This thesis undertakes a systematic, tripartite analysis of the interactions between the fiction and essays of Thomas Pynchon and the philosophy of Ludwig Wittgenstein, Michel Foucault and Theodor W. Adorno, resulting in a solid set of original reference-material for those undertaking work on Pynchon and philosophy, or more generally on philosophico-literary intersections. Premised upon the notion that Pynchon's literature harbours a fundamental hostility to much systematizing philosophical thought, this work avoids a dominating imposition of philosophy, or an application of philosophical (...) thought as a validating Other, by examining those aspects of Pynchon's work that seem ill at ease with, or aggressive towards, aspects of each philosopher's thought. This is explored through the concept of an intra-textual polyvocality and relational situation of philosophical intersection; when Wittgenstein is cited, for instance, who is speaking and what are the connotations of that placement? I do not propose, therefore, a Wittgensteinian / Foucauldian / Adornian Pynchon, but rather explicitly highlight excluded aspects of thought to instead develop a complementary reading; a form of intersubjective triangulation. This polyvocality is examined from a univocal perspective. The specific conclusions of this work re-situate Pynchon, in many cases against forty years of critical consensus, as a quasi-materialist or at least anti-idealist, a regulative utopist and a practitioner of an anti-synthetic style akin to Adorno's model of negative dialectics. In a broader sense, it answers the questions regarding hostility towards philosophical thought in Pynchon's work by demonstrating that no single philosophical standpoint has yet to totally resonate with even one of his novels. Simultaneously, it also shows that a profitable approach can be found in the spaces of philosophical overlap and divergence. (shrink)