In the run-up to the event, Randy J. Hunt did a short interview Allan Chochinov of Core77 about the event’s aims, and how designers employ wit, irony—even subversion—in the service of making a connection with their audience.
The biggest issue, in my mind, is that humor is so culture specific and culturally bound. Americans, Italians and Brits have a very different sense of humor, and there are many variations within these countries as well. So it is an extremely complex issue and not at all easy to standardise and implement in design.