The aim of this thesis is to provide a comprehensive account of the role literature, the ‘literary’, and the notion of a ‘literary culture’ plays in the work of the American pragmatist philosopher Richard Rorty (1931-2007). While these notions are systematically significant in Rorty’s work, no thoroughgoing study of the literary aspect of his oeuvre exists. I undertake this study to understand why Rorty hoped ‘culture as a whole’ would be ‘poeticized’ (CIS p. 53) rather than simply pragmatised, and why he, at the end of his career, stated that his key contribution had been his narrative about the ‘takeover’ by a ‘literary culture’ (PTG p. 4). I ask what work literature and a particular literary vocabulary does for Rorty as he articulates his own brand of pragmatism. Examining Rorty’s narrative as narrative, and foregrounding his constant alignment with the literary attitude, allows me to understand the Rortian project as a break with traditional forms, and, importantly, with the governing forms we impose on history and moral progress. Tracing the roots of the idea of a ‘literary culture’ in Rorty’s work permits me to see CIS as a literary and poeticist response to a question Rorty’s adoption of a literary vocabulary helps him articulate: how we might cultivate a humanist pragmatism – a mode of thought and work that emulates the attitude and writerly practices of the literary artist or critic. And, lastly, looking closely at why Rorty, despite advancing a thoroughly contextualist and functional conception of literature, recommends that we centre liberal-intellectual practice around plays, poems, and especially novels, lets me delineate the morally significant function Rorty takes literature in the narrow sense to be more efficient at performing – the performance of which depends on the cultivation of literary skill. I close by offering some thoughts on Rorty’s readings of Lolita and 1984, on how my findings enables us to become better readers of Rorty, especially of Rorty as a reader of literature, and on what I take Rorty’s attention to literature to imply about the role and importance of the literary (critical) institution in contemporary society.