Study Guide

The Hobbit, or, There and Back Again Cunning and Cleverness

By J.R.R. Tolkien

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Cunning and Cleverness

Chapter 2

A really first-class and legendary burglar would at this point have picked the trolls' pockets – it is nearly always worth while, if you can manage it –, pinched the very mutton off the spits, purloined the beer, and walked off without their noticing him. Others more practical but with less professional pride would perhaps have stuck a dagger into each of them before they observed it. Then the night could have been spent cheerily.

Bilbo knew it. He had read a good many things he had never seen or done. He was very much alarmed, as well as disgusted; he wished himself a hundred miles away, and yet – and yet somehow he could not go straight back to Thorin and Company emptyhanded. (2.42-3)

The thing is, Bilbo has no practical experience of the outside world by the time he finds his first real adventure with the trolls in the forest. But he has read a lot of tales and legends, so he knows how his story is supposed to go. He decides that, as a burglar, he has to pick Bill the Troll's pocket – he can't go back to Thorin "emptyhanded." And, of course, he winds up getting captured. Are there other examples in The Hobbit where Bilbo makes decisions based on his assumptions or other people's expectations? Or does he learn his lesson with this trollish disaster? What can Bilbo's decision in this passage tell us about his character at this point of the novel?

Chapter 5

[Gollum] was anxious to appear friendly, at any rate for the moment, and until he found out more about the sword and the hobbit, whether he was quite alone really, whether he was good to eat, and whether Gollum was really hungry. Riddles were all he could think of. Asking them, and sometimes guessing them, had been the only game he had every played with other funny creatures sitting in their holes in the long, long ago, before he lost all of his friends and was driven away, alone, and crept down, down, into the dark under the mountains. (5.22)

Gollum is trying to stall while he has Bilbo right in front of him, so he challenges the hobbit to a riddle game. Why do you think Bilbo agrees? What might have happened if Bilbo had refused to riddle with Gollum? What does this passage in the novel show us about Gollum's character?

[Bilbo] knew, of course, that the riddle-game was sacred and of immense antiquity, and even wicked creatures were afraid to cheat when they played at it. But he felt he could not trust this slimy thing [Gollum] to keep any promise at a pinch. (5.68)

It strikes us as a little odd that Tolkien spends so much time describing the riddle game when the end result doesn't matter: if Bilbo loses, Gollum will try to eat him. And now that Bilbo has won, Gollum is still going to try and kill him. What's the tone of the riddle chapter in The Hobbit? What does it achieve in the novel's plot and character development?

Chapter 9

For Thorin had taken heart again hearing how the hobbit had rescued his companions from the spiders, and was determined once more not to ransom himself with promises to the king of a share in the treasure, until all hope of escaping in any other way had disappeared; until in fact the remarkable Mr. Invisible Baggins (of whom he began to have a very high opinion indeed) had altogether failed to think of something clever.

The other dwarves quite agreed when they got the message. They all thought their own shares in the treasure (which they quite regarded as theirs, in spite of their plight and the still unconquered dragon) would suffer seriously if the Wood-elves claimed part of it, and they all trusted Bilbo. Just what Gandalf had said would happen, you see. Perhaps that was part of his reason for going off and leaving them. (9.16)

Gandalf's probable reason for leaving the dwarves behind is so they can grow to trust Bilbo. But Gandalf's reason is also Tolkien's reason: he has to develop the relationships between the dwarves and Bilbo before the end of The Hobbit, which can only happen once Gandalf is gone (check out our "Character Analysis" of Gandalf for more on this). We find Gandalf's sudden departure a little contrived, actually – is there a more natural way that Bilbo and the dwarves could have been left on their own to grow to trust one another? There is a similar moment of Gandalf's departure in The Fellowship of the Ring. How does Gandalf's scenes in the Mines of Moria compare with his plan to pursue other business with the Necromancer in The Hobbit? And what evidence do we get before Bilbo and the dwarves enter Mirkwood that Bilbo is going to become an expert at "[thinking] of something clever"?

Chapter 12

"I suppose you got a fair price for that cup last night?" [Smaug] went on. "Come now, did you? Nothing at all! Well, that's just like [dwarves]. And I suppose they are skulking outside, and your job is to do all the dangerous work and get what you can when I'm not looking – for them? And you will get a fair share? Don't you believe it! If you get off alive, you will be lucky."

Bilbo was now beginning to feel really uncomfortable. Whenever Smaug's roving eye, seeking for him in the shadows, flashed across him, he trembled, and an unaccountable desire seized hold of him to rush out and reveal himself and tell all the truth to Smaug. In fact he was in grievous danger of coming under the dragon-spell. (12.62-3)

All of this time, we've been thinking Bilbo's the cunning one. Smaug has just seemed like a toothy, fire-breathing abstract threat, and not necessarily a thinking being. But here we get proof that dragons are surprisingly wily and well-spoken. And they can enchant you with their talking; they can put you under "the dragon-spell." Do we get any sense of Smaug as a character? Does he have any character depth or motivation for what he does?

Chapter 16
Roäc son of Carc

"But [Dain and his dwarves] cannot reach the Mountain unmarked," said Roäc, "and I fear lest there be battle in the valley. I do not call this counsel good. Though they are a grim folk, they are not likely to overcome the host that besets you; and even if they did so, what will you gain? Winter and snow is hastening behind them. How shall you be fed without the friendship and goodwill of the lands about you? The treasure is likely to be your death, though the dragon is no more!" (16.5)

Roäc the raven isn't just a messenger. He also tells Thorin when he's being an idiot. For example, Thorin is counting on Dain and his reinforcements to hold the Lonely Mountain against Bard and the Elvenking. But Dain can't get into the Lonely Mountain without fighting his way through the valley where the elves and men are camped. And then what? Does Thorin just want to stay at war with everyone around him, just for treasure? Tolkien represents treasure as an actual sickness that can overcome your reason just like any other mental illness. This isn't his idea alone; according to Anderson's Annotated Hobbit, Tolkien gets his ideas about the maddening effects of treasure from the Old English epic Beowulf.


"Why do you tell us [about the arrival of Dain and five hundred dwarves]? Are you betraying your friends, or are you threatening us?" asked Bard grimly.

"My dear Bard!" squeaked Bilbo. "Don't be so hasty! I never met such suspicious folk! I am merely trying to avoid trouble for all concerned." (16.32-3)

When Bilbo sneaks down to Bard's camp with the Arkenstone in hand, he's "merely trying to avoid trouble for all concerned." What do you think of Bilbo's plan? Would it have worked to avoid war in the long run if the goblins and Wargs had never turned up?

Chapter 18

There is more in you of good than you know, child of the kindly West. Some courage and some wisdom, blended in measure. If more of us valued food and cheer and song above hoarded gold, it would be a merrier world. But sad or merry, I must leave it now. Farewell! (18.19)

As Thorin is dying, he gives Bilbo credit for "Some courage and some wisdom, blended in measure." Of these two virtues – courage and wisdom – which do you think Bilbo values more? How about Thorin himself, or Gandalf? Why?


When Gandalf saw Bilbo, he was delighted. "Baggins!" he exclaimed. "Well I never! Alive after all – I am glad! I began to wonder if even your luck would see you through. A terrible business, and it nearly was disastrous." (18.14)

Up until Gandalf's surprise that Bilbo has survived the Battle of Five Armies, we don't think we've ever seen Gandalf be wrong before. Can you think of other examples? What are the limits on Gandalf's wisdom? How does Gandalf use his knowledge as a tool earlier in The Hobbit?

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