1. Many reviewers have compared The Phantom Tollbooth to fantasy novels such as The Wizard of Oz and Alice's Adventure in Wonderland. Compare the book to one or both of these classic fantasy tales. How are they similar? Different? Which did you like the most?
2. Juster has played on words and made puns throughout the book (take, for example, the Wicked Which and the awful DYNNE). Pick several words or names from The Phantom Tollbooth and explain what Juster has done to make a joke.
3. The Wicked Which and the Soundkeeper are both women who once occupied positions of responsibility and abused their power. How are they similar? Is one more sympathetic than the other?
4. How does Milo succeed in a quest that the two kings believe to be impossible? Describe his character, the help he receives from Tock and the Humbug, and how the gifts he receives along the way lead to his success.
5. Although some of the demons are frightening, others appear, at least at first, to be likeable, or at worst, worthy of sympathy. They represent faults that all of us have to some degree. Pick several of the demons and describe how they have influenced someone you know, possibly even yourself. What, for example, are some things that you have done to waste time under the influence of the Terrible Trivium?
6. The Phantom Tollbooth was made into an animated film in 1970. Compare the book and the film. Do the songs in the film add to your enjoyment? Is the experience of imagining what happens in the book better than seeing it depicted in a cartoon? Which do you like better?
7. Some people have said that the book is too complicated for young readers, that it contains jokes and wordplay that will go over their heads. Do you agree or disagree? Explain your answer. You may also want to let friends read the book and compare experiences with them.
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