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The Stairs of Cirith Ungol

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'Gollum looked at them. A strange expression passed over his lean hungry face. The gleam faded from his eyes, and they went dim and grey, old and tired. A spasm of pain seemed to twist him, and he turned away, peering back up towards the pass, shaking his head, as if engaged in some interior debate. Then he came back, and slowly putting out a trembling hand, very cautiously he touched Frodo's knee – but almost the touch was a caress. For a fleeting moment, could one of the sleepers have seen him, they would have thought they beheld an old weary hobbit, shrunken by the years that had carried him far beyond his time, beyond friends and kin, and the fields and streams of youth, an old starved pitiable thing.'

J.R.R. Tolkien: The Lord of the Rings: The Two Towers: Book IV,  Chapter 8: The Stairs of Cirith Ungol

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Painted in watercolour. 

See this image under the entry for 'Gollum' on Tolkien Gateway here.

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Tin-Turtle's avatar

I recommended this illustration in my LiveJournal post for International Fanworks Day this year.