Adventureland (2009)
If it’s possible for a movie to make you nostalgic for a time during which you had yet to be born, that’s exactly what Adventureland does. Set in the summer of 1987, the film begins with recent college graduate James Brennan (Jessie Eisenberg) finding out his parents can no longer afford his Euro trip. So, instead of joining his friends on the adventure of a lifetime, he ends up working at an amusement park where the games are rigged and the corn dogs are inedible.
Loosely based on director Greg Mottola’s life, Adventureland is so relatable because it perfectly captures the naiveté and insecurity of post-graduates who still don’t quite have life figured out. This comedy is often as heartwarming as it is funny, making it a standout entry in the twilight of the Apatow-age of comedy.