5 — Ferris Bueller’s Day Off (1986)

Ferris Bueller is selfish, arrogant and smarmy, and Ferris Bueller’s Day Off is all about a dude who breezes through life having yet-another awesome day where the world seemingly bends to his whim.

The movie is still quite a bit of fun. Matthew Broderick is such a delight that he almost (we stress almost) makes up for how obnoxious Ferris is. It’s a breeze to watch. Also, do you know who we like Cameron. And Sloane.

If Ferris were a more likable character, or the movie did not play as if though you’re supposed to like him, Ferris Bueller’s Day Off would be much higher on this list, perhaps at the top. Instead, where it succeeds, it succeeds in spite of Ferris, not because of him.

Like a lot of John Hughes movies, it asks us to root for some sometimes unlikable characters. And pulls it off.