This book provides a first overview and interdisciplinary discussion of imaginary dialogues in American literature and philosophy from the eighteenth century to the present. It combines the perspectives of literary studies, philosophy, linguistics and political history to offer wide-ranging analyses of 19th-century anti-slavery dialogues and the dialogical writings of Thomas Paine, Benjamin Franklin, Charles Brockden Brown, Washington Irving, Edgar Allan Poe, Henry David Thoreau, Herman Melville, Henry James, William James, Charles Sanders Peirce, George Santayana, Gertrude Stein, Jerome McGann, Leon Forrest, Paul Feyerabend, Corey Mesler, Nicholson Baker and Cormac McCarthy. Taking a fresh look at these American writers the essays in this volume explore the important yet marginalized tradition of dialogical writing and highlight the transatlantic nature of many American dialogues.