9. Snake
Sometimes called merely Snake Jailbird, but once given his real name of Chester Turley, Snake is another Hank Azaria creation who thrives on the exceptional voice work of the main cast member. He is Springfield's resident criminal, though his almost perpetual freedom (aside from at least two executions) is testament more to the ineptitude of the town's justice system, rather than his prowess as a felon. His appeal lies with his irresistibly immitatable Valley Boy accent - based on a college roommate of Azaria - and his devil may care reckless spirit, and commitment to being bad without even the slightest hint of remorse. He is Apu's foil, adding a much needed hook for the beleaguered Kwik-E-Mart manager, whose appeal has faded in recent seasons thanks to the restrictions of his octuplet children, and the limited opportunities his character actually offers. The other important dynamic in Snake's make-up is his relationship with Chief Wiggum, who he frequently gets the better of and who he ends up in a Pulp Fiction-style compromising situation with after being kidnapped by Herman, the proprietor of Springfield's military surplus store. It would have been simple to write a typical tale of hardship as Snake's backstory, but the genius of the character is that his origin is brilliantly ludicrous - he was once known as Professor Jailbird, an Indiana Jones-type archaeologist, who lost his way and sought revenge on society when Moe stole the Mayan gold coins he had discovered.
Select Quote: "Um, I must have, like, fallen on a bullet, and it like, drove itself into my gut."