What do the inverted words, "va'Yachalmu Chalom Sheneihem" teach us?
Rashi #1: It means simply that they both had a dream. 1
Rashi #2: It teaches us that each one dreamt his own dream, and the interpretation of that of his friend.
Ha'amek Davar: In Chulin 92a, many interpret the dreams regarding Yisrael. They explain Sheneihem to be the Sar and his companion, i.e. Yosef.
As if the Torah had written 'va'Yachalmu Sheneihem Chalom.'
What is the significance of the fact that the butler and the baker dreamt on the same night?
Oznayim la'Torah: It was the night of Rosh Hashanah, when most dreams come via an angel, and are therefore significant. 1
See Oznayim la'Torah to 41:1.
Why does the Torah add, "Ish k'Fisron Chalomo"?
Rashi: Each dream resembled the interpretation that would be given for it. 1
Ramban (citing the Ibn Ezra): Each one dreamt his dream and the events that Yosef ultimately interpreted, down to the last letter.
Rashbam: They were dreams that were worthy of interpretation, and not just meaningless ones.
Targum Yonasan, and Berachos 55b: Each one dreamt his own dream and the other one's interpretation. 2
Malbim: Each dreamed what was appropriate for him (about wine or bread). Further, it was appropriate for the Sar himself, and not for the worker under him; i.e. the Sar himself would put the cup in Pharaoh's hand, or carry the baskets of baked goods.
Just like Pharaoh's dream resembled the interpretation given for it (as the Ramban explains below to 41:12). However see Ramban's objection to this explanation here. Gur Aryeh explains Rashi slightly differently; refer to 40:5:2.3:1.
Rashi derives this interpretation earlier in the Pasuk, from the words "Chalom Sheneihem."
Why does the Pasuk repeat the fact that they were the Mashkeh and the Ofeh of Melech Mitzrayim, and that they were incarcerated?
Seforno: Even though they were important officers, the fact that they were in jail affected them negatively, and they dreamt like plain butlers and bakers.
Oznayim la'Torah: Because they were therefore unlikely to have thought about serving the king - a further sign that their dreams were (not merely what they thought during the day, but) dictated by an angel. 1
Malbim: Although the Sarim had the dreams, the message was fitting for the Mashkeh and the Ofeh (i.e. their workers), who were in the same prison. Meaning, the baker should have been killed for his great negligence, but the wine-maker deserved to live, for the fly was Ones. But the dreams' message was not fitting for the Sarim; Sar ha'Mashkim was more negligent than Sar ha'Ofim! (Refer to 40:2:151:1.)
Ha'amek Davar: This is why Yosef interpreted in the way that he did. If any of these details were missing, he would not interpret so. 2 It did not depend on being Sarim, so they are not called Sarim.
Refer to 40:5:1.1:1.
This implies that Yosef interpreted based on his Chochmah, without Ru'ach ha'Kodesh, unlike his Perush of Pharaoh's dreams. (PF)
QUESTIONS ON RASHI
Rashi writes: "Each one dreamed his own dream; and the interpretation of his friend's dream." How then should we interpret the verse, "They both dreamed a [i.e. one] dream, each one his [own] dream"?
Gur Aryeh: Both of them dreamed one dream - in essence - in that what they saw portended the future - both for himself, and for his fellow. But what exactly they saw was not identical; for each one saw only the riddle of his own dream, and the outcome for the other's dream. (For example, the butler saw that the baker would be hung; he did not see the three wicker baskets, etc.) 1
Gur Aryeh: This is unlike Mizrachi's understanding of Rashi. Mizrachi finds difficult that the verse implies that each one dreamed his own dream. Gur Aryeh explains how each dream was in fact distinct.
Rashi writes: "'Each one, like the Pisaron of his dream' - Each dreamt a dream that resembled the interpretation that would befall them." How else might I have understood it?
Gur Aryeh: The verse seems to imply that they dreamt the interpretations (as well)! Rashi explains that this was not so; rather, it means that the dreams appropriately matched the interpretations that would follow.
Rashi writes: "... A dream that resembled the interpretation that would befall them." What is the verse telling us with this added phrase?
Gur Aryeh: Do not say that the solution was a farfetched interpretation of the dream's content, and Yosef just happened to interpret accurately. Rather, the solution emerged from the dream itself.
Rashi writes: "'Each one, like the Pisaron of his dream' - ... resembling the interpretation that would befall them." Why does Rashi add these words?
Gur Aryeh: The verse seems to imply that the dream matched the interpretation, whereas the inverse would be more correct - an interpretation should match the dream! Rashi tells us that "Pisaron" means 'outcome;' each dream matched the events that would befall them shortly.
