This chapter aims to locate Machado’s place in the development of literature—more specifically, realism in Brazil. This exploration of the aesthetic mode of realism in Brazilian literature focuses on Machado and his often contentious place within literary movements. More importantly, Gumbrecht addresses how Machado reconfigured realist aesthetics to the demands of his time, engendering a new brand of realism—in stark contrast to the European realist tradition—founded upon a firm philosophical questioning of placing reality into representation. Gumbrecht interrogates Machado’s relationship with realism, centering on the writer’s singular narrative form of instability and self-reflexivity.