Thomas Pynchon has often been hailed, by those at wont to make such statements, as the most significant American author of the past half-century. What is indisputable about this simultaneously beguiling and frustrating, prodigiously sophisticated and irrevocably juvenile, not to say admired and reviled writer, is that his fiction has inspired critical readings that are now as appositely voluminous as his novels themselves. Yet no prior critical effort does full justice to the importance of the face in the work of this notoriously “faceless” author, who even had a brown paper bag over his head when depicted in cartoon form on The Simpsons. In light of this oversight, this thesis seeks to address what might be called—to borrow from his 1990 novel, Vineland—the ‘not-yet-come-to-terms-with face' in Pynchon's corpus. Though always driven by the workings of Pynchon's writing, various theorists—such as Theodor Adorno, Walter Benjamin, Erving Goffman, and Emmanuel Levinas—are called-upon throughout this study in order to aid the conceptualisation of this ‘not-yet-come-to-terms with face'. Particular inspiration is taken from Gilles Deleuze and Félix Guattari's call to ‘dismantle the face' in A Thousand Plateaus. Albeit not in strict adherence to this summons, the first three chapters of this project butcher the face into its dominant component features: eyes, nose, and mouth. These features—as well as the central issues of the final two chapters, the mask and the face respectively—are then traced across Pynchon's entire oeuvre, including his most recent novel, Bleeding Edge, published when this project was already underway. What emerges is a picture of the integral role the face plays in Pynchon's manifold concerns: surveillance, surgery, dentistry, identity, cinema, drugs, the senses, and so on. This thesis ultimately contends that although frequently defaced and effaced in Pynchon's writing, the face is nevertheless a prime locus at which ethical and political possibility surface.

This thesis examines the countercultural politics expressed within the work of the American novelist Thomas Pynchon, contributing to critical work already published on the subject of Pynchon's politics, in which there has been a recent upsurge of interest. Expressions of sympathy with anarchist and anti-Capitalist principles discerned in Pynchon's work are explored in their connection with the author's experience of particular practices and philosophies of the 1960s counterculture. Furthermore, the ongoing significance of sixties politics in Pynchon's more recent production is demonstrated as ideological connections between earlier and later novels are traced. In Slow Learner Pynchon professed admiration for the motive energy of Beat literature, so influential on the formation of the counterculture. With particular focus on Jack Kerouac's On the Road, chapter one demonstrates the impact of the Beat movement, and its limits, in Pynchon's early novels. New Left thought and tactics as manifested across the decade provide the focus of the second chapter, which engages primarily with Gravity's Rainbow's depiction of Communist revolutionaries in Weimar-era Germany. The following chapter considers the role of psychedelic experience and the philosophies of Timothy Leary in Pynchon's The Crying of Lot 49 and Against the Day, arguing that the fantastical has a concrete political role in Pynchon's novels. Black Power, and specifically the political theory of the Black Panther Party, is the subject of chapter four. Gravity's Rainbow's framing of Huey P. Newton's concept of “revolutionary suicide” is central to an analysis which offers insights into the novel's perspectives on the use of violence and on leadership in revolutionary groups. The final chapter investigates the dynamics of Pynchon's ambivalent engagement with the Women's Movement. Betty Friedan's The Feminine Mystique is put forward as an important intertext for The Crying of Lot 49, while Vineland is examined in the context of radical feminism.

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.