This dissertation investigates the problem of historicism from the perspectives of Leo Strauss's political philosophy and Hans-Georg Gadamer's hermeneutics. Both present historicism as a crisis that undermines our ability to properly interpret eras other than our own. Consequently, they develop distinct applications of interpretative theory to explain both how to understand others and—more importantly—how to consider truth itself. On the one hand, Strauss treats historicism as the manifestation of the inherent problems of modernity. By denying the possibility of understanding fundamental questions in the manner that Socrates approaches them, Strauss argues that modernity has abandoned the quest for truth. He thus posits that we can "return" to the fundamental questions of the ancient philosophers themselves as proof that the modern abandonment of classical philosophy was a mistake. Instead of searching for a "new dispensation of Being" or novel tools to understand the world, we can think like the ancients did. In contrast, Gadamer treats the discovery of "historical consciousness" [geschichtliches Bewußtsein] as a serious break between the ancients and moderns. Because we have learned how history "always already" prefigures who we are, this recognition requires us to design new tools for interpreting reality. Fortunately, Gadamer argues that through hermeneutics we can properly interpret truth as an endless conversation that—while always changing—represents a real set of understandings that enable discourse. Although` Gadamer and Strauss have many serious disagreements about the nature of historicism, they both agree that interpretive discourse is the one thing needful for approaching the political problems that undermine the possibility of practicing philosophy.