The present article traces the inevitable turn towards negativity of the idea of hope, following the literary-critical reflections of Georg Lukács, Walter Benjamin, and Theodor W. Adorno. This movement dates back to early modernism, where the transformation of absolute despair into its opposite was still supported by the religious-political climate of the Baroque period. However, according to the three literary critics, due to the impossibility of a positive metaphysics, hope, if it does not wish to become ideological – as false consolation or transfiguration – can only be formulated as an ‘inspite.’ This idea, impressively captured in Theodor W. Adorno’s Negative Dialectics , found literary expressions that range from Baroque theatre to Samuel Beckett’s modernism. Negativity itself, in which these expressions are immerged, must not, however, be declared a meaning-giving, totalizing authority. Such ‘post-metaphysical’ interpretations can be prevented by critically reconsidering the insights of the three literary critics. They do not hypostatize a negative principle from which meaning is to be derived, but rather, in view of the desolate world, prefigure the possibility of a better one.