The episode title is a reference to the film The Italian Job.
The Lamborgotti Fasterossa is virtually identical to the real-life Lamborghini Gallardo. As a play on the names of Italian exotic cars, the Fasterossa's name is also derived from the Ferrari Testarossa.
The song Lisa chants as the cheeses bounce towards the Fasterossa is to the tune of "Italiano Calypso", a song on The Seven Hills of Rome.
Lisa mentions Jean Valjean. Both Bob, Principal Skinner and Arrested Development's Oscar Bluth have worn Valjean's prison number in the past.
This episode marks the first cameo appearance Stan Smith. He, like fellow "plagiarismo" Peter Griffin is shown with their regular skin color rather than yellow skin.
After temporarily escaping from Sideshow Bob in Rome, Marge states that she feels like the Bourne Identity which is the name of a book and movie (which stars Matt Damon in the lead role) about a former assassin with amnesia who is chased around Italy by people working for the CIA.
The rake-to-the-face gag is recycled from "Cape Feare".
The Italian police book features Snake as Invasione Di Casa (Home invasion|home invader), Mayor Quimby as Drinko Drive-O (drunk driving), Peter Griffin from Family Guy as Plagiarismo (plagiarism), Stan Smith from American Dad! as Plagiarismo Di Plagiarismo (plagiarism of plagiarism), and Sideshow Bob as Omicidio Attentato Multiplo (Multiple attempts of Homicide), even though none of them (except Sideshow Bob) were in Italy or even visited Italy at that time.
The two year old town drunk looks and sounds like a young Barney Gumble. He may actually be one of Barney's innumerable children, thanks to the Springfield sperm bank.
When Homer gives an Italian woman a mug with Kentucky emblazoned on it as a peace offering, this may be a reference to "Behind the Laughter", in which the Simpsons are referred to as a "Northern Kentucky family."
When Lisa rips Sideshow Bob's clothes off revealing his prison suit, his prison number is HABF02, the production code of this episode (a running gag on The Simpsons, where the episode's production code is seen on-screen).
The writing in the book of fugitives from America on the opposite page from the pictures appears to be Arabic.
Homer and, to a lesser extent, Bart manifest profound knowledge of the history of Italy in this episode. Homer also shown his liking of Italy in "You Only Move Twice".
When the family visits Pompei, there are the remains of a Roman family strongly resembling the Simpsons, which Homer refers to as "savages."
The PBS logo has the Simpsons' overbite, which was also featured in Mission: Impossible.
In Sideshow Bob's flashback, he is wearing the same clothes as he was at the end of his last appearance, in "The Great Louse Detective".
On Sideshow Bob's globe, Tuscany looks like it is a city, but it is actually a region.
This episode was shown during the Super Bowl XL Halftime show (February 5, 2006).
The name of the village (Salsiccia) means "sausage" in Italian.
Krusty's lines during the musical Pagliacci, with the words changed to "I'm all out of Rice Krispies", is a reference to an operatic Rice Krispies commercial from the 1960s, in which a family is eating breakfast, and the father sings this exact line.
When Homer imitated a sport fanfare, he said 'charge' just before Mr. Burns who is in charge of the power plant entered. The Song the drunk baby that looks like barney sings is Mambo Italiano a song sung by Rosemary Clooney in 1954 Rosemary Clooney was well known until she passed away on June 29 2002.
Homer did attend college—later in life, though. However, his character would be known to forget something like that.
Lisa does not appear to speak much Italian in this episode, despite learning from Milhouse in the previous episode. However, she does translate the old woman's dialogue and correctly identifies all the cheeses that fall off the truck.
Sideshow Bob has a child now, who appears to be older than Maggie, seeing as he can talk, whereas in previous episodes Maggie has existed but Bob has had no son.
Pompeii was spelled "Pompei" when they arrived. Pompei in fact is the correct Italian name of the city.
The Italian language/Italian spoken in the show is a quite literal translation of the English phrases shown as subtitles. It's not grammatically and phonetically correct sometimes, but the literal translation of the English idiomatic expressions would sound nonsensical to an Italian native.
Bob becomes the "Il Mayore" of Salsiccia but the correct Italian word would be "Sindaco". Mayore is probably an intentional Italianization of the term mayor, as the word doesn't even exist in Italian.
When the family is at the Lamborgotti assembly line, the sign shows "Limea Montaggio No. 1". The correct word would be "LiNea". Plus, "No." is the English abbreviation of "Number"; in Italy that would have been "N°", "Num." or simply "N."; "#" is not used in Italy.
When the Italian Police searches the book of American criminals, Sideshow Bob is listed under "omicidio attentato multiplo". The correct Italian term would be "Tentato Omicidio Multiplo". Attentato is a wrong, although largely intelligible, translation of attempted, as the word in Italian means more or less "act of terrorism", and not the act of attempting to do something.
"Plagiarismo" is a Spanish translation from the English "plagiarism". The correct Italian word is "plagio". This was deliberately done so viewers who don't speak Italian could understand the joke.