Socially inept garbage-man Simon Grim is befriended by Henry Fool, a witty rogue and untalented novelist. Henry opens the world of literature to Simon, and inspires him to write "the great American poem." Simon struggles to get his work recognized, and it is often dismissed as pornographic and scatological, but Henry continues to push and inspire Simon to get the poem published.
Seven years after the events of ''Henry Fool,'' Fay Grim (Parker Posey) is coerced by a CIA agent (Jeff Goldblum) to try to locate 'the confession novel' notebooks that belonged to her fugitive husband (Thomas Jay Ryan) whom he believes to be deceased. Fay is launched into a world of espionage as she travels to Paris to retrieve some of the journals, each having mysteriously appeared in the hands of the most unlikely of people. Simon Grim, Fay's brother and Nobel Prize–winning poet because of Henry, remains home with his sister's son, the CIA and his publisher.