Original air date: 12/11/2005
Production code: HABF-02
The Simpsons are going to Italy...to help Mr. Burns retrieve his sports car, and end up in an Italian village where Sideshow Bob is now married and has a son.
Tropes in this episode include:
- All Part of the Show: When Bob's family disguise themselves as extras to kill the Simpsons in the Colosseum, Lisa tells the audience that it's no act and that they're really trying to kill them. Nobody is convinced. This is the same thing that happens to the characters within the Show Within a Show of Pagliacci.
- Artistic License – Cars: Driving a car over an aqueduct is pretty impossible.
- Big Damn Heroes: Just before Sideshow Bob and his family can kill the Simpsons on stage, Krusty shows up via limousine to rescue them. He even gives them a ride back to the U.S. on the condition that they help him smuggle some stolen artifacts.
- Bilingual Dialogue: Many Italian characters seen in this episode are unable to speak English, but otherwise understand it alright.
- Camp Straight: Bob was Mistaken for Gay by Homer, presumably due to his flamboyant, theatrical nature. In fact, he's married and has a son.
- Chair Reveal: Mayor Sideshow Bob reveals himself to the Simpsons this way. In a twist, he's just as shocked to see them.
- Comically Missing the Point:Lisa: Dad, you're driving on an ancient Roman aqueduct.Homer: What am I supposed to use it for? Transporting water to distant urban centers?! [...] Lazy Romans!
- Comic-Book Time: Between his last encounter with the Simpsons and this episode, Bob got married and had a son who's now the same age as or older than Maggie (and fully verbal), despite Maggie not having aged a day.
- Continuity Nod: In the last episode, Lisa learned Italian from Milhouse. While she didn't become fluent, she correctly identifies several Italian meats and cheeses, and translates a bit of the old lady's Italian.
- Crazy-Prepared: Played With. After the Fasterosa is demolished by a wheel of sausage while evading various cheese wheels, Homer reveals that he bought cheese insurance. But Marge points out that it doesn't cover Mortadella.
- Easily Forgiven: Marge is happy to make nice with Bob, who has tried to murder her son and her sister, due to her belief that a person with a family can't be evil.
- "El Niño" Is Spanish for "The Niño": When Bob swears a vendetta on the family, Marge looks in an Italian-English dictionary and is shocked that "vendetta" means "vendetta" in English.
- Even Evil Has Loved Ones: Marge stops being concerned about Bob after discovering that he's now Happily Married with a child, believing that a "family man" can't be evil. In fact, they're more than happy to co-sign his death grudge.
- Everyone Has Standards: Sideshow Bob uses a spinning globe to decide where to start a new life, and vehemently refuses the first choices of Orlando and North Korea. And even though he is considerably more intelligent and cultured than the average Springfieldian, he is still repulsed at the thought of living in Shelbyville.
- Experimented in College: Bob admits to this when Homer is confused to discover that he's not gay.
- Face–Heel Turn: At first Francesca knew nothing of her husband's multiple murder attempts. When she does become aware, she helps Bob try to kill the Simpsons family.
- The Family That Slays Together: Provides the page image.Bob: Revenge is a dish best served... family style.
- Gladiator Games: While in the Colosseum Bart shows his historical ignorance by telling Krusty: "We don't want to be the first Christians to die at the Colosseum."
- Go-Karting with Bowser: Sideshow Bob treats the Simpsons to dinner and Bart and Lisa even play soccer with him.
- Historical In-Joke:Homer: Stupid Italy. Wish you'd never been unified by Victor Emmanuel II. If only you'd stayed a loose confederation of city-states, trading with each other and occasionally warring.Bart: Please help us, Krusty. We don't want to be the first Christians to die at the Colosseum.
- History with Celebrity: The Simpsons turn out lucky as they discover that Krusty is performing an opera nearby. Not only does the clown offer them protection during his upcoming performance but he also saves them from the Famiglia di assassini in the last minute.
- Ignorant of Their Own Ignorance: Marge believes that Bob is a better person because he has a family.Marge: Bart, Bob is a family man now. You can't be a bad person if you have a family.
