The aim of this paper is to show how, taken at face value, it appears that Horkheimer and Adorno’s conception of the culture industry presented in The Dialectic of Enlightenment does not allow for integral freedom--or the very freedom which is at the heart of modernity’s conception of the person and is the basis for its political philosophy. Nevertheless, the text has the resources to support a slightly less pessimistic reading, and provide a role for irony which came to be among prevalent artistic practices for postmodern aesthetics. That is, once the distinction between terrible laughter and reconciled laughter as well as terrible and reconciled humor is understood, the text rewards rational reconstruction to demonstrate the folly of rea...