Focusing on a series of debates on aesthetics and politics, this dissertation represents the intellectual history of one unique mode of exchange between intellectuals from across the political spectrum in twentieth century German thought. Although commonly associated with liberal bourgeois and left-wing influences, such as Hegel, Marx, and Freud, the Critical Theory of those linked to the “Frankfurt School,” I argue, developed out of criticisms and engagements with an array of conservative German intellectuals, many directly affiliated with Nazism. The ideas of such thinkers and artists—in particular, Stefan George, Martin Heidegger, and Carl Schmitt—were not only critiqued by theorists like Adorno and Benjamin but were also often rescued in the very process of their criticism. Redemptive criticism was one of the modes that defined critical theorists engagement with these thinkers, in that they did not simply negate or affirm the thought of their conservative counterparts; rather, deploying their innovative mode of future-past oriented criticism they interacted with the ideas, aesthetics and politics of their political opponents redemptively, by rescuing the truth content of that which they criticized. This redemption or rescue of aesthetic ideas, however, was not simply a secular mode of critique, but included a politicizing messianic valence. For in rescuing the ideas of their interlocutors associated with the right, critical theorists evoked the latent messianic, utopian impulses—what they considered the truth content—of their political adversaries. Thus, by simultaneously criticizing and uplifting ostensibly unredeemable aesthetic ideas and currents, Critical Theory sought to redirect such ideas toward the historical movement of messianic redemption, understood in the secularized sense as the task of liberating humanity from oppressive historical cycles and thus transforming the world. Even when historical and philosophical accounts acknowledge the interaction of Critical Theory and intellectuals across the political spectrum, it is often interpreted in dichotomous terms: either the critical theorists are shown to be profoundly influenced by and compatible with their conservative counterparts, particularly, Heidegger and Schmitt, or they are positioned as inextricably opposed to such thinkers on account of their ties to Nazism. This study therefore seeks to illuminate the history and complexity of the debates on aesthetics and politics in this period—which are often portrayed as exclusive to leftist or Marxist thought in Germany, as argued in Fredric Jameson’s edited collection Aesthetics and Politics and Eugene Lunn’s Marxism and Modernism—by placing them in a wider intellectual historical context that includes thinkers inhabiting a wide range of political and aesthetic positions. In representing the overlooked, often redemptive engagements of critical theorists and their conservative interlocutors, this dissertation seeks to reimagine the birth of Critical Theory and the intellectual-historical milieu in which it developed.