This chapter describes Theodor Adorno as probably the greatest Marxist cultural theorist of the twentieth century. The uses of Adorno's work are related to the fact that he is at once close to and distant from the perspective of postmodernism. Adorno is interested in the forces which restrict or act as blockages or which suffocate the potentiality for critical self-reflection. The chapter considers these blockages in more detail. The endlessly paradoxical character of Adorno's thought is central and certainly the reliance on paradox derives from G.W.F. Hegel's philosophical lineage. The best way to isolate what is specific to Adorno's own way of doing things is via the work of that proto-postmodernist and brilliant Adorno-interlocutor, Walter Benjamin. In his celebrated 'Work of art' essay, Benjamin sought signs of aesthetic and political redemption in the fate of contemporary cultural production.