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The two main characters

The Phantom Tollbooth is a children's adventure novel and modern fairytale by Norton Juster It was published in 1961 with illustrations by Jule Feiffer. It tells the story of a bored young boy named Milo who unexpectedly receives a magic tollbooth one afternoon and, having nothing better to do, decides to drive through it in his toy car. The tollbooth transports him to a land called the Kingdom of Wisdom. There he acquires two faithful companions, has many adventures, and goes on a quest to rescue the princesses of the kingdom—Princess Rhyme and Princess Reason—from the castle of air. The text is full of puns, and many events, such as Milo's jump to the Island of Conclusions, exemplify literal meanings of English language idioms.

Juster claims his father's fondness for puns and The Marx Brothers films were a major influence. Critics have compared its appeal to that of Lewis Carrol's Alice's Adventures in Wonderland and Frank L. Baum's The Wizard of Oz.

The book has been translated into several languages.


In June of 1960 Juster was given a $5,000 grant from the Ford Foundation to write a children's book about cities. He proposed to reveal the "visual delights and pleasures of living in cities..." It is notable that in this proposal, he also wanted "to stimulate and heighten perception — to help children notice and appreciate the visual word around them — to help excite them and shape their interest in an environment they will eventually reshape."

Juster quit his job so that he could work on the book. With the stacks of notecards of research, he felt as if he were in "grade school again, and about to be buried alive under a mountain of facts." Taking a break, he went to Fire Island. He also took notes from an incident that had happened in Brooklyn a few days earlier, wanting to turn it into a short story. A boy about 10 years old, asked "What is the biggest number there is?" Juster stated that "when a kid asks you a question, you answer with another question, so I said, 'Tell me what you think the biggest number there is,'" and Juster repeatedly asked him to add one to the number the boy came up with, leading them to talk about infinity. Juster, back in Brooklyn, wanted to finish the story about "a boy who asked too many questions" before returning to the book on cities.

Around the time he met Feiffer (see below), he also met Judy Sheftel, a young editor whom he would marry in 1961. She suggested that to pull the pieces together, that he write a two page synopsis. She later took the book to the editor Justin Epstein. Epstein later wanted the whole section on Chroma and his orchestra removed,[8] but Juster insisted that it be kept.

The book was published in 1961, without much hope that it would last long. Juster says the book was rescued from the remainders table when Emily Maxwell wrote a rhapsodic review of it in The New Yorker magazine.


Jules Feiffer, who did the drawings, had met Juster some time earlier, and he, Juster, and a third man rented the building together, with Juster doing the cooking for all of them in return for using almost the whole fourth floor, with Feiffer and another man on the third floor. Feiffer was curious about the pacing going on above him (when Juster was writing), and decided to investigate. Juster showed him the early manuscripts. Feiffer liked it, and Juster continued showing Feiffer manuscript pages. Feiffer would draw sketches from the drafts of various sections of the book. There never was a formal agreement about the drawings: since Juster did the cooking, if Feiffer wanted to eat, he had to do the drawings. Feiffer did not like to draw maps (Juster wanted a map) or horses. It became a game, with Feiffer trying to draw things the way he wanted, and Juster trying to describe things that were impossible to draw (such as the Three Giants of Compromise). Juster says that Feiffer got his revenge by drawing him (Juster) as the Whether Man wearing a toga (Juster later wrote that he does not wear togas).

Feiffer was in a panic as the book neared publication, since the text brought out his technical limitations as an artist, e.g. his inability to draw dogs or horses, as well as the precedent of other illustrators such as Edward Ardizzone making him "question his suitability" as a children's book illustrator. For instance, the drawing of the armies of wisdom has four riders on three horses (Feiffer originally drew them on cats instead of horses, and Juster was not amused). Thinking he would have to do many revisions, he drew on cheap tracing paper, which began to disintegrate with time. Later, Feiffer purportedly told himself, "Well, I got away with it." He did consider the double-spread illustration of demons on pages 240–241 to be a success — a drawing which would later remain one of his favorites from the book, being different than his usual style (which would involve a white background), instead using Gustav Dore's drawings as an inspiration.


