7. Ferris Bueller – Ferris Bueller’s Day Off (1986)

An absolute icon of the ’80s, Ferris Bueller is the typical lovable bad boy. He takes his friends on a glorious day of wacky hijinks and adventure, and manages to get himself home before his ruse is found out. Not a hero in the strictest sense, but the audience is supposed to root for him, so he fits the bill.

However, Bueller’s actions are actually incredibly problematic. He leads his best friend and his girlfriend astray (despite the former’s objections) by talking them into skipping school. Technically, this is a crime, and it also could potentially affect their futures, establishing that Bueller’s pursuit of fun comes at the expense for any thought of how it affects others.

Moreover, his constant dismissal of Cameron’s anxieties proves how little he really cares about his friend. In their friendship, it’s Ferris’ way or the highway, and Cameron is forced to play along with his reckless pal’s dangerous ideas. Still, there’s a theory that Ferris is actually a figment of Cameron’s imagination, so maybe the real villain is the rebellious spirit inside of us all?

Also, it’s worth noting that Ferris’ intentions are generally pure – he wants to give his friend a fun day and cheer him up – but it’s his methods that make him far less than heroic.