This chapter argues that several aspects of Bernard Williams’s style, methodology, and metaphilosophy can be read as evolving dialectically out of Wittgenstein’s own. After considering Wittgenstein as a stylistic influence on Williams, especially as regards ideals of clarity, precision, and depth, Williams’s methodological debt to Wittgenstein is examined, in particular his anthropological interest in thick concepts and their point. The chapter then turns to Williams’s explicit association, in the 1990s, with a certain form of Wittgensteinianism, which he called ‘Left Wittgensteinianism’. It is shown how this is not a sudden conversion, but the direct product of Williams’s longstanding critical engagement with Wittgenstein’s methodology and metaphilosophy: Williams arrives at this position by envisaging a Wittgensteinianism that thinks in concrete sociohistorical terms, embraces genuine explanation, and relinquishes its insistence on the purity of philosophy. When properly understood, moreover, this critique turns out to be continuous with Williams’s advocacy of a conception of philosophy as a humanistic discipline. Finally, it is shown that Williams inherits from Wittgenstein a certain understanding of how philosophy can help us to live, in particular the therapeutic ambition to liberate us from distortions in our self-understanding by assembling reminders.