Milo is a boy bored by the world around him; every activity seems a waste of time. He arrives home from school one day to find in his bedroom a mysterious package that contains a miniature tollbooth and a map of "the Lands Beyond". Attached is a note, "FOR MILO, WHO HAS PLENTY OF TIME". He assembles the tollbooth, takes the map, drives through the tollbooth in his toy car, and instantly finds himself on a road to Expectations. He pays no attention to his route and soon becomes lost in the Doldrums, a colorless place where thinking and laughing are not allowed. However, he is found there and rescued by Tock, a "watchdog" with an alarm clock attached to him, who joins him on his journey.

Their first stop is Dictionopolis, one of two capital cities of the Kingdom of Wisdom. They visit the word marketplace, where all the world's words and letters are bought and sold. After an altercation between the Spelling Bee and the blustering Humbug, Milo, and Tock are arrested by the very short Officer Shrift. In prison, Milo learns from Faintly Macabre, the history of Wisdom. Its two rulers, King Azaz the Unabridged and the Mathemagician, had two adopted younger sisters; Rhyme and Reason, whom everyone came to settle their disputes. All agreed that with Rhyme and Reason, nothing is impossible. Everyone lived in harmony until the rulers disagreed with the princesses' decision that letters and numbers were equally important. They banished the princesses to the Castle in the Air, and since then, the kingdom had Rhyme nor Reason.

Milo and Tock leave the dungeon and attend a banquet given by King Azaz, where the guests literally eat their words. King Azaz allows Milo and the Humbug to talk themselves into a quest to rescue the princesses. Azaz appoints the Humbug as a guide, and he, Milo, and Tock set off for the Mathemagician's capital of Digitopolis(called "Numeropolis" in earlier drafts[14]) to obtain his approval for their quest.

Along the way they meet such characters as Alec Bings, a little boy who sees through things and grows until he reaches the ground, and have adventures like watching Chroma the Great conduct his orchestra in playing the colors of the sunset.

In Digitopolis, their first stop is the mine where numbers are dug out and precious stones are thrown away. They eat subtraction stew, which makes the diner hungrier. (In the 2008 British Paperback edition, there is a recipe for Subtraction Stew. This is reprinted in p. 185 of the Annotated Phantom Tollbooth). The Mathemagician erases the mine with his magic pencil eraser, he and Milo discuss Infinity, and Milo proves to the Mathemagician that he must allow them to rescue the princesses.

In the Mountains of Ignorance, the three intrepid journeyers contend with lurking, obstructionist demons like the Terrible Trivium and the Senses Taker. After overcoming various obstacles and their own fears, the questers reach the Castle in the Air. The two princesses welcome Milo and agree to return to Wisdom. When the group leaves, Tock carries them through the sky because, after all, time flies. The demons chase them, but the armies of Wisdom repel them. The armies of Wisdom welcome the princesses home, King Azaz and the Mathemagician are reconciled, and all enjoy a three-day carnival celebration of the return of Rhyme and Reason, the princesses of the land.

Milo says goodbye and drives off, feeling he has been away several weeks. Ahead in the road he spots the tollbooth and drives through. Suddenly he is back in his own room, and discovers he has been gone only an hour.

He awakens the next day full of plans to return to Wisdom, but when he returns from school the tollbooth has vanished. A new note has arrived, which reads, "FOR MILO, WHO NOW KNOWS THE WAY." Milo is somewhat disappointed but looks around and finds that he lives in a beautiful and interesting world.

Critical Reaction

Critics have acknowledged that the book is advanced for most children, who would not understand all the wordplay or the framing metaphor of the achievement of wisdom. Writers like the reviewer in The New York Times have focused on the children and adults able to appreciate it; for them, it has "something wonderful for anybody old enough to relish the allegorical wisdom of Alice in Wonderland and the pointed whimsy of The Wizard of Oz".

It is now acknowledged as a classic of children’s literature. Based on a 2007 online poll, the National Education Center named the book one of its "Teachers' Top 100 Books for Children." It was one of the "Top 100 Chapter Books" of all time in a 2012 poll by School Library Journal.

1970 Film AdaptationEdit

Animation director Chuck Jones adapted the book into The Phantom Tollbooth, a feature live-action/animated film of the same name. The film was met with critical acclaim. Although it has no consensus, it earned an approval rating of 100% on Rotten Tomatoes.

2010 Proposed RemakeEdit

February 2010, director Gary Ross began development of a remake of The Phantom Tollbooth under Warner Bros. with the first draft of the script written by Alex Tse. The release date is currently unknown