The Story of the First Jack-o-Lantern for Halloween

Kimberly Us
7 min readOct 25, 2021

Stingy Jack and the Devil Create the First Jack-o-Lantern

The First Jack-o-Lantern belonged to Stingy Jack. (KimberlyUs)

The devil lay in bed watching the flickering flames of Hell.

His toady, Lickspittle, hopped up. “Sir…Master?” The devil slid a languid glance his way and flicked a piece of ash off his finger. “Stingy Jack is bragging again, Sir.”

“What?” the devil sat up, his cloven hooves sparked as they hit the floor.

“I heard him myself,” the toady explained. “He said,” and the bullfrog puffed himself up as he imitated the human, “I could run a con on the devil himself. No one is craftier than me!”

The devil stood and pointed his finger at the Earth above, “Stingy Jack, you have summoned me with your taunting.” His tail flicked from side to side. Lickspittle had to jump back to avoid the sharp arrowhead point.

The devil grabbed his black cape and headed for Hell’s exit. “Curses,” he mumbled and went back to get his hat. He wedged it down on his head so his horns were covered. “Lickspittle, I will return…with Stingy Jack!” The portal slammed shut with a puff of sulfurous smoke.

Near the bar that Stingy Jack did his bragging in, the devil lay down in the road and transformed himself into a dead man. It wasn’t long before Stingy Jack came along. With a glance here and there, Jack knelt to rifle the dead man’s pockets. The devil grabbed Jack’s wrists with his fierce grip.

“Misery me.” Stingy Jack whispered as he stared into his captor’s goat eyes.”You’re the devil, ain’t you?”

“You’re dead on,” agreed the devil. “I’m tired of your bragging Stingy Jack, I’ve come to take you to Hell.” With a nod, a hole opened up in the ground and the devil tugged on Jack to begin the trip down.

Stingy Jack looked into the bowels of Hell. “Sir, Mr. Devil, sir, before we go, could you allow me one more drink? I’m sure they don’t serve beer in hell.”

The devil licked his lips. He was feeling a bit parched. He barely had time to agree before Stingy Jack began pulling him down the road towards his favorite bar, Foxy’s Irish Pub.

The devil and Stingy Jack sat in a dark corner. The bartender brought them a bottle of whiskey and two glasses. Jack drank swiftly and the devil had to keep pace to protect his pride. Before he knew it, three empty bottles lay on the table. The devil shook his head to clear it, but it was no use. “Let’s go,” he growled and stood.

The bartender rushed over. “Time to pay up, sir.” The devil looked at the man and then at Stingy Jack.

“Everyone knows I ain’t got no money. Look at the sign,” Stingy Jack pointed at the sign over the bar. “Anyone who shares a drink with Stingy Jack must pay the bill. No exceptions”

The bartender nodded. “You must not be from around here if you don’t know your drinking partner. Why Jack here could pull a con on the d–”

“Enough!” thundered the devil. He patted his pockets–they were empty. Stingy Jack had stolen his wallet.

“I’ve got an idea,” whispered Stingy Jack, leaning in so the bartender couldn’t hear him. “Why don’t you change yourself into money to pay the bill, and then transform back once the deal is done.”

The devil agreed. He’d had too much to drink, he felt flustered by the contract on the wall that he’d failed to see.” With a flash that temporarily blinded all, he transformed into money.

Stingy Jack snatched up the money before the bartender and shoved it into his pocket. He thought he heard a groan as the money touched the crucifix he always carried with him. He knew the cross made the devil impotent.

Stingy Jack left the bar and wandered down the road. He felt the money squirm in his pocket. “I’ll let you go, if you promise to give me ten more years on Earth.” He could sense the devil’s agreement so he took the money out of his pocket and tossed it into the road.

The money blazed and the devil reappeared. He shook his fist at Stingy Jack but wouldn’t meet his eyes. “I’ll see you in ten,” he mumbled and opened the portal to Hell and descended.

Ten years passed in the blink of an eye and the devil returned. This time he waited for Stingy Jack during the day, outdoors, away from the bar and booze that had tricked him before.

Stingy Jack walked down the path and the devil blocked his way. “Your time is up.” He smiled with pointed teeth.

“Well, I sure hate to leave this green earth while the apples are in season.” Stingy Jack pointed towards a tree in his yard. High in the branches the devil could see the red fruits shining in the sun.

“You sure you don’t want to pick some? I don’t imagine you have apples in Hell.”

The devil shook his head. The fare was dismal in Hell, primarily burnt meat. Those apples would taste sweet and fresh. He flicked out his snake tongue. He could smell them.

