Grady Tripp is a middle-aged philanderer with a penchant for pot and failed marriages, who is unable to complete the long-awaited follow-up to his award-winning novel. His brilliant student James Leer is a troubled young writer obsessed with Hollywood suicides and prone to fabrication and petty thievery. In their odyssey throuh the streets of Pittsburgh, Grady and James are joined by Grady's pregnant mistress, his hilariously bizarre editor, and an achingly beautiful student lodger. The result is a wildly comic, poignantly moving, and ultimately profound search for past promise, future fame, and a purpose to Grady's life.