This chapter argues that the work of Ivan Vladislavić offers a sophisticated response to the dangers of selective memory—and memorialization—that characterizes some responses to the disappointments of the ‘new’ South Africa. Using Svetlana Boym’s differentiation (in The Future of Nostalgia) between reflective and recuperative forms of nostalgia, the chapter considers the turn to nostalgia in South African letters, and places in that context the negotiation of a ‘critical nostalgia’ in representative work by Vladislavić—including ‘Propaganda by Monuments’, The Restless Supermarket (2001), Portrait with Keys (2006), and Double Negative (2010). It assesses the usefulness of Walter Benjamin’s work (including the ‘Theses’, Arcades Project, and ‘Work of Art in the Age of Mechanical Reproduction’ essay) for engaging with the affective politics and formal provocativeness of Vladislavić’s work, which balances past and future, disappointment and utopianism, a concern with this place and every place.