Study Guide

The Phantom Tollbooth Themes

  • Language and Communication

    In The Phantom Tollbooth, words are very important. In fact, for the folks who live in the Lands Beyond, words are pretty much the most important things in the world. Language is everything to the people of Dictionopolis. It's their bread and butter. Literally! Linguistic tricks, puns, and plays on words can help people to travel [like the car that "goes without saying" (6.56)] or cause them injury [like "falling off a log" (3.86)]. Knowing what to say and when to say it can save your life – or at least, save you from boredom. But in Digitopolis, it's numbers (which you might think of as another type of language) that run the show. And it's the conflict between words and numbers that has created the bitter fight between these two cities. Will they kiss and make up? We sure hope so.

    Questions About Language and Communication

    1. If you had to "eat your words," what would you say and why?
    2. Think of all the different, idiomatic sayings people use (for a start, check out this list). If you said any of them in Dictionopolis, they would come true. Which would you most like to see in action?
    3. The word that Milo steals from the Soundkeeper's fortress is "but." How can such a little word have so much power?
    4. Can you name two examples of language loopholes that allow characters to get out of dodgy or dangerous situations in The Phantom Tollbooth?

    Chew on This

    The lessons Milo learns from King Azaz in the kingdom of Dictionopolis show that words will always be more important than numbers.

    The lessons Milo learns from the Mathemagician in the kingdom of Digitopolis show that you don't need to rely on words to communicate.

  • Time

    When <em>The Phantom Tollbooth</em> begins, Milo takes a lot of things for granted, particularly time. He doesn't see the importance of time and is always either wasting it or rushing through it. He's so bored, he can't seem to make the most of his moments. But during his journey through the Lands Beyond, he meets people who have <em>very</em> different attitudes toward time. Some of them waste it, some of them take advantage of it, and watching them do these things helps Milo realize he really should value his time. With the help of Tock, Milo learns that instead of whiling away the hours complaining of boredom, he can live life to the fullest by going on adventures of the mind.

    Questions About Time

    1. What do you think time means in <em>The Phantom Tollbooth</em>? That's a big question, so tackle this one first: is time important to these characters? Who values time? Who wastes it?
    2. According to the book, why is it important not to waste time? 
    3. What would happen if time really could fly? Wow, what a question.      
    4. Can you name at least one instance when time seems to pass differently for one character than for the others? What is interesting about this moment in the book?
    5. How long does it take for the events in <em>The Phantom Tollbooth</em> to actually take place? Why does more time pass in the Lands Beyond than it does in the real world?

    Chew on This

    Despite the fact that being a watchdog is his life's work, Tock is not actually that great at keeping track of time.

    The selection of a watchdog as Milo's first and most loyal companion on his quest emphasizes the importance of time as a concept in <em>The Phantom Tollbooth</em>.

  • Philosophical Viewpoints

    In <em>The Phantom Tollbooth</em>, everyone in the Lands Beyond suffers from the loss of Rhyme and Reason. These two princesses, while real characters, could also be seen as symbols of what their names represent. Everyone in the Lands Beyond maintains his own unique philosophical viewpoint, and it seems like the more these folks stubbornly stick to their guns, the less wise they become. Their views of the world suffer without the balance of Rhyme and Reason to make them think practically about the way they live their lives. Nevertheless, as Milo travels through these troubled lands, and encounters all these different philosophies, his mind expands with the addition of these new perspectives. Now the trick is to take all this new knowledge and apply it to his own life.

    Questions About Philosophical Viewpoints

    1. Which character's philosophy do you find the most appealing? Which is the least appealing?
    2. Do you see any similarities between real-word philosophies you may have learned about and the philosophies mentioned in <em>The Phantom Tollbooth</em>?
    3. If you could be a member of Alec Bing's family and therefore get a special "point of view," which manner of seeing the world would you want to have and why?
    4. What do you think will be Milo's philosophical viewpoint as he moves forward in his life? What has he learned from his time in the Lands Beyond?

    Chew on This

    The character with the most well-rounded point of view in <em>The Phantom Tollbooth</em> is Milo, because he is sympathetic to all the other characters' points of view and even temporarily adopts some of them.

    When King Azaz and the Mathemagician cast out Rhyme and Reason, they revealed themselves to be as foolish as the demons that populate the land of Ignorance.

