It is not difficult to find both affinities and divergences in the work of Wittgenstein and Brandom but this particular text explores several key issues beyond first impressions and reveals hidden divergences in supposed similarities and occasionally less profound dissimilarities where their philosophies seem to differ radically. Both Wittgenstein and Brandom (as well as Dewey), while agreeing that representations cannot be taken to be primitive, would not approve of Rorty’s drive to jettison the very idea of representation along with that of truth. Wittgenstein, on the other hand, “is averse to any attempt at general, explanatory, theories of how language works” while “Brandom is much more positive about the possibility of general, systematic and explanatory theories of meaning.” The divergence about the builders of Philosophical Investigations § 2 and their language use is traced back to Wittgenstein’s being essentially a worldly pragmatist, while Brandom’s practice is essentially intralinguistic. In the second part, the text takes issue with Brandom’s theory of making explicit, and in the final sections, the paper questions the supposed contrast between expressivism and the ‘motley of language’ and takes a look at Brandom’s strive for a normative realism that distinguishes him from other expressivists.