Cheerfulness or serenity is one of the most important themes in Nietzsche’s philosophy. Throughout his writings, from first to last, he can be found wrestling with conceptions of cheerfulness and promoting a cheerful mode of philosophizing. Despite the importance and recurrence of the theme of cheerfulness in Nietzsche’s entire œuvre, there have been relatively few studies specifically devoted to it. An important debate on cheerfulness has recently taken place in the literature on Nietzsche between Robert Pippin and Lanier Anderson and (...) Rachel Cristy. Both sides of the debate have explored Nietzsche’s practice of cheerfulness in direct relation to Montaigne. According to Pippin, Nietzsche never succeeds in writing with the kind of cheerfulness of Montaigne. In contrast, Anderson and Cristy have contended that both Nietzsche and Montaigne conceive of cheerfulness as a complex, non-naïve spiritual state or attitude that is to be cultivated through the practice of philosophy as a way of life. According to Anderson and Cristy, this is a deep form of love of life that both Nietzsche and Montaigne practice and perhaps achieve at least in part by and through writing. In this essay, we aim to contribute to this debate by offering a threefold argument. First, we argue that Nietzsche conceives of cheerfulness not only as a psychological ideal, as a desirable state or attitude of the spirit, but also as an aesthetic ideal, as a desirable quality or style of thinking and writing. Second, we argue that, in addition to Montaigne, Ralph Waldo Emerson is an equally important but neglected influence on Nietzsche’s conception and practice of cheerfulness. Third, by reconstructing Nietzsche’s self-presentation as a cheerful thinker and writer in the 1886 prefaces and in Ecce homo, we conclude that it is possible to argue that starting from his middle writings Nietzsche thinks and writes cheerfully in some of his works, including a number of his most significant texts. (shrink)