As a reassessment of the southern grotesque, this dissertation places Flannery O’Connor, Carson McCullers, and William Faulkner in context and conversation with the fiction of Fyodor Dostoevsky. While many southern artists and intellectuals have testified to his importance as a creative model and personal inspiration, Dostoevsky’s relationship to southern writers has rarely been the focus of sustained analysis. Drawing upon Mikhail Bakhtin’s deeply positive understanding of grotesque realism, I see the grotesque as an empowering aesthetic strategy that, for O’Connor, McCullers, and Faulkner, captured their characters’ unfinished struggles to achieve renewal despite alienation and pain. My project suggests that the preponderance of a specific type of character in their fiction—a physically or mentally deformed outsider—accounts for both the distinctiveness of the southern grotesque and its affinity with Dostoevsky’s artistic approach. His grotesque characters, consequently, can fruitfully illuminate the misfits, mystics, and madmen who stand at the heart—and the margins—of modern southern fiction. By locating one source of the southern grotesque in Dostoevsky’s fiction, I assume that the southern literary imagination is not directed incestuously inward toward its southern past but also outward beyond the nation or even the hemisphere. This study thus offers one of the first evaluations of Dostoevsky’s impact on southern writers as a group.