Following the lead of Duncan Pritchard’s “Wittgensteinian Pyrrhonism,” this paper takes a further, comparative and contrastive look at the problem of justification in Sextus Empiricus and in Wittgenstein’sOn Certainty. I argue both that Pritchard’s stimulating account is problematic in certain important respects and that his insights contain much interpretive potential still to be pursued. Diverging from Pritchard, I argue that it is a significant and self-conscious aspect of Sextus’ sceptical strategies to call into question large segments of our belief systemen (...) masseby exposing as apparently unjustifiable fundamental propositions which are closely related in their linchpin role to Wittgenstein’s hinge propositions. In the first instance, the result is a more complex account of both a deeper affinity between Wittgenstein’s approach to hinge propositions and Sextus’ approach to what I termarchaipropositions and a divergence between the two. In the second instance, I suggest how the comparison withOn Certaintycan be illuminating for the interpreter of Sextus. In particular, it can help us to see how the Pyrrhonist’s everyday conduct—common assumptions to the contrary notwithstanding—involves rational procedures of justification, in line with a naturalism reminiscent of Wittgenstein. Furthermore, it can help us to reflect on the Pyrrhonist’s attitude to what Wittgenstein would have called her ‘worldview’. Throughout, I suggest that the comparison with Wittgenstein is interesting, although it must be cashed out differently, not only on the interpretation—or, perhaps, strand—of ancient Pyrrhonism which has the sceptic exempt ordinary beliefs from her suspension of judgement, but also on the interpretation which has her disavow all beliefs categorically. (shrink)