Happy Halloween! Stingy Jack Gets a Modern Makeover

The saying goes: The Devil always overplays his hand.

No matter what religious tradition you come from, or if you come from no religious tradition at all–no matter what devil bedevils you–he always overplays his hand. We must be wary, however, not to overplay ours first.

Gather ‘round this All Hallows’ Eve and let us spookily spook together. Let us woooo! like ghosties. Let us boogie boogie.

Here is the tale of Stingy Jack, the progenitor of the Jack-O-Lantern. There are many versions of this tale. Here is mine.

Once upon a time in a SoCal desert town, not too long ago as a matter of fact, there lived in a rough part of town a man named Jack who was known all over for his stinginess, temper, chronic drunkenness, and general bad attitude. One night, drunk and trolling the city streets for a date, Stingy Jack came across a man in black leaning against a light pole. The man looked out of place, dressed as he was and wearing a hat with the brim cocked down over his face. What Jack could see of his face was diabolically bathed in the orange light of the streetlight.

Being well acquainted with the hellish workings of the deceitful soul, Jack instantly recognized this man as The Devil.

The Devil lifted his head and said a little too courteously, “Stingy Jack, heart of my blackened heart, it’s time to go and you know where.”

Jack did know where and it made him tremble to think of it. Jack said, “If Hell is as bad as I think it is, I need a shot before I go. I don’t have any money,” he lied, as is the custom of a stingy man, “so would you mind paying for it? There’s a bar right around the corner.”

The Devil all too courteously acquiesced and, on the spot, changed himself into a five spot. Jack picked up the dough and, chuckling to himself at his own craftiness, wrapped the bill around a silver crucifix he carried in his pocket–the very crucifix he lifted from a dying friend earlier that week.

Wrapped all around the crucifix, The Devil could not change back and was frustrated. He would have thrown a goat-footed fit if a five spot were capable of throwing a goat-footed fit. Jack told The Devil he would release him if, and only if, he would postpone the taking of his soul for another ten years. Jack would be 39 by then, old and crusty by his own estimation, so he wouldn’t care.

The Devil all too courteously acquiesced and Jack set him free.

Ten years rolled by and Stingy Jack found that, at 39, he wasn’t so old and crusty after all and, by his own estimation, he had at least another twenty-some-odd years of bad baddiness in him. When The Devil came for him, as promised, wearing the same black suit and hat, leaning against the same lamp post, and bathed in the same diabolical light, Jack was prepared.

“If you’re taking me to hell,” Jack said, “I’ll need to pay the ferryman, right? Well, no one likes me and no one will lay coins on my eyes, so would you mind shimmying up that light pole and ripping out the copper wire so I’ll have something to pay him with?”

The Devil all too courteously acquiesced and, with the grace of a fireman in reverse, shimmied up the pole to look for the copper wire. While he was up there, Jack pulled the silver crucifix from his pocket and laid it up against the pole. He then surrounded the rest of the pole with crosses he made out of pipe cleaners he bought at The Dollar Store, (he was stingy after all).

The Devil was thwarted again and Jack, older and wiser, did not let him free this time until he promised never to take Jack to Hell. The Devil agreed, Jack removed the crucifix and crosses, and saved the pipe cleaners for the future, just in case, so he wouldn’t have to buy new ones.

Eventually, when Jack was the ripe old age of 66, he did die, shot at a basement poker game for pilfering $5 chips. When he approached The Pearly Gates, St. Peter said, “Slow your roll you stingy so and so. No way, no how are you getting into heaven. You’ve got a rap sheet a mile long.”

Having never been homeless in his life, but also never having had to pay rent because he always found someone’s couch to sleep on and someone’s refrigerator to mooch from, Jack sauntered off to Hell to see if he could crash there.

“Oh no,” said The Devil, “you can’t stay at my house, remember? You aced yourself out of that deal with that whole light pole incident. Devils don’t forget.”

“Aw man!” Jack exclaimed. He said, “Well, if you’re going to leave me out here, could you at least give me a light? It’s dark and the Santa Anas are coming on like crazy.”

The Devil slammed the gate and came back in a moment bearing a chipped plastic pumpkin trick-or-treat bucket with a Dollar Store glow stick dimly flickering within. He tossed it at Jack, nearly knocking his block off, and said, “Deal with that, Jack!” He slammed the gate closed.

Jack slouched and mumbled, took the plastic pumpkin trick-or-treat bucket by its badly fastened handle, and wandered off into the dark.

To this day, we carve luscious pumpkins and put real candles or expensive Halloween store glow sticks in so on this night Jack will be reminded that he was the one who got the raw deal in the end and no, he can’t crash on our couches either.

Happy Halloween everybody! Be nice to the man leaning against the light pole. He’s all too courteous and might buy you a shot if you leave the crucifix at home.


About M. Ashley

Essayist and poet, my work has been rejected by some of the finest journals in America. Fortunately, it also gets accepted from time to time and has appeared in equally fine journals such as Word Riot, Inlandia, Brew City Magazine, and SageWoman among others.. In 2002, I was awarded the Academy of American Poets Prize for Vanderbilt University. For no good reason, I possess an unnecessarily dark humor which is why being third generation California Inland Empirian delights me so. My gods are weird. I once received $350 for writing a smartassed essay on “why the wise use of water is important in my daily life”. I am undoubtedly the Greek god Hermes’ special snowflake. I’m pretty sure I got into college via a series of fortuitous clerical errors. When I had to grow up and get a real job, I decided against it and stayed a writer. I have worked many odd—and I mean odd—jobs to support my habit: Commercial writer for country music hopefuls, resume massager, WalMart fitting room attendant and switchboard operator, telephone psychic.
This entry was posted in Catholicism, Ghosts, Halloween, Holidays, Mythology, Sabbats, Samhain, Satan and tagged , , , , , , , , , , , , , , , , , , , . Bookmark the permalink.

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