“Go ahead,” urged Stingy Jack. “Grab some for yourself, as much as you want, and one for me too.” He walked to the base of the tree and directed the devil to climb.

“You get them for me,” commanded the devil, although the temptation for the apples nearly overwhelmed him.

“Can’t,” said Stingy Jack. “My old knee is too bum to climb. You know us mortals, we age badly.”

The devil nodded. He’d always been repulsed by the aging of mortals. He’d show Stingy Jack how spry he was. In no time the devil was at the top of the tree. He clung to the branch and bit into his first apple. Sweet juice ran down his chin and into his goatee. He sighed with pleasure.

Without a glance at Stingy Jack, the devil ate apple after apple. When he had finally had his fill, he looked down to toss the last apple to Jack. He screeched in horror. The base of the tree was ringed with crucifixes.

“Ha, I told you I could con the devil himself!” crowed Jack. “Not once, but twice I’ve bested you.”

The devil bowed his head. He knew that he’d been beat. “What will you ask for this time?” he mumbled.

Jack stood below the tree and pointed his finger up at the devil. “You must agree to never take me to hell.”

By this time, the devil was rather sick of Stingy Jack and his cons. The last thing he wanted was to have to spend eternity with him. “Agreed,” he said.

Stingy Jack removed the crucifixes and the devil lept out of the tree and raced down to Hell and home.

It was only four years later that Stingy Jack died. A lifetime of trickery and drink demands its toll from the body no matter how clever the mind may be.

After his burial, Stingy Jack went up to the Pearly Gates of Heaven. St. Peter blocked his path. “Surely you don’t think you deserve entrance?” he said in a voice thick with smug.

“Well, I can’t go to Hell so that means I go here,” said Stingy Jack, but his bravado faded under the stern gaze of the angel.

“No. You have lived a life of deceit and sin. You are not welcome here.”

Stingy Jack turned and headed down towards Hell. “Maybe it won’t be so bad down there. I’ll bet that ole devil will be fun to prank.”

He pounded on the lead door to Hell. Lickspittle opened it a crack. “Yes?” he asked.

“I’ve died and am ready to come in,” said Stingy Jack.

“Who is it?” Jack heard the devil ask from behind the door.

“It’s me, you’re old pal Stingy Jack! I’m ready to move in with you. Think of the fun we’ll have together. I’ll bet I can teach you some new tricks,” Jack laughed, but his heart trembled.

The devil flung the door open. Lickspittle stood beside his master holding a lantern. “You are not allowed to enter my home. Remember our deal in the apple tree? Your victory? Your ‘con,’” the devil’s pointed fingernails made quotation marks in the air, “of the devil himself?”

“Yes, but I changed my mind. I will void that deal. You can have my soul.” Stingy Jack stood tall with his chest puffed out, but his knees shook.

The devil chuckled, he loved to have the last laugh.

“Everyone knows deals with the devil are binding. You can not enter.” The devil started to shut the door but Jack put his hand against it.

“What is to become of me? I’m barred from Heaven and Hell.”

“You are doomed to wander for eternity as a restless soul. You will walk the plane between good and evil.” Stingy Jack heard a certain tone in his voice, was he receiving sympathy from the devil?

Stingy Jack fell to his knees, pleading. “Esteemed sir, can you give me anything to ease my journey?” He pointed at the lantern Lickspittle held.

“I can’t give him an artifact from Hell, sir. That would give him power,” Lickspittle said, looking up at the devil.

“Give him an ember. Humans already have the power of fire.”

“What shall I put it in, sir?” asked Lickspittle.

The devil stretched his hand up through the ceiling, up to the Earth and grouped around for something. He felt something round. He pulled it down and handed it to Lickspittle.

“A pumpkin, sir?”

“Yes, hollow it out. Carve a scary face so that no one is tricked into talking with him,” demanded the devil, impatient with himself for once again helping Stingy Jack.

Lickspittle did as he was told and placed the ember inside the pumpkin. “Here you go,” he said, “your own scary lantern.”

Stingy Jack grabbed it. “Not a scary lantern,” he said holding it up and admiring the way the light glowed through the evil eyes and wicked mouth, “a Jack-o-Lantern!”

He turned. The devil and Lickspittle felt a stab of admiration as Stingy Jack skipped back up to Earth.

In the mood for some Halloween fun? Take a Retro Road Trip to the Hollywood Forever Cemetery

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Kimberly Us

Kimberly is a writer, teacher, speaker. She writes about mythology, nature, and bold women who drove social change in midcentury America https://kimberlyus.com/