Some of T. S. Eliot's poetry is a bit like a Coen brothers movie—there are enough quotable lines to keep the geeks happy, enough serious reflection to keep the philosophers happy, and enough scratch-your-head moments to confuse everyone. You'd be hard pressed to find critics willing to admit they don't understand Eliot, but just read their essays and you'll realize they aren't any closer to the truth than you are. If you're a critic, my apologies.
Eliot had a two-part career. Born in St. Louis, Missouri in 1888, he drew on a Classical education to write poetry steeped in allusions and references too numerous to count that was solidly Modernist in its philosophical perspective. In 1927, however, 13 years after expatriating to England, Eliot became a Christian, joined the Anglican Church, and wrote a very different kind of poetry.
Not so very different on the surface, maybe. It still overflowed with learned allusions, but it was no longer Modernist, it was explicitly and glorioiusly Christian. That doesn't mean it was no longer difficult to read (it was), but there was a certain meaning behind it now that wasn't obscured merely for the sake of obscurity.
Of the former kind, the Modernist propaganda,The Love Song of J. Alfred Prufrock andThe Waste Land are probably the most famousand the most difficult.
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