History’s Most Interesting Transvestites

Featured, Pop Culture — By BB Admin on May 8, 2012 12:00 am

Personalities such as Boy George, RuPaul, and even J. Edgar Hoover have introduced cross-dressing, or transvestism, into the mainstream in recent history, as have movies like Psycho, The Rocky Horror Picture Show, and Mrs. Doubtfire. Although women such as Joan of Arc and Hua Mulan cross-dressed centuries ago in order to join the military, modern transvestites often cross-dress for other practical purposes: they feel more comfortable in the clothing of the opposite sex.

Transvestites should not be confused with transsexuals. A transsexual is one who takes on the identity of the opposite sex, either through a sex change or by living as a member of the opposite sex. A transvestite chooses to dress in the clothing of the opposite sex, but does not necessarily identify his or herself as a member of the opposite sex. A transvestite is also not necessarily a homosexual; transvestites often favor heterosexual partners. They simply prefer to wear the clothing of the opposite sex, for whatever reason.

Bonny and Read

Sure, we’ve all heard of Bonnie and Clyde, but what about Bonny and Read? Anne Bonny and Mary Read were women who cross-dressed as pirates on the Revenge in the late 1600s. Bonny was not originally a cross-dressing pirate—she married a pirate and worked on her husband’s crew. It wasn’t until Read later joined the same crew and Bonny developed a secret crush on “him” that Read was forced to reveal to Bonny her identity as a woman. Both women began posing as male pirates and hiding their identities as females. When the Revenge was eventually captured, Bonny and Read were allowed to live longer than the rest of their crew because both women claimed to be pregnant (only Bonny was).

George Sand

19^th Century French novelist George Sand was a woman who took on both the pen name and clothing style of a man. Born as Amantine Aurore Lucile Dupin, the Baroness claimed that she preferred men’s clothing because they were more comfortable, practical, and sturdier than women’s clothing of the era. Her cross-dressing allowed her luxuries typically unavailable to women at the time, such smoking in public and admission to events and venues where only men were welcome. Her masculine pen name contributed to her becoming the first well-known female French novelist.

Shi Pei Pu

Male Chinese spy Shi Pei Pu posed as a woman and maintained a 20-year sexual relationship with French diplomat Bernard Boursicot while stealing government secrets from him all along. Boursicot never discovered that Shi Pei Pu was a man until the men were caught and convicted of espionage in 1986. Boursicot was so devastated and embarrassed to learn his lover was a man, he slit his throat (but lived). This story became the basis for David Henry Hwang’s 1988 play M. Butterfly, and the 1993 David Cronenberg film by the same name. In the play/film versions, the Chinese spy performs in the Peking opera as a woman, and uses this disguise to seduce the French Diplomat (in real life, Shi Pei Pu became a male opera singer after he was pardoned).

Billy Tipton

Depression-era jazz performer Billy Tipton was really a woman named Dorothy Lucille Tipton who began performing as a man in the 1930s and later living as a man in both public and private life in the 1940s. Tipton began dressing in male clothing on stage to better blend in with other performers and to help advance her career as a performance musician—a career mainly limited to men at the time. During her life as a man, Tipton had several long-term sexual relationships with women, none of whom knew that he was really a woman. Over time, Tipton had hidden his true identity from everyone he knew, and his secret was finally discovered by his wife and their three adopted sons when he died in 1989.

Edward D. Wood Jr.

Ed Wood finally earned his claim to fame after his death in 1978 when he was voted “The Worst Director of All Time” and his 1950s horror films gained a cult-status following. Wood’s transvestism was also the subject of his first film, Glen or Glenda?, which doubles as a loose biography of his early adult life. Wood frequently wore women’s undergarments under his clothes, including while in combat in WWII, giving rise to the term “underdressing.” He also had an angora sweater fetish and a tendency to appear on the set to direct in full drag. Wood was a heterosexual and a womanizer in his younger years, but he later married a woman who didn’t mind him borrowing her sweaters once in a while. Wood gained even more notoriety when he became the subject of the 1995 Tim Burton film Ed Wood.

Divine

Harris Glenn Milstead is better known as Divine, his alter-ego, drag persona, and stage name. He is also known as part of Baltimore cult-director John Waters’s entourage, starring in many of Waters’s films. His final performance was in Waters’s 1988 film Hairspray, in which he played both the female character Edna Turnblad and the male character Arvin Hodgepile. Divine died suddenly the week after Hairspray was released, but his legacy lives on in both the Broadway play and 2007 musical film: in all performances of Hairspray, it is customary for Edna Turnblad to be played by a man in drag.

ed note:  Modern Transvestite Extraordinaire:

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