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MORE QUESTIONS
Why was Milo so quick to get in the car and pass through the Tollbooth? Do you
think he was being foolish or just adventurous?
Why is it so important to rescue Rhyme and Reason? What would've happened –
to Milo and to Wisdom – If they were never rescued?
Does The Phantom Tollbooth remind you of any other books you've read? If so,
why? And if not, what makes it unique?
Is Milo a well-developed character? Is he a typical hero? Or is he just a stand-in
for us as readers, who need to open up our minds to a world of learning and
imagination?
What's your favorite pun in The Phantom Tollbooth? Why do you think the author
uses so many puns anyway?
Why does Norton Juster focus on language and math. What about literature?
What about sciences? And hey, what about recess?
If you could buy words, what words would you choose, and why? And how do
you think those words would taste?
Which part of the Lands Beyond would you most like to visit? Which would you
most like to avoid? Why?
Suggested Essay Topics
A. What lessons could the Soundkeeper learn from Dischord and Dynne?
B. Why does Faintly Macabre remain in prison, despite knowing how to escape?
C. Who might the anonymous sender of the tollbooth be? What reasons would he
D. or she have to send it to Milo?
E. What would the King of Wisdom— Azaz and the Mathemagician’s father—
think
F. of the state of things in the Lands Beyond? Would he be pleased with the way
his
G. sons have been looking after the kindgom?
H. What would have happened to Milo if Tock had not shown up in the
Doldrums?
I. Would he have stayed there forever?
Chapters 1-3
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What did Milo think was the greatest waste of time? Why?
How would you describe Milo? Give some examples from the book to support
your ideas.
Why is it fitting that Milo's journey started with the Land of Expectations?
Who did Milo meet in the Land of Expectations? Why was his name
appropriate for him?
Milo meets the Lethargarians in the Doldrums. What are they like?
What is unusual about Tock?
Describe the five ministers that Tock and Milo meet in Dictionopolis.
Chapters 4-6
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Describe the word market in Dictionopolis.
In the word market, Tock and Milo meet the Spelling Bee and the Humbug.
Describe both characters.
Why is the Humbug's name appropriate for him?
What happens when the Humbug and the bee fight in the word market?
Describe Officer Shrift. Explain why his name is appropriate for his character.
Explain how Rhyme and Reason became banished to the Castle in the Air.
Chapters 7-9
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Who do Milo and Tock meet at the banquet? Why is his name appropriate?
This chapter is called ''The Humbug Volunteers.'' What did he volunteer to do?
Find an example of alliteration in Chapter 8.
Find an example of hyperbole in Chapter 8.
The King tells Milo that there is ''one far more serious problem.'' What is it?
What does the King give Milo as a gift to take with him on the journey?
Explain what a ''point of view'' is and give an example.
Chapters 10-12
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What are illusions?
Who is Chroma the Great? What is his job?
Why is the name ''Chroma the Great'' a good choice for him?
Find an example of personification in Chapter 10.
Find an example of a simile in Chapter 10.
What happens when Milo conducts the orchestra?
What gift does Chroma give to Milo? What is it for?
Describe Dischord and his wagon.
What is the DYNNE's job?
Find an example of an oxymoron in Chapter 12.
What do the people of the Valley of Sound ask Milo to do?
Describe how the Soundkeeper saves sounds.
Explain how Milo brought a sound out of her fortress.
Find an example of an onomatopoeia in Chapter 12.
Chapters 13-15
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What happened when Milo let out the word ''but''?
What gift did the Soundkeeper give to Milo? What is it for?
Where did Milo, Tock and the Humbug land after leaving the Valley of Sound?
How did they get there?
What is a dodecahedron? What is unusual about the Dodecahedron in this
chapter?
How are numbers obtained in Digitopolis?
Who do the travelers meet in the mine?
Explain how subtraction stew works.
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How does the Mathemagician travel from place to place?
Phantom
Tollbooth Discussion Questions
Pg 1-70
1. Why does the author select names such as “Expectations” for the destinations
on the map provided with the tollbooth? What might be some similar but different
names for other possible places Milo might travel?
2. Who are the colorful characters Milo meets, and what is interesting about each
one?
Why does the absence of Rhyme and Reason help to make the characters
more? Entertaining?
3. Describe a time when you have been in “the doldrums”. How did you get out?
4. Some of the crimes seem very silly, such as “barking without a license”. What
do you think the author is trying to say by having such crimes? Do members of
your group ever fight about silly things in their lives?
5. Is the small additional penalty of six million years really small? Do members of
your group ever encounter “small” matters that are really rather huge? What?
6. When the humbug says, “Don’t worry, maybe they will take a million years off
for good behavior,” is he really trying to help? Have members of your group ever
had people make comments that sound nice by don’t really help in certain
situations? How do they feel about such “help”?
Discussion Questions
Pgs. 70-142
1. Which is better, words or numbers? Why do you feel that way? Do members of
your group like words better if they enjoy reading the most, and numbers better if
they prefer math? Why is this dispute used instead of an actual war situation? Do
you think the author is trying to make a statement in regard to real war?
