Jesus has just finished telling the crowds how great John the Baptist is, that he is the culmination of all the prophets up to this point but many in the crowd do not acknowledge John or Jesus as who they really are.
16 “But to what shall I compare this generation? It is like children sitting in the market places and calling to their playmates,
Jesus addresses the crowds surrounding him and asks what he should compare them to. He refers to them as “this generation” which is a term coated with Old Testament connotations as this was the language used to describe the disobedient Israelites in the wilderness who rejected God. Typically thought of as the “wicked generation”. This phrasing can be seen in Numbers 32 and Deuteronomy 1. So although he is referring to his contemporaries he is also comparing them to the wicked generation who rejected God.
Jesus gives a short parable to make his comparison clear. He speaks of children sitting in the public areas around a market who call to their playmates. A little explanation is necessary to explain some of the following verses extending from part B of verse 16. In this time and place, young boys were used to sing, play music and dance at weddings and girls were used in solemn mourning practices of funerals.
17 ‘We piped to you, and you did not dance; we wailed, and you did not mourn.’
One group of children calls to another that they “piped” or played something equivalent to a flute and the other children do not dance for the wedding festivities. Another wails for the funeral mourning practices the others do not mourn. Jesus will clarify later that the leader of these little bands are himself and John.
18 For John came neither eating nor drinking, and they say, ‘He has a demon’;
John is presented as the leader of the wailers who are to call people to mourn and lament, he does this through ascetical practices like fasting and abstaining from alcohol as a witness to his call for peoples repentance but the people do not respond to him as they should, like the little children in the parable, when John wails, the people do not mourn, in fact, they go so far as to accuse him of being possessed.
19 the Son of man came eating and drinking, and they say, ‘Behold, a glutton and a drunkard, a friend of tax collectors and sinners!’ Yet wisdom is justified by her deeds.”
Jesus calling himself by the Messianic Title says that he comes as the piping and dancing child but the people do not respond correctly. They again, like John, accuse him of evil things. Considering the pipes and dancing aspects of weddings, its fitting that Jesus applies this part of the parable to himself as scripture does confirm him to be the divine bridegroom. It is supposed to be a sign of joy for the people but instead they spread calumny about him and call him a drunkard. The truly wise will understand these signs but the truly wise are humble whereas the intelligentsia of ancient Palestine were very learned but not humble.
The point is that whether the people are presented with a sign of sombre repentance like John, or a sign of joy like the Messiah, this generation refuses to play ball with either. It isn’t that they reject the way they do their ministries, it’s that they reject those who have been sent by God. Jesus later will say that “this generation” does not know how to understand the times and signs presented to them.
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