2. Billy Madison
It was hard for me to pick only one Adam Sandler movie for this list, because the man embodied PG-13 comedies for a long time. However, although Billy Madison is extremely childish and doesn’t really have much of a plot, the quotability and legacy this movie has was enough for me to put it on this list.
Living off his father’s money his whole life, Billy (Sandler) is distraught to learn that he will not be taking over his father’s company when he retires. In an effort to prove to his father that he isn’t a complete failure, Billy Madison decides he will go back to school, with the stipulation that he must complete all 12 grades in order to take over the family business. Why am I even telling you this? We’ve all seen it and love it, and only snobs turn their nose up at this classic comedy.