Rushmore

Max Fischer (Jason Schwartzman) is an odd friendless teen at a private school with lots of useless extracurricular activities. He get put on academic probation, and falls obsessively in love with elementary teacher Miss Cross (Olivia Williams). He befriends an equally odd wealthy Herman Blume (Bill Murray), the owner of a pipe company. She dates Dr. Peter Flynn (Luke Wilson) which raises the ire of Max. Then Herman becomes infatuated with the lovely teacher and Max gets kicked out of private school.

These are truly uncompromisingly odd characters. They are a quirky unconventional group. They are not immediately hilarious but funny in how wacky Schwartzman gets. The dialog is sharp with a lot of unusual Wes Anderson takes. Bill Murray extends his range starting an acting relationship with Wes. It's a wonderful move forward for Wes and friends.