As with many current traditions, the original tale is filled with much fascination, though, it rarely seems to be told the same way twice. Our modern tradition of carving a pumpkin with an amusing or slightly scary face began with the Irish immigrants who came to America looking for a new life after the potato famine which hit Ireland. In many cases, they found something just as useful-cheap squash.
The Irish tale originally highlighted turnips, most often rotten ones, as the central produce in the story. It's possible that the Irish grew turnips much larger than they do now, or perhaps it's the nature of the 'whopper' to make everything seem that much bigger. Whatever the reason, the Irish made the custom popular using the pumpkin because the large orange squash was cheaper and more easily found than the turnip.
Thus, the tale begins as far back as the mid-1700s with a character named Drunk Jack, Stingy Jack, Jack the Blacksmith and a host of other names. What most accounts agree on is, that Jack was fond of his liquor, but that seems a common thread in Irish folklore and perhaps a bit stereotypical of stories about the Irish. For the purposes of this history, however, Jack is a man with a love for whiskey.
Our tale finds Jack at a local pub where he meets a rather unique guest, the prince of Darkness, Satan. Satan often includes the drinker's immortal soul if he has to be a drinking buddy to someone. On this night, as it was Halloween, Satan was prowling the pubs of Ireland for just such a person and found our Jack.
Now, it can be said that the Irish could drink even Satan under the table and still possessing of his wit, Jack offered the Devil a deal. If Mr. Mephistopheles would pick up the tab, Jack would offer the Devil his soul. The Devil changed himself into a sixpence and instead of paying for the drink, Jack tossed the devil into a money pouch with a silver crucifix and imprisoned the Devil. In exchange for freedom, the Devil agreed to let Jack have another 10 years on earth.
However, after those years lapsed, the Devil again visited his friend Jack. Though most stories paint the Devil as a being of supreme intelligence, this tale shows him as a bit of a dim bulb. Pretending to ready himself for transport to Hell, Jack asks the Devil for an apple off an apple tree. When the Devil climbs the tree to get the apple, Jack carves a cross in the tree, trapping the infernal being again. This time, Jack is smart enough to bargain back his soul in exchange for the Devil's freedom.
Jack would seem to have won, but when he eventually died and went before Peter at the Gates to Heaven, he was denied entrance because of his miserly acts, drinking, and trickery. Thus, Jack traveled to Hell to ask for a spot there, but the Devil denied him entrance. The Devil, however, granted Jack a boon-perhaps out of respect for his wit and the knowledge that he was forever damned-of an ember from the fires of Hell. Jack placed this in a hollowed-out turnip and used it to light his way in the eternal darkness of a man caught in the world between Heaven and Hell.
Perhaps to prevent a visit from Jack or other damned souls, people began carving turnips and even potatoes with scary faces in order to ward off the spirits that may roam on Halloween. When the Irish fled Ireland during the potato famine, the custom came to America, where the Irish found the pumpkin a much more suitable item for carving.