Topics for Discussion
1. Although Milo is the hero of the story, is he a remarkable character? How typical is he of boys and girls today?
2. The Mathemagician thinks that numbers are more important than words; King Azaz believes the opposite. Do you believe that one is more important than the other? Or do you agree with Rhyme and Reason that they are of equal importance?
3. The Humbug is a liar, a fraud, and, as the Spelling Bee says, "A very dislikable fellow." Why, at the end of the book, is he described as "lovable"? What has happened to change our opinion?
4. What does Milo learn from conducting Chroma's orchestra? How does he feel after the episode is over?
5. Milo's parents never appear in the story. Why do you suppose Juster left them out?
6. Among the demons that are described in the book are the Terrible Trivium, demon of petty tasks and worthless jobs; the demon of insincerity; the Gelatinous Giant; the Overbearing Know-it-All; and the Threadbare Excuse. What are some other demons that might be named for bad habits?
7. At the conclusion of Milo's journey into the lands beyond, why does the tollbooth disappear? Why does it not remain so he could reenter the Kingdom of Wisdom again and again?
8. How would you respond to the tollbooth appearing in your room? Knowing what you know about the Kingdom of Wisdom, would you want to go there? How do you think you would react differently than Milo to the situations he faced?