Homer Simpson, Grampa Simpson, Barney Gumble, Krusty the Clown, Groundskeeper Willie, and others
Apu Nahasapeemapetilon, Moe Szyslak, Chief Wiggum, Comic Book Guy, Lou, and others
Mr. Burns, Ned Flanders, Principal Skinner, Waylon Smithers, Kent Brockman, and others
Marge Simpson, Patty Bouvier, and Selma Bouvier
Bart Simpson, Nelson Muntz, Ralph Wiggum, Todd Flanders, and others
Sideshow Bob Terwilliger
Krusty reads Pagliacci, an opera written by Ruggero Leoncavallo in 1892.
The village is named Salsiccia, which means "sausage" in Italian.
The family goes to Italy with the airline Alitalia.
Bob's prisoner number (on his prison clothes) is #HABF02, the production code of this episode.
(The family discovers Sideshow Bob is the mayor of Italy.)
Bart and Lisa: Sideshow Bob!!!
Sideshow Bob: The Simpsons!!!
Homer: Can I be the phantom of the opera?
Lisa: Dad, the phantom isn't in this.
Homer: Oh, but I do a great impression of him! (Imitates the phantom) Ooh, I am the gayest super villain ever! Beware my scented candles!
Lisa: Mozzarella, Parmiggiano, Provolone, Pecorino, Gorgonzola, Fontina, Taleggio, Bocconcini! (Splattering) Mortadella!
Francesca: Roberto, is this true? You tried to make the murder?
Bob: But darling, the boy, drove me to it by exonerating a Harlequin who I had framed for robbery at the Kwik-E-Mart; (depressed) oh, it all sounds so stupid!
Bob: (to Francesca regarding their son Gino) I don't wish to brag, but he's evil at an eighth grade level!
Marge: Boy that Sideshow Bob goes from zero to murder awfully fast.
Bart: At least this time it was Lisa who ruined Bob's life.
Marge: Oh, Homie, isn't Venice romantic? This gondola ride was a wonderful idea!
Gondolier: (singing) When-a, wife looks like that and her husbands so fat, that's immoral. When she kisses that jerk while I do all the work, that's immo...
Homer: Hey, knock it off!
Gondolier: Excusi, no speak-a English. (singing) When that big tub of lard…
Homer: Americano? What the hell could that mean? Why can't you people learn to speak my language? I learned to eat your food!
Homer: You're sending me to Italy?
Homer: Can I take my family?
Homer: Do I have to hang out with them?
Burns: It would be nice.
(Homer groans loudly)
Bob: I needed a fresh start, but where? (Spins globe, covers his eyes and uses a knife to decide where to go. First, he stabs Orlando, Florida) Not in this lifetime! (Spins the globe again, then stabs North Korea) Dammit! (Tries again, Shelbyville) Never! (Tries again, Bartovia) Now cut that out! (Touches globe and rotates it slowly, then stabs Tuscany) Ah, Tuscany!
Brandine: (to Cletus) You are the most wonderful husband - and son - I ever had.
Homer: Holy moly! I always though you were, you know, out loud and proud.
Sideshow Bob: Well, I experimented in college, as one does.
Homer: Yeah, I never went to college.
Sideshow Bob (sardonically) Stop the presses.
(At the leaning tower of Pisa).
Homer: I've seen this in pictures, but you have to actually be there to really experience it. (Camera pans out showing that they are at McDonalds.) A McDonald's that actually serves booze!
Krusty: (Singing at the opera) No more Rice Krispies, We are out of Rice Krispies! (Krusty laughs, then his laugh turns into a cry).
Bart: Krusty you've gotta help us!
Krusty: I don't do gotta.
Lisa: Sideshow Bob has sworn a vendetta against us!
Krusty: A vendetta? What's that, an Italian vending machine? (Simpsons stare blankly at him) Aww, that's my opening joke! And my closer. And my saver! And my topper!
Kelsey Grammer won an Emmy for his performance as Sideshow Bob in this episode.
This episode won the 2007 WGA Award (TV) for Animation.
This episode marks the first cameo appearance of Stan Smith.
Blackboard Joke: None.
Couch Gag: The family enters the living room in the form a playing cards being dealt. Bart is the Jack, Marge the Queen, Homer the King, Lisa an Ace and Maggie is the Joker.
When Bob is spinning the globe looking for a fresh start, it stops on an island called Bartovia and Bob says, "Now, cut that out!" This is a reference to comedian Jack Benny as it was his catchphrase and was even used as the title to his Biography episode.
When Sideshow Bob sings "These feet are made for stomping, and that's just what they'll do..." it is a parody of the song "These Boots Are Made for Walking."
"Les Misérables" by Victor Hugo
Lisa suggests that Bob deserves a second chance like Jean Valjean, the protagonist in "Les Misérables" who became the Mayor of the small town Montreuil-sur-mer. This is not the first allusion to "Les Misérables"; when Bob was in prison, his ID number was 24601, the prisoner number of Jean Valjean.
Sideshow Bob: Revenge is a dish best served...family-style.
An obvious spoof to the old saying, "Revenge is a dish best served cold."
The criminal book shows pictures of Family Guy's Peter Griffin and American Dad's Stan Smith.
This is a reference to how some feel that Family Guy copies ideas, and American Dad copies another copier (as shown in the book).
Title: The Italian Bob
The title is a take on the 1969 and 2003 film, The Italian Job.
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