There are no pictures of Jesus or any of the saints laughing. Is that because none of them were funny or didn't have a sense of humor? No one alive really knows, however, Jesus’ interaction with the Pharisees had great potential for comedy. I do not know whether there was a Hebrew mannerism similar to the rolling of the eyes or not. If there was, then you have to believe that Jesus rolled his eyes when he was challenged with questions like:
Should we pay taxes? (Give to Caesar that which is Caesar's and to God that which is God’s).
A widow marries seven brothers, each one after another brother dies in succession. Who is she married to in Heaven?
We found a sinner, should we kill her!
Who says that you get to say what you’re saying?
I think that Jesus was amazingly patient, but also funny. He was asked so many “Riddle me this, Batman!,” types of questions that he must have laughed at their very nature. He is the Son of God. He could dismiss them, ignore them or possibly have a little bit of humor in his response.
Traps were set for him by the Pharisees and Sadducees again and again. I can imagine the debates the Pharisees had in trying to craft the exact wording for a challenge meant to trip up the Christ. They would take hours debating what question to ask and how. When they finally asked the question, they waited to pounce. Yeah, good luck with that His answers had great humor in their elegant simplicity. In a sentence or maybe two, Jesus revealed the trap and then befuddled the person asking. If you were one of this disciples and you saw the challengers coming, I imagine you might say to each other, “Watch this, this will be good!.”
Humor is not just words. Humor includes tone and timing. The translated Bible that we read now does not always communicate these qualities well. When the gospels are read aloud it is usually with an air of solemnity. A lot of the gospels are solemn. There is no comedy in Jesus’ prediction of His own torturous death. When He chose to chastise, (Peter re: Get behind me satan!), I do not believe that there was any smile.
I would close out my thoughts with this; Jesus was the greatest teacher ever. One of the tools that He used was to teach the importance of humility. A great way to do that is to teach people to understand and laugh at themselves. I think that is why I believe Jesus was funny.