- Idiot Ball:
- Lisa may have accidentally revealed Bob's past to his people, but Bob didn't do himself any favors by getting his Secret-Keeper drunk and inexplicably keeping his old prison jumpsuit, much less wearing it under his clothes.
- During Krusty's opera performance, not only does Homer make eye contact with Gino thus blowing his cover, but he actually waves at him while smiling.
- Impossible Insurance: The Simpsons, for reasons unknown, bought "cheese insurance". Unfortunately, their car gets totalled by a wheel of mortadella (which isn't covered by the insurance, since it's a type of sausage and not cheese).
- In My Language, That Sounds Like...: Homer gives a Kentucky mug to an old Italian woman, who angrily declares "'Kentucky'?! In Italian, this means 'whore'!" and slaps him. It actually doesn't. Intentional Rule of Funny.
- Insufferable Genius: Bob wasn't well-liked in Italy at first due to his propensity for doing things like correcting the Italian pronunciation of native speakers.
- In the Blood: Gino inherited his father's drive to murder Bart, despite never seeing or hearing of him before the Simpsons arrive in Bob's village. When his family decides to get revenge, little Gino is more than happy to make the full switch to evil.
- In Vino Veritas: After Lisa is loosened up by a few glasses of wine, she lets the truth about Sideshow Bob's criminal past slip out.
- Knocking the Knockoff: Sideshow Bob loses his position as mayor of Salsiccia after the town finds out he's a wanted killer in the United States. The Italian police officers confirm this by checking their book of American criminals, which includes Peter Griffin ("plagiarismo") and even Stan Smith (wanted for "plagiarismo di plagiarismo").
- Language Barrier: Homer is vexed that people in Italy don't speak English.Homer: Americana? What the hell could that mean? Why can't you people learn to speak my language? I learned to eat your food!
- Loophole Abuse: Mr. Burns had Homer bring his new car from Italy to save tax money. He also paid for the whole family just because.
- The Mafia: Referred to only once, according to an old village lady their small village is run by the Mafia.
- Map Stabbing: A variation where Sideshow Bob tells the family that he decided to choose the next place to live by spinning a globe and stabbing it with a dagger. When numerous random attempts resulted in the knife landing in Orlando, Florida; Shelbyville; North Korea, and Bartovia, he more carefully spins and stabs the globe so that the dagger lands in Tuscany, Italy.
- Mistaken for Gay: Homer is surprised to see that Sideshow Bob has a wife, as he's always assumed Bob was "out loud and proud." Bob shrugs and says that he "experimented a bit" when he was younger.
- My Country Tis of Thee That I Sting:Bart: What's with the Canadian flag on your backpack?Lisa: Well, some people in Europe have the impression that America has made some stupid choices in the past, oh, five years. So, for the next week, I'm from Canada.Bart: I think Dad may blow your cover.Homer (battling over a flag): That flag is mine! Don't mess with Texas! Shock and awe, losers! Shock and awe!
- National Stereotypes: Several references to Italy are made, including stylish cars, spaghetti, the Leaning Tower of Pisa, Pompeïi, the Pontevecchio Bridge, Federico Fellini, Italian cheese, chianti, Tuscany, The Mafia, vendetta, olive gardens, aqueducts, the Colosseum, opera and Venice. Bart makes a tiny reference to The Adventures of Pinocchio too, after watching a horrible educational video at the start of the episode: "What is this crap? This is worse than 'Wheelchair-nocchio.'"
- Never My Fault: After a drunk Lisa reveals Bob's criminal past, he swears a vendetta on the family even though it was his idea to let Lisa drink wine. He is also at fault for wearing his prison outfit for no apparent reason underneath his clothes.
- Nice Job Breaking It, Hero:
- Lisa did her part by making cracks at Bob's past as a Serial Killer along with revealing his prison uniform, but Homer seals the deal by instinctively crying out "Sideshow Bob!" which tips the Italian authorities about the truth.
- Bob himself is to blame since he encourages Lisa to get drunk which would lead to him being unveiled to everyone.
- No Ending: Even though the Simpsons escape Sideshow Bob and head back to the U.S., the plotline for Mr. Burns' new car is left unresolved.
