You wouldn’t think a movie based on Jane Austin’s Emma would be hilarious, but you’d be wrong. Clueless was the high point of Alicia Silverstone’s career, and with good reason. A high school comedy that actually deals with high stakes issues, Clueless taught all of us how to dress, how to flirt, and that “Searching for a boy in high school is as useless as searching for meaning in a Pauly Shore movie.”