The Riddle-game
The Riddle-game is the central episode of Bilbo Baggins's encounter with Gollum in the orc-mines beneath the Misty Mountains, as recounted in The Hobbit and later confirmed in The Lord of the Rings. It is a contest of wits that determines whether Bilbo will be killed and eaten or guided to safety. More than a mere survival trick, the game becomes the mechanism by which the One Ring passes from Gollum to Bilbo, and thus ultimately to Frodo, setting the entire quest of the War of the Ring in motion.
The Setting and the Stakes
Lost and alone in the dark tunnels after being separated from the dwarves, Bilbo gropes blindly and finds a ring lying on the floor of a tunnel, which he puts in his pocket without knowing its significance. He then descends to the roots of the mountains, where a cold lake lies far from any light. On an island of rock in the water lives Gollum, a loathsome creature who paddles a small boat with his large flat feet, catches blind fish with his long fingers, and eats them raw. Gollum possesses a secret treasure: a golden ring that makes its wearer invisible, which he calls his "Precious" and keeps hidden in a hole on his island. When Gollum encounters Bilbo, he would have attacked at once if the ring had been on him, but it is not, and Bilbo holds an Elvish knife. To gain time, Gollum challenges Bilbo to the Riddle-game, saying that if Bilbo cannot guess a riddle, Gollum will kill and eat him; but if Bilbo wins, Gollum will lead him to a way out of the tunnels.
The Course of the Game
Bilbo, lost in the dark with no hope of finding his own way, accepts the challenge. They ask one another many riddles, and the contest is long and evenly matched. Gollum's riddles are dark and ancient, drawn from his long years in the dark; Bilbo's are more whimsical, drawn from his hobbit knowledge of the world above. At last Bilbo is stumped for a riddle to ask. His hand, groping in his pocket, touches the ring he had picked up and forgotten. In desperation he cries out: "What have I got in my pocket?" Gollum demands three guesses, but fails to answer correctly. The authorities differ on whether this last question was a mere "question" and not a "riddle" according to the strict rules of the game, but all agree that after accepting it and trying to guess the answer, Gollum was bound by his promise.
The Aftermath and the Ring's True Nature
Bilbo presses Gollum to keep his word, but Gollum's heart is black with treachery. He slips away to his island, intending to fetch his ring and then kill Bilho with its power. But the ring is not on the island; he has lost it. His screech of despair alerts Bilbo, who flees. As he runs, Bilbo puts his hand in his pocket and the ring slips onto his finger, making him invisible. Gollum passes him without seeing him and goes to guard the only way out. Bilbo follows Gollum, overhearing his muttering about his "Precious," and realizes that the ring he found is the very treasure Gollum has lost. This gives him hope of escape. At the exit, Gollum crouches at bay, and Bilbo is tempted to kill him with his sword, but pity stays his hand. Instead, he leaps over Gollum and escapes, pursued by Gollum's cries of "Thief, thief! Baggins! We hates it for ever!"
The Deception and the Deeper Significance
Bilbo's first account of the encounter, told to the dwarves and later written in his memoirs, claimed that Gollum had promised to give him a present if he won the game, and that when Gollum went to fetch it, the ring was gone, so Bilbo took it as his rightful prize. This version was a lie, as Gandalf suspected from the first. The wizard eventually forced the true story from Bilbo, and the lie itself became a sign of the Ring's corrupting influence. Gandalf noted that the lies were too much alike for comfort: Bilbo's claim of a "present" echoed Gollum's own talk of a "birthday-present." The Ring had an unwholesome power that set to work on its keeper at once. The Riddle-game, therefore, is not only a contest of wits but the first test of the Ring's power over a new bearer, and the first hint of the deep kinship between Bilbo and Gollum, both of whom were transformed by their possession of the One Ring.