Though irony is a category familiar to rhetoric and literature, its philosophical forms are far less explored, and this is especially true with regards to its articulation in the work of Friedrich Schlegel. Schlegel’s engagement with irony is essential to the Romantic philosophical project, one that is fundamentally concerned with contradiction and posits itself as a challenge to and continuation of idealism. Through exploring his relation to the philosophies of Kant and Fichte, this essay demonstrates that Schlegel can deploy irony (...) as a method of taking up the philosophical paradigm of idealism without limiting himself to their systems. He can use Kant and Fichte against themselves, making sincere philosophical arguments through a brazen playfulness. Further, Schlegel’s concept of irony is shown to be a philosophical faculty that is concerned with the limits of philosophy in language. Irony is much more than a rhetorical device – it is a form that allows Schlegel to approach the limits of discursivity from within and so continually stage instances of philosophical contradiction, undermining systematicity. This centering of contradiction is one of Schlegel’s major contributions to the development of German philosophy, critical of those who precede him and spurning their presuppositions of univocal logic. The outworking of Schlegel’s philosophical concern with irony is unmistakably humorous, full of puns, jokes and witticisms, which nevertheless need to be taken seriously. This paper contends that irony is at the crux of Schlegel’s philosophical project, simultaneously the content and mode of his criticism, the source and justification of his humour, and one of Romanticism’s most significant conceptual developments. (shrink)