Few of us are familiar with the culture Jesus lived in. In our culture, most humor is based on joke telling, verbal ambiguities, and physical comedy. Jewish humor often employed witty hyperbole—clever, startling, over-the-top statements—to get a laugh. Though some comedians today do this and we laugh, when we see Jesus use the technique in the Gospels, we usually don’t get it. Jesus certainly never employed the caustic humor of late-night comedians who ridicule the weak minded or the unfortunate. But He did make hypocrites in positions of power the brunt of his wit.
In The Humor of Christ, Elton Trueblood argued,
There are numerous passages . . . which are practically incomprehensible when regarded as sober prose, but which are luminous once we become liberated from the gratuitous assumption that Christ never joked. . . . Once we realize that Christ was not always engaged in pious talk, we have made an enormous step on the road to understanding 
Did humor come into the universe as the result of sin? No. As I share in my book Happiness, we have a sense of humor because as His image bearers, we are similar to God, who enjoys laughter.
The Dictionary of Biblical Imagery says, “Jesus was a master of wordplay, irony and satire, often with an element of humor intermixed.”  Jesus makes many serious points in humorous ways. “Are grapes gathered from thornbushes?” He asks, “or figs from thistles?” (Matthew 7:16). People who worked the ground in that culture surely smiled at the self-evident answers. When encountering a verse such as this one, which instructs us not to “cast your pearls before swine” (Matthew 7:6, NKJV), a modern reader might wonder why anyone would even think to do such an outlandish thing. But that’s the whole point—no sane person would! Therefore, Jesus was saying, don’t do the spiritual equivalent of that ridiculously stupid thing.
Jesus told people, “When you give to the needy, sound no trumpet before you, as the hypocrites do in the synagogues and in the streets, that they may be praised by others” (Matthew 6:2). No one would do anything so obviously self-promoting. Instead, they’d draw attention to themselves by walking slowly and piously, making their money clearly visible. These self-congratulatory actions, which Jesus characterized as “sounding a trumpet,” undoubtedly produced numerous smiles, smirks, and chuckles.
Can’t you imagine folks looking at each other with amazement and nervous glee when Jesus said, “Woe to you, scribes and Pharisees, hypocrites! For you are like whitewashed tombs, which outwardly appear beautiful, but within are full of dead people’s bones and all uncleanness” (Matthew 23:27)? Jesus was not telling jokes but painting mental pictures with a humorous, satirical sting. Think of the religious leaders’ outrage when Jesus said, “The harlots go into the kingdom of God before you” (Matthew 21:31, KJV). Then think of the approving smiles of the poor and oppressed in the crowds who finally saw someone unafraid to confront these pseudospiritual false shepherds.
Jesus referred to the shrewd and ruthless political leader Herod as “that fox” (Luke 13:32). Since a fox is cunning, this may appear to be a compliment, but it certainly wouldn’t have been lost on the crowd that those pointy-eared varmints were nuisances, not terrors. Jesus was poking fun at a vicious, immoral, murderous tyrant by comparing him not to a lion or a bear but to a fox! Imagine people going home and telling their friends, “You won’t believe what Jesus called Herod!”
Jesus said, “And when you fast, do not look gloomy like the hypocrites, for they disfigure their faces that their fasting may be seen by others” (Matthew 6:16). (“Do not look gloomy” would be a great memory verse for some churchgoers!) The self-righteous religionists of Jesus’ day liked to call attention to their fasting by rubbing ashes on their faces to make them look gaunt and deprived. The more miserable, the more spiritual—or so they supposed. Christ made fun of them for it, and they didn’t like it—but no doubt many of His listeners enjoyed hearing the self-righteous leaders taken to task.
Jesus said of the religious leaders, “They are blind guides. And if the blind lead the blind, both will fall into a pit” (Matthew 15:14). This graphic word picture might have prompted outright laughter. Of course, Jesus wasn’t making fun of the blind; He was critiquing the wealthy, powerful, influential people who prided themselves on their supposed clarity of spiritual vision.
Jesus also used exaggeration for comedic effect. Jesus told the religious leaders they were sightless, missing the whole point of following God: “You blind guides, straining out a gnat and swallowing a camel!” (Matthew 23:24). Straining out a gnat would have been hard work for anyone—but impossible for the blind. And what could be more ridiculous than swallowing a camel? This odd and pithy statement undoubtedly caused laughter to erupt.
The Dictionary of Biblical Imagery says, “The most characteristic form of Jesus’ humor was the preposterous exaggeration.”  It’s important to understand that this form of exaggeration is not falsehood in any sense, because the hearer knows it’s overstatement. The speaker is not misleading anyone; rather, He is appealing to the hearer’s humor to make his point.
Consider the parable of the talents in Matthew 25. Jesus depicts a wealthy man who hands over one to five talents to various servants. Five talents would have been the equivalent of nearly a hundred years’ wages.  In a culture where many people lived hand to mouth, this extreme amount of money would equate to saying, “There was a man who ate one thousand gourds.” The storyteller deliberately paints an absurd picture, with a gleam in his eye, to emphasize his point.
Jesus took hyperbole—a rhetorical art form—to a new level in His story about the king who loaned one of his servants ten thousand talents (see Matthew 18:23-35), an amount so ludicrous it defied comprehension, since the average person made one talent every twenty years.  Imagine the listeners’ expressions when they tried to calculate the sum that the king forgave his servant.
Then Jesus said another servant owed the forgiven servant one hundred denarii (see Matthew 18:28). A denarius was a day’s wage, and although a hundred days’ wages was significant, it was the tiniest fraction compared to the forgiven servant’s debt. The parallel to each person’s debt to God, which is beyond measure, must have had a deep impact. It wasn’t stand-up comedy (which might not have been funny to them anyway), but Jesus’ humor certainly would have resonated with His original audience.
Consider when Jesus asked, “Why do you see the speck that is in your brother’s eye, but do not notice the log that is in your own eye? . . . You hypocrite, first take the log out of your own eye, and then you will see clearly to take the speck out of your brother’s eye” (Matthew 7:3, 5). Surely the ridiculous picture of a log sticking out of a man’s eye produced not only a sense of conviction but also broad smiles.
Elton Trueblood recounted how he noticed Christ’s humor for the first time. He was reading Matthew 7 aloud when his young son burst into laughter at Jesus’ words about a log in the eye. Until then, Trueblood had failed to see Christ’s obvious wit. 
Those who heard Jesus speak knew His keen humor—and they were endeared to Him. The humor of Jesus is far more apparent if we understand His culture and engaging personality. There’s nothing disrespectful about noticing that many of Jesus’ statements are, by design, happily outrageous.
 Elton Trueblood, The Humor of Christ (New York: Harper & Row, 1964), 10.
 Leland Ryken, James C. Wilhoit, and Tremper Longman III, eds., “Humor—Jesus as Humorist,” Dictionary of Biblical Imagery (Downers Grove, IL: InterVarsity Press, 1998), 410.
 See footnote on Matthew 25:15, ESV Study Bible (Wheaton, IL: Crossway, 2008).
 See note on Matthew 18:24, The NET Bible (Biblical Studies Press, 2006).
 Trueblood, Humor of Christ, 9.