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 is in the early stages of pre-production, with an intended 2013 release.
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?
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.
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.
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.
He also starts a long windy speech, when asked to by a waiter, then finds he has to "eat his words", as a pile of his own (no doubt rather dry) words are placed before him.
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.
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.
Judge, Jury and Jailer: Officer Shrift. Fortunately for Milo, he only cares about throwing people in prison, not about keeping them there.
Non-Indicative Name: Tock - his watch makes a ticking sound. It's a sensitive subject for him, and apparently his whole family (he has a brother with the flipped problem - said brother is a watchdog named Tick who makes a tocking sound).
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).
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."
World Of Pun: There's a "watchdog" called Tock who is a dog with a clock in his abdomen. In the city of Dictionopolis people literally "eat their words" off plates. People literally jump to an island called Conclusions. It goes on and on like this.
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.
Year Inside, Hour Outside: Despite the grandiose nature of Milo's adventure, he's only gone in the real world for five minutes.
The movie provides examples of:
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.
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.