The Parable of Two Sons

Jesus’ Parable of Two Sons contrasts tax collectors and prostitutes who accepted the message taught by John the Baptist with the “religious” people who rejected John’s message.

In this parable, Jesus rebuked those who considered themselves to be whiter than white, as opposed to those who were deemed “sinners,” such as tax collectors and prostitutes. It was those “sinners” who accepted John’s message of  repentance.

Jesus told a tale of two contrasting sons.


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par•a•ble [noun] a simple story used to illustrate a moral or spiritual lesson, as told by Jesus in the gospels
synonyms: allegory, moral story/tale, fable

The Parable of Two Sons — Matthew 21:28–32

The Parable of Two Sons is about obedience and disobedience. Jesus’ parable told the priests that they'd claimed to accept the message from God but they'd failed to live up to it by being obedient. Outwardly, they were pious and appeared to be people of God, but God knew their heart, and it was in their hearts that they failed miserably.

Coloring page of 'The Parable of the Two Sons'

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To appreciate this parable about Christian life, it’s important to first put it into context. Matthew chapter 21 begins with Jesus’ triumphal entry into Jerusalem. The purpose of Matthew’s gospel was to demonstrate to the Jewish leaders the fact that Jesus was their long-awaited Messiah. As Jesus entered Jerusalem while seated in a donkey, the crowd responded by shouting “Hosannas” and praises to the King. Jesus — specifically and intentionally — introduced this parable to the chief priests, elders, and Pharisees who’d just questioned his authority after he’d cleared the Temple of buyers, sellers, and money changers (vv. 12–17).

Immediately after cleansing the Temple, Matthew tells us that Jesus cursed a fig tree (vv. 18–22), thereby making a symbolic point. A fig tree was often symbolic of Israel. The fact that this one fig tree had leaves but lacked fruit symbolized Israel’s religious activity (i.e., all the trappings of spirituality but without substance). Israel might have had “leaves of activity,” but it lacked the “fruit of repentance and obedience to God,” which was why Jesus told the priests and elders: “Truly I tell you, the tax collectors and the prostitutes are entering the kingdom of God ahead of you” (v. 31).

This parable introduces us to two brothers whose father told them to work in his vineyard. The first son told his father that he wouldn’t work, but he eventually obeyed and worked all day for his dad in the vineyard. The other son initially expressed obedience but instead disobeyed his dad and refused to work.

Jesus then asked the question, “Which of the two did the will of his father?” The answer is clear: The son who did the will of his father was the one who eventually obeyed and performed work, though initially refusing to do so. Jesus then likened the first son (the obedient one) to tax collectors and prostitutes — the outcasts of Jewish society — because they were people who believed John the Baptist and accepted “the way of righteousness” (v. 32), in spite of their initial disobedience to the Law.

Note: The Parable of the Pharisee and the Tax Collector is another parable that highlights this idiom: “actions speak louder than words.” Both parables have a similar theme of outcasts becoming righteous people in God’s eyes.

A down-to-earth parable about the choices we make

The Parable of Two Sons

God Accepts Those Who Repent and Offer Themselves to Him

Matthew 21:28–32

The Parable’s Setting

The Parable of Two Sons (found only in Matthew) is one of a group of three parables with the same theme built around obedience and disobedience to Christ. These are found in Matthew 21:28–22:14. This Two Sons Parable is the first, followed by the Wicked Tenants Parable (vv. 33–46), then the Wedding Banquet Parable (22:1–14). All three share the same thread, that of the acceptance and rejection of Jesus. Each was told to Jewish religious leaders, illustrating their rejection of Jesus and a pronounced judgment on Israel for its rejection of their Messiah. In this parable, the leaders of Israel represent the second son who claimed obedience but didn’t respect or follow the will of the father.

This Two Sons Parable, along with many others, is split into two parts. Part 1 includes the actual parable of the two sons, contained in vv. 28–30. This first part can be summed up as the father’s invitations and the sons’ responses, followed by the father’s responses to each son.

Part 2 presents the parable’s application element (vv. 31–32), which can be broken into four sections, which theologian Donald Hagner designates as: “(1) the faithful response of the first son; (2) the faithful response of tax collectors and prostitutes; (3) the contrast between the unbelief of the Jewish leaders and the faith of the tax collectors and prostitutes with respect to John the Baptist; and (4) a repeated indictment of the Jewish leaders for their hardheartedness.” Remember: The audience to which Jesus spoke was primarily made up of Jewish leaders, chief priests, and Pharisees.

The Analysis of Jesus’ Teaching

In Matthew’s telling of this parable, Jesus invited the listeners to interact with him when he asked them, “What do you think?” (v. 28). By these words, Jesus put them on notice that he was about to present something to them that would require an answer and they, therefore, would have to give him their strictest attention. He then dove in and told the captivating story of the father asking his two sons to work in the vineyard.

