StudySync | The Hobbit
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CHAPTERS 1–3: An Unexpected Journey
KEY PASSAGE | Chapter 1, Paragraphs 95–96
In this passage from the first chapter of The Hobbit, the hero of our tale,
Bilbo Baggins, listens in as Gloin, one of a party of thirteen dwarves, openly
questions whether Bilbo is a little too fearful and excitable for the dangerous
quest ahead. The thirteen dwarves, led by Gandalf the Wizard, are preparing
to head off to the Lonely Mountain to reclaim their treasure, being held hostage
by the fierce dragon Smaug. Gandalf has endorsed Bilbo as their “burglar” that
will sneak into the mountain on behalf of the party, but Gloin fears that Bilbo’s
anxiety could get them all killed. Bilbo’s desire to prove his bravery—his “Took
side”—finally impels him to interrupt Gloin’s protestations; he puts himself up
to the task and accepts his role as the burglar. Privately, however, Bilbo later
wonders if this decision to join Gandalf and the dwarves on their adventure
was an impulsive one, figuring he might have been better off without trying to
prove his mettle.
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Discussion Prompt: Do you ever feel as though you have two conflicting sides in your own
personality—like Bilbo? Discuss as a group the experience of having competing impulses
or tendencies, offering examples from your own life and comparing them to what Bilbo
experiences in The Hobbit.
VOCABULARY
audacious
au•da•cious adjective
Daring; bold; fearless
The audacious spirit that makes him such a
great businessman can also get him into some
troublesome situations.
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flummoxed
flum•moxed verb
Bewildered; perplexed
The coach’s decision to leave Jerrod out of the
starting lineup without any explanation left the
shortstop flummoxed.
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StudySync | The Hobbit
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obstinately
ob•sti•nate•ly adverb
Done with stubbornness or a refusal to yield
Despite its plea for more funding, the governor
obstinately refused to increase the department’s
budget.
outlandish
out•land•ish adjective
Extremely strange or ridiculous
She has built a reputation as a fashion designer
for outlandish dresses that seem to get stranger
every year.
remuneration
re•mu•ner•a•tion noun
Money paid in exchange for work done
Even though the company is in financial trouble,
the remuneration for the CEO has nearly
doubled over the past three years.
venerable
ven•er•a•ble adjective
Highly respected or revered
In 1978 they both won the Presidential Medal of
Freedom, the most venerable honor a citizen of
the United States can receive.
CLOSE READ
1. As narrator, how does Tolkien introduce the various elements of this story? From what
point in time is the narrator speaking, and what perspective or knowledge does the
narrator have of the history and genealogy of Middle Earth?
2. Why does Gandalf choose Bilbo for this quest? Whose decision is it for Bilbo to come
along—Bilbo’s, Gandalf’s, or some mix of both? Explain.
3. What are Bilbo’s two “sides,” and how do they come into play at different points in the
early chapters? Explain, citing various examples.
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Reading Guide
StudySync | The Hobbit
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4. What does Bilbo do at the trolls’ camp that gets him and the others in trouble? Why do
you think he chose to do this?
5. Who lives in Rivendell, and what is it like there? Briefly describe this place and its
inhabitants.
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Reading Guide
StudySync | The Hobbit
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CHAPTERS 4-6: Captured by Goblins!
KEY PASSAGE | Chapter 5, Paragraphs 88–89
In this passage, we receive more contextual information about the mysterious
ring that holds a strange power over the creature known as Gollum. Living in
a cave and feeding on fish, Gollum’s history with this ring is uncertain, having
come by his “precious” ring so long ago his memory of its origins had become
foggy. For a while he would wear it, until its power made him tired and compelled
him to hide it in a hole—though he finds himself unable to stay away from the
ring for too long. Putting it on, it granted him the power of invisibility, and he’d
hunt for small goblins, sneaking up on his prey and pouncing on them without
even being seen. His plan is to use the ring’s invisibility to kill Bilbo Baggins,
who encounters him deep in the goblin cave. There’s just one little thing about
the ring’s current whereabouts that Gollum doesn’t know.
YOUR STUDYSYNC® TV
Discussion Prompt: By now, you are familiar with the largely episodic structure of the novel,
in which each chapter seems to offer a brand-new self-contained adventure. How might
these independent episodes build towards a larger story? Using this passage and others
as examples, explain how these individual encounters and adventures converge in a larger
narrative or plot.
