Following a successful first novel, writer and professor Grady Tripp (Douglas) is feeling pressure to deliver a brilliant followup, especially from his editor (Downey Jr.), who's just been fired. However, Tripp is struggling with a serious case of writer's block. In the meantime, he teams up with a college student (Maguire) to find a rare jacket once owned by Marilyn Monroe and begins an affair with the dean (McDormand). Simultaneously, a college student (Holmes) boarding with Grady has a bit of a romantic crush on her much older professor.
Based on a novel by Michael Chabon.
Winner of the 2001 Oscar Award for Best Song.