It is often the comedic exaggeration of Jesus that drives less-than funny
Bible commentators mad as they try to figure out such things as how a camel can fit through the eye of a needle. In fact, one scholar argues that "the most characteristic form of Jesus' humor was the preposterous exaggeration... Jesus humor was often biting and harsh, particularly when directed at the pharisees. For example, he called them a bag of snakes, said that their moms had shagged the devil, and mocked them for tithing out of their spice racks.
He also makes the point that Jesus was invited to parties and had many wild people hang around him.
One of the things that disturbs me is that we often associate fun outside of our Sunday meetings. In the meetings we speak somberly, yet when we go out socially our actions and speech change. Could it be that we need to bring fun back into our meetings and build up the sense that we continue worshiping God when we come into the meetings as well as continue to do so when we go back out into the world?
Mark Driscoll and Gerry Breshears Vintage Jesus: Timeless Answers to Timely Questions (Crossway Books, Illinois, 2007) p.40-41