The following is from an old project of mine. It is in rough chronological order, so I cut it off by the 15th century, but some Acharonim still managed to squeeze in. :)
Classic Mussar Seforim
The following is a select list of major works of mussar:
Mishlei (Proverbs) – Shelomo HaMelech (King Solomon). The book of Mishlei is probably the first work devoted entirely to mussar. As such, it provides much of the material that is utilized in all later works of mussar. Because the book of Mishlei is a mussar work, all the commentaries on it are also effectively works of mussar as well. In addition to the standard Biblical commentaries, there are several commentaries written specifically on Mishlei. Many of these are studied as mussar works in their right. Among these are:
- Pirush Rabbeinu Yonah – Rabbeinu Yonah of Gerona (c.1180-1263)
- Pirush HaGra – Rav Eliyahu of Vilna (the Vilna Gaon) (1720-1797)
Pirkei Avos – Talmud. Probably the most widely studied tractate of the Talmud. In addition to all the standard commentaries on the Mishna (such as the Rambam, Bartenura, and Tosefos Yom Tov), Pirkei Avos has been the subject of innumerable special commentaries. Many of these are considered classics in their own right. Among these are:
Pirush Rabbeinu Yonah – Rabbeinu Yonah of Gerona (c.1180-1263)
HaChasid Ya’avetz – Rav Yosef Ya’avetz (d. 1507). Rav Yosef Yaavetz
also wrote a commentary on book of Tehillim (Psalms), and several
books on Jewish belief.
Nachalas Avos – Rav Don Yitzchak Abarbanel (1437-1508)
Medrash Shmuel – Rav Shmuel di Uzeda (1538-1602). One of the most
comprehensive commentaries on Pirkei Avos, the Medrash Shmuel is both
a collection of earlier commentaries and an original commentary. Rav
Shmuel di Uzeda was a disciple of the Arizal and Rav Chaim Vital. He
also wrote commentaries on Megillas Rus and Megillas Eicha.
Ruach Chaim – Rav Chaim of Volozhin (1749-1821).
Avos D’Rebbi Noson, a Talmudic work which expands upon the themes of Pirkei Avos.
Chovos HaLevovos – Rabbeinu Bachya ibn Paquda (Early 11th Century). Arguably the most important mussar work of all time, the Chovos HaLevovos is divided into ten Shearim (“Gates”). In each section, Rabbeinu Bachya precisely defines each concept and the principles related to it. These ten sections are:
Shaar HaYichud (“Gate of Unity”) – a philosophical discourse on the importance of proving to oneself that God exists, and the proper means by which to achieve this.
Shaar HaBechina (“Gate of Discernment”) – on perceiving God’s wisdom and control in the world around us.
Shaar Avodas HaElokim (“Gate of the Service of God”) – on our obligation to serve God.
Shaar HaBitachon (“Gate of Trust”) – on our obligation to trust God.
Shaar Yichud HaMaaseh (“Gate of Unity of Action”) – on the principle of devoting all one’s actions only to the service of God, and how to achieve this.
Shaar HaKeniah (“Gate of Humility”) – on the principle of humility.
Shaar HaTeshuva (“Gate of Repentance”) – on repentance.
Shaar Cheshbon HaNefesh (“Gate of Self-Accounting”) – on the importance of introspection and self-examination and the proper ways to do this.
Shaar HaPrishus (“Gate of Abstinence”) – on the value of separating oneself from physical and worldly pleasures, and the proper way to do so.
Shaar Ahavas HaShem (“Gate of Love of God”) – on loving God.
Sefer HaYashar – Ascribed to Rabbeinu Tam – Rav Yaakov ben Meir (1100-1171). A philosophical mussar work.
Sefer Chasidim – Rabbeinu Yehuda HaChasid (c.1150-1217). A very influential mussar work with substantial kabalistic input.
Shaarei Teshuva – Rabbeinu Yonah of Gerona (c.1180-1263). One of the most important and influential mussar works, the Shaarei Teshuva is considered the basic work on teshuva (repentance).
Igeres HaRamban – Rav Moshe ben Nachman (Ramban) (1195-1270). An extremely brief letter – only two or three pages long – the Igeres HaRamban was written by the Ramban to his son. Despite its brevity, this letter is considered a major mussar classic.
Orchos Tzadikkim – Anonymous (c.13th Century). An extremely popular work, the Orchos Tzadikkim is divided into twenty-eight Shearim.
Orchos Chaim L’Ha’Rosh - Rabbeinu Asher ben Yechiel (Rosh) (c.1250-1327). A very brief work consisting of admonishments to proper behavior and observance. Traditionally divided into seven sections for daily study.
Maalos HaMiddos – Rabbeinu Yechiel (13th Century) – A classic work of mussar that discusses in depth twenty-four middos and their opposites:
• Knowing God
• Loving God & One’s Fellow
• Fear of God & Parents
• Torah Study & the Fulfilment of the Mitzvos
• Humility vs. Pride
• Modesty vs. Immorality
• Shame vs. Arrogance
• Faithfulness vs. Theft
• Honesty vs. Deceitfulness
• Compassion vs. Cruelty
• Amicability vs. Anger
• “A Good Name”
• Yetzer Tov vs. Yetzer Hara
• Teshuva (Repentance)
• Wisdom vs. Foolishness
• Diligence vs. Laziness
• Easily Satisfied vs. Gluttony
• Generosity vs. Stinginess
• Derech Eretz
• Peace vs. Contention & Gossip
Menoras HaMe’or – Rav Yitzchak Aboav (c.14th Century). An extremely popular work, the Menoras HaMe’or was translated into numerous languages including Spanish/Ladino, Yiddish, German, and, most recently, English. Much of the Menoras HaMe’or is made up of extensive selections from the Talmud and Midrashim with commentary by the author.