American Pie

July 9, 1999: Paul Weitz directed this $11 million teen comedy for Universal — until the MPAA slapped it with an NC-17. Weitz edited it down to an R, and Adam Herz's script became the blueprint for a decade of raunch comedies. Jason Biggs as the perpetually flustered Jim, Seann William Scott as the unforgettable Stifler, Eugene Levy as Jim's cringe-inducing dad—the casting was perfect.

$235.5 million worldwide on an $11 million budget wasn't just a hit; it was a cultural mandate. Alyson Hannigan's one throwaway line—"this one time, at band camp"—became immortal, uttered in playgrounds and locker rooms for years. The film smuggled a new vocabulary into every American household and gave audiences permission to be explicit about what teen comedies had always secretly been about.

American Pie 2 landed in 2001 even bigger than the original, followed by American Wedding in 2003—the trilogy raked in over $750 million worldwide (and the franchise closed in on $1 billion once 2012's American Reunion brought everyone back), cementing this as the blueprint every studio tried to copy. The sequels proved this wasn't a one-joke phenomenon; it was a lifestyle comedy, and it set the tone for how openly mainstream media would talk about sex and the teenage body for the decade to come.