History Literature / ThePhantomTollbooth

* AffablyEvil: 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 eight hundred or so years, right?

* 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.]] By making him laugh, the Senses Taker is rendered helpless.]]

* StealthPun: 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."

** There was also the long-nosed, green-eyed, curly-haired, wide-mouthed, thick-necked, broad-shouldered, round-bodied, short-armed, bowlegged, big-footed monster, who was actually the Demon of Insincerity and none of these things. (Although he is drawn as having relatively large feet for his size, resembling something like a hare.)

** There was also the long-nosed, green-eyed, curly-haired, wide-mouthed, thick-necked, broad-shouldered, round-bodied, short-armed, bowlegged, big-footed monster, who was actually the Demon of Insincerity and none of these things.

* AbsurdlyLongStairway: Digitopolis's staircase to Infinity. Doesn't matter how far you go up, you'll never reach the top. Because it's infinity.

** There was also the long-nosed, green-eyed, curly-haired, wide-mouthed, thick-necked, broad-shouldered, round-bodied, short-armed, bowlegged, big-footed monster, who was none of these things.

* OxymoronicBeing: A few, most obviously Canby -- he physically transforms to represent whichever trait he's currently representing. For example, when he's "as tall as can be," he shoots up to a prodigious height; he then shows he's "as short as can be" and immediately shrinks down to nearly nothing.

* AnAesop: Roughly, "the world and learning 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 on Earth]].

* AnthropomorphicPersonification: Many of the kingdom's characters, notably including the Princesses of Rhyme and Reason, the Awful Dynne, and several of the Demons of Ignorance.

* DepartmentOfRedundancyDepartment: King Azaz's cabinet ministers are a literal example: a department of Dictionopolis's government whose collective job includes knowing, and ''using'' at length, all kinds of synonyms for the same thing.

-->"I didn't mean to hurt your feelings," Milo said, not meaning to hurt his feelings.

** And the origin of the book was that Juster had gotten a grant from the Ford Foundation 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 tried to pay back the grant several times, but could never find anyone who would officially acknowledge it. (Though there are also reports that the Ford people were actually aware of and quite happy with what Juster produced with their money.)