Stingy Jack
Centuries ago, amid the myriad of small towns and villages of Equestria, there lived a pony by the name of Stingy Jack, a lazy pumpkin farmer. Jack was known throughout the land as a drunkard, a deceiver, a clever manipulator who would lie, trick, and steal to get his way. He was much disdained by the good ponies of Equestria, and all were wary whenever Jack came near. They would tell tales of his tricks and pranks, how he would deceive others into doing his work for him. None could be as deceitful as Jack.
So great was Jack's infamy that the king of tricksters himself, Discord the spirit of Chaos and Disharmony, grew envious of Jack. Discord could not believe that anyone could be more deceitful than he, especially not some drunkard pony. Discord's envy grew until he could no longer stand it, and he decided to get rid of Jack once and for all, and regain his title as the most deceitful of creatures.
One night, Jack wandered alone in the countryside after another day of drinking and trickey. As he walked, one of the cobblestones on the path morphed and Discord stood before him in all his malice.
"Jack," said Discord in a menacing tone, "I've been hearing that you are the cleverest deceiver in Equestria. I can't allow somepony to upstage me, so I'm afraid I'm going to have to get rid of you. I am taking your soul to Tartarus."
Jack knew that this was his end. He could not hope to stand against Discord himself. But that did not mean he couldn't have some fun first.
"Very well," slurred Jack. "But if I could have but one last request, I'd like to drink cider until I can't drink anymore. Allow me this, and I will go with you to Tartarus."
Discord pondered his request for a moment.
"Alright," said Discord, "I can allow that. Come, follow me."
And so the two went to the local pub and Jack drank more than he ever had before, the cider flowing freely as he enjoyed his last day in Equestria. After some time, he also managed to convince Discord to join him in his drinking. Soon, the two of them were good and sauced, swaying and burping as the alcohol took effect. As the last drop of cider fell onto their tongues, Discord turned to Jack with unfocused eyes.
"I do believe that's enough," said Discord. "It's time we left and get you to Tartarus."
"Wait," said Jack, "we have yet to pay for our drinks. But it seems I have no money." Jack seemed to ponder for a moment. "I have a brilliant idea: why don't you transform into a gold coin, and we'll use that to pay. Then, you can change back when the barkeep isn't looking."
Discord smiled at Jack. "You clever rogue. We get to drink all this for free? I like it. I can't wait to see the fool's face when he realizes he's been tricked!"
"Nor can I," Jack responded with a twinkle in his eye.
And so with a snap of his fingers, Discord changed into a gold coin. But instead of using it to pay, Jack quickly stuffed it in his pocket, which also held an amulet of Celestia's Mark. The Harmony of the amulet prevented Discord from changing back, leaving him trapped in the form of a coin.
"You treacherous cur!" shouted Discord from Jack's pocket. "You tricked me! I demand you release me at once!"
Jack laughed. "I'll agree to release you, but only if you agree to never take my soul and never bother me again. Do we have a deal?"
Discord grumbled and seethed, but he agreed and was released from Jack's prison. He glared at the smirk on Jack's face before disappearing with a flash and a bang. Jack reclined with a cocky smile and believed himself invincible. His greatest trick ever.
Years passed and Jack continued his life of debauchery, taking its toll on his health. Before long, Jack died as he lived: in a drunken stupor.
His soul ascended and he was prepared to enter Heaven before he was stopped by an angelic alicorn.
"You cannot pass trough the Gates and enter Heaven," spoke the shining alicorn. "Your life of drunkenness and deceitfulness has barred your way to Paradise. Now begone."
Cast out, Jack's soul drearily made its way to the Gates of Tartarus, where Discord waited for him. Jack begged Discord to allow him into Tartarus, but Discord only laughed.
"I cannot break our deal," said Discord with a smile. "I cannot take your soul, thus you cannot enter into Tartarus. You are doomed to wander between life and death for eternity, lost and fumbling through the darkness." Discord picked up a red-hot ember and tossed it to Jack. "This shall be your only light, an ever-burning ember."
Jack shrieked as he caught the ember, the pain of the heat searing through his body. Discord laughed before turning his back and casting Jack out of his realm.
Jack wandered, guided only by the ember that caused him such pain to hold, until one day he came across a field of pumpkins. He gave a small smile as he placed the ember in one of the pumpkins to make himself a lantern.
Now, Jack of the Lantern wanders Equestria, unable to move on and doomed to forever be trapped between planes as an aimless spirit. We light jack-o'-lanterns to remind us of Jack's folly and to help guide his pitiable soul as he stumbles in the dark.