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.