The interpretation timeline
Luke 19:41 Douay-Rheims

And when he drew near, seeing the city, he wept over it, saying:

A.D. 253 – 1871 11 witnesses 16 excerpts

Patristic

before A.D. 750
253
A.D.
Origen Patristic
c. A.D. 184–253
“All the blessings which Jesus pronounced in His Gospel He confirms by His own example, as having declared, Blessed are the meek; He afterwards sanctions it by saying, Learn of me, for I am meek; and because He had said, Blessed are they that weep, He Himself also wept over the city.”
“I do not deny then that the former Jerusalem was destroyed because of the wickedness of its inhabitants, but I ask whether the weeping might not perhaps concern this your spiritual Jerusalem. For if a man has sinned after receiving the mysteries of truth, he will be wept over. Moreover, no Gentile is wept over, but he only who was of Jerusalem, and has ceased to be.”
Source
“But our Jerusalem is also wept over, because after sin enemies surround it, (that is, wicked spirits,) and cast a trench round it to besiege it, and leave not a stone behind; especially when a man after long continency, after years of chastity, is overcome, and enticed by the blandishments of the flesh, has lost his fortitude and his modesty, and has committed fornication, they will not leave on him one stone upon another, according to Ezekiel, His former righteousness I will not remember. (Ezek 18:24.)”
Source
339
A.D.
c. A.D. 260–339
“He here declares that His coming was to bring peace to the whole world. For unto this He came, that He should preach both to them that were near, and those that were afar off. But as they did not wish to receive the peace that was announced to them, it was hid from them. And therefore the siege which was shortly to come upon them He most expressly foretells, adding, For the days shall come upon thee, &c.”
Source
“But how these things were fulfilled we may gather from what is delivered to us by Josephus, who though he was a Jew, related each event as it toot place, in exact accordance with Christ’s prophecies.”
444
A.D.
A.D. 376–444
“For Christ had compassion upon the Jews, who wills that all men should be saved. Which had not been plain to us, were it not revealed by a certain mark of His humanity. For tears poured forth are the tokens of sorrow.”
“If thou hadst known, even thou. The Jews were not worthy to receive the divinely inspired Scriptures, which relate the mystery of Christ. For as often as Moses is read, a veil overshadows their heart that they should not see what has been accomplished in Christ, who being the truth puts to flight the shadow. And because they regarded not the truth, they rendered themselves unworthy of the salvation which flows from Christ.”
Source
604
A.D.
Gregory the Great Patristic
c. A.D. 540–604
“(ut sup.) By these words the Roman leaders are pointed out. For that overthrow of Jerusalem is described, which was made by the Roman emperors Vespasian and Titus.”
“(Hom. 39. in Ev.) Or else; The evil spirits lay siege to the soul, as it goes forth from the body, for being seized with the love of the flesh, they caress it with delusive pleasures. They surround it with a trench, because bringing all its wickedness which it has committed before the eyes of its mind, they close confine it to the company of its own damnation, that being caught in the very extremity of life, it may see by what enemies it is blockaded, yet be unable to find any way of escape, because it can no longer do good works, since those which it might once have done it despised. On every side also they inclose the soul when its iniquities rise up before it, not only in deed but also in word and thought, that she who before in many ways greatly enlarged herself in wickedness, should now at the end be straitened every way in judgment. Then indeed the soul by the very condition of its guilt is laid prostrate on the ground, while its flesh which it believed to be its life is bid to return to dust. Then its children fall in death, when all unlawful thoughts which only proceed from it, are in the last punishment of life scattered abroad. These may also be signified by the stones. For the corrupt mind when to a corrupt thought it adds one more corrupt, places one stone upon another. But when the soul is led to its doom, the whole structure of its thoughts is rent asunder. But the wicked soul God ceases not to visit with His teaching, sometimes with the scourge and sometimes with a miracle; that the truth which it knew not it may hear, and though still despising it, may return pricked to the heart in sorrow, or overcome with mercies may be ashamed at the evil which it has done. But because it knows not the time of its visitation, at the end of life it is given over to its enemies, that with them it may be joined together in the bond of everlasting damnation.”
Source

Scholastic

c. 1100 – 1500
1107
A.D.
c. 1055–1107
“That is, of my coming. For I came to visit and to save thee, which if thou hadst known and believed on Me, thou mightest have been reconciled to the Romans, and exempted from all danger, as did those who believed on Christ.”

