Michael Douglas is Grady Tripp, a college professor and award-winning novelist whose latest book is seven years overdue. Among his current crop of students is James Leer (Tobey Maguire), a highly-talented young writer who, at a party held during the college's annual literary festival, accidentally manages to kill the Head of Department's dog. Grady helps James dispose of the beast, but one thing leads to another, and the pair soon find themselves on a strange odyssey involving drugs, bar fights, lost manuscripts, and stolen Marilyn Monroe memorabilia, with Grady reeling from the announcement that his mistress (Frances McDormand) is pregnant, and literary agent Terry Crabtree (Robert Downey Jr) doing his best to get James into bed.