4. Billy Madison (1995)
Taking the phrase "man-child" to new lengths,
Billy Madison stars Sandler as the titular character, a sweet but dimwitted man who lives off of his family's fortune from running a hotel chain. However, when his father decides to retire as CEO and appoint his brother (Bradley Whitford) as the new charge, Billy protests, claiming that going through a crash-course of school again - for his dad bribed his teachers the first time around - will prove his competence. Like many of Sandler's films, it's a nutty, goofy premise, but it certainly never bores, and benefits from some great supporting work, specifically Bridgette Wilson as Madison's hot teacher. The film is perhaps best remembered for the hilariously condescending put-down handed out to Billy during a spelling bee late in the film: "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". Despite being one of Sandler's more popular mid-90s films in retrospect, it grossed only $26m at the box office, and has 45% on Rotten Tomatoes.