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Describing the literal and figurative weeping of the heavens at the time of Enoch, Hugh Nibley writes:[2]

One of nature’s ironies is that not enough water usually leads to too much. Enoch’s world was plagued by flood as well as drought; we are regaled by the picture of lowering heavens ceaselessly dumping dismal avalanches of rain and snow upon the earth. The constant weeping of Enoch and all the saints is matched in the powerful imagery of the weeping heavens and the earth veiled in darkness under the blackest of skies: In the book of Enoch the same imagery is applied to the meridian and the fulness of times as well as the Adamic age.

In this Essay, we will survey examples of the weeping of the heavens from the time of Creation through the time of Noah.
The Weeping of the Heavens at the Time of Creation
Providing a plausible echo of the imagery of the weeping of the heavens in Enoch’s account is an ancient Jewish theme that is always associated with the second day of Creation, when the heavenly and earthly waters were separated by the firmament. According to David Lieber:[3]

The Midrash pictures the lower waters weeping at being separated from the upper waters, suggesting that there is something poignant in the creative process when things once united are separated.

So painful was the command of God for the waters to separate that they were seen as having actually rebelled.[4] As Heschel recounts:[5]

On the second day of creation, the Holy and Blessed One said: “Let there be an expanse (raki’a) in the midst of the water, that it may separate water from water. God made the expanse, and it separated the water that was below the expanse from the water which was above the expanse.”[6] God said to the waters: “Divide yourselves into two halves; one half shall go up, and the other half shall go down”; but the waters presumptuously all went upward. Said to them the Holy and Blessed One: “I told you that only half should go upward, and all of you went upward?” Said the waters: “We shall not descend!” Thus did they brazenly confront their Creator. … What did the Holy and Blessed One do? God extended His little finger, and they tore into two parts, and God took half of them down against their will. Thus it is written: “God said, ‘let there be an expanse’”[7] (raki’a)—do not read “expanse” (raki’a) but “tear” (keri’a).”

Heschel makes it clear “that the waters rebe...