This article proposes that Deleuze’s psychoanalytically inspired theory of humour and irony provides an underappreciated way to theorize acts of resistance that adopt a structurally perverse position towards a law or authority. In his books Coldness and Cruelty and Difference and Repetition, Deleuze explains that the law is susceptible to two kinds of subversive procedure. The first, which he calls irony and which he aligns with sadism, reveals a gap between the law and its principles. The second, which he calls humour and which he aligns with masochism, exposes a gap between the law’s interdictions and their consequences. For Deleuze, humour and irony harbour the potential to overturn or overthrow the law. Drawing on Lacanian psychoanalytic theory and contemporary examples – alt-right ‘free speech’ demonstrations in the United States and protests surrounding Russia’s 2012 parliamentary elections – the article argues that Deleuze overstates the transformative potential of perversion. Nevertheless, his account remains useful for showing the circuitous routes that some subjects take to enjoy their position within the law. Given the global rise in right-wing authoritarianism in recent years, this may prove to be an important insight.