Books that I feel are at least semi-advanced, and probably not for beginners, I have placed in the “Stage Two” section. Within each stage, it doesn’t really matter what order you read them in, but most Rabbis will probably suggest you study about prayer first.
The books in these lists are both of practical Jewish law and of Jewish thought and philosophy. Both Jewish Law and Jewish Thought are of vital importance in Judaism. In Judaism, we believe that one must both believe as a Jew, and act as a Jew. One alone cannot be more than a springboard to attaining the other, and only both can complete a person.
Most of the books in these lists are required reading by most Rabbis for conversion applicants. Those that aren’t will help you in any case.
First Steps in Hebrew Prayer, by Dr. Danny Ben-Gigi — learning how to daven and read prayer book Hebrew. I have seen samples of this book on the internet, and I was impressed. It looks great for beginners, and it has some very vital content.
To Pray As a Jew, by Rabbi Chaim Donin — A guide for the beginner to the prayer book and the synagogue service.
Maimonides’ Principles: The Fundamentals of the Jewish Faith, by Rabbi Aryeh Kaplan. The title speaks for itself.
Artscroll Tanach Series, by Rabbi Meir Zlotowitz. It is an excellent gateway to the Bible, Prophets and Writings for the lay person. It is a multi-volume translation, with commentary and an introduction for a conceptual understanding. I’m not sure that a conversion Rabbi will insist on any particular translation of the Chumash, he may accept any good translation as long as it’s from a reliable Rabbinical source.
This is my G-d, by Herman Wouk. A well-written, basic review of Jewish religion and life by a renowned contemporary writer. It explains Orthodox Judaism, what differentiates it from other forms of Judaism, talks about major Jewish holidays (including ones that non-Jews don’t generally know about, like Shavuot, Sukkot, etc), gives a brief history of Israel, an explanation of what the Torah is, the Written Law and the Oral Law, and some interesting information about the Talmud. All in all, a good summary of modern Jewish observance.
Is it Kosher: Encyclopedia of Kosher Food Facts and Fallacies, by Rabbi E. Seidlitz. This is an
incredibly comprehensive and invaluable guide to the facts about keeping kosher. It even has a very useful guide to reliable kosher certifications and their logos and symbols. I am told that it is required reading by many conversion Rabbis. If it is not, I nevertheless suggest you buy this book and at the very least read whatever parts of it interest you.
The 39 Avoth Melacha of Shabbath, by Rabbi Baruch Chait — Actually, this is a children’s book. However, it is an excellent way for anyone to learn about the modern-day practical applications of the basics of the Laws of the Jewish Sabbath. We owned a copy, and I learned many things from it. Strongly recommended, and also required by many converting Rabbis.
Becoming a Jew, by Maurice Lamm, (JD Publishers). I have not read this one myself, but the author is known to be reliable.
For practical purposes, I suggest studying the Kitzur Shulchan Aruch (Abridged Code of Jewish Law). A handy version is the linear translation, the Metsudah Kitzur Shulchan Aruch (published by Israel Book Shop). This work will give you a lot of basic information you need to know about day-to-day Jewish Law. It will not give you encyclopedic or vast knowledge, and you’ll still have questions to ask, but it will give you a little bit of everything you need to know to live a Jewish life. It is a pretty handy “how-to” book on Judaism, and not just for beginners either. (However, remember that no study of the practice of Judaism is ever complete without first-hand experience.
Being part of a congregation and visiting Jewish homes will be an absolute necessity when learning for the purpose of conversion to Judaism.)
If You Were G-d, Rabbi Aryeh Kaplan. Contains three works. First, a novel understanding of G-d by putting yourself in His role. Second, a work on immortality and the soul. Third, an essay called “A World of Love” that deals with the purpose of creation.
To be a Jew, by Rabbi Chaim Donin — A guide to Jewish observance in contemporary life.
The Book of Our Heritage, by Rabbi Eliyahu Kitov. This three-volume deals with the Jewish
Calendar and the Holidays. It has a wealth of Jewish information, and is extremely useful. It is also an easy read. Many Rabbis insist on including this work, and will test you for that knowledge. I also recommend it very strongly.
For the married, or for those seeking marriage, The Jewish Way in Love and Marriage, by Rabbi Maurice Lamm. This book is a popular authoritative presentation of Jewish teaching on love and marriage in light of the traditions and laws of the Bible.
In that vein, A Hedge of Roses by Rabbi Norman Lamm. This book presents, in brief form, the psychology and philosophy of the laws of Jewish family purity, as well as valuable insights into marriage and married life.
Artscroll Siddur, by Rabbi Nosson Sherman. Includes translation, comprehensive commentary and clear instruction for the beginner. With special sections at the end of the Siddur that discuss laws.
Alternatively, you can use The Metsudah Siddur, by Rabbi Avrohom Davis. A linear Siddur with English translation and anthology of the classic commentaries. This might also be useful if you know a little Hebrew and are trying to advance your knowledge in the language. With a linear translation, it is sometimes easier to figure out which English word goes with which Hebrew word.
The Living Torah, Rabbi Aryeh Kaplan, Moznaim Publishers. A heavily-researched translation of the Five Books of Moses written in modern English. This can be approached in two stages. You can read it first to get a basic overview of the Chumash (Pentateuch), and then later reread with the footnotes to gain a more detailed, intellectual understanding of the Torah. It includes study aids such
as an introduction, notes, maps, tables, charts, bibliography and index. Strongly recommended for the necessary serious study of the Chumash. This is not the only good translation of the Chumash, though it is a very good one. I must point out, however, that as good as it is, it cannot stand alone, which is why I place it in the Stage Two section. You must familiarize yourself with studying Chumash with Rashi, which is the most important and ineluctable commentary. For that, you may need another translation. However, Rabbi Kaplan’s work is excellently researched, and therefore
very usable alongside whatever Chumash you use. Many people recommend it be studied alongside the next selection, The Midrash Says.
The Midrash Says, Rabbi Moshe Weissman. Arranged according to the weekly Torah portions. An excellent collection of Midrashim on the chumash. Midrashim are the Rabbis sermons on Torah subjects, all based on the Tradition as Hashem taught it to Moses. They contain deeper meanings of the Torah, expansive discussions on events that the Torah only alludes to, as well as ethical teachings and Halachic lessons. (Contrary to popular belief, Midrashim are not fictitious tales. They are absolutely true lessons as taught by Hashem to Moses, who taught them to the Children of Israel.)
The Jew and His Home, by Rabbi Eliyahu Kirov. A classic work on Jewish family life. Includes practical Halachic matters, as well as discussions on Jewish marriage, harmony in the home, modesty, raising children and more.
Sabbath: Day of Eternity, by Rabbi Aryeh Kaplan — A blend of the technical framework of the Sabbath with insights that develop its philosophy.
Ethics from Sinai, by Rabbi Irving M. Bunim. Commentaries on a section of the Talmud that discusses some of the ethical teachings and wisdom of Judaism.
For men, Tefillin: G-d, Man, Tefillin, by Rabbi Aryeh Kaplan. Insights to meaning behind Tefilin and practical aspects of the mitzvah.
Also for men, Tzizith: A Thread of Light, by Rabbi Aryeh Kaplan. The author delves deeply into the mystery of the commandment of Tzizith to reveal the link between Tzizith and the ability of man to overcome his faults and reach towards G-d.
As you advance in your studies with a Rabbi, he will assign you reading material according to your abilities and your level of knowledge. It is advisable not to tackle any book without your Rabbi’s advice. There are many books out there from unreliable sources.