Gollum challenges Bilbo Baggins with riddles in J.R.R. Tolkien’s The Hobbit.
Bilbo encounters Gollum beneath the Misty Mountains after becoming separated from the Dwarves. Gollum lives on an island in an underground lake and possesses a mysterious golden ring. Rather than immediately attacking one another, Bilbo and Gollum agree to a riddle contest, with the stakes being guidance or a chance to eat the other contestant.
The contest includes questions about everyday objects, natural phenomena, and time. Bilbo wins after asking, “What have I got in my pocket?” Tolkien later revised this episode when the Ring became more clearly connected to Sauron and its corrupting power.
Gollum was once called Sméagol, a member of a river-folk people. He had possessed the Ring for centuries before Bilbo found it. The character therefore links The Hobbit directly to the deeper history and moral conflict developed in The Lord of the Rings.