There are extensive studies of subjects such as irony in the Gospels, and scholars regularly make comparisons between the parables and jokes. But are any of them actually funny? That is a question that is harder to answer, since jokes often lose all semblance of funniness when translated into another language or another cultural setting.
Nevertheless, there are a few strong candidates for genuinely humorous sayings of Jesus. For instance, although we only have the words recorded, I could imagine Jesus enlisting the assistance of one of his disciples to act out a particular parable in Laurel and Hardy fashion, namely the saying about the man who has what in a modern idiom would be a “telephone pole” in his eye trying to assist someone with a “splinter” in his eye (Matthew 7:3-5). The ducking and swinging arm to reflect the “beam” in the eye could certainly be entertaining.
An even more clearly humorous parable is the one about the wedding feast (in Luke 14:16-24). The invited guests’ excuses for not coming are seriously lame, and it is helpful to find modern equivalents in order to make this clear. One is asked to come (on short notice, but that was normal in this historical-cultural setting) and objects in what is the equivalent of saying “I’ve just bought a house on eBay and I need to go see whether it really does have bathrooms”. The next says in effect “I’ve just bought a used car over the phone and I need to go see if it has wheels”. The last member of the trio is the funniest – sometimes what is not said is as important as what is said. He has just gotten married and so… Unlike the other two, there is no second phrase “I have to do X” to justify the final statement, “I cannot come”. What is left out we have to imagine – perhaps in a modern retelling we’d have the man hem and haw: “Sorry, I’m on my honeymoon and my wife and I….I mean, we’re busy….In fact, we were just about to….Look, I can’t come, OK?”
In some instances, as with any humor, the stories people already knew would have been a key part of the “joke”, and so we have little hope of getting it. But I suspect some of Jesus’ stories sounded to his contemporaries a bit like the following: “Whoever hears my words and does not put them into practice is like the little pig who built his house of straw. The big bad wolf came along and huffed and puffed, and that little pig met an unfortunate end. But whoever hears my words and puts them into practice is like the little pig who built his house of bricks…”
Let me conclude with a modern equivalent of what Jesus apparently said at the end of many of his teaching sessions: If you’ve got ears, use ’em!