So, Dr. James Barry. Genius surgeon, feisty dueler, warrior, breaker of female hearts. The below story and quotations are from Barbara Holland's They Went Whistling, pages 29-30.
He became a medical student at the University of Edinburgh quite young (some reports say as young as 14, others as "late" as 16). He did brilliantly and became a surgeon. Then he signed up for the army, because he liked to kill things as much as he liked to heal them (I shouldn't joke about that since I've started watching Hannibal). Okay, maybe he didn't like to kill things, but Dr. Barry was an opinionated and temperamental man who would bitch-slap you as soon as look at you: he "fought a number of duels in the old-fashioned way, with swords, killing at least one opponent".
It probably didn't help that "He was known on several continents as a breaker of feminine hearts, but he didn't seem to be the marrying kind". He got teased a lot by his army buddies, since he always looked so young and boyish. See this messed up picture, circa 1813, when he first became a doctor:
No, I don't know what's wrong with his head, or where his neck went. I'm not a doctor, but maybe this is the reason he was getting picked on.
Anyway, he traveled all over the world to many British colonies and eventually became the Medical Superintendent-General. He died, relatively famous and well-respected, in 1865 of dysentery. BUT HERE IS WHERE THE STORY REALLY STARTS.
Because, you see, his buddy army doctor from a South African campaign did a routine inspection of the body and thought, "Huh. James sure has a tiny penis. It's so tiny, I can't see it at all. Wait a second . . . " (I might be paraphrasing the doctor's thought-process).
That's right, people, he was a woman.
He fooled people for sixty years, in the army, no less, and rose to the top of his field. "How Barry survived the physical exam essential for enlisting in the first place is a mystery; perhaps he sent a friend of the correct gender. Once in, he seemed a man of unusual physical modesty, but this was held in his favor, as a gentlemanly trait. When contacted [about his death and real gender], his astounded classmates at Edinburgh recalled only that he couldn't be persuaded to take up boxing, but no doubt his swordsmanship made up for this delicacy.
"Nobody ever found out who she was, though you might consider that, after so long, she'd won the right to be whoever she said she was. Her tombstone reads simple, "Dr. James Barry"".
Best Jane Doe story ever.