In this paper, I explore what Robert Clewis, in The Origins of Kant’s Aesthetics, suggests is an ‘analogy’ between humour and beauty. I do this by focusing on Kant’s concept of wit (Witz), which is central to both reflective judgement and humour. By exploring the concept of Witz as a distinctive kind of cognitive activity, I believe a case can be made that the origin of Kant’s mature aesthetic theory in the Critique of the Power of Judgement and his discovery of the principle of taste were, in part, a result of Kant’s thinking about Witz. I therefore share Clewis’s puzzlement about why, in the third Critique, humour, arguably the art of Witz, is not considered to be a beautiful art. I conclude by suggesting a possible reason why Kant thought that a judgement of humour is different from a judgement of beauty.