The Simpsons: Every Sideshow Bob Episode Ranked Worst To Best

Another Bob installment revolving around his other main (non-rake) foe Krusty The Clown, Day Of The Jackanapes retreads some of the ground covered in the character’s season seven appearance, but has a lot going for it in its own right.

The plot spoofs The Manchurian Candidate, with Bart converted by Bob into a glass eyed killer, ready to blow up Krusty at the end of his latest retirement special. Krusty has earned Bob’s ire this time by deleting the back catalogue of shows before Bob’s incarceration - the always enjoyable contrast between the crass, unprofessional star and his erudite, classy sidekick is used to great effect here.

By this point Bob had grown beyond a simple bloodthirsty antagonist, and episodes started to take the opportunity to expand the character, or hint at something of a redemptive arc. The ending of this episode, in which the two erstwhile colleagues make up, is downright sweet, even if this is then undercut by Bob’s impending execution.

Bob would shortly revert to type, but this is a more rounded portrayal of the character at a time in the show when the decline was starting to become all too visible.