The Simpsons: Every Sideshow Bob Episode Ranked Worst To Best
10. Treehouse Of Horror XXVI (Season 27, Episode 5)
In Treehouse of Horror XXVI, Sideshow Bob headlines the segment Wanted: Dead, Then Alive, in which he finally kills Bart but realises he has no life outside of him.
Grammer's ability to still be menacing after over two decades in the role is the segment's greatest strength here, allowing Bob to become a bigger monster than ever as he continuously revives Bart just to kill him over and over again.
Deliciously dark and totally in-keeping with Bob's character, following him as he tries to find purpose outside of his hatred for the Simpsons, Wanted: Dead, Then Alive is violent and worthy of its place in the vast Sideshow Bob canon.
To be honest, this was the last great appearance of the character, and considering he gets his wish and ends the episode dead, he could have comfortably been retired here with no issue.