Stingy Jack is a titular and protagonist villain of a story with the same name from Irish folklore. Stingy Jack was a man who was hated by the locals due to his deceptive nature to the point even the Devil came to hear of this infamous man.
This tale is used to explain origin of the creation of Jack-o'-lanterns due to being named of one of Jack's alias' "Jack of the Lantern" from when he carved his own lantern to light his way when doomed to wander for all eternity.
The exacts vary on why Stingy Jack earned his reputation but generally it is said he was a manipulative con artist and even at times a thief who took advantage of any who were unfortunate enough to meet him, this combined with him being a notorious drunk who refused to help anyone made the locals believe he was worse than even the Devil himself.
The Devil became curious and in some tales envious and sought to meet the cruel man. Jack, who was as usual drunk, wandered the countryside at night until the Devil appeared in front of him. Unlike most people in his situation Jack was quick to form a plan and pretended to not put up a fight but merely asked the Devil for a last request which would be to drink some more at a local tavern before departing to Hell, the Devil decided this was a fair request thus allowed it.
The two spent many hours drinking and as it became clear Jack's thirst was quenched and Jack decides to ask the Devil to pay the for the drinks shocking him, before the Devil could even respond Jack said that the Devil should turn into a silver coin and that way when they both departed it would be deceiving the bartender. This impressed the Devil that even now Stingy Jack was unrepentant so the Devil agreed but instead of going along with the plan Stingy Jack instead places the silver coin in his pocket next to a crucifix (or just a cross in some) which prevented the Devil from turning back while sneaking out of the bar. Upon sneaking out Stingy Jack made the Devil an offer: the Devil would be unable to claim his soul for ten years or else remain trapped, rightfully angered the Devil reluctantly agreed.
For ten years Stingy Jack continued to con others for personal gain but exactly to the day the Devil came once more to haunt Jack when alone in the countryside. Once again cornered Jack feigned defeat any yet again asked one last request but this time for a single apple claiming to be starving to which the Devil decided to accept out of pity. As the Devil climbed a tall apple tree to retrieve an apple Jack made his move by placing several crosses at the base of the tree (or carved one in the tress in some versions) effectively trapping the Devil. Outraged the Devil demanded his freedom which Stingy Jack struck a deal, in return for the Devil's freedom Jack's soul could never be claimed by him thus could never go to Hell, with no choice the Devil reluctantly agreed once more.
After many years Stingy Jack's lifestyle of drinking and conning took its toll, upon death Jack realized much to his horror he could not enter Heaven. As he walked to the pearly gates St. Peter informed Jack that his lifetime of sin and evil made it to where God forbid Jack from finding eternal peace in Heaven. Desperate and feeling exhausted due to the soul not meant to be wandering the world Jack went to the gates of Hell to plead the Devil to let him rest. However due their deal all those years ago and either out of honor towards their deal (or anger over his wounded pride) the Devil refuses to let Jack enter.
When demanding to know what he's supposed to do if unable to enter the afterlife the Devil responds that Jack is wander between the worlds (or the mortal world in some versions) for all eternity, however the Devil does give Jack an ember (or flaming coal) from Hell to forever light his way to mock Jack's plead that he couldn't even see anything in the darkness. With no choice left Jack was forced to hollow out a turnip (later changed to a pumpkin in some retellings) to function as a lantern in the futile hope of finding a place to finally rest earning himself the alias "Jack of the Lantern".
Stingy Jack is portrayed as a selfish man who is able to talk his way out of most situations while also being very deceptive. Throughout the tale Jack proves himself able to manipulate the situation and convince those around him to taking pity on him even if they know he's untrustworthy. As his nickname suggest he is willing and able to trick others to paying his tab which is presumably part of why the locals despised him and implies he is rather greedy. Jack also makes it abundantly clear he has no interest in redemption nor helping other due to lacking remorse. This is even emphasized when he is about to be taken to Hell he comes up with an attempt to con a bartender along with the Devil, even when he finds a temporary escape from his damnation for a decade he merely continues his notorious acts due to enjoying them.
Jack was in his lifetime was known as a skilled silver tongue and a prankster always playing some kind of trick on people. While Jack was able to out smart the Devil so he could live longer but after his death he wasn't allowed into heaven or hell. Because Jack was cursed to wonder forever in darkness, nothingness and on earth Jack was also able to cheat Death/Grim Reaper. Neither God, the Devil, Heaven nor Hell wanted to take Jack even Death couldn't take Jack thus he became a spirit.
Despite being a smooth talker able to get anyone to trust him, believe him and feel pity for him, Jack is also known to rowdy and foul mouthed. Jack is a man who always manages to find a loophole when making deals, gambling and making bets which allow Jack to either win or get away with crimes.
- This tale is in may ways similar to Faust in a man making a deal with the Devil yet doing all they can to escape their own damnation but the main difference is that Jack in lacks any remorse or even noble start at the beginning.
- The tale is as mentioned before the explanation of Jack-o'-lanterns which in olden times was done on Hallows' Eve as it was believed then that the barrier between the worlds was the weakest thus spirits could cross over to the mortal world and the Jack-o'-lanterns were believed to ward off said spirits including Jack.
- Not only does Jack have ties to Halloween but Stingy Jack is also rooted into Samhain as well.
- Stingy Jack made an appearance in the Ghostbusters comic which overall kept the same story with a look at his acts in the present where he attempts to exploit a loophole and have the Ghostbusters catch him to escape his curse by finding eternal rest.
- Stingy Jack was the inspiration for a video game character named, "Pyro Jack," in the series, "Shin Megami Tensei." It follows the same story as Stingy Jack.
- Jack O'Lantern from The Grim Adventures of Billy & Mandy is based on the same Jack from the Stingy Jack legend. While Jack was able to cheat the Grim Reaper in the cartoon just like how he cheated death in the folklore. The difference in the show and the legend Jack meets the Grim Reaper and out smarts him instead of the Devil.
- The legend of Stingy Jack would later on become the inspiration for characters with the name Jack who have pumpkins for heads. Stingy Jack became the inspiration for many characters in cartoons, tv shows, films and novels.
- While his nickname Jack of the Lantern became the origin for Jack-O-Lanterns, Stingy Jack's trickery probably was the origin that started the idea of people playing tricks and pranks on Halloween.
- In the DC Vertigo comics Stingy Jack finds a loophole just like in the Ghostbusters comics. However unlike in the Ghostbusters universe in the DC universe Jack's loophole doesn't last and is doomed to his original fate.
- Much like other shows and series Digimon created their own pumpkin headed character inspired by Stingy Jack called Pumpkinmon. Although Pumpkinmon is not Jack the idea of him having a Jack O' Lantern, being a ghost and his personality come from the story of Stingy Jack.
- Although Pumpkinmon's trickster and pranking ways are inspired by Stingy Jack Pumpkinmon isn't a drunk and his tricks are more playful rather cruel like Jack's.