Sideshow Bob is known for trying to kill Bart over and over again in The Simpsons, and he eventually succeeded in his murderous quest. Bob was introduced in the season 1 episode “Krusty Gets Busted.” As Krusty the Clown’s TV sidekick, Bob got sick of being the butt of Krusty’s jokes and framed him for a robbery. When Bart figured out that it was Bob who committed the crime, he had Krusty cleared of the charges and got the sidekick sent to prison. This sparked a grudge against Bart that lasted for decades.
In the years since Bart thwarted Bob’s first criminal scheme way back in The Simpsons season 1, Bob has been intent on killing him. Despite his various diabolical plots to kill Bart, Bob has become a fan-favorite supporting character beloved by both critics and audiences. Voice actor Kelsey Grammer, who also starred on Frasier, brings a hilarious gravitas to Bob’s signature brand of psychopathic intellectualism. After Bart foiled a bunch of his attempted murders, The Simpsons’ writers paid off this running gag and Bob actually succeeded in killing the spiky-haired troublemaker.
Cape Feare (Season 5, Episode 2)
Sideshow Bob’s obsession with killing Bart Simpson began in the season 5 episode “Cape Feare.” After Bart thwarted his attempts to frame Krusty and kill Selma, Bob wanted revenge. In a parody of Cape Fear, Bob started tormenting Bart with threats after being paroled. This forced the Simpsons into hiding. The Witness Relocation Program sent them to a houseboat on Terror Lake under the alias Thompson. Bob followed them there and attacked Bart in the middle of the night. To buy himself some time, Bart asked Bob to sing the score of H.M.S. Pinafore. Before Bob could finish his performance, the boat drifted into Springfield and the cops arrested him.
Sideshow Bob’s Last Gleaming (Season 7, Episode 9)
In The Simpsons season 7 episode “Sideshow Bob’s Last Gleaming,” Bob attempted to eradicate television for good but had to follow through on his threat when Krusty found a way to get on the air. After trying and failing to destroy Springfield with an expired nuclear bomb, Bob kidnapped Bart and hijacked the Wright brothers’ plane. He planned to fly the plane into the shack where Krusty was using the Emergency Broadcast System, killing all three of them. However, this plan also backfired, as the ludicrously slow plane simply bounced against the shack without doing any damage. Bob was, once again, arrested and taken to prison.
Day Of The Jackanapes (Season 12, Episode 13)
Season 12’s “Day of the Jackanapes” revolves around Sideshow Bob hatching a scheme to kill Krusty the Clown, not Bart, but his plan involved using the boy as a suicide bomber. When Bob learned that Krusty erased all the old shows featuring Bob, he planned to kill his old boss as revenge at the taping of his retirement special. For once, Bob’s plan was a success, but he changed his mind when Krusty used the special to publicly apologize to Bob and take responsibility for turning him into a criminal. So, Bob aborted the plan, saving both Bart and Krusty, and he reconciled with his old TV cohort.
The Great Louse Detective (Season 14, Episode 6)
When Homer was targeted by a killer in The Simpsons season 14’s “The Great Louse Detective,” Bob was recruited, a la Hannibal Lecter, to help catch the culprit. Throughout the episode, Bob was advised to just kill Bart instead of concocting elaborate schemes. After the man trying to kill Homer was identified as the long-lost son of Frank Grimes from the episode “Homer’s Enemy,” Bob decided to follow the advice he received earlier and tried to kill Bart without hesitation. However, he was surprised to find that he’d become so endeared to Bart after holding a vendetta against him for so long that he couldn’t bring himself to do it.
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