Home Horror Entertainment News 31 Scary Story Nights: October 31 “The Strange Story of Jack O’ Lantern”

31 Scary Story Nights: October 31 “The Strange Story of Jack O’ Lantern”

by Waylon Jordan

Well, readers, it seems we’ve finally made it to Halloween night.  We’ve had ghost stories and campfire stories and urban legends galore this month, and here it is, our final tale.  I wavered a lot but finally decided that tonight’s tale would be one of those special to Halloween itself.  It’s The Strange Story of Jack O’ Lantern and I hope you’ll enjoy it as much as I do!

So, one last time, let’s dim the lights, gather around, and enjoy our last Scary Story Night of 2017.

***Writer’s Note:  We here at iHorror are big proponents of responsible parenting.  Some of the stories in this series may be too much for your little ones.  Please read ahead and decide if your kids can handle this story!  If not, find another story for tonight or simply come back to see us tomorrow.  In other words, don’t blame me for your kids nightmares!***

The Strange Story of Jack O’ Lantern as retold by Waylon Jordan

Stingy Jack was the laziest, drunkest, no good layabout in his entire village.  He was constantly playing practical jokes on his neighbors and more than one had caught him stealing pies from windowsills and eggs from their coops.  To Jack it was all good-natured fun, but more than one person had begun using his name as a curse.

One night as Jack stumbled from the pub, he came face to face with the Devil himself.

“Stingy Jack, your time has come.  Tonight you die and it’s hell for you!”

Jack never missed a beat.

“Sure and I’d love to go with you, Satan…can I call you Satan? But how can you take a man without allowing him one more drink?”

“Well, I suppose…,” the Devil replied watching Jack dig around in his pockets.  “What are you looking for?”

“I’ll be damned,” Jack said, throwing the Devil a wink.  “but it seems I’ve spent my last coin.  You wouldn’t happen to have some money would you?”

“I don’t make a habit of carrying money, no,” Satan boomed at Jack, obviously becoming impatient.

Jack began to wail and lament aloud about how he’d soon be leaving the earth without a final drink.  How would his fellow Irishmen respect him in the afterlife?  It went on for so long that the Devil finally interrupted.

“I have no coin, but I can change myself into a coin and after you use me to pay for your drink I’ll change back.”

“THAT, my good Satan, is an ideal proposition!” Jack exclaimed and clapped his hands as the Devil became a shiny silver coin on the ground.

Jack quickly snatched up the coin and dropped it into his pouch  which happened to be marked with a holy cross!

“I’ve got you now, Satan, old boy,” Jack cackled.  “And I’ll never let you out!”

Jack could feel the Devil kicking about inside his pouch and it made him cackle all the more.  Before long, he heard a tiny, though menacing voice from inside his pouch.

“Let me out of here, Jack, or so help me!”

“Let you out?  Why would I do that when you want to take me to hell?  I tell you what, Satan.  I’ll let you out of this pouch on one condition.  You guarantee that I’ll never be allowed into hell and I”ll set you free!”

The pouch ceased moving about and finally the voice from inside said, “Deal…”

With that, Jack turned the pouch over and tossed the coin to the ground.  Immediately, the Devil stood before him and grinned.  “You’ve no idea what you’ve done, Stingy Jack, but one day you will!”

With that, he was gone in a puff of smoke.

Ten years passed, and though Jack had meant to mend his ways, it never came to be.  One night he stumbled drunk from the pub as he had so many times before and was hit by a horse drawn cart, dying instantly.

In the blink of an eye, he stood before the Pearly Gates, and Saint Peter scoffed.

“You’ll never be allowed in here, Stingy Jack.  I’m afraid it’s hell for you.”

In a flash of light, Jack stood before the Gates of Hell.

“Well, well, well,” Satan laughed.  “Jack!  Finally dead?”

“That I am, Satan.  That I am!  And Heaven tossed me out on my own ear,” Jack smiled.

“That is a problem, Jack.  Heaven won’t have you and I gave my word you’d never enter these Gates.  I suppose it’s Limbo for you.”


“Aye, Jack, the great grey void.  A vast landscape of…nothing.”

It was the Devil’s turn to laugh as Jack suddenly realized what he’d done, turning and staring into the grey space of Limbo that touches the earth, but not enough for Jack to ever truly interact.  He would be cut off from everything he’d ever loved.

“Don’t fear, Jack, I’ve got a light for you,” Satan called and he scooped up a burning ember from the flames of Hell and tossed it to where Jack stood.  “The light will never die, Jack.  Not like you!”

And with that Satan, Hell, and all the rest disappeared.  Jack knew he couldn’t pick up that ember so he pulled up a large turnip and carved it out.  He scooped up the ember and carried his light forth into the grey.

They say to this day, on Halloween night, when the veil between our world and the land of the Dead is at its very thinnest you can spy poor old Jack still wandering in the darkness searching for other lost souls like him.  So carve your pumpkins and light them this evening so that Jack won’t feel quite so alone!

Well, that does it.  Another Halloween night in the books.  I hope you’ve enjoyed this series of stories and that you’ve shared them with your friends and families.  Who knows, next year, we might just turn up again for another 31 Scary Story Nights!  Happy Halloween!

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