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Originally it was because he committed an armed robbery on the Kwik-E-Mart, and tried to frame Krusty for it. Bob used to co-star on the Krusty the Klown show. He had Sideshow Mel's job (Sideshow Mel, in fact, was Sideshow Bob's replacement). Bob hated being the butt of all the jokes on the show, and he considered Krusty a talentless hack. Bob wanted Krusty off the show so he could star in it himself, so he disguised himself as Krusty and robbed the Kwik-E-Mart.

Bart didn't believe Krusty committed the crime, and set out to prove it, and in doing so discovered it was Sideshow Bob who did it. Sideshow Bob went to prison and has held a murderous grudge against Bart ever since.

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13y ago

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