VOCABULARY
uncanny
un•can•ny adjective
Mysterious or unnatural; beyond what is normal
Even as a child, Anna had the uncanny ability
to do extraordinarily complex math problems
without the assistance of a calculator.
ingenious
in•gen•ious adjective
Clever; inventive
Credit must be given to the restaurant’s
ingenious layout, which makes it seem twice as
large as it really is.
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antiquity
an•ti•qui•ty noun
The ancient past or items from the ancient past
No other museum in the city has such amazingly
restored relics from the civilizations of antiquity.
queer
queer adjective
(somewhat old-fashioned) Peculiar, strange
Marty has a queer sense of humor, and likes
many things that are too strange for mainstream
audiences.
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StudySync | The Hobbit
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obliged
ob•liged adjective
Indebted or compelled to do something
because of gratitude
Her generosity the last time I was in town
obliged me to help her get a job with the
company.
CLOSE READ
1. What obstacles does the group encounter while attempting to camp on the mountain?
Why do they move camp, and what is the result of this?
2. How does Bilbo get separated from the group while escaping the goblin cave? What
does Bilbo immediately find upon waking up?
3. Who is Gollum? Briefly describe his character and his life in the caves. What is his
objective or purpose?
4. What does Bilbo overhear Gandalf and the dwarves talking about before he comes
forward? What is the one thing Bilbo doesn’t tell the others about his escape?
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5. Do the dwarves ever show any bravery in protecting Bilbo? Do any of their actions
affect or change our opinion about their nature?
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StudySync | The Hobbit
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CHAPTERS 7–10: Through Mirkwood Forest
KEY PASSAGE | Chapter 8, Paragraphs 75–77
In this passage, Bilbo’s battle with the giant spider that attacks him culminates
as he stabs it right in the eyes, then delivers the fatal blow. The battle is so
taxing on Bilbo, he passes out as soon as he has vanquished the spider and
wakes up an unspecified time later with the spider’s dead body still at his side.
As Bilbo comes to, he realizes that his victory over the spider has instilled him
with a newfound sense of strength and confidence, which makes him forget
about his hunger for the time being. In honor of his victory, Bilbo decides to
give his trusty sword a name—Sting—as he returns it to its sheath.
YOUR STUDYSYNC® TV
Discussion Prompt: Analyze the importance of this episode, in which Bilbo kills the spider
and names his sword. How does this episode signify growth for Bilbo’s character? What
qualities is he shedding or acquiring? Based on your assessment, what kind of challenges
do you imagine might lie in his future? Finally, think of an experience or moment from your
own life that marked an important rite of passage for you, and compare and contrast it with
Bilbo’s latest adventure.
VOCABULARY
enchantment
en•chant•ment noun
Magic or wizardry
People in the Middle Ages sometimes used
spells, incantations, and other forms of
enchantment to try to cure diseases.
inquisitive
in•quis•i•tive adjective
Especially curious or inquiring
She’s the most inquisitive child I’ve ever met,
always exploring and asking questions and
never taking a minute to rest.
unimpeachable
un•im•peach•a•ble adjective
Dependable, reliable; unable to be doubted or
criticized
Dozens of speakers talked about John’s
unimpeachable integrity, mourning the loss of a
truly dependable and good-hearted man.
abominable
a•bom•in•a•ble adjective
Deserving of hatred or revulsion
In Nuremberg, former German military officers
and politicians stood trial for their abominable
war crimes.
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famished
fam•ished adjective
Extremely hungry; ravenous
The two-week siege of the city has left many of
its residents famished and desperate.
circuitous
cir•cu•i•tous adjective
Roundabout; winding; indirect
Thanks to the circuitous directions Carissa gave
me, we arrived at the party an hour late.
CLOSE READ
1. Who is Beorn? Describe this character and explain where his allegiances lie. Why
does he agree to help their group?
2. What prompts Bilbo to name his sword? Why is this a significant moment in the
narrative?
3. How are wood elves different from the elves they encountered earlier in the story?
How do the wood elves treat Thorin when he is captured?
4. What are some different situations in which Bilbo’s ring helps him out of a jam? Do
you think the ring makes Bilbo seem tougher than he really is? Explain.
