Two German philosophers working during the Weimar Republic in Germany, between the two World Wars, produced seminal texts that continue to resonate almost a hundred years later. Franz Rosenzweig—a Jewish philosopher, and Martin Heidegger—a philosopher who at one time was studying to become a Catholic priest, each in their own, particular way include in their writings powerful philosophies of art that, if approached phenomenologically and ethically, provide keys to understanding their radically divergent trajectories, both biographically and for their philosophical heritage. Simon provides a close reading of some of their essential texts—The Star of Redemption for Rosenzweig and Being and Time and The Origin of the Work of Art for Heidegger—in order to draw attention to how their philosophies of art can be understood to provide significant ethical directives.