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.
The Italian Bob (Season 17, Episode 8)
When the Simpsons went to Italy to pick up Mr. Burns’ new sports car in The Simpsons season 17, episode 8, “The Italian Bob,” they found that Bob had moved to a town in Tuscany for a fresh start, gotten himself elected mayor, and become a dedicated family man with a wife and son. Bob welcomed the Simpsons into his Italian home on the condition that they keep his criminal past a secret. After a drunken Lisa unwittingly revealed Bob’s secret, he extended his grudge against Bart to the whole family. As Bob tried to kill them at Krusty’s disastrous Italian opera performance, the Simpsons escaped in Krusty’s limo.
Funeral For A Fiend (Season 19, Episode 8)
The season 19 Simpsons episode “Funeral for a Fiend” brought in Grammer’s on-screen family from Frasier to play Bob’s family. David Hyde Pierce played his brother, Cecil, and John Mahoney played his father, Robert Sr. After trying and failing to kill the Simpson family yet again, Bob faked his death during his trial. At the funeral, he locked Bart in the coffin and attempted to cremate him alive in what appeared to be an homage to an iconic scene with James Bond in Diamonds Are Forever. Like 007, Bart escaped at the last second, thanks to Lisa’s perfectly timed intervention.
The Bob Next Door (Season 21, Episode 22)
In season 21’s “The Bob Next Door,” Bart suspected his new neighbor, Walt Warren, was actually Bob in disguise. Marge took Bart to see Bob in prison to reassure him, but that was the real Walt. When he and Bob were cellmates, Bob switched faces with him. Bob planned to kill Bart at the Five Corners, where five states meet. Bob would stand in one state, fire the gun in the second, send the bullet across the third, hit Bart in the fourth, and he’d land dead in the fifth, making the murder impossible to prosecute. Fortunately, the real Walt escaped from prison and arrived in time to save Bart.
Moonshine River (Season 24, Episode 1)
The Simpsons’ season 24 premiere, “Moonshine River,” was the second episode in which the Simpsons vacationed in New York City after season 9’s “The City of New York vs. Homer Simpson.” The episode brought back high-profile guest stars like Natalie Portman and Sarah Michelle Gellar as Bart’s previous love interests. Sideshow Bob made a silent blink-and-miss-it cameo appearance in the episode. He can be spotted in the background of a shot crossing the railway tracks to attack Bart with a knife. Before he reached Bart, Bob was hit by a train.
The Man Who Grew Too Much (Season 25, Episode 13)
Season 25’s “The Man Who Grew Too Much” revealed that Bob had become chief scientist at a genetic engineering company called Monsarno. He even altered his own DNA to give himself superpowers. Bob and Lisa bonded over their shared love of Walt Whitman, but Bob warned Lisa that he could fly into a murderous rage at any minute. When he tried to kill Bart and Lisa with his superpowers at the Springfield Dam, Lisa quoted Whitman. This made Bob realize what a monster he’d become, and he jumped off the dam to take his own life. But when he landed in the water, he remembered he gave himself gills.
Treehouse Of Horror XXVI (Season 27, Episode 5)
The one time that Bob succeeded in killing Bart, albeit non-canonically, was in season 27’s Halloween special, “Treehouse of Horror XXVI.” In the first segment of the episode, “Wanted: Dead, then Alive,” Bob used Milhouse’s phone to trap Bart in the music classroom, where he killed him. However, he found that without an arch-nemesis to pursue, his life was terribly boring. So, Bob created a machine that would bring Bart back to life so that he could keep killing him over and over again. The Simpsons saved Bart in between resurrections, and he used Bob’s machine to turn him into a monster.
Treehouse Of Horror XXVII (Season 28, Episode 4)
Bob returned in the next Simpsons Halloween special, season 28’s “Treehouse of Horror XXVII.” In the opening sequence, he arrived at the Simpsons’ house with Homer’s other enemies, including Kang, the ghost of Frank Grimes, and the leprechaun from “Treehouse of Horror XII.” The Simpsons visited a Christmas tree lot in their Halloween costumes, only to be locked inside and attacked by Bob and his goons. Maggie killed the three living members of the anti-Homer squad, leaving Frank Grimes’s ghost furious.
Gone Boy (Season 29, Episode 9)
In The Simpsons season 29 episode “Gone Boy,” a parody of Gone Girl, Bart went missing and was presumed dead. When Bob found him hiding out with his best friend Milhouse, he attempted to kill them both. He strapped Bart and Milhouse to a Titan II missile and tried to launch it. However, following the advice of his injured prison therapist, he had a change of heart and decided to save them. The epilogue of the episode seemed to close the book on Bob’s story. An older Bob, known as “Elder Bob,” working as a lighthouse keeper, still regretted sparing Bart’s life decades later.
MORE: The Secret Reason The Simpsons Needs Sideshow Bob