The list below includes a few works on prayer that I have found to be helpful in my personal prayer life as well as in my teaching. It is far from comprehensive. Some of the works listed are in Hebrew, although English translations might be available. I tried to limit the list to works written in the past 100 years or so (with one or two exceptions), and have not included books written by Chassidic masters, of which there are many.
1. A multi-volume work in Hebrew, Netiv Binah, by Rabbi Yissachar Jacobson, is a veritable encyclopedia of the philosophy, history and the meaning of tefillah. The author also wrote an excellent book on the weekly Torah portion entitled Binah B’Mikrah.
2. The World of Prayer, written by Rabbi Dr. Elie Munk, provides answers to many philosophical questions about prayer, which renders some specific prayers especially meaningful.
3. Al haTefillah presents Rabbi Yosef Dov Soloveitchik’s view on the halachic framework of prayer in a very lucid fashion. The Rav here demonstrates his unique ability to make halachic details emotionally stirring.
4. There are numerous anthologies, in English translation or in the original Hebrew, of the Chofetz Chaim’s writing on the subject of prayer. If you want to study the Chofetz Chaim on prayer, make sure that the work you choose focuses on his writings rather than biographical anecdotes.
5. Rabbi Avraham Yitzchak Kook has much to say about prayer, especially from a spiritual perspective. His poetic language enhances the beauty of the prayers upon which he comments. His thoughts on prayer comprise the introduction to his commentary on his siddur, Olat Riyah, and a more inclusive collection of his writings on this subject published as Orot HaTefillah.
6. Rabbi Shimon Schwab’s book On Prayer demonstrates his special ability to blend the approach of Rabbi Samson Raphael Hirsch with the teachings of the Lithuanian yeshivah world. Rabbi Schwab never misses an opportunity to demonstrate the relationship between prayer and proper ethical behavior.
7. Praying with Joy by Rabbi Daniel Yaakov Travis is a series of short books about tefillah that is down-to-earth, offering readers an optimistic outlook on life. The series serve as a practical handbook for those who really want to change the quality of their prayers.
8. Rabbi Samson Raphael Hirsch wrote a translation and commentary on the siddur in German, which is available in English translation. This is a must read. Rabbi Hirsch applies his philosophy of “Torah im derech eretz” to almost every prayer in the siddur.
9. Rabbi Jonathan Sacks’ translation and commentary on the siddur is available through OU Press (ou.org/oupress/product/the-koren-sacks-siddur-a-hebrewenglish-prayerbook-standard-size/). His language is majestic and emotionally uplifting. His commentary draws upon a wide range of sources, providing a certain depth to the prayers that is mostly absent in more traditional commentaries.
10. Rabbi Chaim Friedlander includes explanations of various prayers throughout the many volumes of his masterpiece, Sifsei Chaim. Some of the volumes contain entire sections entitled Biurim al haTefillah. These are especially valuablein that they convey the perspectives of the masters of the Musar Movement, and particularly that of Rabbi Eliyahu Dessler, under whom Rabbi Friedlander studied.
Rabbi Dr. Tzvi Hersh Weinreb is executive vice president, emeritus, of the OU.