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There are many commentaries on the siddur. However, most of them focus in detail on the words of the prayers.

I'm looking for a commentary which looks at the "big picture" of each prayer. That is, where each prayer came from, when it was added to the siddur, which communities say it, why it is placed at the point where it is, why it is omitted on certain days, and so on.

(It doesn't actually need to be a commentary per se; it can be in any format, stand-alone or attached to some other work, etc.)

  • Why We Pray What We Pray, although I can't speak very highly of the author at this point – Y     e     z Oct 21 '14 at 2:52
  • @YEZ That was exactly the book that came to my mind! Great look at Kriat Shema at different points of history. I guess don't judge a book by its author? – Mike Supports Monica Oct 21 '14 at 3:29
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    I'd suggest looking at introductions to siddurim. The two best ones that I've seen are the introduction to Siddur Avodas H' (very popular in Israel, especially more Mizrachi/modern communities) and Chief Rabbi Jonathan Sacks' introduction. Neither of these have too much detail but it's a start – הנער הזה Oct 21 '14 at 3:32
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As for me, My Prayer by Rabbi Dr. Nissan Mindel is such a book. It doesn't have quite the academic bent that your question implies, but it does give the history of the prayers and why they are placed where they are.

It does not much touch on the variety of customs in different communities.

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Rav Schwab on Prayer (compiled from taped lectures under the editorship of his eldest son Rav Moses L. Schwab)

Iyun Tefilla, Hebrew version of "Rav Schwab on Prayer"

Rabbi Shimon Schwab was officially "retired," but his mind and conscience never rested. Always a great thinker and teacher, he turned his attention to the Siddur.

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