In this paper we will move from the most interesting issue investigated by William James: the continuity of consciousness. In his Principles of Psychology (1890), James introduced his reflection on the stream of consciousness as a peculiar trait of our thinking's processes. Such an original theme will remain a pivotal topic in all James's works in so far as it can be considered both as the starting point of his epistemological inquiry and as the source of those characteristic traits of his later pluralistic metaphysical outcomes. As it is well known, for all his life James held firm to his psychological acknowledgments and particularly to his functionalist (with a unavoidable tendency to sensationalism) approach to meaning in considering philosophical questions. As James O'Shea has recently shown (2014), such a tension between a general inferentialist and functionalist pragmatic approach to meaning and his attempt to ultimately found meaning in feelings is evident in all James's works and indeed it was never completely solved. This tension is probably connected to James's two main methodological concerns: that of a pragmatist account of experience and that of keeping radical his empiricist appeal to experience. In this view, the psychological analysis of the continuity of consciousness seems to have disclosed to James all those epistemological and ontological problems that he will be seriously considering still in his very last works, and particularly in A Pluralistic Universe (1909) and Some Problems of Philosophy (posthumous). This latter was started in 1905-6 as a notebook for his courses of philosophy and was then intended to become the book in which James should offer the systematization of his metaphysical view. As a matter of fact, in SPP James organizes his discourse around singular metaphysical problems, such as percepts and concepts, the one and the many and novelty. The book remained unfinished, and the last three chapters offer an interesting analysis of continuum, through which James was trying to find a way to keep together real novelty and continuity. Moreover, in PU his general view is explicitly defined as synechistic and it is very interesting to observe that the fifth chapter of this later work is a reformulation of his early position about the continuity of the fields of consciousness that he had treated in his Principles of Psychology (1890). In a few words, in this article we move from the clarification of the epistemological assumptions that James developed through his psychological analysis of the main features of the continuity of consciousness, in order to show – particularly focusing on his most metaphysical texts – how these considerations remain strictly connected to his claim for the priority of perceptual knowledge and to his conception of a pluralistic universe. This effort is justified by the contemporary resonance that James's ideas appear to have regained in many different fields of knowledge – spreading from psychology, to philosophy of mind, epistemology, ethics and religion – a fact which invite us to closely reconsider the texture of James's epistemological reflections and, in a melioristic fashion, to point out his precious insights as useful tools for contemporary discussions.