Phantom Tollbooth
Discussion Questions
Pre-Reading
1. Have you ever complained that you are bored? Under what circumstances might you
feel bored? What can you do to avoid being bored? Do you know anyone who
complains about being bored all the time? What might this person do to reduce
boredom?
2. How does language reveal a person’s character? Do you think it is fair to judge
someone by his or her speech and use of language? What criteria might be used
instead?
3. Discuss the characteristics of a fantasy: imaginary setting, exaggerated characters,
personified animals, curious occurrences, people with special powers. Which books of
fantasy have you read? What was “fantastic” about them?
4. Which is more important words or numbers? Why?
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”?
Phantom Tollbooth
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.
Phantom Tollbooth
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?
Phantom Tollbooth
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?