Stingy Jack and the Allure of the Dark Side
- Jacquelyn Holmes
- Oct 25, 2024
- 5 min read
Updated: Aug 19

Recently I watched a really interesting video on YouTube discussing a medieval perspective on the upcoming holiday of the month, Halloween. It was fascinating for a lot of reasons, and if you'd like to watch it, you can find it here. However, tucked into the discussion was the story of Stingy Jack and the origins of the modern Jack-o-lantern.
Here is a version of the story from The History Channel:
"According to the story, Stingy Jack invited the Devil to have a drink with him. True to his name, Stingy Jack didn’t want to pay for his drink, so he convinced the Devil to turn himself into a coin that Jack could use to buy their drinks. Once the Devil did so, Jack decided to keep the money and put it into his pocket next to a silver cross, which prevented the Devil from changing back into his original form.
Jack eventually freed the Devil, under the condition that he would not bother Jack for one year and that, should Jack die, he would not claim his soul. The next year, Jack again tricked the Devil into climbing into a tree to pick a piece of fruit. While he was up in the tree, Jack carved a sign of the cross into the tree’s bark so that the Devil could not come down until the Devil promised Jack not to bother him for ten more years.
Soon after, Jack died. As the legend goes, God would not allow such an unsavory figure into heaven. The Devil, upset by the trick Jack had played on him and keeping his word not to claim his soul, would not allow Jack into hell. He sent Jack off into the dark night with only a burning coal to light his way. Jack put the coal into a carved-out turnip and has been roaming the Earth with it ever since. The Irish began to refer to this ghostly figure as 'Jack of the Lantern,' and then, simply 'Jack O’Lantern.'"
(If you'd like to read the rest of The History Channel's article about the origins of jack-o-lanterns, click here.)
During the medieval times, people were just built different. Had I been told a story like this as a child, it is unlikely I would have taken up carving my own "Jack of the Lantern" to display at my doorstep for the amusement of myself or my neighbors. In that same vein of thinking, I don't know that it would ever occur to me to carve a gargoyle for my roof, monster faces for doorknockers, death's heads for the eaves or animal totems for the doorposts. In fact, quite the opposite. Our modern minds seem to equate making a place for a monster on the walls signals an acceptance of such a being in our lives. The medieval people seemed to believe that if their own facsimile was scary enough, it might ward off the real thing.
And yet...
Don't we dress up for Halloween in scary costumes? Don't we watch horror movies? Every October we put monsters on the lawn and tread carefully through haunted houses. We don't even wait for Halloween to do some of those things, and the number of true crime documentaries, podcasts and books would suggest that there is an element of horror in many people's every day lives.
For as long as people have been people, there have been stories. Whether they were shared over a fire, around a dinner table, while tucking a child into bed or over the radio waves, they have always existed. Do you know what else has always existed?
Scary stories.
On Halloween night, we open our doors to darkness... and children dressed as goblins. But I would argue that all year long we open metaphorical doors to darkness. I would argue that it is a human condition.
In fact, I would argue that the very rhythm of our lives is a trade off between tension and release. We get stressed, or we are under a deadline, or things are pressurized, or life is hard...and then there is a release. Any woman who has birthed a child will know that there is a very stressful time getting that child into the world, but oh the moment it's over! That baby in your arms is a relief beyond words. If you workout, you know that you feel terrible at times, and then you hit your stride. You get a runner's high. Students feel a tremendous amount of pressure to pass tests, but there is a soaring sense of freedom when the test is over. Stress, then relief.
Are we so programmed to this rhythm that we open the door to darkness, seeking the tension, believing in our guts in the relief on the other side? Is stress, followed by relief the same as darkness, followed by light?
And if so, is this urge necessary to human life?
I would argue that we all have a scary darkness that we are willing open a door to, and look out into the night. If mankind had been unwilling to do this, oceans would never have been crossed, the north and south pole would never have been reached, and we would even now not be pushing to put a human on Mars. Crossing unknown darkness is part of the -seemingly- inborn need to pioneer new territory. Maybe you are safe in your house and you believe, I would have never crossed the ocean, not knowing what was on the other side! But, have you maybe started a business that you couldn't guarantee the success of? Have you quit a job when you weren't sure you had another to replace it? Maybe you married that boy that everyone told you wouldn't amount to anything?
Scary doors are a part of our lives, whether we like it or not. Without them, we are stagnant. And, in case you were wondering, stagnant stinks! However, you will never clear that water without churning up some mud. You can't get to the other side of your story without first addressing the scary door, the tension. Thank God there's usually some kind of relief on the other side!
Maybe the real moral to the story of Stingy Jack is that he set himself up to avoid an eternity of tension (hell), but he didn't make a path for that eternal relief (heaven). He chose neither, and now he must roam the earth, unchanging and homeless.
So friends, I leave you with this: open the door to darkness. Occasionally dare to cross the threshold, even. However, you must either take a roll of string, or you must stock your boat with hard tack. You must either make a path back home, or you must be ready to endure until you reach the new shore.
Go out into the world and dare to get gloriously lost. Face down the tension of that dark night. Morning always comes.
Tell me: what darkness have you crossed? Where did you end up at the end?
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