This chapter explores urban prose, poetry and painting that moves from sense impressions of city streets to statements about American social and political conditions. A strain of American culture, from Ashcan School painting through James Baldwin’s essays on Harlem to Don DeLillo’s set-piece performative protests, insists that the nation’s politics take shape and moods register on city streets. It argues that certain, primarily literary, forms, through their close attention to, and lucid expression of, the way streets feel offer access to experiences that range from jostling crowds to organized protests to violent confrontations. Where the flâneur pursues urban aesthetics and impressions in the spirit of dilettantism, Henry James restlessly analyses New York’s metropolitan scale; insiders and outsiders probe the tensions that shape ethnic enclaves; and in Tillie Olsen’s strike journalism and E. L. Doctorow’s political fiction of mass protests are at once inspiring and monstrous. Where Doctorow and DeLillo describe postmodern withdrawal from the street as a site of meaning, the chapter ends with its reemergence with Occupy and other recent protest movements.