All right, we don't to be jerks here, but looking at the picture up there we're thinking this probably was not one of the more difficult disguises to pull off.
Catalina de Erauso was a Spanish woman in the 1600s who felt that life was too boring for Spanish women in the 1600s. When her family decided she was to be a nun, that was the last straw and she bolted, looking for adventure in the New World.
Under the name "Francisco de Loyola," she fought as a Spanish soldier, and like most soldiers, gambled, dueled, drank and broke hearts. Noble families everywhere tried to set their daughters up with this dashing young fellow, and she strung them along for all the cash and sex she could get before bolting.
Sooner or later, the game was going to be up, and the canny Catalina decided to beat them to the punch by finding a sympathetic powerful man, a bishop in particular, and giving him her side of the story. The end result was that in return for fooling everyone and running away to fight, drink and screw like a man, and telling everyone about it, she returned to Spain a hero and was commended by the king and even the Pope.
She brought about feelings that were strange and deeply confusing.
She may possibly have been the smoothest talker of that era in both the Old World and the New.
Yes, the Chevalier d'Eon was so androgynous the Japanese were compelled to make an anime about him.
The Chevalier, who dressed and acted like a man, was part of an elite French spy corps reporting directly to Louis XV. "He" carried out successful infiltration and spy missions in the Russian court and in England as interim French ambassador.
When a new French ambassador arrived, he did his best to undermine d'Eon as part of a power play, and d'Eon retaliated by publishing a load of French spy secrets while holding back the best ones as a threat. This kept him safe personally but ended his spy career.
Now in retirement, he felt free to let out his big secret: he had been a woman the whole time.
The government was cool with this but demanded that he start dressing as a woman, and he said he was cool with this if the government paid for it, which they did. He went on to have more adventures, participating in the American Revolution, publishing his memoirs and trying to start up a division of women soldiers.
Why did we keep referring to d'Eon as "he" after he came out as a cross-dressing woman? Well, that's the kicker.
After he died, they found out he had a penis the whole time. So... he was what you might call a double crossdresser.
Charley Parkhurst was one of the Old West's legendary characters, maybe because he fit the part so well: Charley was a grizzled old one-eyed stagecoach driver, fearless and hard-boiled. He was also, as you can probably guess, a lady.
Charlotte Parkhurst was an orphaned girl who grew up working in stables and eventually stuck to boys' clothing so she could keep on that path. In Charley's long and adventurous career, she had quite a few close calls, possibly due to the difficulty of hiding her "graciously endowed" rack (as described by the attending physician upon death).
Yet, she managed to keep it up by moving to another location when exposed, or when her likable personality caused friends to cover up for her.
Along the way, she lost an eye to a horse kick or a rattlesnake bite, became the first woman known to vote in a presidential election (52 years before women were granted the vote), became one of Wells Fargo's top stage drivers, and turned to lumberjacking and running a stage business after she retired.
Manlier than 90 percent of dudes today
When she died of cancer, the attending physician commented on his breasts, as mentioned above, and also dropped a bomb when he said "further examination revealed that old 'Cock-eyed Charley' had given birth to a child." Holy shit! How the hell did she explain away that year of her life, and why the hell hasn't somebody made a sitcom about it?
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For more badass spies, check out 5 Spies with Bigger Balls Than James Bond. Or find out about some soldiers who went above and beyond the call of ass-kicking duty, in 5 Real Life Soldiers Who Make Rambo Look Like a Pussy.
And stop by our Top Picks (Updated 3.26.2010) to find out which columnist is actually a woman.