The 10 Best Sideshow Bob Simpsons Episodes, According To IMDb

Sideshow Bob is pretty much universally considered the greatest guest star in the history of The Simpsons. Voiced immaculately by Kelsey Grammer, his poisonous wit and overwhelming desire to simply kill Bart Simpson is pretty much always gripping. An episode featuring the bouncy-haired criminal is always a treat.

We’ve used IMDb to rank the ten best episodes that center on the character from across the history of the show.

10 The Italian Bob (7.0)

A criminally underrated episode from the seventeenth season of the show gives us an insight into what Sideshow Bob had been getting up to in his long hiatus. It turns out he has become mayor for the second time in his life, but this time of a small town in Italy, where the residents have no knowledge of his past.

In fact, he has a wife and a child who seem unaware of any potential harm Bob could do. This all changes when it is revealed his new family is as sinister as him, and they’re all desperate to act on his vendetta.

9 Funeral For A Fiend (7.1)

This season nineteen episode introduces another genius move on the behalf of the writers, as the actor who plays Frasier’s dad (John Mahoney) is brought in as Sideshow Bob’s dad. The episode kicks off with Bob setting another seemingly foolproof trap, but is turned on his head when Bob ‘dies’ from his heart condition.

Despite being an attempted murderer, the entire town goes to his funeral and decide they hate Bart for killing him. Very weird. Luckily for us, he wasn’t dead after all.

8 The Bob Next Door (7.2)

It might not be the single greatest Sideshow Bob adventure we’ve ever been taken on, but ‘The Bob Next Door’ puts the character at the forefront, and that’s all we need. The episode, taken from season twenty-one, is strangely ambitious for The Simpsons.

It hits us with cases of mistake and fake identity, with twists and turns and alternative narratives coming from every corner, but it doesn’t have the same ability to make us laugh as the show could twenty years earlier.

7 The Great Louse Detective (7.3)

Season fourteen is known to be one of those strange middle ground, early-2000s seasons in which the show was just about hanging on to its quality by a thread.

As such, this Sideshow Bob episode doesn’t do him much justice in comparison to some of his previous adventures, but it does give his character a whole new angle. Instead of spending his whole time attempting to kill Bart, he and Homer try and figure out who Homer’s attempted murderer is (it was the son of Frank Grimes) before Bob realizes he actually can’t bring himself to kill Bart anyway.

6 Sideshow Bob’s Last Gleaming (8.0)

Sideshow Bob hates Krusty The Clown, that much has always been true. As much as he wants to kill Bart Simpson, he also wants to kill Krusty. In this episode, he takes things to a very extreme level, apparently gaining control of a nuclear bomb that he will detonate if the people of Springfield don’t stop watching TV.

It might end up being a dud bomb, but the adventure into the Duff Blimp and Bart and Bob’s excursion on The Wright Brothers’ plane is some seriously good viewing.

5 Brother From Another Series (8.2)

This season eight outing is the first encounter we ever had with Sideshow Bob’s brother, Cecil. In a genius move, they got Kelsey Grammer’s on-screen brother from Frasier to play his brother on The Simpsons.

As such, their chemistry is already at a solid 10/10. It turns out that Cecil is just as much of a criminal as Bob himself, and the two end up sharing a cell in jail.

4 Black Widower (8.3)

This season three episode sees Aunt Selma play straight into the hands of Sideshow Bob simply through her overwhelming desire to be married. Everyone seems to assume that Bob has changed (and everyone just forgives him and lets him get away with it, despite knowing that he has attempted to kill Bart many times over) and let him carry on his courtship with Selma.

It ends up being one of the most genuinely dramatic episodes of the show, with a truly explosive finale which Bart and Lisa manage to foil.

3 Sideshow Bob Roberts (8.3)

It seems the American political system can let you get away with pretty much anything. There’s a rapist in the White House in the real world, and an attempted murderer running for mayor in The Simpsons.

Draped in an American flag, he betrays Mayor Quimby and actually succeeds at becoming the man to run Springfield. Bart and Lisa, as they always do, get in the way of Bob’s illegal plans, but we get a lot of laughs along the way.

2 Krusty Gets Busted (8.4)

The very first episode to have the involvement of Sideshow Bob was the penultimate episode of season one. The characters are still finding their feet and the animation style remains a little bit sloppy, but the comedy to come in the next couple of seasons is very clearly being teased out in every frame.

This episode first introduces us to Bob’s hatred of Krusty, as he tries to kill the clown’s career by faking a robbery before Bart involves himself and begins Bob’s newfound hatred.

1 Cape Feare (9.2)

Known to be one of the best episodes of The Simpsons ever, let alone the best Sideshow Bob episode, is ‘Cape Feare’. A 9.2 average after thousands of votes is a hugely impressive feat.

As with many Bob episodes, there are various horror and thriller parodies littered throughout, with the most noticeable being its overarching spoof of the 1962 film of the same name as the episode. It’s a ‘kill Bart’ episode at its absolute finest and most incredibly hilarious.