This dissertation traces the development of Hugo von Hofmannsthal's attempts to find solutions to what he perceived to be the crisis of meaning in his time. I focus primarily on Hofmannsthal's fictional letters and poetological reflections from the post-lyrical phase of his career, also touching on his final drama and political speeches. In the 1990s semiotic, structuralist, and poststructuralist studies of Hofmannsthal's texts allowed critics to uncover the more radically modern dimension of his creative process and work, making possible a poetological turn in the scholarship, with critics becoming far more interested in the poetics and aesthetics of Hofmannsthal's writings. Thanks to this work, a very different image of Hofmannsthal has appeared - one that attempts to overcome the common prejudice against the author as an elitist and cultural conservative who was out of step with his time. This dissertation participates in the latest approach to Hofmannsthal's work inasmuch as it largely focuses on Hofmannsthal's self-reflexive poetological writings from the Erfundene Gespräche und Briefe and on the author's intermedial search for a language that can counteract the reification of language in a positivistic age. The central argument of this dissertation is that the crises of language, of perception, of experience and of identity that Hofmannsthal repeatedly represents in his work fundamentally express a crisis of authorship. Hofmannsthal's preoccupation with these crises reflects his increasing uncertainty about the role of the poet in a modern democratic age, in which not only the social hierarchies but also the hierarchies of knowledge are leveled. I argue that Hofmannsthal radically destabilizes the role of the poet by questioning whether the poet has a necessary role in interpreting experience for the many. But I conclude by suggesting that in an effort to keep this question alive in an age of democratic skepticism about the poet's vocation, Hofmannsthal sees the need to reassert at a rhetorical level the poet's privileged position.