Using Frantz Fanon’s depiction of the colonial city in The Wretched of the Earth (1961) as a starting point, this chapter argues that the very disjunctiveness of Manichean colonial urban forms is key for perceiving, analysing, and indicting the colonial system, as well as for imagining paths for decolonization. Moreover, understanding the city as a site of contestation and anticolonial desires allows us to rethink the role of the urban in world literature studies. In contrast to models that assume the city as a node that endows literary value, this chapter views the (post)colonial city as a crucible in which the critical energies of decolonization emerge, take literary expression, and circulate in new ways. The chapter examines three representative literary examples, all focusing on Asian metropolises: José Rizal’s Noli Me Tangere; Kim Chi-ha’s Five Thieves (Ojŏk); and Arvind Adiga’s White Tiger. Respectively, they depict a racially-divided colonial capital at the end of the nineteenth century (Rizal’s Manila); a recently decolonized, post-civil war city under dictatorship (Kim’s Seoul); and a paradigmatic conurbation of twenty-first-century neoliberal capitalism (Adiga’s Gurgaon).