3. Sideshow Bob
Voiced By: Kelsey Grammer Emmy Winning Episodes: "The Italian Bob" Will the hunter become the prey?
Chances Of Dying? Grammer has had it rough since the end of Frasier, and taking away another chance of a pay-check might be deemed a little cruel, BUT, the reappearance of Sideshow Bob is always a popular event among Simpsons fans, thanks to the exceptional voice work by Kelsey Grammer, and it might not be the worst idea to kill the character off symbolically before his appeal wavers. There's only so much you can do with a murderous, devious plotter, and only so many times he can be foiled before he becomes a threatless comedic supporting figure, and that would be an insult to the legacy of the character. The best opportunity for Bob's end would be to bring back his brother Cecil (voiced equally well by Frasier alumnus David Hyde Pierce) - all of the episodes he has appeared in have been high-points - and have a grand plan hatched to finally do what Bob has struggled to for so long. And let's be honest, any excuse to bring back Cecil is a good one. Sadly for the writers Bob has "died" before, though that ultimately proved to be a hoax, and redoing that for real might be a little too familiar.
How He Should Die It would be retreading old ground, but having a final change of heart and saving Bart from the evil, murderous clutches of someone else - like his brother for instance - might be a fitting, poetic end to the character.