Olive Garden

""Maybe we could have dinner! Perhaps the Olive Garden! It's like dining in the private kitchen of a delightful Italian stereotype!""

- Cinnamon J. Scudworth, Clone High

Italy, mostly known for its food and fat mustachioed people making pasta. There are only two cities in Italy, Rome and Venice (sometimes Sicily if you need The Mafia!). Neither city seems to contain a single building constructed after the 17th century. Rome is heavily populated by gourmet chefs, effete fashionistas and handsome, Vespa-riding homewreckers all too eager to give young female tourists a romantic ride past the Trevi Fountain—oh, and most famous landmarks are within five minutes of each other, too. The Leaning Tower of Pisa is usually found here as well, as opposed to, you know, in Pisa.

Venice, meanwhile, is chock full of handsome, gondola-riding homewreckers all too eager to give young female tourists a romantic ride under the Bridge of Sighs. Either way, men: if your wife or girlfriend steals away on one of these intimate little tours, you're probably flying back home by yourself.

Apparently, Tuscany has swallowed up the rest of the country, as all the surrounding countryside consists of tomato farms and vineyards. If anybody's got any kind of sound system, expect to hear it blasting either "Funiculì, Funiculà", "O Sole Mio", "Santa Lucia" or some famous Giuseppe Verdi aria.

Female Italians are usually dark haired beauties, feisty and wildly slutty, yet for some reason are also very faithful and jealous of their man. In other words, Spicy Latinas through and through.

Expect plenty of Gratuitous Italian.

There's also a dark side to this idyllic country: the time-warped post-war black-and-white Italy that somehow survived till today, directly from neorealistic movies. It's a dangerous and unhospitable country mostly populated of black clad old women that speak quietly and make emphatic gestures, act as superstitious yet religious fanatics, and still don't own a TV set or a vehicle. The only intelligible words these creatures seem to be able to communicate is some distorted provincial dialect like "goomba", and they still claim to vote for Mussolini (Well, you still can...). The remaining population of dark Italy is composed of dark skinned and dark haired (almost Indian looking) scoundrels, good-for-nothing or whores.

In a twist of supreme irony, the whole American continent was discovered by an Italian sailing under the flag of Spain; rather than coming from Rome or Venice said Italian came from Genoa, the sailing/merchant republic which destroyed the Pisans (yes, them of the leaning tower) and scared the Venetians shitless in several naval battles (Back in the day when they went around in heavily armed galleys rather than gondolas, defeating Venetians was an achievement to be proud of, like sinking the U.S. navy). Contrary to the more popular Italian tropes Genoese are famed to be a surly bunch of seldom-smiling, understated, humorless fellows, disdaining songs and dances and preferring pesto to tomato on their pasta. They also have an unjustified reputation of being stingy.

The trope is named after an American chain of casual dining restaurants.

See here for info on the real country.

Anime and Manga

 * Axis Powers Hetalia: North (Venice) and South (Rome) Italy are personified (the former being the main character). North Italy is a ditz who loves good food like pasta, pizza, gelato, and appreciates art and culture. The time when he fought against Mediterranean pirates is shown too. South Italy is more of the mafia image. Both of them are flirtatious. South Italy wails that his brother is eating nothing but potatoes.
 * Porco Rosso takes place on the Adriatic coastline of Italy (with some scenes set in Milan) back when it was ruled by the Fascists. And pigs could fly.
 * Surprisingly subverted in Gunslinger Girl, which takes place Twenty Minutes Into the Future (the only apparent difference being several significant advancements in medicine, and a different political climate) in a very realistic and modern Italy.

Film

 * Roman Holiday features a romatic Vespa ride, this trope in scooter form.
 * Jane Austen's Mafia! had this. Completely with a holiday for the black olives.
 * A Midsummer Night's Dream (1999) is set in Victorian-era Tuscany. It includes that newfangled contraption, the bicycle. It has a soundtrack full of famous Italian arias.
 * Much Ado About Nothing (1993) was filmed in a Renaissance villa in Tuscany.
 * James Bond
 * Although Casino Royale had its climax in Venice, the Daniel Craig James Bond films have gone all over Italy, including Lake Como, the small coastal town of Talamone, and the city of Siena. In Quantum of Solace the latter featured a foot chase during the Palio di Siena horse-race, which would be Siena's equivalent to It's Always Mardi Gras in New Orleans.
 * The Spy Who Loved Me averts the trope by Bond going to Sardinia.
 * For Your Eyes Only featured the northern Dolomiti mountains.
 * From Russia With Love played it straight, ending up in Venice. In all these films, background Italian characters still come across as stereotypes.
 * The Italian Job (1969) takes place in Turin and pretty much averts this trope completely.

Live Action TV

 * Everybody Loves Raymond: Any Italian character and the country itself on the "trip" episode.
 * I Love Lucy: The infamous grape-stomping episode.
 * The Sopranos: Tony and the boys go to Naples in an episode. They meet a female Camorra capo, and her men mock Paulie and Silvio's lack of culture.

Professional Wrestling

 * With his very large family, his love for wine and opera, women swooning all over him, and oh yes, his outrageous accent, WWE wrestler Santino Marella seems to hail from this version of Italy. Of course, since his Face Heel Turn, he only thinks women swoon over him. He's much funnier this way.

Theater

 * The Most Happy Fella is steeped in this atmosphere (Gratuitous Italian and tarantellas abound), though set in the vineyards of Napa Valley, California.

Western Animation

 * In the Jem episode "In Stitches," the two rival bands, "The Holograms" and "The Misfits" are invited to a fashion contest by the owner of a salon in Venice, Italy. Especially irksome as the centres of the Italian fashion industry were Rome from The Fifties to The Seventies, and Milan thereafter.
 * Kim Possible bucks the trend by actually having an episode set partly in Milan. Of course, the villains that episode were criminally-minded fashion designers (hey, at least they did some research!).
 * A Looney Tunes example: In "A Hound For Trouble" the foreign, But Not Too Foreign, Charlie Dog went to this version of Italy, attempting to be adopted by a ludicruously stereotyped Italian chef. At the end, said chef tricked Charlie into "holding up" the Leaning Tower of Pisa while he "went for help".
 * The Simpsons
 * An Italian tour bus in had Mario from Super Mario Bros. mocking Homer. Then an angry Homer starts throwing trash cans at him, and you can pretty much guess where it goes from there.
 * The Simpsons went to Italy. They visit Rome, the Tower of Pisa, and a Tuscan village where Sideshow Bob just happened to be mayor. They see an opera being performed in the Colosseum. In the closing credit montage they visit Venice.
 * Futurama: Mario also serves up stereotypical dialogue as a representative of Italy in a video game reimagining.