrote novels, short stories, and non-fiction books. A womanizer in his youth, Wood later formed lasting relationships with women, eventually marrying Kathy O’Hara, with whom he had a daughter. Ed Wood died of a heart attack at the age of 54. His films have a loyal cult following, and Tim Burton’s film about his life, Ed Wood starring Johnny Depp, won Academy Awards for Best Supporting Actor and Best Makeup.
Divine was the drag persona of American actor and singer Harris Glen Milstead, best known for his work in the films of John Waters. Waters and Milstead first met when they were teenagers. Milstead developed the character of Divine in his 20s, performing in stage shows and in some of John Waters’ earliest films, including Pink Flamingos. The collaboration between Waters and Divine lasted throughout Divine’s life. In a few films, Milstead played male roles, and in Female Trouble and Hairspray, he appeared both as Divine and as a male character. Divine died of an enlarged heart in Los Angeles at the age of 42, just a week after Hairspray’s theatrical release. John Waters has said in interview that he misses Divine very much and still can’t believe he is dead.
Moll Cutpurse: http://upload.wikimedia.org/wikipedia/en/thumb/1/14/Mollcutpurse.jpg/443px-Mollcutpurse.jpg
Abbé de Choisy: http://www.gendercentre.org.au/images/de-choisy.jpg
Chevalier d’Eon: http://upload.wikimedia.org/wikipedia/en/thumb/a/a6/D%27Eon_de_Beaumont_altered_1.png/392px-D%27Eon_de_Beaumont_altered_1.png
Georges Sand: http://www.mtholyoke.edu/courses/rschwart/hist255/at/georges3.jpg
Annie Hindle: http://images.nypl.org/?id=1261090&t=r
Gladys Bentley: http://www.epifanio.eu/nr6/images6/gladysbentley.jpg
Virgina Charles Prince: http://www.advocate.com/uploadedImages/advocate/editorial/advocate_daily_news/princex390.jpg
Billy Tipton: http://upload.wikimedia.org/wikipedia/en/e/e2/Tipton_portrait.jpg
Ed Wood: http://upload.wikimedia.org/wikipedia/commons/e/eb/Glenda.jpg