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The Phantom Tollbooth

The Phantom Tollbooth (1961) is a children's novel and a modern fairy tale featuring wordplay and adventure, written by Norton Juster and illustrated by Jules Feiffer. It tells the story of a bored young boy named Milo who drives through a magic tollbooth into the Kingdom of Wisdom, where he embarks on a noble quest and in the end learns a valuable lesson.

Juster claims his father's fondness for puns and The Marx Brothers' movies were a major influence.

Plot summary

A boy named Milo, who is perpetually bored by life and considers his own to be purposeless, comes home one day to find an anonymous package containing a miniature purple tollbooth in his bedroom. After assembing the tollbooth, he drives through it and is transported to the Kingdom of Wisdom, a metaphorical land. He soon pays insufficient attention to his route and becomes lost in the Doldrums, a colorless realm where thinking is not allowed, whence he is found and rescued by the steadfast watchdog Tock, who joins him on his journey.

Dictionopolis

They arrive in Dictionopolis, one of two capital cities of Wisdom. In Dictionopolis, Milo learns, all the world's letters are grown in orchards; he sees them being sold in a vast marketplace. Humbug and the Spelling Bee get into a fight, where Milo is blamed and sent to prison for six million years.

In the prison, Milo meets a person called "Faintly Macabre, the not-so-wicked Which" [sic], who tells him the history of Wisdom's two rulers, King Azaz and the Mathemagician, and their adopted sisters, Rhyme and Reason. According to this story, the two princesses were unable to settle the long-standing argument between their brothers over whether letters or numbers are more important; for their failure they were banished to the Castle in the Air, high in the demon-infested Mountains of Ignorance. When Milo then tells Faintly Macabre that he was sent to jail here, she tells him Shrift does not intend to keep anyone in the jail, and shows him a way out.

Milo is sent to a banquet with the cabinet members, where he meets King Azaz the Unabridged. King Azaz agrees to allow the princesses to be rescued, providing his brother also agrees. This, however, Milo learns, is an unlikely event, as the brothers have not agreed on anything for years. Milo and Tock then leave Dictionopolis with the blustering Humbug, whom Azaz has sent along as a guide, towards the Mathemagician's capital of Digitopolis.

Journey through Sight and Sound

Entering the Forest of Sight, they meet Alec Bings, a little boy who sees through things and grows until he reaches the ground; they visit the twin cities of Reality and Illusions; and they watch Chroma and his orchestra of color conduct the sunset. After they depart, Alec gives Milo a telescope. Moving on to the Valley of Sound, they encounter Dr. Kakafonous A. Dischord, who dispenses unpleasant noises, and his smoky sidekick the Awful Dynne. In the valley proper (which is completely silent) Milo visits the fortress of the Soundkeeper, creator and cataloger of all sounds, who has withheld the valley's sounds because the inhabitants had stopped appreciating them. As directed by the valley's inhabitants, Milo secretly takes a sound from the Soundkeeper's fortress, which the people of the valley use to break open the palace's sound vault. Milo and his friends then continue their journey, taking a short (and involuntary) detour to the Island of Conclusions. They arrive at Conclusions by "jumping", which happens to each traveller as he makes an unwarranted assumption.

Digitopolis

Approaching Digitopolis, they meet the Dodecahedron, a figure having twelve faces, each of which expresses a different emotion. He takes them to the Mathemagician, who shows them the Numbers Mine, where the world's digits are pulled from the earth like jewels. Milo tricks the Mathemagician into agreeing with his brother to release the princesses, whereupon the Mathemagician takes them to the edge of the Mountains of Ignorance, and provides Milo with a mathemagical wand (a pencil).

