Was my favorite show for more than a decade for me.
I think with so much material to work with, each chip could have a unique design, at least on once face. For me, I would also be making this a tourney set, just so that I have an excuse to do bounties, rebuys, seating chips, etc. I'll reply later depending on what you're looking to do, but man it really seems endless.
Bart/Homer jumping the gorge, tons of assassin episodes/characters (maggie with a gun from who killed Mr. Burns?), Killer Sideshow Bob, and so much more for bounties. The great reveal of the J. standing for Jay could be worked into the Rabbit Hunt buttons, Big Blind button being Moo Moo Homer, etc.
Anyways, good luck and following, excited to see where this goes!