Heathers is a black comedy/satire from the late 80s, not all of the humour is acceptable by today’s standards, it made Christian Slater famous and propelled Winona out of child star into more adult roles.

Idk that it’s exactly what you’re looking for though. Winona plays a popular upper middle class girl (not zero by any stretch) who throws off the shackles of popularity and takes up with the new mystery guy at school. They plot revenge on bullies but it gets out of hand.