Living… in jail, mostly. He has a sworn vendetta against Bart Simpson, the kid who foiled his plan to frame Krusty the Clown and thus sent him to prison. Bob is released from jail several times for various reasons, but mostly he breaks out and hatches another psychopathic plan to exact revenge on Bart Simpson.
Profession… former entertainer. He used to work on the “Krusty the Clown Show." But after being shot out of cannons and subjected to other torturous acts of slapstick, he became bitter toward Krusty and eventually betrayed him. He robbed the Kwik-E-Mart and framed Krusty. Eventually he was caught, and now his “profession” is prison inmate.
Interests… the Republican Party, model boats, and opera. He likes tattoos, especially vicious depictions of Bart Simpson’s head on a platter. Misquoting Shakespeare is another Sideshow Bob favorite. He also has quite a nice singing voice, somewhere between the baritone and tenor ranges.
Relationship Status… mostly single. He once escaped to Italy and married a beautiful Italian woman. But he soon reverted to his murderous ways and tried to kill Bart Simpson, landing him back behind bars, a single man once more.
Challenge… breaking out of prison to kill Bart Simpson, his arch nemesis. Unfortunately for Bob, his murderous plans are always foiled one way or another – usually involving garden rakes, his other mortal enemy.
Personality… psychopathic. He’s something of a mad genius. But he’s generally not as brutal as you’d expect an attempted murderer to be. In fact, he gets pushed around in jail by thugs like Snake, who treat Bob like a nerd.
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