This chapter explores the development of irony from its Romantic and modern conception, as a form of negation that aggregates to become a perspective of scepticism in any received values and perspectives. Søren Kierkegaard’s ironic subject is introduced as one who critiques established norms yet also acknowledges the need for humour to curtail irony’s trajectory toward absurdity and despair. By contrast, Richard Rorty perceives human experience as inescapably ironic, a view supported by an understanding of language as arbitrary and contingent. Rorty’s postmodern ironist remains detached from political and ethical engagements, favouring constant reconfiguration over substantive development or resolution. These views on irony preface a distinctly modern malaise: if irony continually subverts human expression and endeavour, apathy seems just as likely an outcome as faith, hope or love. However, considering irony with reference to Hegel’s determinate negation can reveal an inherent creativity within ironic negation. Rather than cancelling meaning, irony can create space for growth, discovery and the emergence of new forms through a confrontation with their intrinsic limitations. This view is echoed by philosophers Terry Eagleton, Slavoj Žižek, Roger Scruton and Jonathan Lear, whose writings treat irony not merely as a form of subversion but as a basic grammar of critical awareness and a means of developing ideas, social institutions and human capacity.