5. Ferris Bueller's Day Off (1986)
http://www.youtube.com/watch?v=oqQFTq2FIdY Already touched on in the intro, I wanted to leave this off and just make this list the "Honorary Ferris Bueller's Day Off" list, but I just couldn't do it. Ferris Bueller is so cool that, even though it's a fictional film, fan theories abound claiming that even in the make-believe world the movie exists in, Ferris can still only be a figment of one's imagination. Ferris is as hip as that fan theory is dumb. He's loved by everybody, the sportos, the motorheads, even the wastoids; they all know he's quite the righteous dude. So when Ferris jumps into the midst of a Chicago parade and leads the city in his renditions of Twist and Shout and Danke Schoen, it's truly one of the coolest things a character has even done in film.