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I heard a quote once how carefully a person needs to analyze every drop of ink in Rashi, but I don't remember who said it. Does any Rishon (medieval scholar) ever discuss their approach to Rashi's perush on Gemara? Do they ever make diyyukim, or do very close readings of rashi?

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There is a rishon who explicitly says how to analyze Rashi. It is Rabbi Yitzhak Kanpanton from Spain. He was the rabbi of the Abuhav who was the rabbi of the Bet Yosef. He wrote a clear approach of how to learn gemara.

This book can save the world. Nothing like it in the last 500 years. The Chason Ish held highly of the book, as did the Shelah. It is Darchei Hatalmud or Darchei Hagemera.

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avihu aboud, welcome to Judaism.SE, and thanks very much for this information! I deleted the last part of your answer, which was not directly relevant to the question at hand. Any information about yourself that you'd like to share should go in your profile. Also, please consider registering your account, to ensure that the same profile is connected to all of your contributions. –  Isaac Moses Oct 19 '11 at 14:18
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In order to help analyze Rashi you must also know his "buzzwords". In the back of every edition of Masechet Brachos is the Mevo Hatalmud. In the back of the Mevo Hatalmud is a small section called כּללים רשׁי "Klalim Rashi" where many terms are explained.

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The question asked specifically for rishonim's views. Was M'vo Hatalmud written by a rishon? –  msh210 Oct 24 '11 at 7:06
    
It looks like it was written by the kitzur mevo hatalmud which was written by the son of the Mesores Hashas. Not sure if he is a Rishon or early Ahcron. Even so looks like he is a heavy hitter.The Radbaz usually says some of the same points. –  avihu aboud Oct 24 '11 at 19:23
    
Did you just say the Mevo Hatalmud was written by the Kitzur Mevo Hatalmud?? –  Double AA Jul 17 '12 at 18:31
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There are many supercommentaries on Rashi's commentary to Chumash, which do pay very close attention to each word he wrote, but these are written by Acharonim for the most part.

Rashi's commentary was popular already throughout the times of the Rishonim. Here are several famous quotes from Rishonim about Rashi that I know of:

Ramban: (Inro. to commentary on Torah)

ואשים למאור פני נרות המנורה הטהורה, פירושי רבינו שלמה עטרת צבי וצפירת תפארה, מוכתר בנמוסו במקרא במשנה ובגמרא, לו משפט הבכורה, בדבריו אהגה, באהבתם אשגה, ועמהם יהיה לנו משא ומתן דרישה וחקירה, בפשטיו ובמדרשיו וכל אגדה בצורה, אשר בפירושיו זכורה

Rashbam: (Bereshis 37:2)

רבינו שלמה אבי אמי מאיר עיני גולה שפירש תורה נביאים וכתובים נתן לב לפרש פשוטו של מקרא, ואף אני שמואל ב"ר מאיר חתנו זצ"ל נתווכחתי עמו ולפניו והודה לי שאילו היה לו פנאי היה צריך לעשות פרושים אחרים לפי הפשטות המתחדשים בכל יום

Abarbanel: (Intro. to Yehoshua)

כי רע ומר לי המעשה שהרב הגדול רש"י ז"ל נסתפק בפירושיו לספרי הקדש ברוב הענינים עם מה שדרשו חז"ל

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Re: the Rashbam's quote, Rashi has quite a bit in the perush on Chumash that many would not consider "peshuto shel mikra;" i.e. midrash. –  yitznewton Oct 19 '11 at 14:50
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@yitznewton, indeed. See judaism.stackexchange.com/questions/6103/is-rashi-really-pshat –  jake Oct 19 '11 at 19:09
    
Great list of quotes. Also see what the Meiri gas to say towards the end of his Hakdamah to Avos. –  Ish Ploni ViKohen Feb 6 at 17:56
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(The title implies you are speaking about Rash"i's commentary on the g'mara, which was not composed the same way as his commentary on chumash but the question does not make a distinction.)

There are many supercommentaries on the commentary on the Torah, many of whom make statements like that. A great book that analyzes it all is this one: Patterns in Rashi. If you are looking for close readings and diyukim, that is the book for you.

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I clarified the question, thanks. –  Ariel K May 15 '11 at 2:56
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