The Simpsons: Best Sideshow Bob Episodes

Highlights

• Sideshow Bob, voiced by Kelsey Grammar, is a memorable villain on The Simpsons who is known for his criminal plots and desire for revenge against Bart Simpson.
• Some of the standout episodes featuring Sideshow Bob include “Cape Feare,” which establishes him as Bart’s nemesis, and “Brother From Another Series,” where his chemistry with his brother Cecil provides comedic moments.
• While some episodes focus more on Sideshow Bob’s character development and motivations, others showcase his evil deeds and cunning nature, making him a beloved and complex character in the show’s “Golden Age.”

The Simpsons has been on the air since 1989. In that time, the writers have introduced hundreds of new characters to the population of Springfield. However, none of these characters have quite made the same impression as Sideshow Bob.

Voiced by Kelsey Grammar, this former sidekick of Krusty the Clown shows up for a feature episode every few seasons as a villain. Instantly recognizable by his big feet and large red hair, Bob’s episodes normally revolve around a criminal plot or him getting revenge on his enemy, Bart Simpson. It is a rare treat to see Sideshow Bob on the show, but some of his episodes are obviously more favored than others.

9 Day of the Jackanapes

Season 12, Episode 13

As a character who has long been established as an enemy of Bart Simpson, this episode goes out of its way to change Bob’s motives. In the episode, it is revealed that Sideshow Bob is still jealous of Krusty’s success on TV, and so comes up with a plan to hypnotize Bart to blow up the clown. Fortunately, his plan is interrupted when Krusty announces he misses his old friend.

While this episode does involve Bart to some degree, it is strange seeing the show now focus on Bob’s envy of Krusty after so long.

8 The Italian Bob

Season 17, Episode 18

When the Simpsons are sent on a holiday to Italy to retrieve a new car for Mr Burns, they are shocked to run into an old enemy of theirs. Sideshow Bob is currently the mayor of the town they are staying in, and has also been married and had a family in the time since his last appearance.

This episode reveals a new side to the villain, one that seems to have given up his evil ways. However, when Lisa accidentally reveals Bob’s criminal past to the town, he vows revenge. Not only this, but the writers put a new spin on this long-running character by having Bob’s family also join in on his vengeance arc against the Simpsons.

7 The Great Louse Detective

Season 14, Episode 6

In this episode, Homer finds himself the victim of an assassination attempt. To catch the killer, the Springfield police force releases Sideshow Bob in a Hannibal Lecter-style twist. Sideshow Bob does figure out the plot and save Homer, but the reveal ends up being a meta callback to a previous episode.

Fortunately, there are plenty of chances for Sideshow Bob to shine in this episode, and there is plenty of fun to be had exploring the dynamic between Homer and Bob. Plus, this marks the point in his story where he gives up trying to kill Bart as he flees to Italy.

6 Sideshow Bob’s Last Gleaming

Season 7, Episode 9

Sideshow Bob’s Last Gleaming is an odd episode for the character that had already been established. The episode introduces a new premise where Bob hates all television, so he decides to steal a bomb and hold an airshow hostage to get rid of it. Bart and Lisa are able to foil this plan, but Krusty’s attempt to stay on the air causes a dramatic ending to the episode.

This episode does have some great jokes like all episodes of The Simpsons, and it is great to see Sideshow Bob trying to get back at Krusty again. However, this appearance does mark a rare slump for the character in the golden era of the show.

5 Sideshow Bob Roberts

Season 6, Episode 5

In an era of the 90s when radio shows were known for featuring right-wing commentators bemoaning the Clinton presidency, The Simpsons‘ writers decided to satirize this time by making an episode where Sideshow Bob runs for mayor. The villain is successful in his campaign, but Bart and Lisa are able to dethrone the mayor by revealing that he committed voter fraud to get into power.

This episode of The Simpsons is still funny and is able to provide a great commentary on this period of politics. Unfortunately, that doesn’t leave much time for Sideshow Bob to do what he does best. This is definitely an episode for the older fans of the show.

4 Brother From Another Series

Season 8, Episode 16

At the same time as Sideshow Bob was making waves on The Simpsons, his voice actor, Kelsey Grammar, was the star of the hit sitcom Frasier. As such, the show decided to make the most of this fact by introducing Bob’s brother to the show, who was voiced by David Hyde Pierce. Pierce played opposite Kelsey Grammar on Frasier, so the pair’s chemistry in this episode is electric.

In the episode, Bob is released from prison to live with his brother Cecil. His brother is working on building a dam but plans to embezzle the money for the project and frame Bob. In a rare twist, Sideshow Bob must team up with Bart and Lisa to stop this plan. However, Bob is still blamed for the crime alongside Cecil, despite saving the town from a flood.

3 Krusty Gets Busted

Season 1, Episode 12

This episode marks the first speaking appearance of the character. It is also the episode that establishes Sideshow Bob’s criminal streak. When Krusty is arrested for robbing the Kwik-E-Mart, Bart starts to lose faith in his hero and Bob gets to be the lead of his own TV show. However, some careful sleuthing from Bart reveals that Sideshow Bob framed Krusty, and set up the iconic rivalry between the two.

This episode is fairly tame compared to later Sideshow Bob episodes, but it is always great to see where the villainous character originated.

2 Black Widower

Season 3, Episode 21

In Sideshow Bob’s second main appearance on the show, he manages to step up his villainy even further. Marge’s sister, Selma, reveals that she is dating someone new, but Bart is horrified when it is revealed her new man is none other than Sideshow Bob. The pair quickly get married, but once again, Bart figures out that Bob is only marrying Selma for her money and is even planning on killing her.

This reveal puts Bart on Bob’s radar once again and shows just how evil Sideshow Bob can be. He has moved on from petty crime and is now capable of committing murder.

1 Cape Feare

Season 5, Episode 2

Cape Feare may just be Sideshow Bob’s most character-defining episode. Parodying the movie Cape Fear, this episode reveals that Sideshow Bob is now trying to kill Bart after the boy has foiled two of his schemes already. When Bob starts sending death threats, the Simpson family undergoes witness protection and leaves Springfield. However, this isn’t enough to fool the villain, and Sideshow Bob manages to keep following them.

This episode is one of the highest rated of the golden era of the show and has some of the best jokes of the series. Fans remember Cape Feare as the episode that establishes Sideshow Bob as Bart’s nemesis, but it is also the one that features the hilarious bit with the rakes.