Film stills via Rag Pony
Heathers (1988) is an outstanding presentation of dark humour and teen angst at its best. Winona at the prime age of seventeen, glorious costume and set designs, which fit perfectly with the reflections of late 1980s pop culture and the social hierarchy of your typical American high school. Trivia note: Winona was a huge fan of Paul Westerberg, of The Replacements, and convinced the director to name the high school in the film after the musician. I love Paul Westerberg. And is Heathers super-cool.