This dissertation examines the shiing social, political, and religious significance of poets in south- ern India and the Deccan during the fourteenth- and fieenth-centuries. To this end, the project centers on the career of Gaurana, a poet and scholar om a family of courtly brahmans in Telugu- speaking south India (present-day Telangana and Andhra Pradesh). Modern historians and literary scholars have interpreted Gaurana’s compositions in Telugu dvipada—typically considered a non-elite genre—as evidence that he affiliated with the Vīraśaivas, an egalitarian devotional movement. How- ever, through an analysis of his Telugu compositions and his neglected treatises in Sanskrit poetics, I argue that Gaurana’s relationship to the Vīraśaiva poets and similarly inclusive literary traditions was one of competition and appropriation rather than collaboration.,Chapter Two examines Gaurana’s Lakṣaṇadīpikā (A Light on the Properties) project, two Sanskrit treatises on poetics and poetry’s metaphysical characteristics. It demonstrates that Gaurana offered an unprecedented and systematic synthesis of multiple Sanskrit knowledge systems to argue for brah- manical prerogatives in the poetic profession. In order to reconstruct the literary world and poetic forms to which Gaurana laid claim, Chapter Three traces the conceptual and compositional history of cāṭuprabandha, the panegyrical genres detailed in the Lakṣaṇadīpikā. Chapter Four analyzes Gaurana’s Telugu dvipada poetry to grasp how his compositional choices align with his theoretical positions and situate him relative his poetic predecessors and contemporary competitors. Finally, focusing on his Navanāthacaritramu (The Deeds of the Nine Naths), Chapter Five explores Gaurana’s relationship to Śaivism, Srisailam, and his monastic patrons. Utimately, the dissertation traces changes in the char- acter of literature, the development of vernacular cultural practices, and the ways in which literature registered transformations in the political culture of late medieval south India.