This chapter attempts to explore possible connections between some forms of art and economic modelling. It synthesises some common insights across selected works of René Magritte and M.C. Escher. Building on them, it explores their relevance to understand certain aspects of mathematical modeling in social sciences, especially in economics. It argues for a more prominent recognition and even a celebration of the relatively unsung virtue of modeling: to highlight paradoxes and impossibilities that lie beneath various representations. Despite their subversive character, I argue that creative disjunctions can play an important epistemological role by advancing our understanding of the nature and limitations of models, at the same time opening up space for new concepts and conjectures. A case for the fruitfulness of such an approach in economics is illustrated by drawing examples from the works of Kenneth Arrow, Piero Sraffa and Vela Velupillai.