Why does Sideshow Bob hate Bart Simpson?

The Simpsons is known for its one-off adventures, usually resorting to giving Homer a job for one episode before he goes back to the nuclear power plant, rather than relying on long storylines spanning seasons and only occasionally (bar the opening sequence) telling running jokes. One well The Simpsons has returned to again and again throughout its lengthy run is the character of Sideshow Bob and his hatred of Bart Simpson. But fans of the series might not be aware of where this particular storyline started as it did air over thirty years ago, as well as how their relationship changed and evolved over time. 

The first season of The Simpsons, which began in 1990, introduced many of the Springfieldians that populate the show’s world. One of those characters is Krusty the Clown. Krusty hosts a children’s comedy variety show, which usually plays the popular cartoon, ‘The Itchy and Scratchy Show’. Sideshow Bob, voiced by Kelsey Grammer, is introduced as Krusty’s sidekick and workplace punching bag in the twelfth episode of the first season, Krusty Gets Busted. In the episode, Krusty seemingly robs the Kwik-E-Mart. With Homer as a witness, Krusty is arrested, but Bart refused to believe that his boyhood idol was guilty of theft and he set out to prove that Krusty was framed. 

With his sister Lisa’s help and a number of clues to help him along, Bart figures out the truth, that Sideshow Bob was tired of being used by Krusty and tired of the show’s lack of substance, so he framed Krusty. They ultimately figured out that in the Kwik-E-Mart, Homer stepped on the faux-Krusty’s shoe causing him to yell out in pain. Remembering that Krusty had small feet so he could not possibly fill out the shoes and that Sideshow Bob had enormous feet, Bart accused Sideshow Bob on television and he was then arrested by police. Bob blamed Bart for his arrest.

Sideshow Bob’s next appearance was in the 21st episode of season three called Black Widower. This was the episode that made Sideshow Bob a recurring character. In the episode, Sideshow Bob and Bart’s Aunt Selma form a relationship after they become pen pals while Bob is in prison. He was released from prison and proposed to Selma, and even though Bart protested, they got married. Bart became increasingly worried that Bob was only married to Selma for her money, and paid close attention to their relationship. While on their honeymoon Bart figured out that Bob was planning to kill Selma by using her lack of the sense of smell to hide the scent of gas. After Bart contacted the authorities, saved Selma, and proved that he was guilty of attempted murder, Bob went to prison yet again.

In the second episode of season five, Cape Feare, the red-haired Robert Terwilliger is cemented as Bart’s nemesis, as this is the first time Bob has attempted to kill Bart in earnest. In hindsight, it’s actually quite funny that Bob doesn’t plot to kill the youngster after he put him in prison once, but only after he did it twice. In this episode, Bart is getting death threats in the mail, and the family figures out that they are coming from Sideshow Bob. The Simpsons pack up their things and go into Witness Protection as the Thompsons. They set themselves up in a houseboat, not realizing that Bob followed them there. Tying up the family, Sideshow Bob corners Bart on the boat and threateningly asks him if he has any last requests. Bart tricks Bob into singing the “H.M.S. Pinafore”, which is just long enough for the authorities to find the boat, and Bob is sent to prison for the third time. 

After being thwarted for the third time, Sideshow Bob runs for mayor in season six, in the episode titled Sideshow Bob Roberts. From prison, with the aid of a Republican radio host and a secret cabal, Bob not only managed to get released from prison and run for mayor, but he also beat Mayor Joe Quimby to become the Mayor of Springfield. Being Bart’s nemesis, he used his newfound influence to ruin the lives of the Simpsons, making Bart start school from scratch and building a freeway on top of their house. 

Bart and Lisa then set out to prove that Bob did not win the election fairly. At first, they couldn’t figure it out, that is until Weyland Smithers, part of the cabal that rigged the election, pointed the siblings in the right direction. They were able to figure out that many of Bob’s votes came from the dead, including pets, and managed to throw Sideshow Bob in prison yet again. 

However, Sideshow Bob’s and Bart’s relationship was not always filled with animosity. In season eight episode 16, Bob is freed under the condition that he works with his brother Cecil. Cecil was voiced by David Hyde Pierce who played Niles in Frasier alongside Kelsey Grammer, which is why the episode is titled Brother from Another Series. But this time it’s Cecil who attempts to frame his ex-con brother by blowing up the Springfield Dam. By the end of the episode, Bob, Bart, and Lisa work together to bring Cecil’s scheme to an end. But Sideshow Bob is still arrested and sent back to prison, this time accompanied by his brother.

You would think after somewhat patching things up with Bart he would have left him alone, but no, in season 12, episode 13, Day of The Jackanapes, Bob tries to murder both Bart and Krusty at the same time. Krusty decides to retire after he gets one too many notes from the network executives in charge of his television show. During an interview with Kent Brockman, the news anchor, Krusty says that his show didn’t get good until they fired Sideshow Bob and that he has erased all of the tapes of the shows featuring Bob. Devastated and enraged, Sideshow Bob organizes to get out of prison.

