2. Billy Madison
Back to school. Back to schooool. Billy Madison put Sandler on the Hollywood map in this flick where a witless spoiled dimwitted rich kid goes to school in hopes of saving his fathers business. This is Sandler simultaneously at his stupidest and funniest. Watching Billy Madison is akin to watching a 90 minute Saturday Night Live sketch that defies staleness and keeps the running joke of a grown man in school rolling with plenty of steam. He falls in love with his teacher, argues with children about Donkey Kong and Mortal Kombat, there are cameos from the late great Chris Farley featuring some of his most iconic lines, and even more off-color scenarios. It is also my personal favorite and most quotable Sandler comedy.
Principal: Mr. Madison, what you've just said is one of the most insanely idiotic things I have ever heard. At no point in your rambling, incoherent response were you even close to anything that could be considered a rational thought. Everyone in this room is now dumber for having listened to it. I award you no points, and may God have mercy on your soul. Billy: Okay, a simple "wrong" would've done just fine.