The Simpsons: Every Sideshow Bob Episode Ranked Worst To Best

The Simpsons’ guest casting - like the show in general - takes a sharp dip after a certain point, but in season eight, they were still capable of greatness. Casting David Hyde Pierce as Sideshow Bob’s brother Cecil was both a moment of genius and a real no-brainer, reuniting Kelsey Grammer with his Frasier co-star to play another pair of bickering siblings.

Bob episodes often hinge on a mystery, but this one plays its cards early - Bob has reformed in prison, but no one is willing to believe him. His attempts to rebuild a normal life, thwarted at every turn by Bart’s tenacity, are a highlight (for the purposes of the episode, Edna Krabappel is the most desirable woman in town).

But the best content comes from Bob and Cecil’s relationship. They become the Crane brothers, trading off quips about wine and sarcastic bon mots. Grammer and Pierce are two of the funniest sitcom actors in the business, and their unbeatable chemistry translates to animation.

The twist sees Cecil unmasked as the villain, but an unfair arrest for Bob sees the status quo returned by the closing credits. The sixth Sideshow Bob episode is probably the last great one, but it’s one of the finest moments of the season.