It's almost tragic that the most badass escaped slave story most people know is Django Unchained. Because in real life, not only did slaves frequently escape, but they often did it without help from free whites, and without murdering several hundred people. Instead, what they had was cleverness and the audacity to try ridiculous plans that by all rights should never have worked.
5 A Couple Cross-Dress Their Way Out of Slavery
In 1848, a slave in Georgia named William Craft hit upon a brilliant plan to escape from his life of bondage: His wife, Ellen, was very light-skinned, and with some forged papers she could easily pass for white. So, why not just pose as her slave and get on a train heading north? There's no way that plan can turn into some kind of wacky Three's Company-style farce!
Wait, there was one problem -- in those days, it was pretty much unheard of for a white woman to travel alone in the company of a male slave, presumably because white men were wary of the enormous sex party that would inevitably break out in just such a situation. For the plan to work, the dainty Ellen would have to be disguised as a white man (she in no way looked like one of those). So, in true wacky '80s sitcom style, they wrapped most of Ellen's face in thick bandages and a pair of tinted glasses. Then, just to make sure that this disguise would attract as much attention as possible, they threw on a huge top hat. Since Ellen couldn't write, they also put a fake cast on her right arm so she wouldn't be asked to sign her name.
"You just put an 'X.' What's your first name?"
"Uh ... Malcolm."
With Ellen now resembling the invisible man in disguise as a mummy, they boarded a train to Philadelphia, only to find that they would be sitting across from a close friend of Ellen's master, who had known her for years. Luckily he didn't recognize them. Unluckily, he kept trying to start a conversation, forcing Ellen to pretend to be deaf to avoid talking to him. She kept this up for the rest of the journey, probably thinking that at any moment somebody was going to spring out and announce that it had all been a practical joke.
Finally, at their last stop in Baltimore, a suspicious railroad employee refused to allow William to board the train to Philadelphia without proof that he did actually belong to Ellen. However, the other passengers were so sympathetic to the thought of the clearly deathly ill "young man" wandering around Philly without his faithful slave to help him, they insisted that both be allowed to board. And with that, they were free.
The Granger Collection, New York
"Your master, Willy Wonka, clearly needs you!"