The Tolkien chapter featuring Bilbo’s riddle contest with Gollum is titled “Riddles in the Dark.”
In this chapter, Bilbo becomes separated from the dwarves beneath the Misty Mountains and encounters Gollum beside an underground lake. The two agree to ask one another riddles, with Bilbo’s life at stake if he loses. During the encounter, Bilbo finds a mysterious golden ring and uses it to escape after Gollum fails to locate him.
The chapter changed substantially between editions. In the original 1937 text, Bilbo presents the Ring as something Gollum willingly gives him after the riddle game. For the 1951 revision, Tolkien rewrote the episode so that the Ring’s corrupting nature and Gollum’s deception fit the larger mythology of The Lord of the Rings. The revised version became the canonical account familiar to modern readers.