This thesis examines five books by the American author Philip Roth commonly referred to as the “Roth Books,” which are The Facts: A Novelist’s Autobiography(1988), Deception (1990), Patrimony: A True Story (1991), Operation Shylock: A Confession (1993), and The Plot Against America (2004). These books, held together by the author’s proper name, are often viewed as texts that conflate fiction and nonfiction or demonstrate the “fictionality” of all factual narrative accounts in compliance with well-known postmodernist and poststructuralist theories. Contrary to this view, I argue that a valid understanding of the Roth Books demands that we acknowledge that these works represent a series of quite different ways for the author to transform his own life into written form, a creative act which is manifested in both fictional and nonfictional writing. In the attempt to argue this view, I turn to a field of study where the question about criteria for distinguishing fictional from nonfictional narrative literature has occupied a prominent place: narrative theory. However, my theoretical and methodological point of departure does not align itself with the “standard” paradigm in narrative theory with its origin in classical, structuralist narratology. Rather, the thesis promotes a pragmatic and rhetorical perspective which is argued to better account for how we read and make sense of different narrative texts. In opposition to standard narrative theory, where all narratives are considered to adhere to the same model of communication, I argue in favour of a view where narrative fiction and narrative nonfiction are conceived as distinct communicative practices. I open the thesis by showing that Roth’s books contribute to the discussion on how to distinguish fictional from nonfictional narrative texts (Chapter 1). I then continue by approaching the distinction between fiction and nonfiction in general theoretical terms (Chapter 2). And in what follows (Chapters 3-5), I present a reading where the Roth Books are juxtaposed against each other. This reading demonstrates how these texts, although in some sense related, because of their divergent qualities and differing intentions still communicate differently with their readers, inviting a readerly attention that is dissimilar from one work to the other.