If I was really going to begin at the beginning, I think the Epic of Gilgamesh would have been the earliest reasonable work of the Western Canon. After a little research, however, I wasn't confident that there was a definitive "Epic of Gilgamesh" that wasn't mostly a later reconstruction. Not worth the effort-- not part of the project.
At some point I purchased Harold Bloom's The Western Canon to use as an overall guide, but it doesn't extend to ancient times. During my used-book purchasing spree at the Fairfax County libraries I came across another Bloom work, Where Shall Wisdom Be Found, that seems to cover ancient literature-- enough for my purposes, anyway. And Bloom starts with a comparison of Job and Ecclesiastes, followed by a comparison of Homer and Plato.Perfect. Job it is.

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