Jesus uses the phrase “this generation” to describe the Jewish people who are hearing his preaching and witnessing his miracles, yet they refuse to believe John was Elijah and Jesus is the Messiah. This generation is a brood of vipers or a wicked and adulterous generation (12:39; 16:4) who will be judged by Nineveh (12:41).
Jesus compares this generation is like children playing in the marketplace saying, “We played the flute for you, and you did not dance; we sang a dirge, and you did not mourn.” The Pharisees and others who opposed John and are now opposing Jesus are “like disagreeable children who complain that others will not act according to their desires and expectations” (Davies and Allison, Matthew, 2:262). They would disapprove of whatever Jesus said or did!
The point of this enigmatic saying is to contrast the ministry of John and Jesus: John came fasting, Jesus came feasting. Yet they were both were rejected. John lived an ascetic lifestyle like Elijah in the wilderness, he was neither eating nor drinking, but “this generation” declared he had a demon.
“This generation” described Jesus as a “glutton and a drunkard” because he was constantly sharing meals with his followers. But many of Jesus’s followers were “tax collectors and sinners.” To be a “friend of sinners” is an insult on a par with saying John has a demon.
Perhaps this saying intentionally contrasts John’s call to repentance as mourning at a funeral to Jesus’s call to participate in his ongoing messianic banquet, dancing at a wedding. In Matthew 9:15 Jesus referred to himself as a bridegroom, saying it was inappropriate to fast while the bridegroom was present. In that context, Jesus called the tax collector Matthew to follow him, and then Matthew hosted a banquet in his home to celebrate. The Pharisees complain that Jesus is eating with “tax collectors and sinners” and the disciples of John the Baptist ask why Jesus does not fast (like John did).
If Jesus is the like a bridegroom, then his ministry is like a wedding celebration. If this is the case, then it is inappropriate to fast. Commenting on the Markan parallel, Anderson argues Jesus is merely making a contrast between his disciples (who are feasting) and the disciples of John (who are fasting) (Mark, 107). Cranfield suggests the disciples of John the Baptist are fasting because of the recent death of John. This would explain the contrast between wedding and funeral imagery in the saying without assigning the saying to the later church (Mark, 111).
Jesus concludes with another enigmatic saying: “Yet wisdom is justified by her deeds.” As with the modern saying, “the proof is in the pudding” (or better, “the proof of the pudding is in the tasting”). Matthew 11 began with John’s question, “are you the coming one?” Jesus’s answer is, “I am doing the messianic deeds which prove my claim to be the messiah.”
It is difficult to imagine that Jesus was “soft on sin.” But what made these people “sinners” in the eyes of the Pharisees is that they dd not conform to the traditions the Pharisees considered important. Jesus reached out to sinners rather than push them away. Imagine how different the church would be if this was practiced consistently!