Clueless is without a doubt the ultimate in high school movies. The era of Phoebe Cates came to an end when the adorable girl from the Aerosmith videos decided to play the part of a lovable, and often gullible, rich girl.
While Clueless avoided the faults of the teen sex comedies that would follow (looking at you, American Pie, and all your weird franchised nostalgia,) they did manage to include Boston ska band the Mighty Mighty Bosstones in a dance scene, who I just discovered are still a band. Someone please tell me why ska is still a thing.