This article discusses how authors such as Olivia Laing and Ivan Vladislavic are positioning homelessness as a form of resistance against “good life” fantasies and neoliberal success narratives (Berlant, 2011). Laing’s quasi-autobiographical novel interweaves multiple narratives of New York residents, including openly queer and homeless artist David Wojnarowicz, to explore the collective isolation of individuals within the confines of a globally interconnected neoliberal metropolis. Laing’s novel redefines our connection to city living and the importance of creating community spaces in the face of mass, systemic, isolation. Similarly, Vladislavic turns to the streets of Johannesburg to create interlacing narratives of South African figures through vignettes. By presenting the “street people” of the novel as a resourceful and supportive counter-cultural group, Vladislavic presents a version of homelessness that centres on reclaiming the streets through a focus on community rather that neoliberal individualism. Consequently, both novels create and empower counter-neoliberal alternative spaces of community for homeless figures and juxtapose them against the expectations of individualism and material success associated with twenty-first century neoliberal living. This article’s primary analysis is informed by work on neoliberalism, psychogeography and urban living and draws on key thinkers such as David Harvey (2014) and Michel De Certeau (1988), alongside Judith Butler and Athena Athanasiou (2013). My research is informed by the wider cultural context of neoliberalism, and overall, explores the depiction of homeless figures in The Lonely City and Portrait with Keys and argues that both novels reclaim the city streets through their depiction of homeless communities by positioning homeless characters as a form of resistance and an alternative to the individualistic nature of twenty-first century neoliberal living.