Both sons are compared metaphorically. You might see the father as God, the vineyard as Israel, and the two sons as two categories of people: those who obey and those who don’t. More likely, the two sons stand for the Jewish rulers and the Jewish common people who made no special claim to religious excellence; the rulers regarded them as very careless about the will or law of their Father, God; they made disparaging contrasts between their own conduct and that of the common people. But it was these same common people who repented and did the will of God when they heard John the Baptist’s preaching.

By the first son’s refusal to do as his father asked, he wasn’t only disobeying, but was, at the same time, rebelling against his father’s authority. Eventually, the first son changed his mind and obeyed his father’s directive.

Jesus tells us in v. 30: “Then the father went to the other son and said the same thing. He answered, ‘I will, sir,’ but he did not go.” The Jewish rulers, though all the while professing to be zealous for the will of God, utterly refused to enter the kingdom or work therein, as God bade them to do by the voice of John the Baptist.

The father then gave direction to the second son who responded in a way that might remind us of Elijah’s response to God: “Here am I.” The second son initially agreed to go (v. 30); he even strengthened the affirmation of his agreement by referring to his father as “sir” (or “lord” in some translations). However, after acting in opposite ways to the first son, the second son refused to work in the vineyard, breaking his promise with his [F]ather.

Then Jesus asked the critical question (v. 31): “Which of the two did what his father wanted?” “The first," they answered. They gave the correct answer without perceiving that, by so doing, they confirmed that Jesus’ parable had condemned them.

He asked his follow-up question to the crowd that had gathered. Those answering which son did the will of his father weren’t aware of the upcoming judgment that was about to be inflicted on them as a result of what they were about to say. The elders and chief priests answered with an, Of course, the first son was in the will of his father. Jesus continued with the correlation by expressing that those who deemed themselves to be “righteous” hadn’t heeded the words of repentance spoken by John the Baptist. By rejecting John’s directives, they effectively rejected Jesus.

Jesus said to them, “Truly I tell you, the tax collectors and the prostitutes are entering the kingdom of God ahead of you. For John came to you to show you the way of righteousness, and you did not believe him, but the tax collectors and the prostitutes did. And even after you saw this, you did not repent and believe him” (v. 32).

The Parable of Two Sons (Matthew 21:28-32)

For us, today, a problem sometimes arises when we’re so “confident in our righteousness” that we “trust that it will save us and justify us before God.” When we move from living righteously to expecting our righteous living to give us a good standing before God, we’ll have committed a fatal error. In this case, we’ve permitted “righteousness” to become “self-righteousness.” I think it important to appreciate the wording in Matthew’s account pertaining to “the changing mind” of the first son. The word given in the translation to mean “change one’s mind” can also be seen as repenting or feeling regret or remorse.

Jesus went on to insult his listeners by painting a picture of so-called “sinful” tax collectors and prostitutes entering the kingdom before the “righteous” religionists. It’s important to realize that by allowing others to enter God’s kingdom before (or preceding) the Pharisees didn’t exclude the Pharisees themselves from doing similarly. On the contrary, they were welcomed into his kingdom, as are all of God’s children, then and today.

I find it interesting that, although the Pharisees might have chosen to repent, this parable puts them at the end of the line. Nevertheless, whether they’d be at the front, middle, or end of the line isn’t relevant here. The point is, Jesus intentionally invited into his kingdom those who’d previously rejected him. 

A Hearty Way to Apply This Parable Today

Today, it doesn’t seem so strange to disobey a parent’s request. Our society is full of disobedient youngsters lacking respect for adult figures of authority in their lives. During the time of Jesus’ ministry, things were looked at completely differently. The importance of the personal relationship stressed here is essential to appreciate; it helps illustrate the weight of a child’s decision to follow a father’s request. In this parable, Jesus condemned those who merely said but didn’t do. He’s emphasizing the importance of faith with works. For those of us who call ourselves believers, our actions must match our statements.

A second chance: An encouraging aspect of this parable is the acceptance of those who may reject God at first, but, in the end, decide to follow the teachings of Christ. The first son rebelled against his father as many believers do today; thankfully, God always accepts those who want to return and offer themselves back to him. Likewise, God also invites those who resemble the Pharisees to enter his kingdom. Each “child,” “son or daughter,” or “Hearty Boy” has the chance to become part of God’s glory. He also provides us with second chances. When we decide to follow him we must make a sincere, devoted, active, hearty effort to seek and remain in him.

“Truly I tell you, the tax collectors and the prostitutes
are entering the kingdom of God ahead of you”
(Matthew 21:31b).