Riddles in The Dark by Alan Lee (1997)

This 1997 watercolor illustration by Alan Lee, titled Riddles in the Dark, depicts the fateful meeting from Chapter 5 of The Hobbit. The painting shows Bilbo Baggins cornered on the edge of a black, subterranean lake deep under the Misty Mountains, holding out his glowing Elven blade, Sting, to keep the creature Gollum at bay. Having crept out from the darkness in his small boat, a bone-thin, skeletal Gollum reaches a long, pale hand forward while staring at the hobbit with large, luminous eyes. Lee’s mastery of damp, moss-covered stalactites and the murky reflection on the water's surface perfectly illustrates the tense, quiet atmosphere of their high-stakes riddle contest, which ultimately reshapes the entire fate of Middle-earth through the discovery of the One Ring