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:

* BigNo: Comic Book Guy when he fails to prevent Homer's ice cream from melting.
* BribeBackfire: Homer was sent to prison for attempted bribery.
* CantGetAwayWithNuthin: To replenish goverment funds, the new laws make it so many things people do normally are heavily fined crimes. They even work so people will be forced to commit more crimes since complaining about being fined, and adding up the total of your fines is also illegal.
* 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, even counting his endless laziness, Leaving a bag full of money clearly marked 'bribe' on a desk in the middle of city hall and not expecting to be arrested is a stretch.
* KilledOffForReal: Fat Tony
* LuckyTranslation: In Brazil, "bribe" doesn't translate as anything that resembles "bride". Fortunately, a Brazilian word for "bribe" is "propina". Homer says he meant to write "pro Bina"(to Bina)[[note]]In that case, Bina is described as the groom. Had Bina been a woman, Homer would say "pra Bina"[[/note]] and the money was a wedding gift.
* 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 ''Film/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.
* TakeThat: The FBI is described as "out of control".
* WhatHappenedToTheMouse: Despite the ContinuityNod to [[Recap/TheSimpsonsS18E1TheMookTheChefTheWifeAndHerHomer The Mook, the Chef, the Wife and her Homer]] referencing Fat Tony's late wife, and the fact that her grave describes her as a "Loving wife and mother," there is no mention at all of Michael, not even when his father dies, making him an orphan.