The three parables in 21:28-22:14 together respond to the Jewish leaders, critiquing them harshly (compare van Tilborg 1972:47-52). Ancient Mediterranean culture demanded that sons honor and obey their parents, especially when they still lived on the father's estate (see Keener 1991:98, 197). The parable's point is obvious enough in Matthew's context: the repentant (3:2) son does the father's will (7:21; 12:50); the unrepentant son is unfruitful (3:8), claiming to do but not doing (23:3). Thus the latter stands for Israel's religious leaders, in contrast to the humble who heed John and Jesus.The issue is not that the tax collectors and the prostitutes were good (compare 9:9; 18:17; cf. 19:17); it is that the religious and political elite were worse, being treasonous (22:5-10). Jesus provides a question after a parable (as in Is 5:3-4; Mt 21:40).

The interpretation of this parable follows naturally after 21:23-27: Jesus and John represent the same source of moral authority, and those who rejected John's way of righteousness showed the hypocrisy of their own claims to be God's servants. The repentance of more openly sinful people did not provoke them to jealousy for their own spiritual status (compare Rom 11:14).