This dissertation is a study of the Mahābhārata epic’s reception history in medieval South India. It focuses on an early, but understudied, translation of the epic into Old Kannada, the Sāhasabhīmavijaya (SBhV) of Ranna. This work has typically been read from a historico-political perspective, which casts the poet’s patron, Satyāśraya of the Western Cāḷukyas, onto the role of Bhīma, one of the epic heroes. Thus, the SBhV is usually deemed to be a “double narrative” that maps Satyāśraya and the Cāḷukya dynasty’s claims to power over South India onto the world of the Mahābhārata and its heroes. However, this dissertation departs from such an approach in favor of a more literary orientation, arguing that the SBhV retells the epic through the alternate perspective of Duryodhana, the leader of the Kauravas and the narrative’s traditional anti-hero. To unpack this unique re-interpretation of the Mahābhārata, it draws on a narrative critical method, especially influenced by Mieke Bal and Gérard Genette. Narratology has been useful in providing a vocabulary to think through the specific ways in which the SBhV orders the sequence of the epic’s narrative anew, gives it a different rhythm, and disrupts our expectations through focalization. This dissertation contends that it is possible to trace the SBhV’s literary response to the epic tradition and its immediate social location in medieval Karṇāṭa by concentrating on the minutiae of the narrative and the modes in which it narrates the Mahābhārata. It demonstrates that the epic is filtered through the Kaurava’s interpretive lens. In other words, the SBhV’s telling of the Mahābhārata is framed by Duryodhana’s perspective, his values and biases. These narrative innovations are explored through a series of connected essays that focus on themes like dharma, mourning, and friendship.