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Let’s start with certain basisc shall we? No one who aspires to be a Jewish intellectual can be without the Rav’s The Halachik Man. Leo Levy’s Torah and Science is also an important little book (literally, it’s less than 200 pages). Eliezer Berkovitz’s Not in Heaven offers a well thought out, if slightly controversial, formulation of the workings of the Halachik system. Aryeh Kaplan’s books also make for a good read duing one’s teenage years. Although reviled in the chareidi world, R. Norman Lamm’s Torah U’Maddah should be read (You don’t need to agree with it in order to learn from it). If one has the time and the ability, R. Teichtal’s Eim Habanim Smeicha is priceless. As far as history is concerned, although not written by a Jew, James Carrol’s Constantine’s Sword is probably the best exposition on the development of anti-Semitism ever. These are the titles that popped into my head now, but I’m sure I could come up with a different list on a different day.