Historians of modern Germany have often drawn connections between the German culture of inwardness and the rise of fascism. As a generation of post-war historians has argued, the idealization of interiority and the valorization of the aesthetic by the German middle-class was at once a symptom for its lack of real political power and a key source for the emergence of fascism. However, this interpretation fails to consider figures whose emphasis on inwardness and art, far from being consistent with the politics of fascism, offer a standpoint from which to critique it. The first to provide a fully-realized historical account of the intellectual friendship between Thomas Mann and Theodor W. Adorn, my dissertation argues that Adorno and Mann, when confronted with political exile from Nazi Germany, were forced to renegotiate the German bourgeois cultural tradition and its attendant ideology of inwardness. Rather than rejecting German bourgeois culturetout court, however, Mann and Adorno engaged with its central paradoxes through a sustained critical attention to the role of melancholia in the constitution of a cosmopolitan self-reflexivity. By differentiating between the pernicious elements in the German culture of inwardness and its emancipatory potential for critical thinking, Adorno and Mann offer intellectual models in which melancholy loss is transfigured into art and philosophy. As my dissertation shows, a complete investigation of Adorno and Mann's works in tandem not only sheds new light on our understanding of nineteenth-century German bourgeois culture and its putative connections to fascism; more significantly, I suggest, it provides us with hitherto unexplored critical venues for reassessing a tradition of cosmopolitan thought that was prevalent among exiles during this catastrophic period of German history.