Henry Fool is a 1997 dark comedy starring Thomas Jay Ryan in a story about a passionate novelist frustrated with his lack of success in the literary world and his confusion about what success even means. Henry Fool (Ryan) is a dark character with a criminal history. He's devoted to his art but can never break into the mainstream. Henry runs into a garbageman named Simon Grim (James Urbaniak), and the two social outcasts strike up a friendship. Henry teaches Simon about literature, a world of expression that Simon is immediately drawn to. However, when rough-around-the-edges Simon quickly ascends to dizzying heights of popularity and acclaim for his poetry, Henry Fool is left feeling abandoned and untalented, still incapable of finding a market for his own work. Parker Posey co-stars as Fay Grim, Simon's sister and Henry's love interest. Henry Fool is written and directed by Hal Hartley, who also wrote and directed the sequel, Fay Grim.