9. Ferris Bueller - Ferris Bueller's Day Off
Ferris is one of those guys who you think is so cool in high school -- or as the secretary would say, he's a righteous dude. He skips school, has amazing adventures in Chicago with his best friend and super hot girlfriend, cons his parents and teachers, and basically just sticks it to the man 24/7. But something happens when you're out of high school and college. You rewatch this movie, and you realize that Ferris is kind of a jerk. He bullies his friend, comes up with these ridiculous hijinks, and for what? To go to the Sears Tower? An art museum? A snooty French-style restaurant? Sure, the parade is fun, but Ferris is so into himself I'm surprised he doesn't break up with Sloane and just date himself. As much as I loved this movie as a kid and it will always have a special place in my heart, sometimes I really do want to punch Ferris in his smug little face.