I had a theology professor once who used to talk about how filled with humor the parables of Jesus are, but how we lose most of it because we don't get the cultural context. Jesus often poked fun at the social structures of his times, including the pomposity of religious leaders. There's almost always an ironic twist in his stories that challenged the status quo.

I doubt he would have been such a popular dinner guest if he was as dour as he is sometimes portrayed in contemporary preaching. Wouldn't you love to have been in the room when he kicked back after a meal and told the stories that didn't make it into the Gospels?