This thesis is a comparative analysis of select works by Hieronymus Bosch and Otto Dix that examines the grotesque as a visual signifier of the desire for social stability during periods of social crisis. Drawing upon theories of the grotesque developed in the twentieth century by Wolfgang Kayser, Mikhail Bakhtin, Geoffrey Galt Harpham, and Noël Carroll, this thesis advances a definition of the grotesque that centers on its social function: as a pictorial strategy, the grotesque attempts to visualize paradox, estrangement, and contradiction in social, political, or religious identity as a means to effect a proscriptive, moralizing, and didactic critique. It examines works by Bosch and Dix in reference to the onset of the Reformation in the Netherlands and the aftermath of World War I in Weimar Germany, respectively. By attending to the circumstances of each historic crisis, the artists' social and artistic position, and particular works, this study presents an argument for the moral symbolism within the grotesque that activates its critical voice within society. The images of the grotesque that were produced by Bosch and Dix during these periods of social unease provide a recognition of contemporary human error in accordance with the socially-entrenched Christian moral code. In doing so, both artists created an instantly recognizable yet disturbing reality, one that captured the terms, shifts, and concomitant fears of each historical crisis by pointing to and away from society.