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The Simpsons (1989) - 22x09 - Donnie Fatso

 
Plot Outline
Homer spends New Year's Eve in the Springfield Penitentiary after getting caught bribing an official. An FBI investigator (guest voice Hamm) offers to reduce his jail time if Homer agrees to go undercover as an informant to investigate Fat Tony (guest voice Mantegna). When Homer forges a special bond with Fat Tony and his family, he becomes conflicted between his obligation to the government and his loyalty to his new family. After an unexpected turn of events, Fat Tony's cousin Fit Tony (Mantegna) seeks to settle a score with Homer, but winds up teaching him an important lesson


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