This chapter explores Richard Rorty’s pragmatist model of ‘conversational philosophy’. By experimenting with new descriptions and novel vocabularies, he aimed to break through old impasses where the conversation has lagged or stalled or been abandoned. For Rorty, experiments in ‘re-description’ potentially reignite the conversation, allowing us to undertake acts that we have never undertaken before. In this view, the point of philosophy is not to mirror the world but to enlarge our cultural repertoire, allowing us to realise new achievements. The chapter applies this approach to the work of the maverick American human geographer, William Bunge (1928¬–2013). Bunge understood maps to be geography’s language, and he believed that by changing the vocabulary of cartography he could break through the crust of previously held conventions, creating something new, potentially changing society and social relations for the better. The chapter looks at three different phases of Bunge’s experiments in cartographic re-description: his early work within spatial science on formal map transformations; his later work in black inner-city Detroit; and his last substantive work on the Nuclear war atlasto warn against atomic Armageddon.