2. Why are the names “officer Short Shrift” and “Faintly Macabre” appropriate for
these characters?
3. Why should Dictionopolis, a land of words and language, be located in the
Foothills of Confusion?
4. What is funny about Humbug “cheerfully” volunteering to accompany Milo and
Tock on the journey to find Rhyme and Reason? How would a Humbug’s company
affect a group of travelers on a trip? Have members of your group ever traveled with
a Humbug?
5. Although most of the Humbug’s other statements are false, do you think there is
any truth to his pronouncement that “History is full of Humbugs”?
6. Do you think there are equal hazards in using too few or too many words? Which
might be more dangerous? Provide examples as evidence to support your opinion.
7. Have you ever used rhyme and reason to settle a problem that you had? Why is
this often more effective than force?
8. Tell about the cities of Illusion and Reality. What are the people Like? Are real
people in real cities similar to the residents of these two cities in the book? Why or
why not?
9. What do you think it would be like to be born in the air, and to have to grow down
to the ground before you became an adult? What problems do you think you would
have? How would floating children affect games such as soccer and basketball?
Would there be any advantages?
10. Would members of your group like a noise doctor who would diagnose children
as having too little noise? How would that affect different situations? How would that
affect adults?
11. A cacophony is a terrible noise. Think of things that you think would be
cacophonous. Discuss these with your group
Discussion Questions
Pgs. 142-210
1. Do you agree with the Soundkeeper that you need unpleasant sounds in order to
Appreciate pleasant sounds? Might it be necessary to always have contrasts in
order to appreciate anything in the world?
2. Do you think Milo should have stolen the sound from the Soundkeeper and
restored sound to the valley? Would the members of your group have done the
same thing?
Why?
3. Have members of your group ever landed in a situation similar to the Island of
Conclusions? What comments did they make to get them into such a situation?
What are some good rules about not jumping to conclusions?
4. The Dodecahedron says, “…as long as the answer is right, who cares if the
question is wrong?” Which do you think is more important, the question or the
answer?
5. What would happen if you could only eat when you were full, and only sleep when
you were awake? What other things like that can you think of that would cause
similar problems? Would you like to eat subtraction stew and why? Do you think it
would make a good diet food?
6. How could diamonds and rubies and emeralds be a nuisance? What
characteristics do you think make something valuable?
7. Have you ever joked about a family with 2.3 children and thought about what the
.3 of a child would be like? How could .3 of child function? Would he or she
complete .3 of his or her homework? Do you like this character in the story and why
or why not? Would you like .3 of a car to drive? Would there be a shoe store that
offered .3 of a pair of shoes?
Discussion Questions Pgs. 210-255
1. What are the useless jobs the Terrible Trivium gave to Milo, Tock and the
Humbug? What are
some jobs members of your group may have to do that they feel are useless? Are
those jobs as useless as what the book characters have to do? Would there be any
useless jobs in Expectations?
2. What does the author use jello for a giant that doesn’t like change? Have
members of your group ever made things with jello? Do you think the author of this
book used a jello character before people thought of ways to change jello into
different shapes? What “unchangeable” substance would an author use today to
show unchanging features?
3. Do you agree with the Princess of Reason that “you learn more by being wrong
for the right reasons than you do by being right for the wrong reasons?” Discuss this
statement with your group, finding as many examples as possible to support your
argument,
4. Time “flies” in the story. Make a list of other idioms and how they could be used in
this book.
5. Can you think of any examples in the real world where wisdom overcame
ignorance?
6. Why was it important for Milo, Tock, and Humbug not to be aware of the fact their
journey to find Princesses Rhyme and Reason was impossible? Have members of
your group ever tried to do something someone told them was impossible? Did they
succeed? Did people tell them they would fail? Are you able to name some
nonfiction stories where people used perseverance and were able to overcome
obstacles no one thought they could?
7. Now that Milo has found the world to be an interesting place once more, what are
some things members of your group think he might want to do?
8. Do you think Milo will still be bored by everything? What big lesson did he learn
from his experiences?
9. The Phantom Tollbooth is considered a modern classic. What qualities determine
a classic?
Which of these qualities can you see in this book? What other books have you read
that you consider classics?
10. Contrast the first and last sentences in the book. State in your own words the
most important lesson this book teaches.
11. Although this is considered a children’s book, many people say it is written just
as much for the enjoyment of adults. What do you think? Why is it grouped with
books for children?
Should it be?
 Discuss the theme of wisdom and ignorance in the novel. Does the book seem
optimistic about most people's ability to achieve wisdom?
 Give three examples in the novel of words or phrases that have a literal or
physical being in the Lands Beyond. How does the meaning of these words or
phrases inform the reader about the character, place or thing in the Lands
Beyond?
 Name three of the gifts that Milo receives on his journey. Explain how he uses
those gifts in his quest to save the princesses Rhyme and Reason.
 Milo does a heroic thing by rescuing the princesses. Does Milo fit your idea of a
hero? Why or why not? Support your answer with examples from the book.