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!"
4 Lewis Williams Is Switched With a Body Double Mid-Trial
As a young boy, Lewis Williams escaped from slavery in Kentucky and grew up free in the abolitionist stronghold of Cincinnati. Things went wrong in his early 20s, however, when he decided to visit a local psychic to find out if a girl he liked was into him. Somehow he also ended up confiding that he was actually an escaped slave. Astonishingly for a woman who made her living ripping people off, the psychic immediately betrayed him to his former owner in exchange for a reward. Williams was seized by bounty hunters and taken before a judge to be extradited to Kentucky.
The New York Times
While the bounty hunter took him away, the girl he asked about finally said "I love you." He said "I know."
And they would have gotten away with it, too, if the leader of the black community in Cincinnati hadn't been a stone-cold badass by the name of Reverend William Troy. No sooner had he heard about the arrest than he was dreaming up a plan so insane that no one would see it coming.
And certainly not that douche psychic from earlier.
As luck would have it, Troy knew another young man who bore a striking resemblance to Williams. And he also knew that some white people have famously questionable skills in the field of advanced telling black people apart. So when Troy heard that Williams had been seized, he made sure that a crowd of his fellow abolitionists rushed over and packed into the courtroom. Then they simply waited until everyone else was distracted by a dramatic legal argument, at which point Williams and his double quickly switched places and Williams crawled out the door on his hands and knees, hidden behind a wall of hilariously large old-timey women's skirts.
To give him time to escape, Williams' lawyers allowed the trial to continue for several more hours before a bailiff finally noticed that the defendant was an entirely different person. Williams' troubles weren't over there, though, and the house he was hiding out in was surrounded by suspicious policemen. Again, Troy swung into action with another of his patented wacky schemes. And as in the previous entry, it was cross-dressing to the rescue.
How has Tyler Perry not made this movie yet?
So, Troy disguised Williams as his daughter in petticoats, crinoline, and a large bonnet with a veil. The fugitive walked right out the front door and past the crowd of policemen on the arm of a "gentleman caller." Another life saved due to the heroic power of shenanigans.