Slightly updated!
Springfield had so many prisons for a single city, and its criminals had the highest recidivism rates in the United States. Bob believed Springfield could break a world record with the number of prison riots it had; there were likely more riots in Springfield Penitentiary alone than California had disasters. The overcrowded prison was a ticking time bomb of noisy, uncouth, temperamental, unrestrained sorts, barely kept in line by the spineless, frequently inebriated, and easily bribed guards.
All sorts of things could set off a riot in Springfield Penitentiary. In other prisons, a riot would be caused by inhumane treatment. Here, a riot could start over something as minor as a broken television.
Bob had started one such riot. It had happened after a week of being served canned banana pudding at meals. Bob had never much liked bananas. As a boy, he was repulsed by their mushiness and how easily they bruised, along with those odd little strings on them. His dislike for the fruit only became worse after years of being hit by Krusty's banana cream pies. It also didn't help that the pudding served in the prison was one of Krusty's many product endorsements. Seeing the faces of Krusty and Mr Teeny on a pudding can had triggered an odd sort of PTSD in Bob, and he'd thrown the pudding at a guard. After that, things were a blur. Bob recalled vague images of running and screaming and other foods being tossed around. His next clear memory was of being tossed into solitary.
New arrivals started fights and riots too. Springfield Penn received plenty of new arrivals, and they would always upset the already tenuous social dynamics. Cecil had once offended another inmate with his haughty demeanour, and he'd been sucker-punched as a result. Bob's sense of brotherly obligation had caused him to threaten the offender with a shiv. That hadn't ended well, to say the least. The fighting had carried on for six hours, ending with nearly everyone involved getting crammed into the infirmary, which was crowded to begin with.
Bob grew to enjoy his stays in solitary confinement. The padded room was sound-proofed, and so he could remain undisturbed by riots. It eventually became Bob's coping mechanism during chaotic times to imagine that he was in that soft, quiet room, or to mentally sing excerpts from Gilbert and Sullivan operettas. Currently, he favoured one of the composers' lesser-known works, The Sorcerer. Imagining himself performing as the titular sorcerer, John Wellington Wells, was one of his more innocent happy places. Sometimes, Bob would willingly take part in a riot, just so that he could be sedated or put in his padded cell, in order to get some peace.
How low he'd sunk.