Heathers (1989)
I've generally tried to avoid all things high school related since I graduated 6-years ago but I've been told time and time again that if you're into dark comedy, then this one is a must-see. I can see where they're coming from, it's a very perverted version of the typical John Hughes formula and as someone who hated high school I would be lying if I said I didn't glee in satisfaction when the popular students died horrible deaths, and then laughed when their deaths only further cemented their popularity. In many ways Christian Slater's character kind of reminds me of myself in high school, quick witted, offset, and slightly deranged.