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The Phantom Tollbooth
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Discussion Questions: The Phantom Tollbooth by Norton Juster
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The Phantom Tollbooth is a children's adventure novel and modern fairy tale (or contemporary fantasy) published in 1961, written by Norton Juster and illustrated by Jules Feiffer. It tells the story of a bored young boy named Milo who unexpectedly receives a magic tollbooth one afternoon and, having nothing better to do, decides to drive through it in his toy car. The tollbooth transports him to a land called the Kingdom of Wisdom. There he acquires two faithful companions, has many adventures, and goes on a quest to rescue the princesses of the kingdom--Princess Rhyme and Princess Reason--from the castle of air. The text is full of puns, and many events, such as Milo's jump to the Island of Conclusions, exemplify literal meanings of English language idioms.
Why is Milo so bored before he goes to the Lands Beyond?
Why does the Humbug come along on Milo's journey?
Why does Milo fail at conducting Chroma's orchestra?
What lessons could the Soundkeeper learn from Dischord and Dynne?
Why does Faintly Macabre remain in prison, despite knowing how to escape?
Who might the anonymous sender of the tollbooth be?
What reasons would he or she have to send it to Milo?
What would the King of Wisdom—Azaz and the Mathemagician's father—think of the state of things in the Lands Beyond? Would he be pleased with the way his sons have been looking after the kindgom?
What would have happened to Milo if Tock had not shown up in the Doldrums? Would he have stayed there forever?