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Review: The Hobbit – Chapter 5: "Riddles in the Dark"

Introduction

Chapter 5 of The Hobbit, "Riddles in the Dark," is one of the most pivotal and iconic moments in J.R.R. Tolkien’s legendarium. This chapter not only introduces Gollum, one of the most complex and tragic figures in The Lord of the Rings, but also marks a defining moment in Bilbo Baggins’ character development.

Stranded in the goblin tunnels beneath the Misty Mountains, Bilbo stumbles into Gollum’s domain, where the two engage in a battle of wits through a game of riddles. This encounter is not merely an entertaining exchange; it is a symbolic and psychological duel that determines Bilbo’s fate. Furthermore, it is in this chapter that Bilbo acquires the One Ring, an event that will shape the fate of Middle-earth itself.

Tolkien masterfully blends suspense, mythology, and moral ambiguity in this chapter, making it a turning point in both Bilbo’s journey and the larger history of Middle-earth.


Plot Summary

After being separated from the company in the goblin tunnels, Bilbo awakens alone in the dark. As he gropes his way forward, he accidentally stumbles upon a subterranean lake, where he encounters Gollum, a strange, emaciated creature who speaks in hissing, fragmented speech. Curious and suspicious of Bilbo, Gollum proposes a game of riddles: if Bilbo wins, Gollum will show him the way out, but if he loses, Gollum will eat him.

The two engage in a tense battle of wits, exchanging riddles drawn from old folklore and mythology. Bilbo, though frightened, proves to be a formidable opponent, answering Gollum’s riddles correctly and countering with his own. However, when Bilbo nearly runs out of riddles, he accidentally asks a question instead of posing a proper riddle—"What have I got in my pocket?" Unable to answer, Gollum loses the contest.

Realizing that Bilbo must have something valuable, Gollum becomes suspicious and retreats to find his "precious"—the One Ring. However, unbeknownst to him, Bilbo has already found it earlier in the dark. When Gollum discovers that the Ring is missing, he flies into a rage, inadvertently revealing its power of invisibility. As Bilbo flees, he instinctively slips the Ring onto his finger and vanishes, allowing him to escape Gollum and the goblin tunnels undetected.

This marks Bilbo’s first true moment of independence and resourcefulness, setting him on a path of transformation from a hesitant adventurer into a cunning and capable hero.


Analysis

The Symbolism of the Riddle Game

The game of riddles between Bilbo and Gollum is far more than just a test of intelligence—it is a symbolic struggle for survival. Riddles, by their nature, require wit, adaptability, and deep cultural knowledge, making them a fitting challenge for Bilbo, who lacks physical strength but excels in cleverness.

This contest also echoes ancient mythological traditions, where riddles are often used to test a hero’s worthiness. Much like Oedipus solving the riddle of the Sphinx, Bilbo’s success in this intellectual duel allows him to move forward in his journey. However, unlike Oedipus, Bilbo’s victory is partly accidental—his final "riddle" ("What have I got in my pocket?") is not a true riddle at all, highlighting the role of fate and luck in his survival.

Gollum: A Tragic and Complex Figure

Gollum, introduced in this chapter, is one of Tolkien’s most psychologically rich and disturbing creations. He is both a pathetic and terrifying figure, alternating between sly cunning and desperate loneliness. His eerie speech patterns, referring to himself in the plural ("we" and "us"), hint at a fractured mind, torn between his original self and the corrupting influence of the Ring.

Unlike the goblins, who are purely antagonistic, Gollum evokes pity as well as fear. He is not inherently evil but has been twisted by centuries of isolation and obsession with the Ring. This makes him one of Tolkien’s most nuanced characters, setting the stage for his deeper exploration in The Lord of the Rings.

Bilbo’s Growth: From Luck to Agency

Up until this point, Bilbo has mostly relied on Gandalf and luck to survive. However, in "Riddles in the Dark," he begins to demonstrate ingenuity and resourcefulness. While luck still plays a role—especially in his accidental discovery of the Ring—Bilbo must rely on his intelligence, quick thinking, and growing courage to outwit Gollum.

The moment Bilbo uses the Ring to escape marks a turning point in his character arc. Instead of waiting for Gandalf’s help, he acts on his own initiative, foreshadowing his later feats of bravery. His decision not to kill Gollum, despite having the perfect opportunity, also highlights an emerging sense of morality and compassion—traits that will become crucial later in the story.

The Ring: A Dark Omen

At the time of The Hobbit’s original publication, the Ring was merely a magical trinket that made its wearer invisible. However, in light of The Lord of the Rings, its significance becomes far more sinister.

Bilbo’s discovery of the Ring is presented as an accident, reinforcing Tolkien’s theme of fate and unintended consequences. While it initially seems like a blessing, granting Bilbo protection and stealth, it also subtly foreshadows the burden and corruption that the Ring will bring in the future. The moment Bilbo first slips the Ring onto his finger is a quiet but monumental turning point in Middle-earth’s history—one that will ultimately lead to the War of the Ring.


Themes and Symbolism

Fate and Luck

Bilbo’s survival is due in part to luck—his stumbling upon the Ring, his accidental final question, and Gollum’s mistake in revealing the Ring’s power. However, luck alone is not enough; Bilbo also proves his worth through his wit and courage, reinforcing the theme that even the most unlikely individuals can shape destiny.

The Power of Words

Tolkien emphasizes the power of language and storytelling through the riddle game. Words, rather than weapons, determine the outcome of this confrontation, reinforcing the idea that intelligence and cunning can be more powerful than brute strength.

The Corrupting Influence of the Ring

Though the Ring appears benign in this chapter, its effect on Gollum hints at its true nature. Gollum’s obsessive attachment to the Ring, referring to it as "my precious," foreshadows the way it will consume others, including Bilbo and Frodo in The Lord of the Rings.


Writing Style and Tone

Tolkien’s narrative shifts in tone in this chapter, moving from the lighthearted adventure of earlier chapters into a darker, more suspenseful atmosphere. The setting of the goblin tunnels is claustrophobic and eerie, enhancing the tension of Bilbo’s encounter with Gollum.

The riddle contest itself is expertly written, with Tolkien drawing on traditional folklore riddles that add depth and authenticity to the exchange. Additionally, the contrast between Bilbo’s hesitant but hopeful demeanor and Gollum’s sinister yet tragic nature creates a compelling dynamic that keeps readers engaged.


Conclusion

"Riddles in the Dark" is a masterfully crafted chapter that serves as a major turning point in The Hobbit and in Middle-earth’s history. It introduces Gollum, one of Tolkien’s most complex characters, and establishes Bilbo’s transformation from an uncertain adventurer to a clever and resourceful hero.

Beyond its immediate impact on The Hobbit, this chapter lays the groundwork for The Lord of the Rings, with Bilbo’s discovery of the Ring setting into motion one of the greatest sagas in fantasy literature. Through its suspenseful storytelling, rich symbolism, and character development, "Riddles in the Dark" remains one of Tolkien’s most memorable and influential chapters.


 

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