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.
Brittany Murphy's life was cut short, but her career lives on in Tai's famous insult to Cher, calling her a "virgin who can't drive." Even though this movie is 26-years-old, teenagers everywhere can relate to the bizarre high school dynamic.