Focusing on the work of Stuart Dybek and a case study of the literature of South Shore, this chapter considers how the neighborhood literature of Chicago has taken shape in response not only to literary antecedents but also to historical changes in the city’s neighborhood order. The emergence of the New Chicago, a post-industrial metropolis that developed through and around the old familiar industrial city, created new possibilities for the city’s writers. Stuart Dybek’s stories of Pilsen/Little Village have made him the dean of the New Chicago’s writers, putting him at the head of a cohort that ranges from Gwendolyn Brooks to David Mamet, Nelson Algren to Gabriel Bump.

Looking back at the mid-twentieth century, we can assemble a cohort of works that paint a composite portrait of neighborhoods as the industrial city as it reached full maturity, with decline approaching or already under way.In the postwar decades, neighborhood literature shifted in its response to the challenge of representing cities as the postindustrial metropolis, primarily organized not around turning raw materials into finished products but around handling information and providing services, began to emerge around and through the receding industrial city.As the postindustrial city matured in the final decades of the twentieth century and the opening years of the twenty-first, neighborhood literature took on the task of mapping it with greater nuance.One city that experienced a postindustrial renaissance in neighborhood stories was Boston; the many movies set there deploy the equipment of genre fantasy to consider what has been gained and lost in the changes that shaped the postindustrial city. They are, in part, about the possibilities opened up by this transformation.