The soundtrack features songs by Newman , Bobby Darin , The Who , Free , Eels , The Guess Who , Bill Withers , Betty Carter , Peggy Lee , The Folk Implosion , Gomez , and Bob Dylan , as well as two cover versions — The Beatles ' " Because " performed by Elliott Smith , and Neil Young 's " Don 't Let It Bring You Down " performed by Annie Lennox . Produced by the film 's music supervisor Chris Douridas , an abridged soundtrack album was released on October 5 , 1999 , and went on to be nominated for a Grammy Award for Best Soundtrack Album . An album featuring 19 tracks from Newman 's score was released on January 11 , 2000 , and won the Grammy Award for Best Score Soundtrack Album . Filmmaker considered the score to be one of Newman 's best , saying it " [ enabled ] the film 's transcendentalist aspirations " . In 2006 , the magazine chose the score as one of 20 essential soundtracks it believed spoke to the " complex and innovative relationships between music and screen storytelling " .