The interpretation timeline
Judges 9:8 Douay-Rheims

The trees went to anoint a king over them: and they said to the olive tree: Reign thou over us.

A.D. 311 – 1849 5 witnesses

Patristic

before A.D. 750
311
A.D.
c. A.D. 260–311
“But lest I should appear to some to be sophistical, and to conjecture these things from mere probabilities, and to babble, I will bring forward to you, O virgins, from the Old Testament, written prophecy from the book of Judges, to show that I speak the truth, where the future reign of chastity was already clearly foretold.…Now it is clear that these things are not said of trees growing out of the earth. Inanimate trees cannot be assembled in council to choose a king since they are firmly fixed to the earth by deep roots. But on the whole these things are narrated concerning souls that—before the incarnation of Christ—luxuriated too deeply in transgressions, who approach God as beggars asking for mercy so that they may be governed by his pity and compassion. This mercy is what Scripture expresses by the figure of the olive, because oil is of great advantage to our bodies: it takes away our fatigue and ailments and offers light. For all lamplight increases when nourished by oil. So also God's mercies entirely dispel death, assist the human race and nourish the light of the heart. Consider the laws [which were in effect] from the first created man successively on to Christ. Weren't they imaginatively set forth in these words by the Scripture, in opposition to which the devil has deceived humanity? In it the fig tree has been associated with the command given to the man in paradise, because, when he was deceived, he covered his nakedness with the leaves of a fig tree; and the vine [has been related] to the instruction given to Noah at the time of the deluge, because he was mocked when overpowered by wine. The olive signifies the law given to Moses in the desert, because the prophetic grace, the holy oil, had failed from their inheritance when they broke the law. Lastly, the bramble aptly refers to the law that was given to the apostles for the salvation of the world: by their instruction we have been taught virginity, which is the only figure that the devil has not been able to make into a deceptive image. For this reason, also, the four Gospels have been given, because God has four times given the gospel to the human race and has instructed them by four laws, the times of which are clearly known by the diversity of the fruits. For the fig tree, on account of its sweetness and richness, represents the delights of man, which he had in paradise before the fall. Indeed, as we shall afterwards show, the Holy Spirit frequently takes the fruit of the fig tree as an emblem of goodness. But the vine, on account of the gladness produced by wine and the joy of those who were saved from wrath and from the deluge, signifies the change produced from fear and anxiety into joy. Moreover, the olive, on account of the oil that it produces, indicates the compassion of God, who again, after the deluge, bore patiently when people turned aside to ungodliness, so that he gave them the law and manifested himself to some, and nourished by oil the light of virtue, which is now almost extinguished.”
Source
430
A.D.
Augustine of Hippo Patristic
A.D. 354–430
“And no one has been so illiterate as to think that similar fables of Aesop, related for the same purpose, ought to be called lies. But also in the sacred writings such passages are found, as in the book of Judges the trees look for a king to rule over them and speak to the olive and the fig and the vine and the bramble. Surely, all this is invented in order that we may reach the matter intended by means of a narrative [that is] fictitious, to be sure, but bearing a true and not a false signification.”
Source

Scholastic

c. 1100 – 1500
1105
A.D.
Rashi Jewish
1040–1105
“The trees went about resolutely. This is a parable. The olive tree. Asniel ben Kenaz, a tribesman of Judah, who are entitled "olive", as it is said, "Refreshed olive tree, with fruit beautiful in appearance, etc."”

Post-Reformation

c. 1650 – 1900
1771
A.D.
John Gill Reformed
1697–1771
“The trees went forth on a time to anoint a king over them,.... This is an apologue or fable, and a very fine and beautiful one; it is fitly expressed to answer the design, and the most ancient of the kind, being made seven hundred years before the times of Aesop, so famous for his fables, and exceeds anything written by him. By the trees are meant the people of Israel in general, and the Shechemites in particular, who had been for some time very desirous of a king, but could not persuade any of their great and good men to accept of that office: and they said unto the olive tree, reign thou over us; a fit emblem of a good man, endowed with excellent virtues and qualifications for good, as David king of Israel, who is compared to such a tree, Psa 52:8, Jarchi applies this to Othniel the first judge; but it may be better applied to Gideon, an excellent good man, full of fruits of righteousness, and eminently useful, and to whom kingly government was offered, and was refused by him; and the men of Shechem could scarcely fail of thinking of him, and applying it to him, as Jotham was delivering his fable.”
Source
1849
A.D.
1774–1849
“Us. By this parable, Joatham expostulates with the men of Sichem, who had so basely requited the labours of Gedeon, and had given the preference to the son of a servant, who was of the most savage temper. (Haydock) — In a spiritual sense, which the Fathers chiefly regard, heretics and schismatics act in this manner, and choose rather to be governed by those who will allow them to follow their passions, than by such governors as God has appointed, though the latter be endued with the grace of the Holy Ghost, and with all virtues, signified by the olive and other fruit trees. They prefer the bramble, or the worst dispositions, like Nemrod, Mahomet, Antichrist, &c., who, after persecuting the virtuous, and Catholics for a time, (2 Thessalonians ii.) will, in the end, prove their ruin, though they themselves be involved in the common destruction. “Fire shall rise (says Ven. Bede, q. 6.) against this bramble, Antichrist, and shall devour him, and all his together.” (Worthington) — The use of parables has been very general. (Menochius) — Agrippa brought the Roman plebeians, who had retired to the sacred mount, to a sense of their duty, and to a love of mutual harmony with the nobles, by observing that the members once refused to supply the wants of the belly, because it did not labour like the rest. (Livy ii.) — In the application of these parables, Maimonides justly remarks, that we must consider their general scope, and not pretend to explain every circumstance; (More. Neboc.) a remark which Origen had already made. Many things are only added for the sake of ornament. (Haydock) — Thus we need not imagine that the people of Sichem offered the sovereign authority to many, who refused to accept of it, and at last only prevailed upon Abimelech. Gedeon had, indeed, rejected a similar offer, (chap. viii. 22.) and his other sons not endeavouring to retain the authority of their father, the Sichemites acceded to the petition of Abimelech, to anoint him king. This expression does not always imply a material unction, though such was used among the Jews. It signifies the granting of all the power of a king; in which sense it is applied to foreign princes, (Isaias lxv. 1.) and to Jesus Christ, (Daniel ix. 24.) who received the reality of that sovereign dominion, of which this unction was only a figure. (Calmet)”
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.