Why do we go out into the street? R' Chiya b' Aba said: 'to express that we've cried out in private and were not answered; let's degrade ourselves in public.' Reish LaKish said: '[this is to express] that we have been exiled, and our exile should atone for us.' What is the practical difference between these approaches? The difference is whether it is sufficient to be 'exiled' from one synagogue to another [to experience the instability of displacement].
And why do we take the Ark out to the city street? R' Yehoshua b' Levi said: '[this is to express] that we had a dignified thing, but it has been degraded by our sins.'
And why do we cover ourselves in sackcloth? R' Chiya b' Aba said: 'to express that we are as worthy as animals.'
And why do we put dust on the Ark? R' Yehuda b' Pazi said this is like [the verse] 'I am with him in distress' (Psalms 91:15). Reish LaKish says [this is like the verse] 'in all their distress, it is distress for Him' (Isaiah 63:9). R' Zera said 'when I first saw them putting ashes on the Ark, my whole body felt perturbed!'
And why do we put dust on each person's forehead? This is debated between R' Levi b' Chama and R' Chanina; one says [this represents] that we are as worthy as dust, and the other says this is to recall the ashes of Isaac. What is the practical difference? The difference is whether we can use any dust, or specifically ashes.
Why do we go to the cemetery? This is debated between R' Levi b' Chama and R' Chanina; one says [this represents that] we are as worthy before You as the dead, and the other says it is so the dead may plead for mercy on our behalf. What is the practical difference? The difference is whether we can go to a non-Jewish cemetery.
(טו) יִקְרָאֵ֨נִי ׀ וְֽאֶעֱנֵ֗הוּ עִמּֽוֹ־אָנֹכִ֥י בְצָרָ֑ה אֲ֝חַלְּצֵ֗הוּ וַֽאֲכַבְּדֵֽהוּ׃
(ה) ...לפיכך כל אחד ואחד חיב לומר, בשבילי נברא העולם.
(5) Therefore, every person must say, “For my sake the world was created.”
It happened that they said to Choni the Circle-Drawer 'pray that rain will fall'. He said to them 'go out and bring in the paschal ovens [made of clay] so them do not disintegrate.' He prayed and no rain fell. What did he do? He drew a circle and stood within it and said 'Master of the World! Your children directed their faces toward me, as I am [seen as] a son of Your house before You. I swear in Your Great Name that I will not move from here until You have mercy upon your children!' Rain began to drizzle; he said 'this is not what I requested, but heavy rains to fill cisterns and caves!' Rain began to pour fiercely; he said 'this is not what I requested, but rains of will, blessings, and generosity!' Rain fell as they were ordered, until the Jews went from Jerusalem to the Temple Mount, because of the rain. They came and said to him, 'just as you prayed for the rain to fall, so too you should pray for the rain to cease. He said to them, 'go and see if the Stone of Claimants has been washed away.' Shimon b' Shetach sent a message to him: 'if you were not Choni, I would have you excommunicated! But what can I do to you, that you rebel before G-d and He does your bidding?! [You are] like a son who throws a tantrum before his father, and his father does his bidding, as it says, 'Your father and mother will rejoice, and those who raised you will be gladdened' (Proverbs 23:25).
בעתם בלילי רביעיות ובלילי שבתות שכן מצינו בימי שמעון בן שטח שירדו להם גשמים בלילי רביעיות ובלילי שבתות עד שנעשו חטים ככליות ושעורים כגרעיני זיתים ועדשים כדינרי זהב וצררו מהם דוגמא לדורות להודיע כמה החטא גורם שנאמר (ירמיהו ה, כה) עונותיכם הטו אלה וחטאתיכם מנעו הטוב מכם
וכן מצינו בימי הורדוס שהיו עוסקין בבנין בהמ"ק והיו יורדין גשמים בלילה למחר נשבה הרוח ונתפזרו העבים וזרחה החמה ויצאו העם למלאכתן וידעו שמלאכת שמים בידיהם:
At their time: Wednesday nights and Shabbat nights [when the rain would not disrupt people's routines]
As we found in the days of Shimon b' Shetach, when rain would fall on Wednesday nights and Shabbat nights, until the wheat was the size of kidneys, and the barley like olive pits, and the lentils like golden denarii [currency], and the made a model of these to demonstrate to later generations how much [damage] a sin causes, as it says (Isaiah 5:25) 'Your iniquities have disrupted these things, and your sins have prevented good from you'.
And so we found in the days of Herod, when they were busy building the Temple, and rain would fall at night, and the next day, the wind would blow, and the clouds would disperse, and the sun would shine, and the nation would go out to their work, and they would know they were engaged in sacred handiwork.
Prayer in the Teachings of R' Soleveitchik (part 2), Rav Aharon Lichtenstein (summarized by Aviad Hacohen) [VBM, May 1996)
Would we dare act in this way before a king of flesh and blood? Would we shout, demand, request and plead? Where do we find such audacity? How do we allow ourselves such "chutzpa" in our relationship with God?
This led the Rav to speak at length of the necessity for the existence of "permission" (a "mattir") for tefilla, something that would serve as a license of sorts, and in this regard he pointed towards a number of halakhot. For instance, it is stipulated that tefillat nedava, a "voluntary prayer" (i.e., not one of the mandatory, regular communal prayers), must include something innovative. It is not sufficient to simply repeat the tefilla which one has already recited, for this novelty serves as his "permission" to add a non-mandatory prayer...
... The forefathers prayed; so did Moshe Rabbeinu and King David. It would seem, therefore, that even if it seems somewhat paradoxical and even if it contradicts the conclusion we would reach were we to focus on the fundamental, theological, ideological-philosophical aspects alone - it is indeed acceptable, and even desirable.
We are in fact commanded to pray...This indicates both the obligation to pray and the permission to do so. Were it not for the obligation, there would be no permission.
Here the question is directed not towards the issue of permission to pray...so much as towards man's very ability to pray: Is it existentially possible for a person to stand in God's presence?
“Prayer is a vital need for the religious individual. He cannot stop the thoughts and emotions, deliberations and troubles which surge through the depths of his soul, his hopes and aspirations, his despair and bitterness...Prayer is essential. In other words, prayer is justified by virtue of the fact that it is impossible to exist without it.”