Rushmore (1998)

Rushmore was a 1998 comedy-drama film directed by Wes Anderson and co-written by Anderson and Owen Wilson.
It was about a teenager named Max Fischer (played by Jason Schwartzman) and his friendship with the rich industrialist Herman Blume (played by Bill Murray), and their love for elementary school teacher Rosemary Cross, (played by Olivia Williams).
The soundtrack was scored by regular Anderson collaborator Mark Mothersbaugh (Devo) and features several songs by bands associated with the British Invasion of the 1960s.

The film not only helped launch the careers of Anderson and Schwartzman, it also established a second career for Bill Murray in independent cinema.
Murray went on to dramatic roles in Wild Things, Cradle Will Rock, Hamlet (as Polonius), The Royal Tenenbaums and Lost in Translation.

Rushmore won Best Director and Best Supporting Male awards at the 1999 Independent Spirit Awards and Bill Murray earned a Golden Globe nomination for Best Performance by an Actor in a Supporting Role in a Motion Picture.

Rushmore came in at number 34 on Bravo's "100 Funniest Movies" and the film was ranked number 20 on "The Cult 25: The Essential Left-Field Movie Hits Since '83" list by Entertainment Weekly.

After this film, Jason Schwartzman went on to do I Heart Huckabees and The Darjeeling Limited.
Olivia Williams went on to do The Sixth Sense, A Knight's Tale and yes, an uncredited role in X-Men: The Last Stand as Moira MacTaggert.

Murray, Wilson and Schwartzman would later reunite on The Darjeeling Limited, directed by Anderson.