Crank up “Monster Mash” and grab your sexy Harambe costume, because Halloween is upon us. Halloween is known for candy-induced comas and crazy costume parties, but the shining symbol of this spooky holiday is the jack-o’-lantern. Pumpkins are a fall staple, but rip out that pumpkin’s insides and replace them with a candle, carve up its skin, and you’ve got yourself a jack-o’-lantern. While the images that people create—creepy faces, witches and ghosts—are all representative symbols of Halloween, the story behind the jack-o’-lantern—and the person it is based on—is even more of a reason for it to be the face of the holiday centered around fear and trickery.

The Origin Story

The jack-o’-lantern was derived from an Irish myth that follows a man nicknamed “Stingy Jack.” According to the story, Stingy Jack invited the Devil to have a drink with him. Living up to his nickname, Jack wasn’t too excited about paying the bill, so he convinced the Devil to turn himself into a coin so the two of them could pay for their drinks.

Jack never paid for the drinks.

Instead, he kept the coin in his pocket next to a silver cross, preventing the Devil from turning back into his old self. He eventually allowed the Devil to return to his original form, under the condition that he would not bother Jack for a year, and if Jack died, the Devil would not claim his soul.

Fool Me Once…

A year passed, and the Devil did not learn his lesson. This time, Jack tricked him into climbing a tree to pick a piece of fruit, and when the Devil was up high, Jack carved a cross in the trunk, trapping the devil in a leafy cell.

Jack’s conditions for letting the Devil down were similar to the previous ones: the Devil could could not claim Jack’s soul when he died and he could not bother him for another ten years.

Stingy Jack eventually died and, after seeing what he had done, God did not allow Stingy Jack into heaven. However, because of their deal, the Devil was not allowed to claim Jack’s soul either. So instead, he sent Jack out into the world with a single burning coal to find his own hell.

Jack put the coal into a carved out turnip, and has been roaming the earth ever since.

Original jack-o’-lanterns in Europe were made out of turnips, beets or potatoes; but in America, the popularity and accessibility of pumpkins allowed for people to use them to make their jack-o’-lanterns.

Jack: The Devil Slayer

On first glance, the Devil just looks like a fool in this story. He let a mere man fool him twice, forcing him to bend to his will. But instead of showing the faults of the Devil, I think the story is meant to show the prowess of Jack.

The Devil is known to many as the face of fear, evil and trickery. In order for a man to beat the Devil at his own game, he must be very cunning. To be the best you have to beat the best.

But Jack was not just able to trick the Devil once; he tricked him twice. Initially, that second encounter must have been very awkward—I know I would hate running into the guy I turned into a coin. But tricking the devil twice shows not only his craftiness but also his persuasion and charm.

The devil had to be wary of being fooled again, so how would Jack even temporarily get back on his good side? Crack a smile, unbutton a few buttons on his shirt and turn on the charm. Climbing up a tree would put the Devil in a very vulnerable position, so assuming the Devil is not completely incompetent, the fact that Jack was able to get him to do that shows that his charm and persuasion were of the highest order.

Also, it says a lot that the Devil would not even let this guy into hell. Yes, they did make a deal, but I imagine the Devil still wanted to stay as far away from Jack as possible after he was humiliated twice. If the Devil would have let him into hell, this story might have ended with Jack being the ruler of the underworld.

So it seems appropriate that the man who tricked the Devil is not the face of Halloween.

Now Jack is the ultimate anti-hero, his trickery and scheming indirectly bringing joy to all jack-o’-lantern and Halloween lovers alike. So think of Jack the next time you see a jack-o’-lantern, but beware: if Jack could fool the Devil, who is to say he couldn’t fool millions of people into celebrating a holiday centered around him? Happy Halloween…