The Hobbit cover

The Hobbit

J.R.R. Tolkien (1937)

A reluctant homebody is dragged out his front door into a world of dragons and dwarves — and comes back someone else entirely.

EraModernist / Pre-WWII
Pages310
Difficulty☆☆☆☆ Accessible
AP Appearances2

Essay Questions & Food for Thought

30questions designed to challenge assumptions and provoke original thinking. These can't be answered from a summary — you need the actual text.

#1Author's ChoiceMiddle School

Tolkien's opening sentence — 'In a hole in the ground there lived a hobbit' — was written on the back of a blank exam paper. Why is this sentence so effective? What does it do in three words that most first sentences take three paragraphs to accomplish?

#2Modern ParallelMiddle School

Bilbo has Baggins blood (respectable, unadventurous) and Took blood (wandering, curious). Is this a useful way to think about human personality — that we inherit competing impulses? What does modern psychology say about nature versus nurture?

#3Author's ChoiceHigh School

The trolls (Bert, Tom, and William) speak in Cockney dialect. Why does Tolkien give them working-class English accents? What does this choice do to how we perceive them as threats?

#4StructuralMiddle School

Bilbo wins the riddle game by asking 'What have I got in my pocket?' — which is not a proper riddle. Does cheating to survive make you a cheater? Is Bilbo morally compromised by this?

#5StructuralHigh School

Bilbo feels pity for Gollum and decides not to kill him, even when killing him would be safer. In The Lord of the Rings, this act of pity is the thing that ultimately destroys the Ring. Can Tolkien's plot retroactively justify Bilbo's moral instinct? Or does the instinct have to stand on its own?

#6Historical LensHigh School

Tolkien invented two complete Elvish languages (Quenya and Sindarin) before writing any story. What does it mean to build a world backwards — language first, stories second? How does this affect the depth of the world?

#7Author's ChoiceHigh School

The narrator of The Hobbit addresses the reader directly — 'you see,' 'I should tell you,' 'as I was saying.' This voice almost entirely disappears in The Lord of the Rings. What does this change cost? What does it gain?

#8Author's ChoiceMiddle School

Smaug is killed by Bard, not Bilbo. Why does Tolkien deny his protagonist the dragon-slaying? What would be lost if Bilbo killed Smaug?

#9Modern ParallelHigh School

Dragon-sickness — the greed that overcomes Thorin near the end — is presented as a disease rather than a character flaw. Does this make Thorin more or less sympathetic? Is greed better understood as sickness or as choice?

#10StructuralMiddle School

Bilbo gives away the Arkenstone — Thorin's most prized treasure — to prevent a war. Thorin calls this theft and betrayal. Bilbo calls it 'doing it for the best.' Who is right?

#11Historical LensHigh School

Tolkien fought at the Battle of the Somme in WWI, where nearly all his close friends were killed. How does this experience shape the Battle of Five Armies and Thorin's death?

#12StructuralMiddle School

Bilbo names his small blade 'Sting' himself, in the moment of using it. In Tolkien's world, naming things is an act of power. What does it mean that Bilbo claims this power — and that he does so in the middle of a fight with spiders?

#13Author's ChoiceHigh School

Gandalf leaves the company at the edge of Mirkwood and says his other business is urgent — but doesn't explain what it is. In The Lord of the Rings, we learn he was fighting Sauron's early manifestation. Is this acceptable narrative withholding, or is it a plot hole?

#14Historical LensHigh School

The dwarves' names in The Hobbit — Fili, Kili, Dwalin, Balin, Bifur, Bofur, Bombur, Dori, Nori, Ori, Óin, Glóin, and Thorin — come directly from the Norse Völuspá (the Catalog of Dwarves). What does it mean to write a 'new' myth that explicitly borrows names and structures from ancient myths?

#15Modern ParallelHigh School

The Master of Lake-town escapes Smaug's attack in a boat loaded with gold while people drown around him. He later lets people starve rather than use the recovered treasure. Is he a villain, or just the most honest portrait of institutional leadership in the book?

#16StructuralMiddle School

The Wood-elves of Mirkwood imprison the dwarves even though the dwarves have done nothing wrong. The elves are not evil. Does their action make them antagonists? Can someone be both 'good' and an obstacle to the protagonist?

#17Historical LensHigh School

Tolkien explicitly rejected allegory his entire career, saying The Lord of the Rings was 'not about' WWII. But The Hobbit was published in 1937, as European fascism rose. Can you read the story without the historical context? Should you?

#18Modern ParallelMiddle School

Bilbo returns home to find himself legally declared dead and his belongings auctioned off. He buys them back at higher prices. He is 'not quite respectable' for the rest of his life. What has he traded? Was it worth it?

#19StructuralHigh School

The eagles appear twice — to rescue the company from goblins and wargs, and to turn the Battle of Five Armies — both times at the last possible moment. Is this a deus ex machina problem, or does Tolkien earn these rescues? How?

#20Author's ChoiceMiddle School

Gandalf tells Bilbo at the end: 'You are a very fine person... but you are only quite a little fellow in a wide world after all.' Is this kind, condescending, honest, or all three?

#21Author's ChoiceHigh School

Smaug's conversation with Bilbo is a contest of wits between the most dangerous creature in the story and the smallest hero. How does Tolkien use sentence length and formality to show who has more power in this exchange?

#22Modern ParallelMiddle School

The Hobbit is a children's book in which multiple characters die, a city is destroyed, and the protagonist is nearly executed by his employer. At what point does a 'children's book' stop being a children's book?

#23Historical LensHigh School

Tolkien's dwarves are in some ways coded with antisemitic stereotypes common to 1930s British culture — gold-obsessed, driven from their homeland, clannish, excellent craftsmen. Tolkien was horrified when this was pointed out. Can an author be racist without intending to be? Does intent change the analysis?

#24Absence AnalysisHigh School

The Hobbit has no significant female characters. Tolkien added none in revision. Does this matter? How would the story change if it did?

#25StructuralMiddle School

Beorn is a man who can become a bear, or a bear who can become a man — even the narrator is not sure. Why does Tolkien leave this ambiguous? What does it mean for identity to be genuinely uncertain?

#26Modern ParallelHigh School

Tolkien's world has a consistent internal geography, calendar, and history — he drew maps, invented moon-letter systems, and worked out the exact date of Durin's Day. Does this level of internal consistency change how you read the story? Does it matter if a fictional world is 'real' internally?

#27StructuralMiddle School

Thorin's death speech — 'If more of us valued food and cheer and song above hoarded gold, it would be a merrier world' — is only possible because he's dying. He couldn't say it before. Why does death sometimes unlock truths that living prevents?

#28Modern ParallelHigh School

Compare Bilbo's pity for Gollum to modern debates about rehabilitation versus punishment in criminal justice. Is pity the right response to someone who has done harm? Is it practical?

#29Historical LensMiddle School

The Hobbit began as a story Tolkien told his children. How does knowing the original audience — specific children in a specific household — change how you read the narrator's voice, the comic passages, and the moments of reassurance during danger?

#30Modern ParallelHigh School

Peter Jackson's three-film adaptation of The Hobbit (2012-2014) runs nearly 9 hours. The book is 310 pages. What does this expansion tell you about the difference between a story told in words and a story told in images? What does each medium have to add that the other cannot?