History Literature / ThePhantomTollbooth

* AbsurdlyLongStairway: Digitopolis's staircase to Infinity.

* AnAesop: Roughtly, "the world and education are so interesting!" At the end, [[spoiler: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]].

* AgreeToDisagree: How Milo gets the Mathemagician's permission to rescue the princesses of Rhyme and Reason. Milo makes the Mathemagician realize that by preemptively never agreeing with King Azaz, [[LogicBomb they're actually still in agreement, because they agree that they will never agree]].
* AlphabetArchitecture: The buildings of Dictionopolis, where words rule everything.
* AnthropomorphicPersonification: Many of the kingdom's characters, notably including Rhyme and Reason, the Awful Dynne, and several of the Demons of Ignorance.

* CardboardPrison: The prison of Dictionopolis, which has a switch that opens up an entire wall to allow people to freely walk out. {{Lampshaded}} by Faintly Macabre, who notes that Shrift is all about throwing people into jail, not keeping them locked up.
* TheCavalry: [[spoiler: The great massed armies of Wisdom, led by Azaz and the Mathemagician, and including nearly every key personage of the two kingdoms, arrive just in time to save the day when the demons of Ignorance are about to overwhelm Milo, Tock, and the Humbug.]]

* ExplainExplainOhCrap: This is basically the Mathemagician's reaction to Milo pointing out that he has [[AgreeToDisagree technically been agreeing]] with his brother King Azaz for over 20 years.

* FakeTown: The aptly-named Illusions appears to be a fancy city but isn't a real city. Despite this, a few people who live in the neighbouring city have mistaken it for a real city and moved in.

* TheGuardsMustBeCrazy: Officer Short Shrift is known for handing down {{Longer Than Life Sentence}}s, but can't be bothered to enforce them. All he does is take people to jail and lock them in through the entry point. They only stay until they figure out [[CardboardPrison they can just walk out through a door at the bottom]].

** 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.

* LiteralMetaphor: ''Lots'', mainly in Digitopolis. Tock is a watchdog, a dog who's also a watch. The Spelling Bee is a large bee that likes to spell. Half-baked ideas are cakes with debunked proverbs on the frosting. The Senses Taker is a demon who actually takes senses. And many, many more.
* LogicBomb: King Azaz and the Mathemagician automatically disagree with each other on everything, and as a result, Dictionopolis and Digitopolis can't cooperate or even make amends with each other. Milo neatly sidesteps this by explaining to the Mathemagician that this means that the two of them are actually in complete agreement at all times--since they've agreed to disagree!
* LongerThanLifeSentence: [[HangingJudge Officer Shrift]] regularly sentences offenders to prison terms of millions of years, merely because he can. Subverted in that he's not good at keeping track of time and thus assumes that anyone who escapes his city's CardboardPrison has already served out his or her sentence. (That, and it's a CardboardPrison that can be exited just by walking out one door.)

* NonActionGuy: The Humbug, occasionally bordering on TheLoad.

* NonIndicativeName: Thanks to parents who got a bit over-eager and named them before they were first wound up, we have Tock, whose watch actually makes a ticking sound, and his brother Tick, whose watch makes a tocking sound. It's a sensitive subject in their family.

** Milo meets "the tallest short man in the world," a fellow who turns out to be perfectly average in height. He also meets the shortest tall man in the world, the fattest thin man in the world, and the thinnest fat man in the world. Spoilers: they're all the same guy.

* AnAesop: Roughtly, "the world and education is so interesting!" At the end, [[spoiler: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]].

A movie adaptation, an animated feature with a live-action framing device, was released in 1970, produced and co-directed by the legendary Creator/ChuckJones, making him one of only two ''WesternAnimation/LooneyTunes'' directors to direct a feature that wasn't a compilation of old cartoons (the other being Frank Tashlin). Juster is on record as disliking the film intensely, possibly because a lot of his incidental wordplay and allusion is streamlined out in favor of some catchy but extremely [[TheSeventies Seventies]] songs about finding your dreams by following your heart. Nevertheless, there's a lot to be said for Jones' typically cute and energetic character designs, especially the ones that have Mel Blanc's voices.

