With the publication of Dewey’s lost (but now found) manuscript posthumously titled Unmodern Philosophy and Modern Philosophy, we find his most developed account of the failures and fortunes of modern philosophy that appeals to human culture as a vehicle through which to both understand and criticize philosophical tradition. In this unfinished work, Dewey makes the familiar point that while we live in a modern age, our ideas, attitudes and institutions are still too wedded to the unmodern ways of thinking bequeathed to us from previous generations. Dewey’s analysis depends on this central insight: changes in the material conditions of human life do not necessarily result in changes to our beliefs, ideals, traditions and institutions. However, a potentially liberating element remains in modern epistemology, when it presents older philosophical views as opaque, here suggesting that future epistemological accounts must emphasize a greater need for transparency through exposing ideas, bias, and even institutions, to a more critical engagement with experience. My paper provides a preliminary account of how these ideas might be exploited in developing a more positive theory of cultural criticism.