Maybe Sideshow Bob Likes Having Bart Simpson Around

A lot of people don’t like Bart Simpson. He’s wreaked havoc on Principal Skinner and Edna Krabappel’s lives time and time again, and in many episodes of The Simpsons, he drives Homer nearly insane. But no one hates him more than Sideshow Bob (as voiced by Kelsey Grammer), the criminal mastermind who has been foiled by Bart (with help from Lisa) on countless occasions.

For all the hate that Sideshow Bob has for Bart (who he will kill in the non-canon “Treehouse of Horrors” episode this year), though, is it possible that he might actually like him a little bit, too? Let’s explore the surprisingly complicated relationship between these two characters by remembering their shared history.

Bart Foils Sideshow Bob’s First Two Criminal Plots

Before Sideshow Bob hated Bart, he hated his boss, Krusty the Klown. Despite being a classically trained actor, Krusty forced him to play the role of the buffoon (his replacement, Sideshow Mel, would encounter the exact same problem). This leads to Bob’s first criminal plan: framing Krusty for armed robbery so he can take over his show.

Unable to accept that his hero is a criminal (which is ironic, since Krusty is certainly a shady character), Bart brings in Lisa to help him clear Krusty’s name. They find Sideshow Bob out, and he gets sent to jail. Case closed?

At this point, one can easily assume that Sideshow Bob certainly had some resentment toward Bart, though it had yet to reveal itself. That wouldn’t happen until “Black Widower,” when Sideshow Bob marries Aunt Selma and tries to murder her, but again he is foiled.

Sideshow Bob Wants Revenge Against Bart At All Costs

“Cape Feare,” the third episode to feature Sideshow Bob, centers around his attempts to wipe out Bart at all costs. After sending Bart numerous threatening letters written in his own blood, Bob tracks down Bart when the family attempts to escape through the witness protection program. He is in the perfect position to do away with Bart once and for all while adrift on a boat, but he foolishly decides to sing the entire score of H.M.S. Pinafore and winds up floating all the way back to Springfield and Chief Wiggum by the time he’s done.

Sideshow Bob’s next two episodes, “Sideshow Bob Roberts” and “Sideshow Bob’s Last Gleaming,” are undeniable classics, but neither really explores his relationship with Bart that much, even though Bart and Lisa thwart Bob’s attempts at running Springfield into the ground as mayor and his effort to silence television.

Sideshow Bob Actually Reforms… For One Episode

In “Brother From Another Series,” everyone assumes that Sideshow Bob is running another scam on the people of Springfield when he gets out of prison and swears that he has reformed, but this time, it’s actually his brother Cecil (played by David Hyde Pierce, Kelsey Grammer’s brother on Frasier), who is the true villain of the episode, with Sideshow Bob doing everything in his power to stop him.

Of course, Chief Wiggum assumes Sideshow Bob must have had something to do with Cecil’s attempt to blow up Springfield Dam, so he sends him to jail, where he goes back to his old ways.

Is Sideshow Bob Actually Capable Of Killing Bart?

Four years later, in “Day Of The Jackanapes,” Sideshow Bob’s Krusty hatred is reignited when it’s revealed that he taped over all episodes of The Krusty The Clown Show that Sideshow Bob was featured in. After taking a job at the school (um, why does Skinner hire Sideshow Bob when he knows about his past? Does he hate Bart that much?), he hypnotizes Bart and straps him with explosives that will kill both Bart and Krusty, eliminating his two biggest enemies. He has a change of heart, however, when Krusty sings a song about how he regrets treating Sideshow Bob so cruelly over the years. This marks the second time when Sideshow Bob could have easily gotten away with murder, but somehow screwed it up. For all of his anger at Bart for foiling his schemes, he’s pretty good at foiling himself.

At this point, one gets the impression that Sideshow Bob needs Bart in his life and that his bloodlust is what keeps him going, but to actually murder him would ultimately leave him (and the show) empty.

This is confirmed in the “The Great Louse Detective” when Bob has a chance to kill Bart in cold blood but decides not to because he’s “grown accustomed to his face.” If you’re counting, this is the third time he could’ve murdered Bart, but didn’t. For Sideshow Bob, the chase is better than the catch, so rather than finish the job once and for all, he keeps letting go. Perhaps knowing that he could’ve killed Bart all those times was victory enough.

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