4. Clueless
Clueless tells the tale of Beverly Hills raised Cher in the glory years of high school. Throughout her high school adventure we witness Cher and pal Dion wear some ridiculous outfits, think of clever ways to get out of P.E. class, give the most interesting and insightful arguments in debate class, give hopeless new students make-overs, play match maker to friends and teachers, attend some raging valley parties, all while learning how to drive. Now that is quite the high school experience. You watch Clueless for the insane advice of Cher and Dion. You watch Clueless to find out just how sympathetic your teachers might be to a bad relationship. You watch Clueless to see Ty get made into the most popular girl of the trio all thanks to her "near-death" experience at, where else, but the shopping mall. You watch Clueless to see Cher's disaster date with Christian. You watch as Cher finally lands the perfect man...her step-brother...well, ex-step-brother, (still doesn't make it any less weird.) But mostly you watch Clueless and wonder how the hell Paul Rudd does not age. It is mind-blowing, and that alone makes it worth watching every time it airs.