- Not Me This Time: Bart Simpson isn't the one at fault for ruining Bobs' new life in Italy; it's Lisa.
- Not So Above It All: Happens with both Marge and Lisa.
- For once, Homer was actually willing to not mess up, and initially declared he was ready to go home as soon as they picked up Burns' new Ferrari. Marge, for once, was the one asking them to see the sights, and even Homer was genuinely surprised to see her as such.
Homer: Marge, are you asking me to disobey?- The moment Lisa finds out she's old enough to drink wine there and gets drunk, she cuts loose like an old pair of slacks, and is, ironically, the one responsible for their predicament near the end (when she's usually the one trying to solve a problem) when she blabs about Bob being a convict to the crowd and accidentally exposed his prison uniform.
- For all his disdain for Springfield and its citizenry, Bob, selecting random locations on a globe to find a new place to live, firmly draws the line at Shelbyville.
- Old-Fashioned Fruit Stomping: After the Simpsons are shocked to discover that Sideshow Bob became the mayor of an Italian village, he explains that a group of villagers exhaustedly try to squash berries, but they then discover Sideshow Bob's uniquely humongous feet and have him make wine. They chose him as the mayor and he stayed there and had a family.
- Opera: The final scene takes place at an opera. Sideshow Bob disguises himself as Pagliaccio (Pagliacci), and gives a far better performance than Krusty did.
- Pop-Culture Pun Episode Title: Of The Italian Job.
- Retcon: Homer at one point says he never went to college, despite going to college in the episode Homer Goes to College. Then again, maybe that's why Bob said "stop the presses." Or maybe that's just him not remembering it, which wouldn't be that surprising. (Alternatively, since he's replying to Sideshow Bob's comment that he Experimented in College "as one does," he could simply mean that he never went to college as a young, unmarried man.)
- Riddle for the Ages: Why is there a country that resembles Bart in both name and shape?
- Secret-Keeper: Sideshow Bob convinces the Simpsons to keep his murderous past a secret from everyone on the condition of fixing their car and allowing them all the services his humble little town has to offer.
- Shout-Out: The song Sideshow Bob sings while squashing grapes with his feet is a reference to Nancy Sinatra's song "These Boots Are Made For Walkin'".
- Similar Squad: The Simpsons find a dead one in Pompeii, stumbling on plaster casts of a family consisting of a heavyset father strangling a slingshot-wielding brat in one hand and drinking from a bottle with the other, while looking on are a horrified daughter and a big-haired, baby-holding matriarch wagging a finger.Homer: Savages!
- Sins of Our Fathers: Yes, even Maggie is being targeted by Sideshow Bob in spite of her innocence just because she's a Simpson.
- Spaghetti and Gondolas: Can be seen in the village. Justified, as this stereotype refers to the Tuscany region and the village is indeed in Tuscany. According to Mr. Burns, they spent at least a month in Italy, so it makes sense that they could visit every major city in the episode's time.
- Take That!:
- Ms. Krabappel's class is horrified and bored having to watch the multi-cultural cartoon made by PBS
- According to an Italian police book, Peter Griffin is wanted for plagiarism and Stan Smith for plagiarism of plagiarism.
- When Bob is trying to decide where to get a fresh start, he randomly stabs his knife into a spinning globe and it lands on Orlando, FL and Bob remarks "Not in this lifetime!"
- While Homer is doing his best Donald Trump impression to the Italian crowd, Lisa warns him that he's posing like Benito Mussolini.
- Translation by Volume: The elderly woman Homer approaches doesn't know any English, so he decides to shout out all of the details of the Lamborgotti Fasterossa in her face.
- "Ugly American" Stereotype: Homer really goes to town with this at the airport, picking up a huge flag he brought along for some reason and waving it while yelling things like "Remember the Alamo!". For her part, and to her embarrassment, Lisa knows about this stereotype and was trying to prevent it affecting her by pretending to be Canadian.
- Vacation Episode: The Simpsons travel to Italy.
- Who Writes This Crap?!: Krusty says this when his opera act (which he was improvising) starts to go south.
