Are there examples of the Buddha showing humour in the Pali Canon? Leading on from this question - are there any examples of the Buddha showing a sense of humour or a certain lightness in his teachings within the Pali Canon? I was once told that it is possible to find examples where he perhaps approaches teaching with a gentler approach depending on his audience. Certainly the Buddha gives the lions roar but does he sometimes give the cheeky wink too?
You could say the Buddha and arahants had a peculiar form of humour, as Konrad suggested in his comment above. The hasituppādacitta (smiling-producing mind) is a citta unique to enlightened beings. While they can also smile due to beautiful-functional cittas, the hasituppādacitta is rootless, containing none of the wholesome or unwholesome roots. 

This means they would smile at things ordinary folk wouldn't, like brahmas being born as pigs (Dhp-A 338), or ghosts being tortured for past misdeeds (Dhp-A 71).