The Snowdon portrait was the first picture of Tolkien I ever saw (in a promotion leaflet from the German publishers of the Silmarillion, way back in the late 70s, which also contained, as a teaser, the first chapter of the Sil I ever read - Of the Darkening of Valinor, IIRC). At the time, he seemed to belong with those trees - to my younger eyes, he looked as old as the earth, as weird, ancient and otherworldly as the world of his tales. I didn't notice the look of old age and loss, but now you mention it, it's obvious.
(By the way, the trees strongly remind me of those on Tolkien's own painting of Taur-nu-Fuin/Mirkwood.)
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Und aus dem Erebos kamen viele seelen herauf der abgeschiedenen toten.- Homer, Odyssey, Canto XI
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