There is an old Irish legend, about a drunk called Stingy Jack.
This man tricked the Devil into not claiming his soul when he died, but being such a rogue was denied Heaven also. He was doomed to travel the darkness between Heaven and Hell for all eternity; with only an everlasting coal from the fires of Hell to provide him light on the road. This coal was placed into a hollowed out turnip and thus the first Jack O'Lantern was born. Full story here
When the Irish emigrated to the US at the time of the potato famine, they took the tradition of carving jack o'lanterns with them; but turnips were not as plentiful in the new land, so they started to carve pumpkins instead.
Read about the potato famine here.
Being half Irish, I knew the myth that was Stingy Jack, so when I decided to paint a picture of a carved pumpkin - what else could it be called, but "Theatrical Halloween"