The central aim of this dissertation is to bring into dialogue certain themes, methods, and concepts drawn from, on the one hand, the 2^nd century CE Mahāyāna Buddhist thinker, Nāgārjuna, and, on the other, the Neo-Pragmatist philosopher, Richard Rorty (1931-2007). I highlight two core types of exegetical disagreement amongst Madhyamaka scholars in their philosophical readings of Nāgārjuna’s central texts (the Mūla-madhyamaka-kārikā and the Vigraha-vyāvartanī), and I re-articulate these debates through a Rortyan Neo-Pragmatist lens. I describe these two types of ongoing disagreement, which I characterise using the metaphor of an oscillation, as metaphilosophical and metalinguistic. They are thematically intertwined – the former is a disagreement over whether we should read Nāgārjuna as primarily engaging in philosophy and the latter is a disagreement over whether we should read Nāgārjuna’s statements as primarily useful to follow for the goal of liberation or accurately capturing facts about reality. In analysing what these Western interpreters are doing in their philosophical readings, I introduce Rorty as a lively conversational partner with whom to revisit their methodological preferences and conceptual presuppositions. My aim is not to conclusively settle these exegetical debates. Instead, I propose that Rorty’s work can give us some valuable conceptual resources for sidestepping their disagreements because of its extensive engagement with metaphilosophical and metalinguistic motifs in Western academic philosophy. My core argument is that by focussing on Rorty’s articulation of semantic anti-representationalism, that is, the view that the function of language is not to “mirror” or re-present the world, we can reconceptualise these exegetical debates as structured by forced choices which can be avoided. Therefore, the Rortyan (second-order) perspective that I will develop in this dissertation stands at a right angle to the (first-order) contemporary exegetical field where the idiom of representationalism is not directly opposed. I will argue that by not clearly rejecting the idioms and the imageries of representationalism from the outset, the interpretive terrain of Madhyamaka becomes associated with representationalist presuppositions, especially of a semantic variety, and it is these presuppositions that generate and sustain the exegetical debates. Once we have reconfigured, with the help of Rorty, the scholarly terrain anti-representationally and pointed to ways of bypassing these exegetical impasses, I then trace the implications of re-reading Nāgārjuna as an anti-representationalist. In so doing, I show that my proposals have the additional advantage of giving us Neo-Pragmatist tools with which to re-read Nāgārjuna’s Madhyamaka in a way that renders his message less exegetically tortuous and more straightforwardly intelligible.