The Rescue

In the mountains, Milo, Tock, and the Humbug meet various demons representing manifestations of ignorance, whose deceits are thwarted by gifts Milo has received from several of his hosts. The defeated demons then arouse the whole population of their realm, who pursue the travelers. With the demons close behind them, the protagonists climb to the Castle-in-the-Air, where the two princesses welcome Milo. The enraged demons, meanwhile, chop off the base of the staircase, causing the Castle to begin to float away. Because "time flies", Tock is able to carry the others safely back to earth, where the combined armies of Wisdom are waiting. The armies then drive back the demons. The two leaders welcome the princesses home and begin a celebration to mark their return. Milo thereafter returns home, where he learns to his surprise that the entire adventure, which seemed to him weeks long, has only lasted an hour. Milo whimsically reflects on the idea that a great deal can be accomplished in a short duration, and he looks forward to his next adventure through the tollbooth. Coming home from school the next day, he finds the tollbooth has vanished. All that he finds is a note which says that he can now find his own way to Wisdom. He soon begins to appreciate life and live each moment with curiosity.

Characters

Main characters

Milo, a boy, the main character. Presented as a sort of "everyman" whose personality is that of an observer of his adventures.
Tock, a "watchdog" resembling a clock mounted on the legs of a dog, who becomes a loyal companion to Milo. The job of a watchdog runs in his family in the ancestral line and consists of making sure that people do not waste time. He can sometimes be irascible, but is essentially a benevolent character.
The Humbug, a large, bombastic, beetle-like insect who acts as the anti-hero. One of Milo's companions. He is a liar, a glutton, frivolous, condescending, arrogant, choleric, and almost never able to provide a correct answer to any question except when he has no intention of doing so. As his name suggests, he is prone to exaggerating and inventing falsehoods about himself.
King Azaz the Unabridged, ruler of Dictionopolis and lover of words. A large, choleric, fierce, bombastic, but benign figure.
The Mathemagician, ruler of Digitopolis and lover of numbers. Similar in personality to his brother (Azaz), but more refined and thoughtful. As his name suggests, he is clad in a variation of the archetypal "wizard's raiment", consisting of a long robe and conical hat decorated with the symbols of his speciality. He carries a pencil that is sufficiently large to be used as a walking stick, which is his most ready tool.
Rhyme and Reason (also known as The Princesses of Sweet Rhyme and Pure Reason). Adopted daughters of the Old King of Wisdom, without whom the kingdom lacks its namesake and falls into disorder. It is implied that Rhyme is more lighthearted than her sister, possibly to reflect the difference in their roles. The names are derived from the phrase "without rhyme or reason", which is a Shakespearean quotation used to indicate an absence of logic.
Faintly Macabre, (Aunt Faintly) the Not-So-Wicked Which. She is King Azaz's great-aunt and sometime regulator of the words used in public. When she became avaricious and hoarded all words for herself, Azaz ordered her imprisoned, in which state she remained until the return of Rhyme and Reason to the Kingdom of Wisdom.
Alec Bings, a boy of Milo's age and height who "sees through things". Like the other members of his family, he grows downwards from a fixed point in the air until he reaches the ground.
Chroma, conductor of the world's color.
Dr. Kakofonous A. Dischord, a distributor of noise possessing extremely large ears. The initial "A" stands for "AS LOUD AS POSSIBLE!".
The Awful Dynne, an emotional, noise-loving creature formed of blue smoke; an accomplice of Dr. Dischord, who raised him from infancy. He is remarked to have had a grandfather called The Dreadful Rauw ("dreadful row"), who died during "the Great Silence Epidemic of 1712".
The Soundkeeper, ruler of the Valley of Sound, and keeper of a large collection of previously-uttered noises; a stern woman who actually prefers silence, and at one point banned sound in her valley because she felt the locals had abused the privilege of having it. Adapts very quickly to the loss of her control over sound and soon rationalizes it to herself. She is enthusiastic in whatever her interest is, regardless of self-contradiction.
The Dodecahedron, an inhabitant of Digitopolis having twelve faces, whereof each shows a different emotion. Used at one point to indicate the universality of numbers.
Officer Shrift, apparently Dictionopolis' entire police force, who enjoys arresting and imprisoning people, but is not concerned with keeping them incarcerated. He is taller sitting down than standing up, and is almost twice as wide as he is tall. His name is a pun on the phrase "short shrift."
The Whether Man, a semi-official who tries to send travellers beyond Expectations, Milo's first stop on his trip. Often comically distracted and absent-minded. His name is openly suggested to be a play on "weather man."
The Lethargarians, a group of small creatures dwelling in the Doldrums, whose purpose is to exert every variation of "doing nothing". They are perpetually sleepy, but seem to follow and continue each other's conversation even when they have been asleep. Each assumes the color of the surface on which he is lying.
The Spelling Bee, an expert at word-construction who quarrels violently with the Humbug.
The Half Boy, a boy who is only .58 of a person. He comes from the "average" family, which has 2.58 children. He is the .58.
The Giant, the Midget, the Fat Man, and the Thin Man, A very ordinary-looking amateur advice-distributor who explains that he is at once the world's shortest giant, tallest midget, thinnest fat man, and fattest thin man.
Canby, a frequent visitor to Conclusions who is as much "as can be" (hence his name) of any possible quality.
King Azaz's advisors/cabinet, includes the Duke of Definition, Minister of Meaning, Count of Connotation, Earl of Essence, and the Undersecretary of Understanding.

