I have to bring up Gary Baseman. First of all he is one of the best entertainment artists of all time. He is a movie producer, painter, toy designer, and humorist. His collectors items of toys are wide known to be thought provoking, innovative, playful, and cultural. My favorite board game of all time is Cranium, who Gary Baseman is the creator of the board figures in the game. You can exchange their pop off wigs or hats to create the character of your choice. I have yet to see his paintings in person, but I defenitely will be searching for his next show.
His "dunce" series is also fun to look for. These collector pieces were made at quantities of 500 each design.