1 Cross-Dressing to Join the Army
Until recently, women have rarely been allowed to serve as soldiers. So what was a gal to do if she wanted to serve her country? Naturally, disguise herself as a man and join the troops. At least 400 Civil War soldiers were women in drag. These included Union Army soldier “Frank Thompson” (also known as Sarah Edmonds), whose small frame and feminine mannerisms (rather than causing suspicion) made her an ideal spy, as she could spy on the Confederates disguised as … a woman!
She wasn’t the first woman to don a male disguise and join the army, though. During the Revolutionary War, women fought as men on both sides. Hannah Snell, for example, joined the British army to find her husband, who had walked out on her to enlist. Once her true sex was discovered (thanks to a pesky groin injury), she became a national celebrity in Britain, and made a postwar career of performing in bars as the “Female Warrior.”
Kathryn Johnston was the first girl to play Little League. In 1950, she cut her hair, called herself Tubby, and made a team in Corning, N.Y.
2 Cross-Dressing to Keep a Royal Family Together
With all the power struggles that went on in the court, the French royal family would go to great lengths to avoid sibling rivalry. In one of the more extreme cases, Philippe I, Duke of Orleans (1640–1701), was raised as a girl to discourage him from any political or military aspirations. This would make things easier for his brother, the future King Louis XIV. Philippe wore dresses and makeup, enjoyed traditionally feminine pursuits, and was even encouraged toward homosexuality.
A girlie man he might have been, but he married twice and even had a mistress. When necessary, he could even lead an army into battle. (This is the nation, after all, that gave us that famous cross-dresser Joan of Arc.) A brave commander, he would go into battle wearing high heels, plenty of jewelry and a long, perfumed wig. One of his wives claimed that Philippe’s biggest fear when going into battle was not bullets, but the possibility of looking a mess. He avoided gunpowder (with the black smoke stains) and didn’t wear a hat, to avoid ruining his hair.
3 Cross-Dressing to Commit Espionage
There have been many instances of cross-dressing spies, but one of the most impressive deceptions in history was carried out by Shi Pei-Pu, a singer with the Beijing Opera (in which, traditionally, all roles are played by men). In 1964 he disguised himself as a woman to seduce Bernard Boursicot, an attaché in the French Foreign Service. Their affair lasted 20 years (on and off), during which Boursicot passed several official documents to Shi, believing that “her” safety was at risk if he didn’t participate. After they were separated in 1965, Shi came back into Boursicot’s life by claiming to be pregnant, and even revealed a baby boy. They later lived as a family. The happy couple was eventually arrested for espionage in 1983, and Shi’s secret was revealed, Crying Game style, to the stunned Boursicot.
4 Cross-Dressing to Get Rowdy
Hindu women in India have traditionally lived inhibited lives, tending the home for their families. But on one night each year, in the city of Jodhpur, they come to life at the so-called Festival of Fun. Dressed as noblemen, complete with turbans and large fake mustaches, they walk the streets in gangs, brandishing sticks, beating any males who are foolish enough to be out there.
The festival celebrates an ancient domestic dispute between the Hindu god Shiva and his wife Ganwar. While the women sing devotional songs asking the goddess to return to her husband, they also take this as their only opportunity to do what they long to do all year: behave like men. Their husbands, respecting the tradition, let them go wild. It sounds like fun (as long as you’re not a clueless male who forgot to stay at home that night), but one thing concerns me: If a woman’s disguise is especially good, does she risk being mistaken for a man and beaten up by her friends?
The famous leg featured in posters for The Graduate belongs not to Anne Bancroft, but to a then-unknown Linda Gray (later of Dallas).