Reformation

c. 1500 – 1650
1637
A.D.
1567–1637
“And when He, &c. To show the bowels of His love to it. How dear to Him was the salvation of the Jews, for to this had He been sent by the Father as the Messiah and Saviour. He wept therefore among all the joys of His triumph, and amidst the happy declamations of those who congratulated Him and shouted Hosanna, that He might temper their joy, by a mixture as it were of gall He wept as well over the blindness, obduracy, and ingratitude of the people of Jerusalem, because they would not receive Him as their Messiah and Saviour, as for the vengeance of God towards them and the destruction of their nation by Titus ; and because He saw His own labours and sufferings for them frustrated and rendered of no effect These three causes wrung tears from Christ, from the vehemence of His grief So S. Cyril, Bede, Theophylact and others. In trope , Origen says, “ Christ fulfilled all the beatitudes in His own Person. He said, ‘Blessed are they that mourn/ and He therefore wept””
Source

Post-Reformation

c. 1650 – 1900
1714
A.D.
Matthew Henry Reformed
1662–1714
“The great Ambassador from heaven is here making his public entry into Jerusalem, not to be respected there, but to be rejected; he knew what a nest of vipers he was throwing himself into, and yet see here two instances of his love to that place and his concern for it. I. The tears he shed for the approaching ruin of the city (Luk 19:41): When he was come near, he beheld the city, and wept over it. Probably, it was when he was coming down the descent of the hill from the mount of Olives, where he had a full view of the city, the large extent of it, and the many stately structures in it, and his eye affected his heart, and his heart his eye again. See here, 1. What a tender spirit Christ was of; we never read that he laughed, but we often find him in tears. In this very place his father David wept, and those that were with him, though he and they were men of war. There are cases in which it is no disparagement to the stoutest of men to melt into tears. 2. That Jesus Christ wept in the midst of his triumphs, wept when all about him were rejoicing, to show how little he was elevated with the applause and acclamation of the people. Thus he would teach us to rejoice with trembling, and as though we rejoiced not. If Providence do not stain the beauty of our triumphs, we may ourselves see cause to sully it with our sorrows. 3. That he wept over Jerusalem. Note, There are cities to be wept over, and none to be more lamented than Jerusalem, that had been the holy city, and the joy of the whole earth, if it be degenerated. But why did Christ weep at the sight of Jerusalem? Was it because "Yonder is the city in which I must be betrayed and bound, scourged and spit upon, condemned and crucified?" No, he himself gives us the reason of his tears. (1.) Jerusalem has not improved the day of her opportunities. He wept, and said, If thou hadst known, even thou at least in this thy day, if thou wouldst but yet know, while the gospel is preached to thee, and salvation offered thee by it; if thou wouldest at length bethink thyself, and understand the things that belong to thy peace, the making of thy peace with God, and the securing of thine own spiritual and eternal welfare - but thou dost not know the day of thy visitation, Luk 19:44. The manner of speaking is abrupt: If thou hadst known! O that thou hadst, so some take it; like that O that my people had hearkened unto me, Psa 81:13; Isa 48:18. Or, If thou hadst known, well; like that of the fig-tree, Luk 13:9. How happy had it been for thee! Or, "If thou hadst known, thou wouldest have wept for thyself, and I should have no occasion to weep for thee, but should have rejoiced rather." What he says lays all the blame of Jerusalem's impending ruin upon herself. Note, [1.] There are things which belong to our peace, which we are all concerned to know and understand; the way how peace is made, the offers made of peace, the terms on which we may have the benefit of peace. The things that belong to our peace are those things that relate to our present and future welfare; these we must know with application. [2.] There is a time of visitation when those things which belong to our peace may be known by us, and known to good purpose. When we enjoy the means of grace in great plenty, and have the word of God powerfully preached to us - when the Spirit strives with us, and our own consciences are startled and awakened - then is the time of visitation, which we are concerned to improve. [3.] With those that have long neglected the time of their visitation, if at length, if at last, in this their day, their eyes be opened, and they bethink themselves, all will be well yet. Those shall not be refused that come into the vineyard at the eleventh hour. [4.] It is the amazing folly of multitudes that enjoy the means of grace, and it will be of fatal consequence to them, that they do not improve the day of their opportunities. The things of their peace are revealed to them, but are not minded or regarded by them; they hide their eyes from them, as if they were not worth taking notice of. They are not aware of the accepted time and the day of salvation, and to let it slip and perish through mere carelessness. None are so blind as those that will not see; nor have any the things of their peace more certainly hidden from their eyes than those that turn their back upon them. [5.] The sin and folly of those that persist in a contempt of gospel grace are a great grief to the Lord Jesus, and should be so to us. He looks with weeping eyes upon lost souls, that continue impenitent, and run headlong upon their own ruin; he had rather that they would turn and live than go on and die, for he is not willing that any should perish. (2.) Jerusalem cannot escape the day of her desolation. The things of her peace are now in a manner hidden from her eyes; they will be shortly. Not but that after this the gospel was preached to them by the apostles; all the house of Israel were called to know assuredly that Christ was their peace (Act 2:36), and multitudes were convinced and converted. But as to the body of the nation, and the leading part of it, they were sealed up under unbelief; God had given them the spirit of slumber, Rom 11:8. They were so prejudiced and enraged against the gospel, and those few that did embrace it then, that nothing less than a miracle of divine grace (like that which converted Paul) would work upon them; and it could not be expected that such a miracle should be wrought, and so they were justly given up to judicial blindness and