8. Billy Madison (1995)
When Billy Madison hit theaters, critics dismissed it as low-rent comedy for the MTV-pilled. But audiences rallied around it, cementing it as a classic that created a star out of Adam Sandler, who plays the dimwitted, spoiled son of a CEO who must repeat his entire schooling to win control of his father’s company. This has effectively been the story of Sandler’s whole career: His is the face of critically unpopular comedies that earn repeat viewings and loyalty from “normal” people. Whether or not Billy Madison is actually good – it’s pretty good, really!– its true importance lies in setting up Sandler’s ball before he spiked it one year later.
