This chapter explores the shared circumstances, collaborations, and socializing that drew modernist poets and painters together in New York, but also the critical discourse of medium specificity that insisted on the separation of their endeavors. William Carlos Williams established proximity with the Stieglitz Circle painters, admiring (and occasionally acquiring) their work, which he rendered in ekphrastic poems. While Wallace Stevens’ early career was also shaped by encounters with these artists, his poetry maintained a distance from while suggesting parallels with visual art. The chapter moves from Williams’ and Stevens’ contrasting approaches through Clement Greenberg’s assertions of medium-specificity to Frank O’Hara’s at once intimate and ambiguous relationship with midcentury American painting and painters. O’Hara’s collaborations with Grace Hartigan and Larry Rivers suggest close connections but no fixed relationships between writing and painting. The chapter concludes with Glenn Ligon, whose late-twentieth-century paintings catch the messiness of preceding word–image encounters but convey an urgent need for communication that extends beyond the dialogue between writing and painting.

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.