Rushmore (1998). (Entertainment Weekly's list)
This was the second movie for Wes Anderson and probably my favorite of all of his movies. (Bottle Rocket, The Royal Tenenbaums and The Life Aquatic with Steve Zissou are some of his other films.)
This stars Jason Shwartzman and Bill Murray, in one of his most brilliant dramatic/comedic roles to date, and Olivia Williams. This is a quirky, charming and extraordinary tale of a young school boy too brilliant for his age - and that gets him into all sorts of trouble.
The music was filled with classic rock gems from the 1960's from bands like Cat Stevens, The Who, The Faces and The Kinks. I own the album and the movie, of course! I recommend both. There really isn't much more that I can say except that I adore this film and the soundtrack and it so deserves to be on this list.
Rushmore (Soundtrack from the Motion Picture) - Various Artists