The Italian Bob

"The Italian Bob" is the eighth episode of "The Simpsons"' seventeenth season. 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 and is the first time the Simpsons visit Italy. It is also a sequel to "The Great Louse Detective".
The episode is a reference to the 1969 British caper film "The Italian Job". Among the locations the Simpsons visit in this episode are Pisa, Pompeii, Tuscany, Rome and Venice.
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. The family flies over on Alitalia, and have a great time touring the country, despite Homer and Bart's mockery of the culture and history of Italy. Lisa tries to pass the family off as Canadian to avoid potential ridicule from Europeans who believe Americans make stupid choices, though this backfires when Homer brings in an American flag to smooch off the other passengers. After two huge food wheels—one made of Mortadella and the other of cheese—land on their car and crush the hood, they slowly push it into a small (fictional) Tuscan village nearby called Salsiccia (sausage), and are told that the mayor speaks English.
The Simpsons are shocked to find out that the mayor is none other than Sideshow Bob, who is equally shocked to see them. He explains that after he last attempted to kill Bart, he wanted a new life away from Springfield. Bob decided to get a fresh start elsewhere by using a knife and globe to "randomly" settle 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 Bart, 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 the Simpsons not to tell anyone, and they agree in order to have the car fixed.
One month later, Bob hosts a farewell party in the village for the Simpson family. However, that goes awry when Lisa gets intoxicated on wine and starts to spout off about him being an attempted murderer. He leads her away from the table, but as she stumbles backwards, she 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. Bob is so angry at this that he has had enough with the rest of the family, and swears a vendetta to not only kill Bart, but "all" of the Simpsons. The family flees in the fixed car, but Bob follows them on a motorcycle (a Ducati 999). Homer drives into a ditch and onto a Roman aqueduct, eventually landing on top of Trajan's Column in the Roman Forum. Bob's wife and son catch up with him, and though Bob initially promises to give up his vendetta, Francesca professes her love and loyalty to Bob and offers to help him take revenge "as a family".
Meanwhile, the Simpsons are wondering what they should do next, since they are in a foreign country with no car and no money whatsoever. Lisa 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. Lisa warns the audience that the Terwilligers are about to actually kill her and the family, but Bob tricks the audience by performing the climax of "Vesti la giubba". Before Bob and his family can finish off the Simpsons, though, Krusty's limousine picks them up; Krusty needs them to smuggle an ancient artefact back to America. The Terwilligers are disappointed at first, but then walk away plotting revenge together, with Gino chasing a butterfly and Francesca and Bob grinning maliciously.
Reception.
Kelsey Grammer won the Emmy Award for Outstanding Voice-Over Performance for his voice portrayal of Sideshow Bob in this episode. This marks the third time a credited guest star for the show has won an Emmy, the other two being Marcia Wallace and Jackie Mason although Wallace and Mason both won theirs as a joint win with the rest of the main cast the first time the category was awarded in 1992. 
John Frink won the at the 59th Writers Guild of America Awards for his script to this episode.
In 2009, IGN's Robert Canning placed "The Italian Bob" last on his list of the "Top 10 Sideshow Bob Episodes" (at that time, ten episodes revolving around the character had aired). Canning wrote that the episode "falls lowest in the ranking for a few reasons, but the biggest of these is the fact that Bob had no intention of killing Bart. Plus we're in Italy. Plus Bob is married and has a son. All the things we love about a Sideshow Bob episode—the vengeance, the familiar settings and characters, the elaborate scheming—were missing from this half-hour. Without it, Bob wasn't nearly as entertaining, and the episode didn't result in a whole lot of laughs."