This chapter discusses literary representations of the ‘peripheral’ city, highlighting depictions of the urban landscape as dreamlike and anachronistic in modernist and proto-modernist texts. From Dostoevsky to Machado, Kafka to Joyce, the clash between imperial and Westernising discourses, on the one hand, and the perceived incompleteness of urban modernity at the periphery of Western Europe, on the other, played a key role in the critical and experimental urban aesthetics that emerged from the late nineteenth century. Chronicling literary responses to the complex modernity on display at the margins of European culture, the chapter builds towards a theory of modernism at the urban semi-periphery – or metrocolonial modernism.