This dissertation examines competing and coalescing narratives concerning the distant past in Sri Lankan Buddhist and Tamil Hindu literature from the 14th-16th centuries. I argue that a more capacious view of the island’s early history emerged during this period, extending chronologically to a point much earlier than the lifetime of the Buddha. The dissertation considers ways in which Sinhala literature reflected changing demographic realities through the imagined past, incorporating aspects of Hindu Purāṇas and Sanskrit epics. I trace the identification of the island of Sri Lanka with the literary “Laṅkāpura,” the abode of Rāvaṇa, demon-king antagonist of the Rāmāyaṇa. I argue that that aspects of reconfigured historical imagination of the late medieval period endure to the present day, accounting for the now popular notion that Rāvaṇa was an ancient Sinhala king of Sri Lanka.