Stingy Jack

Happy Halloween!

I thought it would be fun to do a portrait of Stingy Jack to celebrate the holiday this year.

Stingy Jack is the legendary figure that the Jack O' Lantern is based off of.  Here's the legend of Stingy Jack copied and pasted from this web-site:

According to the story, Stingy Jack invited the Devil to have a drink with him. True to his name, Stingy Jack didn't want to pay for his drink, so he convinced the Devil to turn himself into a coin that Jack could use to buy their drinks. Once the Devil did so, Jack decided to keep the money and put it into his pocket next to a silver cross, which prevented the Devil from changing back into his original form. Jack eventually freed the Devil, under the condition that he would not bother Jack for one year and that, should Jack die, he would not claim his soul. The next year, Jack again tricked the Devil into climbing into a tree to pick a piece of fruit. While he was up in the tree, Jack carved a sign of the cross into the tree's bark so that the Devil could not come down until the Devil promised Jack not to bother him for ten more years.

Soon after, Jack died. As the legend goes, God would not allow such an unsavory figure into heaven. The Devil, upset by the trick Jack had played on him and keeping his word not to claim his soul, would not allow Jack into hell. He sent Jack off into the dark night with only a burning coal to light his way. Jack put the coal into a carved-out turnip and has been roaming the Earth with ever since. The Irish began to refer to this ghostly figure as "Jack of the Lantern," and then, simply "Jack O'Lantern.

I didn't exactly follow this version of the legend.  I saw another version once where the devil carried Jack's head off to hell, leaving Jack with a hellfire ember to light his way.  Jack carved a turnip into a face and dropped in the burning ember, and used that to replace his own head.  That version seemed like more fun to draw.