* EverythingsBetterWithPrincesses: Quite literal with the Princesses of Sweet Rhyme and Pure Reason, of the Kingdom of Wisdom. 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 TheQuest that the Kingdom becomes sane again... everything ''is'', in fact, better with them in charge.

* NonNaturalNumberGag: Milo learns of a [[LiteralMetaphore perfectly average family]] with exactly 2.58 children, among other similar quirks. The 0.58 child doesn't seem to be any worse for the wear, and is the only one who can drive their fractional car.

* TheMagicGoesAway: [[spoiler:The Phantom Tollbooth disappears the following day]]...but it's okay, since Milo has learned to appreciate the magic of the Real World in which he lives.

* NeverTellMeTheOdds: The quest was ''literally impossible''--[[AchievementsInIgnorance but since nobody told Milo, it became possible]].

* NonIndicativeName: Thanks to parents who got a bit over-eager and named them before they were first wound up, we have Tock, whose watch actually makes a ticking sound, and his brother Tick, whose watch makes (...wait for it...) a tocking sound. It's a sensitive subject in their family.

* WorldOfSymbolism: With the tollbooth itself guarding the entrance.

* LongerThanLifeSentence: [[HangingJudge Officer Shrift]] regularly sentences offenders to prison terms of millions of years, merely because he can. Subverted in that he's not good at keeping track of time and thus assumes that anyone who escapes his city's CardboardPrison has already served out his or her sentence.

* LovableCoward: The Humbug.

* NonHumanSidekick: Tock and the Humbug.

* ObstructiveBureaucrat: The Senses Taker, who asks incredibly obscure questions, and wants the answers accurately recorded in ink and in triplicate.

* ParentalBonus:
** If you're under the age of 12, it's a given that you're not getting about a fifth of the jokes.

* DividedWeFall: The kingdom is literally falling apart ever since the powers of Dictionopolis and Digitopolis each tried to claim superiority. Because almost ''everything'' in the kingdom is absolutely literal or an AnthropomorphicPersonificantion, the feud is causing a breakdown of the kingdom.

* [[JudgeJuryAndExecutioner Judge, Jury and Jailer]]: Officer Shrift, who merely changes costumes in response to Milo's protests first that 'only a judge can sentence you' and then that 'only a jailer can put you in prison'. Fortunately for Milo, he only really cares about throwing people in prison, and not in the slightest about keeping them there.

* YearInsideHourOutside: Despite the grandiose nature of Milo's adventure, he's only gone in the real world for five minutes in the movie. In the book, he's gone for an hour.

* AnAesop: Roughtly, "the world and education is so interesting!" The page quote opens the book. At the end, [[spoiler: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]].

* AgreeToDisagree: How Milo gets the Mathemagician's permission to rescue the princesses--by making him realise that by preemptively never agreeing with Azaz, [[LogicBomb they're actually still in agreement]].
* AlphabetArchitecture: The buildings of Dictionopolis.

* TheAtoner: King Azaz sends Milo and company off on their quest to rescue the princesses very much out of contrition for banning them in the first place (and/or watching his realm go steadily downhill as a result). The Mathemagician eventually comes around for this reason as well, but he's rather stubborn at first due to the fact that Azaz is on board with the idea.

* ABoyAndHisX: A boy and his '''watch'''dog.

* TheCavalry: [[spoiler: The great massed armies of Wisdom, led by Azaz and the Mathemagician, and including nearly every key personage of the two kingdoms]] arrive just in time to save the day.

