Blanchot’s writings are distinctive for the ways that negativity takes place in them in terms of the experience of literature, the possibility of the work, and the nature of its language. However, this role in his thinking is unique and is not to be subsumed to the negativity found in the thought of Hegel or Heidegger, although it partakes of aspects of both. Instead, negativity for Blanchot operates at the level of the ontological status of language, which oscillates undecidably between the assertion and negation of meaning and thereby affects the experience of literature and the possibility of the work with an irreducible ambiguity. To explicate the significance of this negativity it is necessary to turn to another figure for whom it has become as central, Adorno, whose Hegelian background is much stronger, but who also works against this tradition to form his own negative understanding of dialectics that is crucially exemplified in the work of art. For Adorno, the work of art exists as a particular model of its historical and material context, one that both demonstrates its contradictions and also indicates what has been obscured by them. The negativity of the work is thus both that of the critique that it levels against this context and of the possibilities that it negatively raises in its place. To study the two writers together it is necessary to find the place where their thinking converges, which occurs most critically in the area of post-Kantian aesthetics and the question of autonomy.