There was a long standing taboo in Thailand against monks being photographed smiling. Ajahn Chah was the first prominent bhikkhu who allowed his image to be recorded while looking cheerful. Certainly many of his teaching stories have a playful or humourous flavour. The same could be said of many other Thai ajahns. Similarly, the Zen tradition is full of quirky anecdotes and Vajrayana has its trickster figure in Milarepa.
But did the founder, Gotama Buddha, have a sense of humour? Some might think the idea irreverant. I would beg to differ, I don't think a healthy sense of humour, a clean enjoyment of ambiguity, paradox and the foibles of human nature, is incompatible with the highest state of liberation.
One obstacle in appreciating the Buddha's wry wit may be the stilted formal language of the suttas; recorded in Pali which was probably not a natural language but a kind of artificial prakrit, an Indic esperanto. The language itself has a structure that lends itself to formality or even gravity in expression, and the use of formulaic passages as a mnemonic device adds to this.
Translations have also been problematic in this way. The newer versions by Bhikkhu Bodhi, Maurice Walshe and some others are written in a more natural English prose, but one sometimes gets the feeling that the early translators of the Pali Text Society were trying to emulate the prose style of the King James Bible to attain the neccessary gravitas.
Nevertheless, some of the Buddha's wit does make it through the layers of transmission. This is especially true of many of his parables. From Digha 23, a parable concerning attachment to views and opinions;
Once there was a swineherd...[who] saw a heap of dry dung that had been thrown away, and he thought: 'there's a lot of dry dung someone has thrown away, that would be food for my pigs. I ought to carry it away. And he spread out his cloak, gathered up the dung, and made a bundle and put it on his head...there was a heavy shower of unseasonable rain and he became spattered with oozing, dripping dung to his finger-tips, but still carried his load of dung. Those who saw him said, 'You must be mad! You must be crazy!' [and he answered] 'You're the ones who are mad! You're the ones who are crazy! This stuff is food for my pigs!'This spoken to one Payasi, a stubborn-minded fellow doggedly holding onto his own pile of metaphorical dung, long after the "rain" had made it worthless.
Or, what about the story found in the Kevatta Sutta (Digha 11) where a monk uses psychic powers to travel up through the successive heavens seeking the answer to a Dhamma question. Each level of gods is unable to answer him, and refers him upstairs; "Surely the gods in the next higher realm will know!" He continues until he reaches the realm of the Great Brahma who does a routine reminiscent of the Wizard of Oz;
"So the monk approached the Great Brahma and, on arrival, said, 'Friend, where do these four great elements — the earth property, the liquid property, the fire property, and the wind property — cease without remainder?'On being asked a second and a third time, at last;
"When this was said, the Great Brahma said to the monk, 'I, monk, am Brahma, the Great Brahma, the Conqueror, the Unconquered, the All-Seeing, All-Powerful, the Sovereign Lord, the Maker, Creator, Chief, Appointer and Ruler, Father of All That Have Been and Shall Be.'
"Then the Great Brahma, taking the monk by the arm and leading him off to one side, said to him, 'These gods of the retinue of Brahma believe, "There is nothing that the Great Brahma does not know. There is nothing that the Great Brahma does not see. There is nothing of which the Great Brahma is unaware. There is nothing that the Great Brahma has not realized." That is why I did not say in their presence that I, too, don't know where the four great elements... cease without remainder. So you have acted wrongly, acted incorrectly, in bypassing the Blessed One in search of an answer to this question elsewhere. Go right back to the Blessed One and, on arrival, ask him this question. However he answers it, you should take it to heart.'Maybe it's just me, but it seems like this passage was intended to be funny.
There are many other examples that could be cited; Moggallana's encounter with Sakka in Majjhima 37, (another one making fun of the gods), or the charlatan Patikuputta in Digha 24 who wants to challenge the Buddha but cannot get up from his seat, ("What is the matter, friend Patikuputta, is your bottom stuck to the seat or is the seat stuck to your bottom?") or so many more.
But my personal favourite, for it's quiet understated humour, is from Majjhima 12, the Greater Discourse of the Lion's Roar. The Buddha is speaking to Sariputta and recounting his early struggle for enlightment. Bear in mind, both are elderly men at this time, roughly the same age'
Now I recall having eaten a single rice grain a day. Sariputta, you may think that the rice grain was bigger at that time, yet you should not regard it so: the rice grain was then at most the same size as now.I don't know why, it cracks me up.
Or as my teacher Kema Ananda once said, "The universe is a huge joke. If you don't find it funny, that's because you haven't reached the punch-line yet."