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An examination of the artist/cartoonist David Shrigley’s work through the prism of philosopher Simon Critchley’s writing reveals a melancholic space of play where humour and obliquity allows the difficult but necessary expression of the unspeakable. A historical overview of melancholy and a close reading of the philosophical and psychoanalytical subtexts of humour in and through drawing opens up a reading of Shrigley’s work illuminated by the triad of nihilism, humour and a long historical strain of melancholy. Critichley, whose work on humour sits within the larger context of his work on nihilism, expands from Freud on melancholy and humour to articulate a self that is constituted as a mournful melancholic. Shrigley’s manipulations of the tropes of drawing produce a wistful ironic distance equivalent to Critchley’s self that ‘smiles and finds ourselves ridiculous in our own impossible mourning’. Shrigley’s work explodes this state towards materialism, immateriality and loss apposite to the work of Benjamin, Derrida and Agamben.