hardness. The peaceful things are not hidden from the eyes of particular persons; but it is too late to think now of the nation of the Jews, as such, becoming a Christian nation, by embracing Christ. And therefore they are marked for ruin, which Christ here foresees and foretels, as the certain consequence of their rejecting Christ. Note, Neglecting the great salvation often brings temporal judgments upon a people; it did so upon Jerusalem in less than forty years after this, when all that Christ here foretold was exactly fulfilled. [1.] The Romans besieged the city, cast a trench about it, compassed it round, and kept their inhabitants in on every side. Josephus relates that Titus ran up a wall in a very short time, which surrounded the city, and cut off all hopes of escaping. [2.] They laid it even with the ground. Titus commanded his soldiers to dig up the city, and the whole compass of it was levelled, except three towers; see Josephus's history of the wars of the Jews, 5.356-360; 7.1. Not only the city, but the citizens were laid even with the ground (thy children within thee), by the cruel slaughters that were made of them: and there was scarcely one stone left upon another. This was for their crucifying Christ; this was because they knew not the day of their visitation. Let other cities and nations take warning. II. The zeal he showed for the present purification of the temple. Though it must be destroyed ere long, it does not therefore follow that no care must be taken of it in the mean time. 1. Christ cleared it of those who profaned it. He went straight to the temple, and began to cast out the buyers and sellers, Luk 19:45. Hereby (though he was represented as an enemy to the temple, and that was the crime laid to his charge before the high priest) he made it to appear that he had a truer love for the temple than they had who had such a veneration for its corban, its treasury, as a sacred thing; for its purity was more its glory than its wealth was. Christ gave reason for his dislodging the temple-merchants, Luk 19:46. The temple is a house of prayer, set apart for communion with God: the buyers and sellers made it a den of thieves by the fraudulent bargains they made there, which was by no means to be suffered, for it would be a distraction to those who came there to pray. 2. He put it to the best use that ever it was put to, for he taught daily in the temple, Luk 19:47. Note, It is not enough that the corruptions of a church be purged out, but the preaching of the gospel must be encouraged. Now, when Christ preached in the temple, observe here, (1.) How spiteful the church-rulers were against him; how industrious to seek an opportunity, or pretence rather, to do him a mischief (Luk 19:47): The chief priests and scribes, and the chief of the people, the great sanhedrim, that should have attended him, and summoned the people too to attend him, sought to destroy him, and put him to death. (2.) How respectful the common people were to him. They were very attentive to hear him. He spent most of his time in the country, and did not then preach in the temple, but, when he did, the people paid him great respect, attended on his preaching with diligence, and let no opportunity slip of hearing him, attended to it with care, and would not lose a word. Some read it, All the people as they heard him, took his part; and so it comes in very properly as a reason why his enemies could not find what they might do against him; they saw the people ready to fly in their faces if they offered him any violence. Till his hour was come his interest in the common people protected him; but, when his hour was come, the chief priests' influence upon the common people delivered him up.”
1771
A.D.
John Gill Reformed
1697–1771
“For the days shall come upon thee,.... Suddenly, and very quickly, as they did within forty years after this: that thine enemies; the Romans, and such the Jews took them to be, and might easily understand who our Lord meant: shall cast a trench about thee, and compass thee round, and keep thee in on every side: which was not only verified in the Roman armies closely besieging them; but particularly in this, as Josephus relates (t) that Titus built a wall about the city, of thirty nine furlongs long, and thirteen forts in it which reached ten furlongs, and all done in three days time; by which means they were pent up, starved, and famished, and reduced to inexpressible distress. (t) De Bello Jud. l. 6. c. 8.”
Source
1832
A.D.
1849
A.D.
1774–1849
“He wept. St. Epiphanius tells us, that some of the orthodox of his time, offended at these words, omitted them in their copies, as if to shed tears, were a weakness unworthy of Christ: but this true reading of the evangelist is found in all copies, and received by all the faithful; and the liberty which those who changed them took, was too dangerous ever to be approved of by the Church. Neither do these tears argue in Jesus Christ any thing unworthy of his supreme majesty or wisdom. Our Saviour possessed all the human passions, but not the defects of them. The Stoics, who condemned the passions in their sages, laboured to make statues or automata of man, not philosophers. The true philosopher moderates and governs his passions; the Stoic labours to destroy them, but cannot effect his purpose. And when he labours to overcome one passion, he is forced to have recourse to another for help. (Calmet) — Our Saviour is said to have wept six times, during his life on earth: 1st, At his birth, according to many holy doctors; 2ndly, at his circumcision, according to St. Bernard and others; 3rdly, when he raised Lazarus to life, as is related in St. John, chap. xi.; 4thly, in his entry into Jerusalem, described in this place; 5thly, during his agony in the garden, just before his apprehension, when, as St. Luke remarks, (Chap. xxii.) his sweat was as drops of blood trickling down upon the ground; and 6thly, during his passion, when he often wept, on account of his great distress of mind, occasioned principally by the knowledge he had of the grievousness of men’s sins, and the bad use they would make of the redemption he was, through so many sufferings, procuring for them. (Dionysius)”
Source
1871
A.D.
1871
“when beheld . . . wept--Compare Lam 3:51, "Mine eye affecteth mine heart"; the heart again affecting the eye. Under this sympathetic law of the relation of mind and body, Jesus, in His beautiful, tender humanity, was constituted even as we. What a contrast to the immediately preceding profound joy! He yielded Himself alike freely to both. (See on Mat 23:37.)”
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.