5. Chief Wiggum
Voiced By: Hank Azaria Emmy Winning Episodes: "Worst Episode Ever" & "Moe Baby Blues" Will the world's worst police chief bumble his way to the grave?
Chances Of Dying? Again, like Bleeding Gums Murphy, Maude Flanders and Doctor Marvin Munroe, Wiggum's death would fit the established pattern of supporting characters meeting their maker, though again, like Comic Book Guy, he is far more popular, and far funnier than any of those characters, even if his bit is a little limited. Chief Wiggum's problem is that his comedic impact is limited to him being a poor cop - which has been explored a lot - or his sometimes hilarious relationship with Ralphie. That might see him deemed as expendable, no matter how devastating it would be for his son (again, that might be seen as a plus point if the show are aiming for a genuinely upsetting episode.)
How He Should Die Any number of ways, considering how poor a police chief he actually is. Poetically, Snake killing him would fit, but turning him into a murderer might be a step too far, given that he thrives on a roguish bad-boy charm rather than an outright malevolence.