AbstractPierre Hadot is best known as a historian of ancient philosophy and for advocating the relevance of ancient thinking for contemporary lives. What is less well known is that he was one of the first French philosophers to take a serious interest in the work of Wittgenstein, publishing between 1959 and 1962 two essays on the Tractatus and two on the Philosophical Investigations, since republished as Wittgenstein et les limites de langage (Paris: J. Vrin, 2010). Only two of these essays are available (and not widely) in English translation. Part of my goal is to argue that they deserve the attention of anglophone readers. My focus here is on Hadot's remarks about the Philosophical Investigations. Hadot argues that this work produces a self‐defeating paradox because it claims that we can speak intelligibly only within a language‐game, but Wittgenstein, like the philosophers he criticises, tries to transcend language‐games in the presentation of his views. Despite this criticism, Hadot is inspired by Wittgenstein's discussion of the multiplicity of language‐games to argue that the texts of ancient philosophy are not part of the same language‐game as those of modern philosophy and must be approached as ‘spiritual exercises’, rather than as bodies of doctrine or theory. Wittgenstein is thus a key inspiration for Hadot's historiographical method. I argue that Hadot is too impressed by a faulty analogy between the Tractatus and the Investigations and that he gives a problematically reductive interpretation of Wittgenstein's talk of language‐games and implausibly attributes to Wittgenstein a reverence for ‘the ordinary’ that supposedly takes the place of his earlier wonder at the existence of the world. Many commentators since Hadot have made similar errors, so his case remains instructive. I conclude by suggesting, nonetheless, that something like Hadot's proposals about historiographical method may be justified by a better reading of the Investigations.