Based on a novel by Michael Chabon, the film tells the story of Grady Tripp (Michael Douglas), a Pittsburgh professor-writer struggling with writer’s block. To complicate matters, his wife has just left him, and he is having an affair with the school’s chancellor (Frances McDormand). All the while, he and one of his students (Tobey Maguire) are trying to find a rare jacket once owned by Marilyn Monroe, and another student (Katie Holmes) has a bit of a crush on him.