5. How does Thorin Oakenshield act once the party reaches Lake Town? What
inferences can we make about his character at this point in the story?
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StudySync | The Hobbit
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CHAPTERS 11–13: The Desolation of Smaug
KEY PASSAGE | Chapter 12, Paragraphs 4–6
In this passage, Bilbo responds to Thorin’s insistence that Bilbo be the first one
to enter into the Lonely Mountain, into the lair where the fierce dragon Smaug
is dwelling. Initially, Bilbo is hesitant to proceed, feeling that he has already
extended the dwarves a couple of great favors in rescuing them, and feeling
he is already owed some kind of reward. However, without any further urging
on Thorin’s behalf, Bilbo talks himself into accepting the challenge, musing out
loud that he has begun to feel more confident in his luck. Only a few of the
dwarves make any offers to accompany Bilbo inside the lair, and their offers
are timid and half-hearted. This display of diffidence, in the narrator’s opinion,
demonstrates the true nature of dwarves: they are not great heroes, for the
most part, and can be especially calculating when it comes to money—but
they are decent enough as long as expectations of their character are kept in
check.
YOUR STUDYSYNC® TV
Discussion Prompt: Based on Tolkien’s analysis of the dwarves’ character, what can Bilbo
expect from the dwarves? What shouldn’t he expect? How does this fixed notion of the
nature of dwarves fit into the overall picture of Middle Earth? How and why does Tolkien
issue a blanket statement, of sorts, regarding all dwarves?
VOCABULARY
threshold
thresh•old noun
The strip of material that forms the bottom of a
doorway that you step over when you enter a
room or building
The threshold at the old cottage was unusually
high, so the old man warned guests to step
carefully when they entered.
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thrush
thrush noun
A medium-sized bird inhabiting wooded areas
The bird-watching group stopped under a tree
and listened to the melodic fluting of a thrush.
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pretense
pre•tense noun
A false claim or appearance
He lied to his sister and told her he couldn’t
make dinner, under the pretense that he had
urgent business to attend to.
infuriate
in•fur•i•ate verb
To enrage someone
Any attempt to explain what happened or
apologize would only infuriate her further.
dubious
du•bi•ous adjective
Doubtful or suspicious
Most of Hannah’s friends doubted her dubious
claim that she’d suddenly inherited a fortune.
fleeting
fleet•ing adjective
Momentary; brief; not lasting for a long time
Their fleeting romance was over in less than a
few weeks, but he would remember it for the
rest of his life.
CLOSE READ
1. How does the scenery change as they approach the Lonely Mountain? How does
the change in setting affect the characters and the tone of the narrative?
2. Describe Bilbo’s use of another weapon—his intelligence—to find a way into the
Lonely Mountain. How does Tolkien insinuate or imply the “answer” to this puzzle
before the characters have figured it out? Why do you think he does this?
3. When do we finally see Smaug? Despite the narrator’s omniscient knowledge of
Middle Earth, why do you think the narrator saves the full description of Smaug
until Bilbo sees him in the Lonely Mountain?
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StudySync | The Hobbit
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4. Describe the “battle” between Bilbo and Smaug, and its ultimate result. What does
it tell us about these two characters?
5. Why does Bilbo take the Arkenstone? What can you infer from his decision to conceal
it from Thorin and the other dwarves?
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StudySync | The Hobbit
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CHAPTERS 14–16: Dwarves, Elves, and Men
KEY PASSAGE | Chapter 16, Paragraphs 40–43
In this passage, Bilbo receives praise and honor from Bard and the Elvenking for
his bravery and cunning in swiping the Arkenstone from the dwarves’ fortune.
Having just presented the Arkenstone to the Elvenking to help in negotiations
with the greedy Thorin Oakenshield, Bilbo receives an offer to stay with the
humans and elves, to be revered and protected. Bilbo politely declines the
Elvenking’s offer, however, stating that he has a sworn duty to his dwarf friends
with whom he has traveled on his long adventure. Nothing can dissuade Bilbo
from departing at once, so the humans and elves prepare an escort for him to
return to where the dwarves are camped. Along the way, he is congratulated
in surprise by an old and trusted friend.
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Discussion Prompt: Why do you think Bilbo returns to the dwarves instead of staying with
the elves? What does his choice tell you about Bilbo? Do you think he’s making the right
choice? Why or why not?
