In academic and popularist text, Western interest in Zen pivots around its 'new age' spiritual appeal. Captured in titles like 'Zen and the art of X' or 'the Zen of Y', these texts explore the self-realisation necessary to relieve individuals of their often worrisome and frequently unwholesome 'selves'. Research and discussion of humour in education has been mainly concerned with its ability promote learner attention, motivation, comprehension and retention, or to facilitate positive teaching and learning relationships and environments (Powell and Anderson , 1985). Zen is introduced in terms of a 'healing deconstruction' (Loy 1996) that is radically anti-essentialising, in ways that have yet to be properly accounted for by poststructuralism. As well, Zen focuses on existential concerns and is interested in embodiment as knowledge, as uses impermanence, suffering and death as resources for technologies of self. As a philosophical/psychological tradition, Zen offers a form of praxis for living a life in which humour is understood to be one of its significant resources. Humour provides a space for serious contemplation on issues that are often repressed or silenced. Taking the comedic dimensions of Zen teaching as a focal point, this paper explores humour as pedagogy. It highlights practices such as the strategic use of paradox, irony, incongruity, unconventionality and distancing; the dissolution of dualisms; and the deployment of radical scepticism in Zen teachings, to argue for a more encompassing consideration of the pedagogic dimensions of humour.