What if Disney would've first start making animated TV series since the 1950s?/The Simpsons/Road to Italy

"Road to Italy" is the eighth episode of the seventeenth season of The Simpsons. It first aired on the Fox network in the United States on December 11, 2005. It features Kelsey Grammer in his ninth appearance as Sideshow Bob. In this episode, Mr. Burns' Stutz Bearcat finally breaks down, so he decides to buy a new Italian sports car, and asks Homer to pick it up for him, but when Homer gets kidnapped by a enemy from Itchy's past, Brain and Stewie go to Italy in his place, but end up in a small town where the residents aren't aware of the criminal past of their new mayor - Sideshow Bob, who is now married and has a son Among the locations they visit in this episode are Pisa, Pompeii, Tuscany, Rome and Venice.

The "Road to" episodes which have aired throughout various seasons of The Simpsons were inspired by the Road to... comedy films starring Bing Crosby, Bob Hope and Dorothy Lamour, though this episode was not originally conceived as a "Road to" show.

Plot
After Mr. Burns gets teased about his old car by the kids at Springfield Elementary School, he sends Homer to pick up a brand new Lamborgotti Fasterossa car (a parody of the Lamborghini Gallardo) in Italy. While Homer tries to prepare for his travel, he ends up being kidnapped by a gang of cat mobsters, which Brian then decides to volunteer to go in Homer's place while Itchy is going to rescue him. Brian and Stewie (who said he and Rupert always wanted going to Italy) fly over on Alitalia, and have a great time touring the country, despite Stewie's mockery of the culture and history of Italy (causing an embarrassed Brian to pretend to be Canadian so no one will assume that he is not with Stewie, though this backfires when Stewie brings in an American flag to smooch off the other passengers). After two huge wheels, one made of Mortadella and the other of cheese lands on their car and crushes the hood, they slowly push it into a small (fictional) Tuscan village nearby called Salsiccia (sausage), and are told that the mayor speaks English.

Brian and Stewie are shocked to find out that the mayor is none other than Sideshow Bob, who's equally shocked to see Brain. He explains that after he last attempted to kill Homer (and Marge), he didn't return to jail and wanted a new life away from Springfield. Bob decided to get a fresh start elsewhere by "randomly" settling on a new destination in Italy (but only after passing over Orlando, North Korea, Shelbyville and, ironically, "Bartovia"). After a rough start, the Italians warmed up to him when he helped them crush grapes into wine using his enormous feet. After that, they elected him as mayor of their tiny village. As a result, Bob no longer has any intention of killing Homer, and he reveals that he has a family. He introduces them to his wife, Francesca and his son, Gino. They know nothing about his past life in America. Bob begs Brian and Stewie not to tell anyone, and Brian agree in order to have the car fixed.

Bob hosts a farewell party in the village for the duo. However, that goes awry when Brian gets intoxicated on Wine and starts to spout off about him being an attempted murderer. He leads him away from the table, but as he stumbles backwards, he rips off his suit to reveal his prison uniform. The village finds out that Bob is a robber and attempted killer, and they sack him as Mayor. Brian and Stewie take off in the fixed car, and Bob swears a vendetta on them, as well. Brian and Stewie flees, and Bob follows them on a motorcycle (a Ducati 999). Brian drives into a ditch and onto a Roman aqueduct, eventually landing on top of Trajan's Column in the Roman Forum. Bob's wife Francesca and Gino son meet him, and though Bob initially promises to give up his vendetta, Francesca tells him, "If that dog have dishonored you, they've dishonored our family. We take revenge as a family."

Brian and Stewie are wondering what they should do next, since they are in a foreign country, have no car and no money whatsoever. Brian spots a bus with a poster advertising Krusty the Clown's performance in the opera Pagliacci. They meet up with him at the Colosseum in Rome, and he puts them in as unnoticed extras. However, Bob, Francesca, and Gino find them and corner them on the stage while Krusty, who went through a trap door, flees the stage, allowing Bob to perform the climax of Vesti la giubba. Before Bob and his family can finish off Brian and Stewie, though, Krusty's limousine picks them up; Krusty needs them to take one of his awards back to America. The Terwilligers are disappointed at first, but then walk away, grinning maliciously and plotting revenge together.

Itchy takes a bus to New York City upon leading the mobsters had brought Homer there. After several flashbacks about his life in New York before returning to Springfield to be in Bart's born day, Itchy discovers the leader of the mobsters is his old nemesis from his past, Warren T. Cat (the antagonist from Don Bluth-Steven Spielberg's classic An American Tail) who wants revenge at him for killing his wife, and confronts him in the MAD magnazine building (where he took Homer hostage) after battling and murdering his henchcats, and kills him after a fight which ends up with Itchy killing Warren by beating him up with a flying pan. Homer then thanks Itchy and hides in the valut to pay some money to somebody.