VOCABULARY
foreboding
fore•bod•ing verb
Warning; foreshadowing
Billowing gray clouds in the sky that day were
foreboding a heavy rainstorm.
alighted
a•light•ed verb
Descended or landed
The bird alighted in the middle of the field,
searching for worms and any other prey it could
find in the ground.
recompense
rec•om•pense noun
Compensation or amends that are paid, usually
for harm or a loss that’s been suffered
The judge ordered the company to pay millions
in recompense to the woman for failing to warn
her about potential health risks.
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tidings
ti•dings noun
Information; reports; news
The unemployment report brought good tidings
for the president, as the rate of joblessness had
declined for a third consecutive quarter.
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StudySync | The Hobbit
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counsel
coun•sel noun
Advice or counseling, given formally
You should seek counsel from an attorney
or legal professional to explore your options
moving forward.
hasty
hast•y adjective
Prone to acting too quickly or without sufficient
forethought
It would be better to wait and see if he improves
at his job, rather than making such a hasty
decision.
CLOSE READ
1. How is Smaug finally defeated? Describe the chain of events responsible for bringing
the evil dragon down.
2. Why does the thrush go off and fetch the raven Roac?
3. How does Thorin Oakenshield react when he hears that there are others who want
a claim of the dwarves’ fortune? What do you think would be a fair agreement?
4. What does Bilbo want to happen in the siege between the dwarves and the humans/
elves at the Gate? How does he orchestrate this?
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StudySync | The Hobbit
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CHAPTERS 17–19: The Battle of the Five Armies
KEY PASSAGE | Chapter 18, Paragraphs 15–18
This passage describes the final moments of Thorin Oakenshield, who lies
mortally wounded on the ground as Bilbo approaches him. Knowing that he will
soon die, Thorin bids Bilbo a farewell and offers an apology for his harsh words
earlier at the Gate, when he learned that Bilbo had swiped the Arkenstone
from the dwarves’ treasure. Bilbo kneels in sadness and says goodbye to
Thorin, stating that it has been an honor to share in their adventure. Thorin’s
final words are an ode to Bilbo’s character, as he tells the little hobbit that he
is filled with great virtue. He has learned a great lesson from Bilbo, and it is the
lesson that he wishes to impart from his deathbed: the world would be a better
place if more of its inhabitants were like Bilbo Baggins.
YOUR STUDYSYNC® TV
Discussion Prompt: As a group, discuss how The Hobbit manages the relationship between
good and evil. Is Tolkien’s Middle Earth a moral universe? Could Thorin’s story be considered
a cautionary tale, and if so, how can its lessons be applied to the real world? Why might
Tolkien have chosen to embed a real-life lesson within a fantasy novel?
VOCABULARY
sufficient
suf•fi•cient adjective
Adequate; enough for a specific purpose
The little money she made at her job was not
sufficient to pay for her rent and other monthly
expenses.
reconciliation
rec•on•cil•i•a•tion noun
The action of restoring friendly or peaceful
relations after a period of strife
UN leaders hope that the two formerly allied
nations can come to a reconciliation soon.
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heedless
heed•less adjective
Unmindful; showing little or no care or concern
Heedless of the danger, he climbed into the
burning apartment building to rescue his dog.
presumption
pre•sump•tion noun
A belief in the truth or veracity of something
before it has been proved
Her presumption that her new job would be
easier soon proved quite untrue.
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extravagant
ex•trav•a•gant adjective
Very showy or lavish
Having just signed a sixty-million-dollar contract
with his new team, he bought extravagant gifts
for his friends and family.
prosperity
pros•per•i•ty noun
The state of having wealth or success
A booming job market and shipping industry
brought prosperity to the region.
CLOSE READ
1. What is Bilbo’s explanation for why he gave the Arkenstone to Bard and the
Elvenking? How does Thorin react to this?
2. Who are the Five Armies? Whose allegiances lie with whom, and how do their
allegiances shift or change?
3. What part do the eagles play in the Battle of the Five Armies? How would you
describe their role in the world of Middle Earth?
4. What is the explanation for why Gandalf left the party earlier in Mirkwood Forest?
What did he accomplish while he was away?
5. How is Bilbo viewed differently by the other hobbits upon his return? How is he
different now from the way he was when he first left the hobbit lands?
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