Humour has recently emerged as an important research topic in International Politics. Scholars have investigated how states and state leaders practice humour as part of their diplomatic exchanges, in misinformation campaigns, and nation-branding. Important knowledge has been gained as to how humorous practices partake in constituting identities, managing recognition, and international anxieties or contesting global orders. Yet, little attention has been devoted to interrogating the risk that humorous practices may give rise to in international politics, to the underside of humour's productive power. This article aims to begin unpacking these risks both theoretically and empirically. To do so, it engages with the critical thinking on humour by Kierkegaard and Foster Wallace in particular, suggesting three challenging implications: (1) humorous entrapments; (2) facile forms of detached engagement; and (3) ambiguous blurring of fiction and reality. It then shows how these unfold empirically in: Iran's meme war with the US, a Yes Men's parody during COP15, and the Pyongyang Nuclear Summit, developing a three-pronged analytical strategy for studying humorous practices and their different relations to formations of power/knowledge.