The first part of this essay examines the importance of Leopardi for Nietzsche qua philologist. Rather than being a way to reduce the influence of Leopardi’s thought on Nietzsche, I argue, the focus on philology is of special importance. Leopardi uses the issue of philology in both the Paralipomeni (section a) and the poem to Angelo Mai (section b) to present a critique of contemporary cultural, historical and political practices with a specific focus on language as the site of memory and of the self. In the figure of the philologist as Columbus Novus, Leopardi advances a new understanding of philology that sees time itself as an artistic production, wherein the philologist does not reconstruct the past but generates it as a dimension of the future. The second part of the essay argues that the reflections on Leopardi’s philology in the notes We Philologists are parallel to the critique of history presented in the second untimely meditation, On the Uses and Disadvantages of History for Life, wherein Leopardi becomes the exemplar of an over-historical approach (section c). The emphasis on the future found in both the notes on the philology and in the second untimely meditation, evolves in dialogue with Leopardi on the meaning of philology and history that culminates in the Gay Science in the wager of the eternal return (section d). In Zarathustra (section e), the eternal return as an alternative historical and philological mode that brings about the philosopher of the future is analogously developed as an answer to Leopardi’s cosmic pessimism.