Why did they have to rush Yosef from prison?
Seforno: Because there is a fixed time for a person to go free; when that time arrives, he goes free immediately, not a moment later. 1
Because when a despotic king like Pharaoh calls for someone, the servants jump to it.
Seforno: See Yeshayah 56:1. That is also what happened when the time came to leave Egypt - See Shemos 12:39, and that is what will happen when we go out of the current Galus. See Malachi 3:1.
What is the significance of the fact that Pharaoh himself called for Yosef?
Oznayim la'Torah: Because had they not taken Yosef out of jail in the name of the king, he would have wondered why they were taking him out, and who knows where they were leading him. 1 Now he knew that he was being taken out to greatness.
Oznayim la'Torah: Bearing in mind that he was being held in a prison for prisoners who faced the death-sentence.
Seeing as they rushed Yosef out of prison, why did he first shave?
Rashi: In order to pay the king homage.
Seeing as they rushed Yosef out of prison, why did he first change his clothes?
Seforno: "One does not enter the gate of the king wearing sack-cloth." 1
How could Yosef shave his beard and sideburns? And Midrash says that he came in front of Pharaoh on Rosh Hashanah. How could he shave on Yom Tov?
Moshav Zekenim #1: He shaved the next day. 1
Moshav Zekenim #2: He could shave due to danger of [appearing unkempt in front of] the king.
Bartenura: If the one being shaved does not move his head to help, it is only an Isur mid'Rabanan; it is permitted due to honor of the king.
He did not address shaving the beard. Gur Aryeh implies that he shaved only the head. One opinion (Nazir 58a) permits shaving the entire head, including the sideburns (the beard is not included - PF).
Why does it say "Es Yosef," and not 'El Yosef'?
Ha'amek Davar: It says that "Pharaoh sent;" this hints that the messengers were royal courtiers, and they returned together with Yosef.
QUESTIONS ON RASHI
Rashi writes: "'From the pit' (Bor) - [I.e.] from the jail." Why didn't Rashi explain this above, when Yosef said "they placed me in the pit" (40:15)?
Gur Aryeh #1 (citing Mizrachi): In that verse, we could have explained that Yosef had initially been placed in a pit, before being placed in the jail with the butler and baker (39:20; 40:3). Here, we know that he was already in jail, and we are forced to explain that the "pit" means a jail.
Gur Aryeh #2: Pasuk 40:15 was in Yosef's own words; he might refer to the jail as a pit to express how deeply he had been lowered. But this Pasuk is the Torah's narrative, it is not using a descriptive expression. Rather, the word "Bor" includes any structure one digs into the ground.
Rashi writes: "'He cut his hair' - Because of respect for the king." What is Rashi explaining
Gur Aryeh #1 (citing Mizrachi): Do not explain that he shaved just like anyone who leaves jail; 1 for Yosef did not yet know if he was being set free, or if he would be sent back to jail!
Gur Aryeh #2: Pharaoh had sent for him; it seems disrespectful that he would delay [to take care of his own needs] by shaving. Rashi explains that on the contrary, his intent was to honor the king.
See Moed Katan 13b.
