I am looking to delve into the teachings of Rav Joseph B. Soloveitchik (1903-1993). Any recommendations on a good starting point?

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@intuit, Welcome to Judaism.SE, and thanks for bringing your question here! As the others have pointed out, your question will be more answerable if you specify it a bit more. – Isaac Moses Jun 6 '11 at 16:55
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Although I personally have not read his works, I have a number of friends who were inspired by The Lonely Man of Faith. Additionally, Halachic Man seems to be a must read. Although chronologically Halachic preceded Lonely by a couple of decades, Lonely is more fundamental.

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This is, of course, assuming that @intuit is interested in R' Soloveitchik's philosophical teachings. If, though, he is more interested in R' Soloveitchik's Talmudic methodology, this certainly would not be the place to start. – jake Jun 6 '11 at 18:20
I am interested in his philosophical teachings. – intuit Jun 6 '11 at 19:21
I was privileged to attend a chabura on LMoF. It is awesome, but I needed the initiation in 20th-century theology, the background of the sefer, and RYBS's basic conceptual framework to really get the most out it. – yitznewton Jan 5 at 22:39
Also: Abraham's Journey is wonderful. – yitznewton Jan 5 at 22:39
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I'm no scholar of the Rav, but I found the Rosh Hashannah and Yom Kippur Machzors and the Haggada based on his teachings to be eye-opening introductions to his oeuvre. They're full of references to his other published works, so if you see a passage you find particularly interesting, you can follow it up by studying the work it was excerpted from.

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The Bergen County Beis Medrash has lots of Audio Shiurim from Rav Soloteitchik. That may be a good place to start.

There are also 164 of the Rav's shiurim available for download here. (linked to from here)

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I think the first one I read was קול דודי דופק, both very deep and very readable at the same time, a nice introduction to his way of writing, and philosophical methodology.

@YDK's suggestions of Man of Faith and Halachic Man are also good to go with.

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In my opinion the best place to start is Here:

The Rav Thinking Aloud:on the Parsha

It is simpler then the other books that have some heavy philosophy and language. They are cross referenced to his other books so if you like an Idea you can find it and the person who wrote it was a close talmid. Plus it is on the Parsha so it makes it very usefull.If you want the Plain The Rav Thinking Aloud not on the Parsha it has most of his viewpoints on the important issues and it is an easy read

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