The Phantom Tollbooth
L-I-T Guide
Literature In Teaching
By Norton Juster
A Study Guide for Grades 4 to 8
Prepared by Barbara T. Doherty and Charlotte S. Jaffe
Illustrated by Sandralynn Veech and Karen Birchak
Meet the Author
Norton Juster
Norton Juster was born in Brooklyn,
New York, on June 2, 1929. His father,
who was an architect, loved puns and word
play. Norton went to the local public
schools. His dream was to become an
architect and after high school he enrolled
in the University of Pennsylvania to study
architecture. In 1952 Juster won a
Fullbright fellowship and he used to funds
to travel to England to study city planning.
In 1954 he joined the United States
Navy and served until 1957. During his
years of service Juster worked at many
assignments, including the planning of new
airfields. Upon completing his service in
the Navy, Norman Juster returned home
and began his career as an architect. While
working as an architect, Juster also taught
architecture and environmental planning at
Hampshire College. He remained on the
staff of the college from 1970 to 1992.
While all of this was going on, Mr. Juster began to write stories as a way to relax and
have fun. As he wrote he remembered the feelings he sometimes had as a boy—feelings of
being bored. He remembered wondering why he had to learn all those “unimportant things”
in school. Out of those memories he wrote The Phantom Tollbooth. It was published in
1961. Since then it has been translated into at least twelve other languages. In 1969 it was
made into a full-length animated MGM film. In 2008 the Kennedy Center for the
Performing Arts began a six-month tour of the story as a stage show. Another of his books,
The Dot and the Line, was made into an Oscar-winning animated film. His latest book,
The Hello, Goodbye Window, was published in 2005. In it he featured his wife and his
granddaughter. He has also written two books for adults.
© Educational Impressions, Inc.
The Phantom Tollbooth
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Meet the Illustrator
Jules Feiffer
Jules Feiffer, the artist whose imaginative drawings add to the quality and fantasy of
The Phantom Tollbooth, was born in the Bronx, New York, in 1929. As a young boy, he
enjoyed reading comic books and drawing his own cartoons. At the age of seven he even won
a gold medal for one of his drawings in a local contest. Feiffer eventually went on to create
cartoons for The Village Voice, as well as editorial cartoons for The New York Times. In 1986
he received the Pulitzer Prize for his editorial-cartoon work.
In addition to his cartoons, Jules Feiffer wrote plays, screenplays, and novels. He also
published more than twenty books. His books for children include The Man in the Ceiling
and I Lost My Bear. During his career, Feiffer taught at many prestigious colleges, including
the Yale School of Drama.
Jules Feiffer and author Norton Juster were close friends. They lived in the same
duplex-apartment building in New York City when Juster began to write The Phantom
Tollbooth. Feiffer explained, “Norton would read a chapter or two, and I would scribble something. I'm not sure I ever agreed to be the illustrator. We just took it for granted.”
Feiffer's distinctive pen-and-ink style appears to be sketchy, but the artist took great
care in planning the illustrations. “I always try to make my drawing appear seamlessly on the
page, as though it wasn't even crafted,” the artist states. His latest illustrations are found in
the children's book, Which Puppy? It was written in 2009 by Kate Feiffer, his daughter.
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The Phantom Tollbooth
© Educational Impressions, Inc.
The Phantom Tollbooth
Written by Norton Juster
STORY SUMMARY
Milo seems disinterested in life and bored by his surroundings. After returning from
school one afternoon, he unexpectedly discovers that a large and mysterious box has been
placed in his bedroom. In it are parts and instructions for assembling a tollbooth. Milo builds
the tollbooth and climbs into his toy car. Following the map that was also in the package, he
sets out towards the Lands Beyond to seek adventure.
As he drives through the tollbooth and down the road toward Dictionopolis, he passes
through a land called Expectations. There he meets the peculiar Whether Man, who fails to
help him with directions. Next, Milo wanders into a monotonous place aptly named The
Doldrums. Nothing much occurs or gets done in The Doldrums. However, it is there that Milo
meets Tock, who is known as a watchdog because he has the body of an alarm clock. Tock
decides to accompany Milo on his journey.
The two travelers finally arrive in Dictionopolis. At the Word Market Place they meet
The Humbug, a large beetle-like insect who becomes another invaluable travel companion.
Milo learns the origin of the dispute between King Azaz, the ruler of Dictionopolis, and his
brother, the Mathemagician, ruler of Digitopolis. King Azaz thinks that words are more
important than numbers, and his brother thinks the opposite. When their two sisters failed to
settle the argument, they were banished from Wisdom and sent to live far away in the Castle
in the Air. Milo and his friends begin a quest to find and free the missing princesses and bring
peace back to Wisdom.
Along the way to their first destination of their quest, Digitopolis, the travelers meet an
array of colorful characters: Alec Bings, a boy who grows downward instead of upward;
Chroma the Great, a conductor of music, colors, and nature; and Dr. Dischord, a collector of
unpleasant noises. Eventually Milo meets the Mathemagician. After gaining his approval, the
three friends continue their journey
through the treacherous Mountains of
Ignorance to the Castle in the Air. They
rescue the princesses, Rhyme and Reason
return to the kingdom, and the three friends
are hailed as heroes.
After a tearful goodbye, Milo
returns home. When he arrives, he finds
that the tollbooth has disappeared and that
a note suggesting that he is now able to
find adventure himself has been left in its
place. Milo will never be bored again.
© Educational Impressions, Inc.
The Phantom Tollbooth
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