From the 2005 Monster Bash, a painting that made me laugh when I saw it:
I talked with the artist, who told me that Sara Karloff was amused by it. Sadly, I can't remember the artist's name, though from the painting his last name is obviously (and appropriately, given the colors here) "Pinkney".
Here's a photo of the artist:
If anyone knows this talented painter with a great sense of humor, please tell him to contact me! I want to see more of his work!
Update: The artist's name is Dwayne Pinkney, and I expect we'll be seeing many more examples of his talent for genre portraiture.