Claes Oldenburg’s commitment to familiar objects has shaped accounts of his career, but his associations with Pop art and postwar consumerism have overshadowed another crucial aspect of his work. In this revealing reassessment, Katherine Smith traces Oldenburg’s profound responses to shifting urban conditions, framing his enduring relationship with the city as a critical perspective and conceiving his art as urban theory. Smith argues that Oldenburg adapted lessons of context, gleaned from New York’s changing cityscape in the late 1950s, to large—scale objects and architectural plans. By examining disparate projects from New York to Los Angeles, she situates Oldenburg’s innovations in local geographies and national debates. In doing so, Smith illuminates patterns of urbanization through the important contributions of one of the leading artists in the United States.