If America worships success, then why has the nation's literature dwelled obsessively on failure? This book explores encounters with failure by nineteenth-century writers – ranging from Edgar Allan Poe and Herman Melville to Mark Twain and Sarah Orne Jewett – whose celebrated works more often struck readers as profoundly messy, flawed, and even perverse. Reading textual inconsistency against the backdrop of a turbulent nineteenth century, Gavin Jones describes how the difficulties these writers faced in their faltering search for new styles, coherent characters, and satisfactory endings uncovered experiences of blunder and inadequacy hidden in the culture at large. Through Jones's treatment, these American writers emerge as the great theorists of failure who discovered ways to translate their own social insecurities into complex portrayals of a modern self, founded in moral fallibility, precarious knowledge, and negative feelings.