Ferris Bueller (Matthew Broderick) from Ferris Bueller’s Day Off (1986)

As with The Goonies, the fact that sister Jeannie (Jennifer Grey) has a few years on Ferris doesn’t mean the younger sibling doesn’t get the run of the Bueller household, as you can see for yourself here. Ferris uses his wit, audacity and disregard for rules to run rings around everyone, from his parents to the school principal to his best friend Cameron (Alan Ruck from Succession).

When Ferris wants to ditch school, steal someone else’s reservation at a fancy restaurant or indulge in a little impromptu singing on a parade float, well, he just does it. What’s worse, he seems to suffer no negative consequences for anything he does—even though wrecking your best friend’s father’s Ferrari is probably a pretty good reason to be grounded for at least a few weeks.

With his devil-may-care attitude and his longstanding rivalry with the dim-witted Principal Rooney (Jeffrey Jones), Ferris is the epitome of teenage cool—but honestly, if you had a him as a little sibling, wouldn’t you hate him just as much as Jeannie does?