The interpretation timeline
Isaiah 5:21 Douay-Rheims

Woe to you that rue wise in your own eyes, and prudent in your own conceits.

1167 – 1875 7 witnesses

Patristic

before A.D. 750
date
unknown
c. A.D. 132
“That the Black One may find no means of entrance, let us flee from every vanity, let us utterly hate the works of the way of wickedness. Do not, by retiring apart, live a solitary life, as if you were already [fully] justified; but coming together in one place, make common inquiry concerning what tends to your general welfare. For the Scripture saith, "Woe to them who are wise to themselves, and prudent in their own sight!"”
Source

Scholastic

c. 1100 – 1500
1167
A.D.
Ibn Ezra Jewish
1089–1167
“Woe unto them that are wise, etc. They do not know how to discern between good and evil, yet think themselves wise.”
1256
A.D.
Thomas Aquinas Catholic
1225–1274
“Woe to you who call evil good. Here is set down the vanity as to the excusing of sin; and first as to the effect, evil for good: Micah 7: they call the evil of their own hands good; second as to the understanding, light for darkness, truth for error: John 3: men loved darkness more than light; third as to the affection, bitter into sweet, esteeming the life of sin sweet. Wisdom 14: and it was not enough for them to have erred concerning the knowledge of God, but living in a great war of ignorance, they call so many and so great evils peace. Woe to you who are wise. Here is set down the third vanity as to the presumption of sinning, which concerns three things. First, the wisdom of the heart, both in speculative matters, who are wise: Proverbs 3: be not wise in your own estimation: and in practical matters, prudent. Romans 12: do not be prudent in your own estimation. Second, as to the power of the body for sinning: who are mighty to drink: they boast that they can drink much, and become drunk, on account of the custom of the land in which mixed wine is drunk. Below, 41: let the islands be silent toward me, and let the nations change strength. Proverbs 2: they rejoice when they have done evil, and exult in most wicked things. Third, as to authority, who justify — that is, you say that you are of such great authority that at your own pleasure you can justify the impious, so that whatever pleases you may have the force of law: below, 10: woe to those who make unjust laws, and who, writing, have written injustices. Proverbs 17: and he who justifies the impious, and he who condemns the just. Micah 3: and if anyone has not put something into their mouth, they sanctify war against him. Because of this, as it devours. Here he threatens punishment. And first he sets down the punishment of consumption under the metaphor of fire. Because of this, that you draw iniquity, setting for yourselves a root in sins. As the flame of fire burns up the stubble which it touches, and the heat of the flame burns that which is distant: for persecution kills those it takes captive, and afflicts others: Deuteronomy 32: without, the sword shall lay them waste, and within, dread: so their root shall be as ashes, as to those things in which they trusted — whether fathers or kinsmen — and their offshoot, the sons, shall go up as dust; in which is noted the strength arising from those causes. Malachi, last chapter: and all the proud, and all who do wickedness, shall be stubble, and it will set them ablaze. Second, he sets down the process and order of the punishment; and first he sets down the cause of the punishment, and especially as to the first vanity, whence he says: for they have cast away the law, despising it in heart, and have blasphemed the holy word of Israel, mocking with the mouth. Jeremiah 32: they have not obeyed your voice, and have not walked in your law. Second, the anger of the one who punishes; therefore he was angry: he speaks after the manner in which the process of anger occurs in men. Psalm 105: the Lord was angry with fury. Third, the infliction of the punishment: and he stretched out his hand, of power to strike, which, folded, he had held back in sparing. Zephaniah 2: and he shall stretch out his hand over the north, and destroy Assyria, and make the beautiful one a wilderness. Fourth, the effect of the punishment in the destruction of the great ones: the mountains were troubled, that is, the great ones, from fear. The Gloss says that he speaks hyperbolically. But against this: then the prophet would have exceeded the truth. And it must be said that in some writings, "hyperbolically" is taken for an excess of truth simply, but in sacred Scripture for an excess of truth according to the opinion of men; as if he were to say: the trouble will be beyond what could be believed. Or otherwise, hyperbole is a certain trope, and in figurative expressions one thing is said and another is understood. Hence there is no falsity as to the sense which it intends to convey, just as also in metaphor; as if he were to say: so great will the trouble be, that the mountains, if it were possible, would be troubled. Psalm 45: the mountains were troubled, etc. And as to the vileness of bodies, they became carcasses. Jeremiah 8: they shall not be gathered nor buried; they shall be as dung upon the face of the earth. The same, 16: they shall die of grievous deaths, and shall not be lamented, and shall not be buried; they shall be as dung upon the face of the earth.”
Source

Post-Reformation

c. 1650 – 1900
1771
A.D.
John Gill Reformed
1697–1771
“Woe unto therm that are wise in their own eyes,.... And yet betray such stupidity and sottishness, as to call things by their wrong names; and make such a perverse judgment of them, as before described. This is a true description of the Scribes and Pharisees in Christ's time; who said, "dost thou teach us? are we blind also?" Joh 9:34. and prudent in their own sight; being wise above what was written; leaving the word of God, and following the traditions of the elders.”
Source
1849
A.D.
1871
A.D.
1871
“Fifth Woe--against those who were so "wise in their own eyes" as to think they knew better than the prophet, and therefore rejected his warnings (Isa 29:14-15).”
1875
A.D.
Keil & Delitzsch Lutheran
1861–1875
“The fifth woe: "Woe unto them that are wise in their own eyes, and prudent in their own sight." The third woe had reference to the unbelieving naturalists, the opponents of prophecy (nebuâh); the fourth to the moralists, who threw all into confusion; and to this there is appended, by a very natural association of ideas, the woe denounced upon those whom want of humility rendered inaccessible to that wisdom which went hand in hand with prophecy, and the true foundation of which was the fear of Jehovah (Pro 1:7; Job 28:28; Ecc 12:13). "Be not wise in thine own eyes," is a fundamental rule of this wisdom (Pro 3:7). It was upon this wisdom that that prophetic policy rested, whose warnings, as we read in Isa 28:9-10, they so scornfully rejected. The next woe, which has reference to the administration of justice in the state, shows very clearly that in this woe the prophet had more especially the want of theocratic wisdom in relation to the affairs of state in his mind.”
Source
Modern · 1953 →

The in-app commentary runs from the Fathers to the early-modern record, then stops — that's where the public-domain sources end, not where the reading does. For the modern reading, follow the sources directly.