Tom Goes to the Mayor: Glass Eyes
(S02E14) If you check out the Adult Swim schedule grid, the words "Worst episode ever" are written next to this particular episode. The men and monkeys who run Adult Swim have never been above a bit of self deprecation, but I actually thought this episode was pretty damn hilarious.
The show opens with the Mayor poking Tom in the eye with a sharp metal rod. It's okay, though, because Tom's eye is made of glass. It seems he had an accident while playing with his step-sons. Tom, however, isn't there just to have his eye poked buy the inquisitive Mayor, he's there to sell hoagies for the annual Father/Son Barrel Goat Hunt, in which the father/son teams hunt the dreaded barrel goat, a creature that is driven insane by the scent of pickle barrels. The Mayor has never heard of a hoagie (he pronounces it "hoogie") before, and he can't get enough of the sandwiches. He also takes a liking to Tom's glass eye and buys two for himself, which of course makes it difficult for him to see and move around.
Tom Goes to the Mayor is, among other things, about the convoluted nature of business and civic organizations. Somehow the money from the hoagie sales and the barrel goat hunt are filtered through the Donnigton Group, an organization that donates eyes to eyeless children (not blind children, but children who actually have no eyes), and then somehow the money goes to Two Eyes for the Third World.
It turns out there are no barrel goats, so the Mayor decides to use regular zoo goats instead. The object of the hunt is for one person to hold the goat while the other shoots it. The goats escape and run amok, but Tom manages to capture one, and, against Tom's better judgment, the Mayor shoots an arrow at the goat. The arrow bounces off Tom's glass eye, ricochets and bounces off one of the Mayor's glass eyes, and then enters Tom's real eye. Tom's only hope is to get another glass eye from Two Eyes for the Third World, but that means he has to live in the third world for one year to achieve orphan status and be eligible for one.