Sideshow Bob plots to hypnotize Bart Simpson and turn him into a living bomb to blow Krusty up during his final celebratory show. Luckily for Krusty, he started talking about how much he missed his old friend, Bob, even though he framed him for robbery. At the last second Mr. Teeny, the monkey, saves the pair from the explosion by throwing the bomb at the network executives. Unfortunately for Bob, his change of heart was not enough to stop him from going back to prison. 

Yet again, there is another episode where Sideshow Bob does not attempt to kill Bart but rather helps the Simpsons. The season 14 episode, The Great Louse Detective, tasks Sideshow Bob with following Homer Simpson to try and discover who is attempting to kill him. After discovering that it is Frank Grimes Jr. who has a vendetta against Homer for tormenting his father to his death, Grimes is arrested. Bob is strapped with a shock collar for the entire episode, until the very end when he escapes, after deciding to sing to Bart rather than killing him.

In the season 17 episode The Italian Bob, Bob had left behind any desire he had to murder any Springfield citizen, let alone Bart. He just wanted to live with his new wife and son in peace in Italy. Unfortunately for him and the Simpsons, they ventured into the town where he had become mayor and Lisa drunkenly let it slip that Bob was an ex-con, which seemingly ruined his new idyllic life. His wife and son embraced his secret, however, joining Bob in his hunt to kill the Simpsons. It just so happened that at the same time Krusty was performing in The Colisseum, where the Simpsons took refuge. Unfortunately, the Terwilliger family was not that far behind them. The Simpsons did manage to get away though, but so did the Terwilliger clan.

The next episode that Bob appears in brings in his family, the Season 19 episode, Funeral for a Fiend. After getting caught for attempting to kill Bart, a trial is held, and Bob’s entire family is present: his parents, his father (voiced by John Mahoney who voiced Frasier’s father in Frasier), his brother Cecil, and his wife and son. After telling the court about his heart defect, Bob pulls out nitroglycerin to treat it. Thinking the nitroglycerin is dangerous, Bart throws it out the window, and seemingly, Bob dies.

Feeling extremely guilty about Bob’s death, Bart ventures to his funeral, where Bob is really alive and the family attempts to murder him. Fortunately, Lisa realized that they wouldn’t have put extra space for Bob’s large feet in the coffin unless Bob were still alive. Realizing that his father was a doctor and could have stopped his heart temporarily, they saved Bart before it was too late, and the entire Terwilliger family was thrown into prison.  

Sideshow Bob’s next attempt to kill Bart might be the most far-fetched. In the season 21 episode, The Bob Next Door, Bob’s prison bunkmate was about to be released, so he drugged the man and traded faces with him. Bob, then taking his identity, moved into the house next to the Simpsons. When Bart heard his voice he knew that it was Sideshow Bob but he could not prove it. After Marge took him to the prison Bob was supposedly in and saw who they thought was Bob, Bart let his suspicions lapse slightly, until Bob kidnapped him and attempted to murder Bart at the point where five states met, for the perfect crime. Fortunately for Bart, Bob was too much of a perfectionist and he was distracted enough to get caught by different states’ police. So he cut open his face for nothing, as he failed again to kill Bart. 

There was one time where Sideshow Bob’s hatred fueled him enough to actually kill Bart. In the Treehouse of Horror episode of season 24, Sideshow Bob manages to murder Bart Simpson, although he almost immediately is filled with regret and sets out to bring him back to life, reanimating him.

In the season 29 episode Gone Boy, Bart has gone missing. After Springfieldians searched for Bart and could not find him, he was presumed dead. Knowing in his heart that only he could kill Bart Simpson, Sideshow Bob broke out of prison. But instead of going through with his plan, Sideshow Bob let Bart live and let him be, working out some psychological issues with his therapist while he was in prison. 

After Sideshow Bob’s last outing he escapes and hides in a lighthouse. In Bob’s most recent appearance, the season 31 episode, Bobby, It’s Cold Outside, his days of hunting Bart Simpson are seemingly over. However, someone in Springfield is stealing the packages off of people’s porches and Lenny Leonard leaves a clue as to who the culprit is: the letters SB. Sideshow Bob works with the Simpsons to prove that he isn’t the box bandit and together, with Bob hiding in a tiny box, they discover that it was Mr. Smithers and Mr. Burns that were behind the theft. Having helped save the day, Bob retreats to his lighthouse, leaving Bart unscathed. 

There you go, every possible reason Sideshow Bob may have had to hate Bart Simpson. But when you really think about it, did he hate him? In most of the encounters they had throughout the series he does not actively attempt to kill him, even though the show wants us to think that Bob hates him. There has been a Sideshow Bob appearance every few years, let’s hope that The Simpsons goes on long enough for another appearance, one where hopefully Bob finally puts down his knife for good.