Rushmore (1998)

I've heard a lot of good things about Wes Anderson's Rushmore over the years but, for some reason or another (I can't recall any of those at the moment), I never checked it out. 

The film follows Max Fischer (Jason Schwartzman), a nerdy, precocious 15-year-old kid who earned a scholarship to the exclusive prep school Rushmore, where he is not doing very well in any of his classes as he doesn't bother to study and spends all of his time enjoying (too) many extracurricular activities. His life takes an unexpected turn as he befriends a depressed middle-aged local industrialist, Herman Blume (Bill Murray), and falls for a recently widowed teacher, Ms. Cross (Olivia Williams). 

Bottle Rocket (1996)

Having seen all of Wes Anderson most recent films, and having adored every single one of them, I decided to check out the rest of his filmography, starting with Bottle Rocket, his debut.

The film follows a group of friends who decides to rebel against the norms of everyday life to pursue a career of professional criminals. After Dignan (Owen Wilson) rescues Anthony (Luke Wilson) from a voluntary mental hospital, they convince their friend Bob (Robert Musgrave), who has a car, to join them and rob a library. After successfully pulling off the heist, they hide out in a roadside motel where the group of friends eventually breaks down and things take a turn for each one of them.