Abstract The aim of this paper is twofold. In the first instance it is an attempt to offer a new perspective from which to reflect on the meaning and philosophical presuppositions of Friedrich Schlegel’s defence and use of (romantic) irony, as well other related notions: humour, wit, and other comic devices. I propose to situate this perspective within a revaluation of pleasure and joy. To do this in a new way (although not in opposition to authors such as Manfred Frank, Elizabeth Millan-Zaibert, or Gary Handwerk), I refer to one of Schlegel’s earliest texts devoted to The Aesthetic Value of Greek Comedy from 1794. In addition, this paper questions the extent to which Schlegel’s position is tenable in the aftermath of the ‘death of God’. For this, I reflect briefly on the ways in which Nietzsche’s writings and notion of life-affirmation respond to Schlegel’s vindication of romantic irony.