American Pie (1999)

Here it is, the end-of-the-’90s teen romp that spawned a million imitators, virtually invented the term MILF, forever altered the popular perception of what goes on at band camp, and changed the way you think about Uncle Sam's most patriotic dessert. We're talking, of course, about the iconic teen sex comedy American Pie (1999). While it essentially relaunched the genre that had died out after the 80's, the film's plot is pretty classic: a group of high-school seniors takes a vow that they'll all lose their virginity by prom night. All the boy have different schemes. The class jock Oz (Chris Klein) decides to join choir and chase after Mena Suvari, Kevin (Thomas Ian Nichols) thinks he can use his mouth to convince his girlfriend Vicky (Tara Reid) that going all the way would feel amazing for her. And he doesn't use words to do so. Finch (Eddie Kaye Thomas) ends up lusting after the legendary cougar mother of class a-hole Stifler (Seann William Scott), played by Jennifer Coolidge. But it's Jim (Jason Biggs) whose attempts are the most painful. After getting caught jerking off into a pie to feel what the real deal feels like, he decides to go for the the foreign exchange student Nadia (Shannon Elizabeth). Unfortunately, when she's pleasuring herself on the bed and not so sad to see Jim walk in on her, he spews his goo way too early, and is forced to go to prom with the secretly freaky band geek Michelle (Alyson Hannigan). Tons of gross out gags from this one became iconic, but nothing was more memorable than Nadia's nudity. At one point, the boys decide to set up a webcam in Jim's room to watch Nadia change her clothes. But Nadia doesn't just get topless. She finds Jim's porn and starts getting off to it, before he shows up and creams his pants when she decides to let him in on the action. Can't blame him. You can not go from doing a Dutch Apple to fornicating with the hottest foreign exchange student ever set to screen! Hilariously parodied by having the foreign exchange student in Not Another Teen Movie (2001) constantly topless, including in school, the scene was instantly unforgettable. The sequels and spinoffs might have diluted the brand, but the original's greatness can never be tainted. The levy was dry, but our boxers weren't after watching American Pie!