Buzz Lightyear from the Disney/Pixar Toy Story franchise is mentioned by Lisa at one point when she said that his voice actor, Tim Allen as one of many stories of redemption in literature.
The episode title is a reference to the 1969 film The Italian Job. The film was remade in 2003 with BMW-designed, modern Minis and an American cast.
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 from Les Miserables. Both Bob and Principal Skinner have worn Valjean's prison number in the past.
This episode marks the first cameo appearance of Stan Smith from American Dad!. 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).
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).
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."
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 "We are 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.
This episode could be seen as a sequel to the previous episode "The Last of the Red Hat Mamas," as Lisa contemplated visiting Italy and had learned Italian from Bart's friend, Milhouse.
Although Lisa doesn't speak much Italian in this episode, she does translate the old woman's dialogue and correctly identifies that fall off the cheese truck and hit Mr. Burns' new car as Lisa learned Italian and was contemplating visiting Italy.
Homer did attend college—later in life, though. However, his character would be known to forget something like that.
Sideshow Bob has a child now, who appears to be older than Maggie, seeing as he can talk, however Maggie, Bart and Lisa still remain the same age they were before Bob even fled to Italy and conceived his son.
Pompeii was spelled "Pompei" when they arrived. Pompei in fact is the correct Italian name of the city.
Sideshow Bob was in his original coloring scheme on the bottle of Chianti Di Salsiccia.
When Homer gives the Italian woman the Kentucky mug, Kentucky does not actually mean "whore" in Italian. The Italian term for "whore" is "puttana".
This episode marks a huge turning point in the series, as in the episode and all others after it, Sideshow Bob is trying to the whole Simpsons family; whilst previously he was only wanting to kill Bart.
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. So saying that the mayor understands English should be Il Sindaco capisce inglese.
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.
When Homer says to Lisa, "It's called a hangover, sweetie," his five o'clock shadow turns yellow then back to tan.
In the same scene as the last one, the collar of Homer's shirt teleports from in front of the seatbelt to behind it.
In the plane scene, Lisa is sitting beside Homer, but when Homer starts ripping off the cables from the seat, Maggie is sleeping beside him in a baby seat.