Bart Simpson is the primary target of Sideshow Bob’s relentless vendetta. Bob blames Bart for foiling his evil plans and has made numerous attempts to exact revenge on the mischievous boy throughout the show’s long-running history.

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.

After Krusty was arrested, Bob took over the show and turned it into an educational one, introducing children to elements of high culture and including a psychological segment called “Choices”, though he kept the popular Itchy & Scratchy Show. Bart exposed Bob as the real robber on his TV show, and he was arrested, swearing revenge on Bart.

Throughout the episode, Bob wrestles with the recent meetings he'd been having with a therapist in prison, forcing him to sit down and consider his obsession with killing Bart. Bob has to confront his inner demons, and Bart openly calls him out on his continued obsession.

After being paroled from prison, Bob targeted Bart directly, threatening him repeatedly and forced the Simpsons to move to Terror Lake as part of the Witness Relocation Program. Bob followed them to their houseboat and, after subduing the family, prepared to kill Bart.