44. Billy Madison (1995)
Director: Tamra Davis
Stars: Adam Sandler, Darren McGavin, Bridgette Wilson, Bradley Whitford, Norm MacDonald
Like Nas with Illmatic, Adam Sandler's first project stands as his greatest work. Let's not cast such serious praise on Billy Madison, though; instead, let's acknowledge the quintessential "stupid" comedy for its unflinchingly juvenile humor, its barrage of sophomoric one-liners, and how it laid the groundwork for overgrown man-kid characters to come, like Will Ferrell and John C. Reilly in Step Brothers.
It doesn't get much funnier than Sandler threatening elementary school kids for their snack packs or smack-talking his way through spelling bees. Sandler's goofball schtick may have lost some of its punch today, but back in 1995, he was an infantile-minded powerhouse, and Billy Madison is his crown jewel of funny childishness. —MB