4. Edward Rooney - Ferris Bueller's Day Off (1986)
Ferris Bueller's Day Off is a movie about an incredibly popular high school student who decides to skip school for a day, bring his super hot girlfriend along so he can make out with her as much as possible, and rope his anxious best friend into doing a bunch of things he doesn't want to do. It's a great movie. The undoubtable villain of the piece, though, is one Mr. Edward Rooney, the Dean of Ferris' school, and the one man who dedicates his entire existence to stopping Ferris from having his precious day off (this is back in the '80s, when teachers still cared, and there was hope for humanity still tucked away in schools). And though the movie attempts to make Rooney look like a real bore, what with all the scrapes that writer/director John Hughes implements, the man is just doing his job. And to be fair, Ferris is kind of annoying in the sense that he's so smarmy about everything he does. He's also a liar, a theft and a but of jerk to best friend, Cameron, who spends much of the infamous "day off" staring into space looking like he's contemplating suicide. No, Rooney isn't cool, nor is he supposed to be - but the point is that he doesn't want his students skipping school and pretending to be sick so they can trapse around art galleries and crash cars through glass windows. We challenge you to find teacher nowadays who gives as much of a damn as this guy does about education.