ABSTRACT While a common view in the literature is that Nietzsche cannot successfully argue against Schopenhauer’s pessimism, a detailed explanation of why this is so is lacking. In this paper I provide such a detailed analysis. Specifically, a consideration of three of Nietzsche’s strategies for a revaluation of pain and suffering reveals two problems: the problem of ‘the direction of revaluation’ and the ‘dilemma of the intransigence of hedonism’. According to the first, the success of a revaluation cannot be guaranteed (...) on strictly argumentative grounds and can in principle bring about a revaluation that proceeds in the opposite direction than the one desired. According to the second, Nietzsche’s revaluations are of no significance since they either ground an un-Nietzschean affirmation of life, or they do not engage pessimism’s hedonistic perspective on the basis of which it condemns life. I then examine two strategies that Nietzsche can be seen to employ in his attempts to revalue the hedonistic perspective itself and explain why they too are unsatisfactory. The analysis illuminates the nature of the dialectical stand-off between Nietzsche and Schopenhauer and clarifies the limitations of Nietzschean revaluations as a philosophical tool. (shrink)