15 Most Unexpectedly Depressing Movies Of All-Time

9. Adventureland (2009)

The problem with Adventureland is that it was marketed like it was another Superbad. If you've seen Adventureland, you'll know that it wasn't, and you'll also recall the feeling that it left you with as the credits began to roll: something akin to an "uncomfortable depression." It didn't help as far as expectations were concerned that it was directed by Greg Mottola, who - yes - also directed Superbad. No wonder people were critical in the aftermath! The film, set in 1987, concerns Jesse Eisenberg's confused and semi-likeable (except not really) protagonist, James Brennan, as he takes on a summer job at the theme park of the movie's title. What you'd probably expect from that premise alone is tons of sexy girls, wacky hi-jinks and crazy characters, and that's what you sort of get (we said "sort of"). To be frank, Adventureland is clouded in a strange melancholia. It's difficult to watch it without feeling genuinely glum. The romance at the centre is filled with dark moments. It doesn't offer anything close to "a good time at the movies." Which isn't a bad thing - it was just the last thing anybody likely expected in the wake of its funny trailer and Superbad.