* [[DamselInDistress Damsels in Distress]]: Princesses Rhyme and Reason, although they certainly don't seem to be in much distress when Milo finally gets to them. They are however very glad to be set free.
* DarkestHour: Yes, Milo and his friends have finally found the princesses of Sweet Rhyme and Pure Reason. However, all of the demons that they've bested to get there have called their friends in revenge, and as our heroes race frantically for safety in Wisdom, the demons launch an all-out assault, intent on destroying Rhyme and Reason once and for all. [[spoiler: They're saved by King Azaz and the Mathemagician leading TheCavalry.]]

* DividedWeFall: The kingdom is literally[[note]]almost ''everything'' in the kingdom is absolutely literal[[/note]] falling apart ever since the powers of Dictionopolis and Digitopolis each tried to claim superiority.

-->"No noise is good noise," exclaimed the Humbug happily, trying to catch the spirit of things\\

** 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.

* ExplainExplainOhCrap: This is basically the Mathemagician's reaction to Milo pointing out that he has [[{{AgreeToDisagree}} technically been agreeing]] with his brother King Azaz for over 20 years.

* FauxAffablyEvil: The Terrible Trivium.
* ForbiddenZone: The Mountains of Ignorance.

%% * TheGoodKingdom: Initially a single Kingdom of Wisdom, now ruled by Princesses Rhyme and Reason. Later joined by Dictionopolis, Digitopolis and unnamed others that presumably represent other fundamental learning concepts.
* GotVolunteered: While King Azaz ponders launching a quest to rescue Rhyme and Reason, the Humbug--ever the sycophant--is hyper-enthusiastic about the idea, describing the many and complicated hazards of same in great detail and suggesting Milo and Tock are the perfect choices to complete it. This backfires spectacularly on the bug when Azaz not only decides to sponsor the quest based on the bug's description, but 'volunteers' him to go along, given his obviously complete understanding of the problems involved.

* TheGuardsMustBeCrazy: Officer Short Shrift is known for handing down {{Longer Than Life Sentence}}s but can't be bothered to enforce them. All he does is take them to the jail and lock them in through the entry point, and they generally only stay until they figure out [[CardboardPrison they can just walk out through a single door at the bottom]].

* IntangibleTheft: The Senses Taker is an ObstructiveBureaucrat who takes away the main character's senses. [[spoiler:The one sense he can't take away, however, is their [[JustForPun sense of humor.]]]]
* InTheDoldrums: Trope Namer (kind of) and possibly the TropeCodifier. It's home to the [[AnthropomorphicPersonification anthropomorphic personifications]] of boredom, and you get there by not thinking.

* ExactWords: 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.

* DerangedAnimation: The Demons of Ignorance truly look insane and sketchy compared to Creator/ChuckJones's usually smooth works.

** AnimatedAdaptation: Once Milo leaves his home to the kingdom.

* DividedWeFall

** 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.

* FreudianTrio: Milo is the Ego: a determined AudienceSurrogate who serves as the heart of the team. Tock is the Superego: the careful "voice of reason" who provides several of the book's lessons about the importance of thinking. The Humbug is the Id: a more silly, self-centered character who is not too intellectual and provides comic relief.

* FreudianTrio: Milo is the Ego: a determined AudienceSurrogate who balances the team. Tock is the Superego: he can seem gruff, but is often the "voice of reason" and is used to express many of the book's pro-education messages. The Humbug is the Id: a bit more impulsive and self-centered, and his main goal usually seems to be his own comfort and safety.

* FreudianTrio: Milo is the ego: a determined AudienceSurrogate who balances the team. Tock is the superego: he can seem gruff, but is often the "voice of reason" and is used to express many of the book's pro-education messages. The Humbug is the id: a bit more impulsive and self-centered, and his main goal usually seems to be his own comfort and safety.

* NonIndicativeName: Thanks to parents who got a bit over-eager and named them before they were first wound up, we have Tock, whose watch actually makes a ticking sound, and his brother Tick, whose watch makes (...wait for it...) a tocking sound.