This paper focuses on the work of two photographers—Helen Levitt and Jansje Wissema— who extensively documented children playing in streets and produced images of the drawings made by children on city streets and walls. These images are read in relation to the work of the Burning Museum Collective, a group of artists based in Cape Town, South Africa, who draw on archival images and make use of photography as a form of resistance. The paper argues for the way in which an engagement with photographs of urban spaces can provide a means for thinking about transnational histories, neoliberalism, gentrification, forced removals, and the politics of restitution.