This article examines the changing practice of urban portraiture in reference to a selection of postmillennial texts written by Ivan Vladislavić. These generically diverse texts trace and reflect on transformations sweeping Johannesburg after the fall of Apartheid, to some extent a metonymic representation of South Africa. An immediate impulse to inquire whether and, if so, how the writer explores the boundaries of portraiture, derives from an explicit textual and visual thematisation of the practice in two of Vladislavić’s works, i.e. the collection of “verbal snapshots” entitled Portrait with Keys and his joint interdisciplinary project, TJ& Double Negative, involving the writer and David Goldblatt, a South African photographer. The article concentrates primarily on the uses and adaptations of the city portrait genre. Vladislavić’s foregrounding of the genre category invites us to consider a series of questions: How does Vladislavić proceed with the appropriation and transformation of the traditional practice of city portrait? Do the portrayals of Johannesburg merely address the past? To what extent does Vladislavić propose contemporary adaptations of the practice? What happens to such categories as realism, accuracy, and likeness? What knowledge does portraiture generate? Finally, the article reflects on whether Vladislavić responds to the need for a new epistemological project in rendering the urban.