The Phantom Tollbooth

There was once a boy named Milo who didn't know what to do with himself -- not just sometimes, but always.
 When he was in school he longed to be out, and when he was out he longed to be in. On the way he thought about coming home, and coming home he thought about going. Wherever he was he wished he were somewhere else, and when he got there he wondered why he'd bothered. Nothing really interested him -- least of all the things that should have.

A classic children's novel by Norton Juster (and illustrated in most versions by Jules Feiffer) that has also become a favourite among adults for its intricate cleverness, rapid-fire wit and boundless imagination.

Milo is a bored little boy. Then one day he comes home from school (he's a latch-key kid) and discovers a very singular box in his room. Within are the pieces to construct a toy tollbooth. Having nothing better to do, he follows the included instructions, drives through the tollbooth in his toy car, and suddenly finds himself driving down a road under a distant sky.

Along his surprising journey he meets such colorful characters as King Azaz the Unabridged, King of Dictionopolis and the realm of words; the Mathemagician, ruler of Digitopolis and everything number-related; Tock, the loyal watch dog (literally); the oversized Spelling Bee; the shifty-but-lovable Humbug; Faintly Macabre, the not-so-wicked Which; Chroma the Great, conductor of the sunrise; the Soundkeeper, who greedily keeps all sound to herself; and the sadly missing Princesses Rhyme and Reason, locked in the Castle in the Air and desperately in need of rescue from the demons of the mountain of Ignorance.

There is also a movie version, produced by the legendary Chuck Jones. A lot of the incidental wordplay and allusion is streamlined out, in favor of some catchy but extremely Seventies songs about finding your dreams by following your heart. There's a lot to be said for Jones' typically cute and energetic character designs, though, especially the ones that have Mel Blanc's voices.

As of Summer 2010 a new film version was in the early stages of pre-production, with an intended 2013 release. However, as of August 2016, the film has still not been made, the project has jumped production companies, and a whole new scriptwriter has taken over.

Tropes used in The Phantom Tollbooth include:
  • Achievements in Ignorance
  • An Aesop: The page quote opens the book. At the end, the tollbooth vanishes, but on reflection, and looking around, Milo wonders how he would have found the time to go back even if it hadn't, when there was so much to do right there.
  • Affably Evil: The Terrible Trivium is a polite, refined gentleman -- so polite and refined, you wouldn't mind doing a few minor, insignificant tasks for him. Heck, you can spare a few thousand years, right?
    • Something of a self-referential Truth in Television, since Juster has said he wrote the book while he was supposed to be writing a different book about city architecture for kids.
  • Agree to Disagree
  • All-Natural Gem Polish: Averted.
  • Anthropomorphic Personification
  • Backstory
  • Big Damn Heroes: Just when the terrible creatures of Ignorance are about to descend on Milo, Tock, the Humbug and the princesses, the cavalry comes in the form of damn near every single person our heroes came across on their journey.
  • The Blank: The Terrible Trivium, and in the movies Rhyme and Reason.
  • A Boy and His X: A boy and his watchdog.
  • The Cavalry: After rescuing the princesses from the Castle in the Air, Milo and his companions are chased down by all the demons of Ignorance, only to be saved at the last second by an army consisting of EVERYONE THEY'VE MET ON THEIR JOURNEY THUS FAR. Phantom Tollbooth could be considered the best example of this trope.
  • Clap Your Hands If You Believe: The cities of Reality and Illusions (I guess?).
  • Distressed Damsels: Princesses Rhyme and Reason.
  • Divided We Fall
  • Everything's Better with Princesses: Quite literal with the Princesses of Sweet Rhyme and Pure Reason, of the Kingdom of Wisdom. They are apparently high enough in authority that their brothers King Azaz and the Mathemagician, rulers of their own respective countries, appeal to them when there's a dispute... and once they're banished, Wisdom goes to Hell in a handbasket. It's only after they're rescued in The Quest that the Kingdom becomes sane again... everything is, in fact, better with them in charge.
  • Exact Words: When Milo asks the Mathemagician to show him the biggest number there is, the Mathemagician shows him a number 3 that's twice his own height. Milo corrects himself and asks for the longest number there is, and the Mathemagician shows him a number 8 that's as wide as the 3 was high.
    • Earlier, when Milo is asked what kind of meal he'd like, he asks for "something light" and gets platters filled with literal light. Then he asks for "a square meal" and gets blocks of food that taste awful.
  • Fantasy World Map
  • Forbidden Zone
  • Fun with Acronyms: Inverted. Dr. Kakofonous A. Dischord's middle initial stands for "AS LOUD AS POSSIBLE"
  • Golden Mean Fallacy: Embodied by the Triple Demons of Compromise: one tall and thin, one short and fat, and the third "exactly like the other two".
  • Grows on Trees: Words do because money doesn't.
  • Home, Sweet Home
  • Hurricane of Puns
  • Insane Troll Logic: Oh, so, so much.

Dodecahedron: Why, did you know that if you a beaver two feet long with a tail a foot and a half long can build a dam twelve feet high and six feet wide in two days, all you would need to build Hoover Dam is a beaver sixty-eight feet long with a fifty-one-foot tail?
Humbug: Where would you find a beaver that big?
Dodecahedron: I'm sure I don't know, but if you did, you'd certainly know what to do with him.

