Clueless - 1995
This classic coming-of-age film follows shallow and rich Cher Horowitz (Alicia Silverstone) navigating her high school days. Of course, the plot thickens as Cher's popularity is challenged by a newcomer (iconic Brittany Murphy). Despite Cher's efforts to "help" Tai, things backfire for the privileged student and she's forced to take a shot of reality.