What exactly, is the Berachah that Yaakov gave Asher?
Rashi: He blessed his land that it should yield an abundance of olives. 1
Targum Onkelos: He blessed him that his land should be fruitful and that it should produce delicacies of kings.
Targum Yonasan: That his land should yield juicy fruit and that it should produce spices and cosmetic-herbs.
Hadar Zekenim: He will put on his own table delicacies of kings.
Indeed, Moshe blessed him in the same way (See Devarim 33:24), a Berachah that was fulfilled in full, as indicated by the story cited in Menachos 85b.
What does "kingly delicacies" refer to?
Rashbam: It was an oil-tax that the kings of Yisrael imposed on the Bnei Asher, to provide them with fine cosmetic oil, to smoothen the skin and remove the hair. 1 Ha'amek Davar - Even though they used much oil, they had so many olives that they were not reluctant to make kingly delights from olives less than a third grown, even though they could have ripened and produced regular oil. It is called Shemen Sateches (Shabbos 80b).
Targum Onkelos: Refer to 49:20:1:2.
Targum Yonasan: Refer to 49:20:1:3.
Malbim: It is all delicious Peros.
See Menachos 86a.
Why does it say, "me'Asher Shemenah Lachmo"?
Moshav Zekenim (to 49:19) #1, Hadar Zekenim (to 49:19): It refers to the previous verse. '[Gad will be] blessed financially even more than Asher,' in order to support his many troops.
Moshav Zekenim (to 49:19) #2: It hints to the 40,000 from Asher who would go to greet David (Divrei Hayamim I 12:37).
Ohr ha'Chayim: Asher will attain this by themselves - either due to its merit, or through its efforts.
Malbim: From Asher, all the Shevatim brought oil to put in their Lechem (food).
Ha'amek Davar: Not only the land caused the abundance of oil. Also Bnei Asher caused this, like the very wealthy man who used to tend to the field himself (Menachos 85b).