  • It Was a Gift: Several people Milo meets give him gifts that prove useful against the demons.
  • Impossible Task: Getting to the land of Infinity. "Just follow that line forever, and when you get to the end, turn left." Or alternately, you can go up a staircase that never ends.
    • Filling out the Senses Taker's questionnaire, which includes such questions as "why you were born", "the schools you haven't attended", "the number of books you read each year", "the number of books you don't read each year", every clothing size you can think of, and then the names and addresses of six people who can verify this information. And it should go without saying that these forms need to be filled out in triplicate and a single mistake means you have to write them all over again.
    • Completing the tasks the Terrible Trivium has laid out for you. Well, strictly speaking it's not impossible, they just take an insane amount of time. To wit:
      • Moving a pile of sand from one place to another, with a tweezers,
      • Transferring water from one well to another, with an eyedropper, and
      • Digging through a cliffside with a needle.
  • Judge, Jury and Jailer: Officer Shrift. Fortunately for Milo, he only cares about throwing people in prison, not about keeping them there.

"Six million years already? My, how time flies!"

  • Kangaroo Court: Officer Shrift runs one of these.
  • The Kingdom
  • Lovable Coward: The Humbug.
  • Never Tell Me the Odds: The quest was literally impossible--but since nobody told Milo, it became possible.
  • Non-Human Sidekick: Tock and the Humbug.
  • Obstructive Bureaucrat: The Senses Taker.
  • Oxymoronic Being
  • The Quest
  • Painting the Frost on Windows: At one point, Milo meets Chroma, a conductor whose orchestra provides color to the world, with each instrument providing a specific color. Upon stopping at Milo's request, everything turns white with black outlines.
  • Parental Bonus: If you're under the age of 12, it's a given that you're not getting about a fifth of the jokes.
    • The conflict between Dictionopolis and Digitopolis was Juster's jab at the "Two Cultures" mentality described by C. P. Snow; the position taken by Rhyme and Reason is much like that of Snow himself (who was both a physicist and a novelist).
  • Portal Slam
  • Punny Name: Pretty much everybody.
  • "Reading Is Cool" Aesop
  • Real Life Writes the Plot: Feiffer drew the book's pictures because he happened to be living in the same apartment building as Juster at the time of the book's writing.
    • And the origin of the book was that Juster had gotten a grant to write a nonfiction book on architecture but he had an idea for a story that he had to get out of his head. The text describing the cities of Reality and Illusion are the only surviving bits of what he wrote before he got sidetracked (and sidetracking you from what you're supposed to be doing is what the Terrible Trivium does). He reportedly has tried to pay back the grant several times, but can't find anyone who will acknowledge it.
    • In the book, the Whether Man is a portrait/caricature of Juster, evidently revenge for including the Triple Demons of Compromise.
  • Shaped Like Itself: The tollbooth package; "for its size it was larger than almost any other big package of smaller dimension that he'd ever seen."
  • Shout-Out: Doctor Dischord's personality was a deliberate shout out to Groucho Marx's stage and screen persona.
  • Stealth Pun: Among other examples, the Everpresent Wordsnatcher, a bird that lives to misinterpret what others say, is actually native to the land of Context, "but it's such a nasty place, I prefer to spend all my time out of it."
    • Canby's puns are as stealthy as can be.
  • Trapped in Another World
  • Wonder Child: The princesses were foundlings.
  • World of Symbolism: With the tollbooth itself guarding the entrance.
  • Worthless Yellow Rocks: They keep cluttering up the Numbers Mine.
  • Writers Cannot Do Math: An in-universe example. Of course, the point was that there is no greatest possible number, but when Milo is for asked the highest number he can think of, he replies, "nine trillion, nine hundred ninety-nine billion, nine hundred ninety-nine million, nine hundred ninety-nine thousand, nine hundred ninety-nine". Even if he hadn't known that "quadrillion" comes after "trillion" (and not everyone does), with the "999s" he's doing, it should be obvious to him that the next number is ten trillion.
The movie provides examples of:
  • Always Identical Twins: Although they are never described or drawn as such in the book, King Azaz and the Mathemagician are this in the movie. They even have the same voice actor.
  • The Cameo: When Milo is in class and many people are speaking at once, the voice of Bugs Bunny can be heard. In fact, nearly every famous voice artist of the day, from Daws Butler to June Foray to Candy Candido gets a bit part somewhere in the film.
  • Deranged Animation: The Demons of Ignorance truly look insane and sketchy compared to Chuck Jones's usually smooth works.
    • When Milo messes with the sky, it results in this.
  • Dramatic Thunder: Occurs whenever Milo announces that he's going to the "Castle in the Air."
  • The Film of the Book
  • Hypocritical Humor

Humbug: If there's one thing I can't abide, it's a hypocrite.

  • Medium Blending: Starts out in live-action San Francisco.
  • Mel Blanc: One of the few theatrical feature length films he worked on. As already noted, he performs multiple characters in the film: Officer Shrift, several Lethargians, three royal palace guards, the Word Seller in the market at Dictionopolis, the Dodecahedron, the Demon of Insincerity, and the Overbearing Know-It-All.
  • Non-Standard Character Design: The Demons of Ignorance are drawn grotesquely and sketchy compared to the smooth and cartoony style of the cast.
  • Pain-Powered Leap: King Azaz is asking if there are any volunteers to help Milo on his quest, and at first no one comes forth. However, the Spelling Bee sneaks up and stings the Humbug in the butt, causing the Humbug to stand up suddenly and making everyone think he was volunteering. Later on, in Milo's car Humbug exhibits a delayed reaction and finally leaps up in the air with a scream (and apparently lands right back in the car).
  • Our Demons Are Different.
  • Villain Song: "Don't Say There's Nothing to Do in the Doldrums" performed by The Lethargians, a group of sinister lazy slimy creatures (voiced by Mel Blanc and Thurl Ravenscroft).
  • World-Healing Wave: Done by Rhyme and Reason after being set free.
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