This chapter argues that US urban labor literature depicts cities as sites of geographic, social, and political contestation. The chapter focuses on three historical periods: the early twentieth century, when the immigration surge from southern and eastern Europe transformed the several US cities, especially New York; second, the long 1930s, when economic collapse, internal migration, and the new union power recast labor’s possibilities; and third, the post-1970s era, when globalization, deindustrialization, and immigration from Latin America and Asia dismantled the industrial working class and created new terms on which to imagine labor’s claim to the nation’s increasingly transnational cities. Cutting across the antinomy of division and solidarity labor literatures of the city –– realist, modernist, and in more speculative modes –– depict the deeply contradictory nature of urban space for working people, who are the source of so much of the city’s social and economic wealth, yet can win their share of it only through collective struggle. Texts include Ridge, “The Ghetto”; Wright, Native Son; LeSueur, The Girl; Russell Banks, Continental Drift; and Riker’s film The City/La Cuidad.