This book examines how pain is represented in a range of literary texts and genres from the nineteenth-century United States. It considers the aesthetic, philosophical, and ethical implications of pain across the works of Ralph Waldo Emerson, Harriet Jacobs, Emily Dickinson, Henry James, Elizabeth Stuart Phelps, and Alice James, as the national culture of pain progressively transformed in the wake of the invention of anesthesia. Through these writers, it argues that pain, while undeniably destructive, also generates language and identities, and demonstrates how literature participates in theorizing the problems of mind and body that undergird the deep chasms of selfhood, sociality, gender, and race of a formative period in American history. Writing Pain considers first Emerson’s philosophy of compensation, which promises to convert pain into gain. It then explores the limitations of this model, showing how Jacobs contests the division of body and mind that underwrites it and how Dickinson challenges its alleged universalism by foregrounding the unshareability of pain as a paradoxical measure of togetherness. The book investigates next the concurrent economies of affects in which pain was implicated during and after the Civil War and argues, through the example of James and Phelps, for queer sociality as a response to the heteronormative violence of sentimentalism. The last chapter on Alice James extends the critique of sentimental sympathy while returning to the book’s premise that pain is generative and the site of thought. By linking literary formalism with individual and social formation, Writing Pain eventually claims close reading as a method to recover the theoretical work of literature.