3. Clueless (1995)
Probably not the first film that springs to mind when someone says “comedy”, but almost certainly the first when they say “’90s”. No film quite embodies a decade like Clueless, with its vapid but emotionally intelligent teens, singular sense of style, and excellent high school story. For the latter, it has Jane Austen to thank, as it’s loosely based on her 1815 novel Emma.
Alicia Silverstone stars as Cher Horowitz, a wealthy and popular teen living in Beverly Hills. After taking “clueless” transfer student Tai (Brittany Murphy) under her wing, Cher finds herself embroiled in a whirlwind of high school drama . Oh, and it also stars the apparently ageless Paul Rudd as Cher’s ex-step-brother, Josh.
What makes Clueless so great is that it’s comedy is written so carefully into its script. It manages to poke fun at the vapid teens of the ’90s without feeling mean-spirited, and it also tells an excellent story to boot. Hard to imagine anyone arguing with its inclusion on this list (only maybe at its placement).