An FBI agent and Homer (who's trying to work off his criminal charge for bribery) infiltrate Fat Tony's mob, and meet Fat Tony's cousin, Fit Tony.

!! Tropes:

* BribeBackfire: Homer was sent to prison for attempted bribery.
* ContinuityNod: In [[Recap/TheSimpsonsS18E1TheMookTheChefTheWifeAndHerHomer The Mook, the Chef, the Wife and her Homer]], Fat Tony mentioned his deceased wife Anna Maria. After he died, he was buried next to her grave.
* ExactWords: At his trial, Homer requested for a side bar. Once the judge granted it, he tried to whack Bart with it.
* IdiotBall: Even for Homer, Leaving a bag full of money clearly marked 'bribe' on a desk in the middle of city hall and not expecting to be arrested.
* KilledOffForReal: Fat Tony
* SeriesContinuityError: When Moe got caught setting his bar on fire, he explained it was either that or installing a ladies lounge but, in [[Recap/TheSimpsonsS8E3TheHomerTheyFall The Homer They Fall]], Moe told Homer that he turned a woman's bathroom into his office because no women have ever come in the bar, though that's a mistake too, as Moe hired a female bartender on the episode with the Flaming Moe's drink, Marge came into the bar on "Episode 23: Bart Gets Hit By a Car," Lisa was in the bar on "Homer Defined," there were women in the bar on "Homer vs. The 18th Amendment," Moe had a "Ladies' Night" sign on the wall in the early episodes, and Ruth Powers (the divorced mom from "New Kid on the Block" and "Marge on the Lam") tried to get a free beer with a coupon on "New Kid on the Block."
* ShoutOut: To ''TheWizardOfOz'' when Moe tried to find a place where he could suggest Homer to bribe his way out of his New Year fines.
* SuspiciouslySimilarSubstitute: Fat Tony's cousin Fit Tony, who looked like Fat Tony except for [[ExactlyWhatItSaysOnTheTin being fit instead of fat]] but even that eventually changed and Fit Tony is now Fat Tony.