The Demons of Ignorance

The Terrible Trivium, a humanoid demon whose face lacks features and who seduces passers-by with mindlessly easy but pointless tasks that take an incredibly long time to accomplish.
The Demon of Insincerity, a rabbit/kangaroo like demon. Its only purpose is to mislead anything or anybody that comes nearby.
The Gelatinous Giant, a giant hidden in the mountains of Ignorance.Shaped like a large mountain. Extremely cowardly and especially afraid of ideas.
The Triple Demons of Compromise, a demonic team of three negotiators; one is short and fat, one is tall and thin, and the third looks "exactly like the other two". They can never truly go anywhere because, rather than reach agreements, they constantly compromise.
The Horrible Hopping Hindsight, a demon which has its eyes on its rear end. It never sees where it is going, only where it has been, and always thinks that each movement could have been better.
The Everpresent Wordsnatcher, a monstrous filthy bird who deliberately misinterprets whatever a person says. He has ambitions of being a demon, but is said to be only a nuisance, and is suggested to have previously met the Humbug.
The Senses Taker, a demon who distracts passers-by by supplying them with illusions of things they would rather be perceiving. His name may be a play on "census taker".
The Overbearing Know-it-All, a spherical demon with spindly legs. He constantly talks, offering his own incorrect opinions to anyone nearby, and all are in danger of being crushed under him. He is often accompanied by the Gross Exaggeration.
The Gross Exaggeration, an especially ugly demon, "whose rows of wicked teeth were made only to mangle the truth". A frequent companion of the Know-It-All.
The Threadbare Excuse, a humanoid demon that clings to anyone who will give him a ride. He is always heard murmuring weak reasons for not doing things, and also has a vice-like grip on anyone who holds him.
The Gorgons of Hate and Malice, two disgusting slug-like demons that leave oozing trails behind them.
The ugly Dilemma, a horned demon whose name implies his purpose. He is said to blow clouds of steam from his nostrils.
Others: Other demons are shown in the illustration, but are never named. They may be the same demons alluded in the passage describing Milo's flight to the Castle in the Air, but are not fully described there.

Film, TV or theatrical adaptations

In 1969, animation director Chuck Jones adapted The Phantom Tollbooth into a full-length feature animated film.
In 1995, Juster adapted Tollbooth into a libretto for an opera version.
Various stage adaptations have been created and performed. In 2004, The Phantom Tollbooth was adapted as an official theatrical screenplay by Patrick Sayre and Cole Taylor.
In 1987 composer Robert Xavier Rodriguez adapted a chapter of The Phantom Tollbooth into "A Colorful Symphony" for narrator and orchestra.