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16. Superbad (2007)
Key players: Michael Cera, Jonah Hill, Bill Hader, Seth Rogen, Emma Stone
Why it's great: "Superbad" is only five years old, but it is arguably one of the greatest teen comedies ever (and it obviously qualifies for this R-rated comedy ranking). Written by Rogen and Evan Goldberg, the Greg Mottola directed comedy takes the familiar storyline of two "geeks," "nerds," etc. having a momentous life-changing night but gives it a dramatic twist: will our two heroes (and best friends) be honest with each other about separating as they head to college after so many years as a dynamic duo? It's a growing up moment that's rarely addressed in popular media, but almost everyone has gone through. Granted, without crazy policemen, losing your virginity and crashing parties all at the same time (well, maybe for some of us).
- Gregory Ellwood