Rushmore (1998)

[cakefactory]

I HATED it on first watch and absolutely loved it on second. If you haven't seen any other Wes Anderson movies, I don't know if you'd like it or not. If you're looking for a zany Bill Murray performance you're not going to get it. The main character of the film is an extremely immature but brilliant teen who falls in love with his teacher, and Bill Murray is a lonely rich guy in a loveless marriage who falls for the same teacher. It is a quirky film with plenty of laughs, but it doesn't shy away from the awkwardness and pain of the various characters. If you can remember what it was like to be a stupid, impetuous teenager in love with someone you could never have, then you'll probably be able to relate to the main character and love it. If not, you'll probably just find him obnoxious and terrible and might hate the movie.

I think Royal Tenenbaums might be the "easier" entrance into the Wes Anderson filmography, but I think Rushmore is widely considered his best. I like them about equally.