This story is not a retelling of the original Irish tale. This version owes a great deal to another seasoned story-teller, Carpathian. (My hat is off to you, good sir.) Of course, I've added my own flairs, as all story-tellers do.
A long time ago in Ireland, there was a wicked knave known as Jack. Jack was a very bad man. He was a highwayman, a robber, and a murderer. He was often quite cruel, mean to small dogs, children and the prostitutes in town. As a highwayman, Jack was often not content to simply rob travelers; he often slit their throats and tossed their bodies in the woods.
One Autumn, on a bright, crisp day, Jack was seated under an apple tree, enjoying the sunshine, when someone suddenly tapped him on the shoulder.
He was astonished to see a spirit with horns standing there. Now, Christians call this fellow the Devil, but I think we know he is the leader of the Wild Hunt, the Lord of the Greenwood.
The spirit said, "Come along, Jack. You've been murdering too many people in my woods. I'm collecting you now. You're coming with me."
Jack realized who he was up against, and he was a crafty old fellow, and he looked up in the tree and said, "Alright then. But before we go, could I have that last apple up there in the tree? I bet it's a long trip to where we're headed and I'm awfully hungry. We can share it."
Indeed, high up in the tree was one bright red apple, still hanging on the branches. Apparently this seemed like a reasonable request. So the spirit scrambled up the tree. Quickly, Jack pulled out his knife and carved a magic sign at the tree's base. Christians say it was a cross. Be that as it may, whatever it was, it trapped the spirit up in the tree.
The spirit up in the tree screeched and screamed.
But old Jack said, "You thought you had me. Now I've got you. You just stay in that tree." And off he went, chuckling to himself.
Now, it'd be nice to say that Jack had learned his lesson and decided to change his ways. But he didn't. He was still a murderer and a robber, a card cheat. He still kicked small dogs and was mean to the whores. If anything, he was worse then ever.
Years passed and, of course, Jack died, as all mortals must. So his soul journeyed up toward the bright and shining land. But the guardian of the gate stopped him when Jack arrived.
"Why, Jack! What are you doing here? You can't come here. You've been a highwayman, a murderer and a robber. You've shown no kindness or charity to anyone. You've been wicked and mean your whole life. Why, you even kicked small dogs for no reason. These are the pleasant plains and beautiful fields meant for kind souls. You've done many evil deeds and you're not even the least bit sorry about it. I'm sorry, but you can't come here."
Well, Jack wandered off, search for somewhere else to go. Eventually, he found his way down to the underworld, to the realm of the mighty one, the Lord of Shadows, the Master of the Wild Hunt.
When demanded entrance, the Lord himself came.
"You!" screeched the angry spirit. "You trapped me in that tree for two years, until I could grow the bark back over that sign you carved. What are you doing here?"
Jack answered, "I have no place to go."
"Oh, no! You come to my home? And ask for entrance here after how you treated me? Be gone! I have no use for you!"
Jack said, "Where am I to go?"
"I care not. Off with you to the outer darkness!"
So Jack wandered off into the outer darkness between the worlds. There were terrible things there in the darkness and the cold. The dark faerie of the Unseely Court wandered here, and there were more terrible things still in the darkness. But Jack was a tough old SOB. And he wandered for many years, over many lands, all over the British Isles and in time all over the world. He saw many frightening and terrible things.
Then one night, as he sat lonely and sad, a gentle faery spirit passed him. The faery spirit took pity upon him, there sitting alone in the dark. She plucked an Autumn vegetable from the field. Maybe it was a pumpkin or a gourd, some say it was a turnip. She hollowed it out, carved a face, and placed a glowing light inside.
"Here, Jack," and she handed him the glowing lamp, "this will light your way in the dark and protect you between the worlds."
And that is the reason why, even today in America, we hollow out pumpkins and carve on faces to frighten away malignant spirits. The Irish custom, of course, was to place a lit candle in a hollowed-out turnip.
And that is the story of Jack O' the Lantern.