Simon Grim (James Urbaniak) is a garbage man whose life is about as unpleasant and uneventful as it can get; he doesn't care much for his job, and he shares a house with his cranky mother Mary (Maria Porter) and his morally suggestible sister Fay (Parker Posey). One day, Henry Fool (Thomas Jay Ryan) appears, claiming to be a writer in the midst of a major project entitled "Confessions," and needs a place to stay. After moving in with Simon and his family, Henry encourages Simon to begin writing himself. When several of Simon's pieces are posted on the Internet, he quickly develops a huge and rabid following and is acclaimed as one of the great authors of our time. Henry, however, isn't able to get anywhere with his own book or his own life. As Simon's star begins to rise, Henry's life spins slowly downward.