The Wedding Singer
Adam Sandler is an unlikely romantic hero – part goofy man-child, part rageaholic. (If you want to see what that combination looks like in a romance without jokes, watch him in Paul Thomas Anderson's weirdly intense Punch-Drunk Love.) Still, he has a vulnerability that's often sweetly appealing, never more so than in The Wedding Singer. Sure, it's funny when he shows off the rage side, particularly during a mopey tirade on the bandstand after his bride dumps him at the altar. But you also root for him to win adorable Drew Barrymore away from her wealthy douchebag fiancé. The '80s nostalgia aspect makes for a nice joke, but it's just gravy – except for how it allows Billy Idol to show up and serve as Sandler's wingman.