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:
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.