Middle-earth would never be the same after J.R.R. Tolkien’s The Hobbit. However, everything really changes after Chapter 5, “Riddles in the Dark,” and it all happens in just about 19 pages! The consequences of its events start to become obvious in The Hobbit, but it’s really when you get to The Lord of the Rings that you see just how crucial this chapter is.
In “Riddles in the Dark,” Bilbo Baggins finds himself alone and lost. Still in a daze from a fall, he crawls around and finds a small ring that he just sticks in his pocket without a second thought. He eventually comes across some water and meets the creature Gollum. In an attempt to learn more about Bilbo, Gollum suggests they tell each other riddles, and the game begins.
If Gollum wins, he gets to eat Bilbo. If Bilbo wins, Gollum will do what the hobbit wants. A trading of clever riddles follows as each tries to think of one to stump the other, until finally Bilbo sticks his hand in his pocket, remembers the ring, and asks simply, “What have I got in my pocket?”
This eventually wins Bilbo the game, and he asks an upset Gollum to show him the way out. Once Gollum discovers his ring is gone, though, he suspects Bilbo and gets frighteningly angry. While Bilbo tries to run, he puts on the ring accidentally, and confirms to Gollum that he's got it. Bilbo realizes he’s invisible, and the One Ring's power allows him to follow Gollum out of the lair. But Gollum smells the hobbit and blocks the way. For a moment, Bilbo considers killing him, but then shows pity and mercy and leaves Gollum behind while escaping from goblins.
This is a brilliant chapter for so many reasons (and done justice in the film, too, as you can see above). The verbal game between the two, as one is hungry and one frightened to death about being eaten, is fun to see play out, and the conclusion is one that changes the course of many fates.
The ring changes Bilbo’s life, and helps him in his adventure with the dwarves. He also brings the ring into the Shire, putting the hobbits and Bilbo’s family at the center of world-changing events. Even Bilbo showing Gollum mercy and not killing him has repercussions. Bilbo taking the ring from Gollum forever makes the creature hate the hobbit, and his knowledge of who has the ring leads those who want it right to it, kicking off the quest to destroy it.
It’s a fantastic chapter within The Hobbit, and one of the best in all of Tolkien’s works, as it masterfully makes a little riddle game of extreme importance to the entire saga.