Face to Typeface: on Reading and Redemption is about reading literature. More precisely, it is about making sense of signs, about the movement, in other words, from the material sign that we see to an image or figure or idea of that sign that we understand. As such, it aims to move beyond current theoretical approaches to literary criticism, which for the past several decades have been caught in the critique of representation. The classical model of representation is derived from Platonic mimesis, the view that the literary image is a representation or copy of the world, which the critique contends is fundamentally flawed because language displaces the things it purports to represent and is thus destined to miss its mark, to fail. My dissertation does not take issue with that critique, but rather with the aporia that it tends to produce. This project is guided by a very simple question: if language and interpretation are indeed caught in a tautological loop in which the one continuously repeats the other, as I believe they are, then why do we continue to read texts that are essentially "made up," texts that are about things and people who do not exist and events that never happened? Moreover, what kind of knowledge do such texts impart to us and how do we account for the joy we experience in reading them? Throughout the chapters that compose this dissertation, I answer these questions by turning to Walter Benjamin's concept of redemption and Gilles Deleuze's reworking of Spinoza's "third kind of knowledge," which is the highest form of knowledge and which is also named "beatitude" because it produces the feelings of love and joy. I continually emphasize the materiality of the text, the sign, and argue that reading is first and foremost a face-to-typeface encounter that always, potentially at least, opens up the possibility of what Benjamin describes as redemption and what Deleuze understands as "a non-subjective living love." My first chapter considers the precise use and function of the literary figure by tracking the figure of the knight of courtly love as it surfaces in texts by Kierkegaard, Deleuze and Guattari, Erich Auerbach, Michel Foucault. My second chapter examines the figuration of surface in literature and in love, in particular the idea that "meaning" lies behind or beneath the surface, through a discussion of Plato's Symposium, its influence on Shelley's poetry and poetics, and on Walter Benjamin's theory of allegory. My third chapter considers Samuel Beckett's deployment of the letter M. I argue that the materiality of the sign of M, in which each arch mirrors the other, is a kind of rebus--both an image that reflects and a sound that resounds, a typographic composite of narcissus and echo. I further argue that Beckett also had in mind the medieval practice of using the letter M to allude to the human face, and that as such M marks the site of specifically human and linguistic condition. My fourth chapter is about how the aesthetic image, whether linguistic or visual, can be a vehicle of knowledge, and specifically the type of knowledge that produces feelings of love and joy.