  • Freedom and Confinement

    <em>The Phantom Tollbooth</em> is all about freedom. Milo is free to travel and have imaginative adventures, so long as he has the tollbooth to take him there. So it's strange, then, that he keeps getting himself trapped in sticky situations. In fact, Milo has to rescue himself and many other characters and things along the way, including the sounds imprisoned in the Soundkeeper's fortress, and Rhyme and Reason, who are trapped in the Castle in the Air. Plus, we can't forget the harrowing adventure that ensues when his entire posse gets trapped in the Island of Conclusions. You'll notice that whenever these people or things get trapped, the key to escape seems to be tucked away in their own minds somewhere. All you need to do is keep that mind open, and see where your wits lead.

    Questions About Freedom and Confinement

    1. Why are Milo and Tock able to leave the jail? Why isn't Faintly Macabre able to leave the jail?
    2. What could have stopped Milo from passing through the tollbooth in the first place?
    3. If Rhyme and Reason are so brilliant and smart, why can't they rescue themselves from the Castle in the Air?
    4. Which escape in The Phantom Tollbooth did you find the most believable? Which was the one for which you had the hardest time suspending your disbelief?

    Chew on This

    When King Azaz and the Mathemagician banished Rhyme and Reason from the Kingdom of Wisdom, they really confined themselves and their people to a world <em>without</em> wisdom.

    Perhaps Rhyme and Reason had the power to return to Wisdom at any time, but didn't want to do so until the people they had left behind showed their true appreciation for what had been lost.

  • Cunning and Cleverness

    Sometimes it might seem as though every single one of the characters in <em>The Phantom Tollbooth</em> is smart. They're able to approach the world in different ways than we do, and they can manipulate language and ideas to get out of dicey situations, or come up with delicious desserts (you know, whatever's required). The longer Milo stays in the Lands Beyond, the more cleverness he picks up, and by the time he visits the Mathemagician, he's ready to deploy a logic bomb he's spent chapter after chapter secretly getting ready. It seems that traveling to the Lands Beyond has unlocked Milo's smartness chip, and he gets to show us all just what he's learned.

    Questions About Cunning and Cleverness

    1. What is the one thing that neither King Azaz nor the Mathemagician can tell Milo, and why is it so significant?
    2. How does Milo get the Mathemagician and King Azaz to agree to his plan?
    3. What is the smartest action taken in the book? Who takes it?
    4. Which character receives the greatest punishment for his/her cleverness? Which receives the greatest reward?

    Chew on This

    Milo proves his worthiness as a candidate to rescue Rhyme and Reason when he convinces King Azaz and the Mathemagician to agree.

    Milo is a great example of a hero because he tries things out. He's smart, but he's not afraid to admit when he doesn't know the answer to something.

  • Education

    This book is all about learning, but sneakily so. On the surface, The Phantom Tollbooth seems like an exciting quest fantasy, with bad guys, sidekicks, and beautiful princesses. But, as Adam Gopnik says, The Phantom Tollbooth's "real subject is education" (source). All the elements of the quest really show off the importance of learning different subjects, and despite what King Azaz and the Mathemagician say, proving that both words and numbers are super-important parts of Wisdom. After each episode in his quest, Milo has discovered another important thing about education. He's learning as he goes along, and by the time he gets home, he's figured out that he can create his own magical quest anytime he wants.

    Questions About Education

    1. Did this book make you more excited to learn about words or numbers? If so, how?
    2. Which of Milo's education-related gifts would you like to receive yourself?
    3. What is the most important lesson any character learns in <em>The Phantom Tollbooth</em>? Why?
    4. Who is the book's most inspiring teacher? What makes him or her inspiring?

    Chew on This

    Ultimately, all Milo's experiences in the Lands Beyond show him what his own school couldn't: learning is important and can help him get through whatever obstacles life throws his way.

    The fact that words and numbers are so deeply separated in the Lands Beyond raises serious doubts about how Rhyme and Reason will be able to unite them after returning.

  • Versions of Reality

    In <em>The Phantom Tollbooth</em>, the different zones of the Lands Beyond may seem really out there at first. It's true that both the Lands and their people can stretch the laws of physics, mathematics, and language in ways we may never have thought possible. Part of the Lands' magic, though, is that all of their characteristics are connected to the ordinary habits and characteristics of our own world. Traveling to the Lands Beyond is a bit like looking into a funhouse mirror, as the expressions and ideas we may rely on or take for granted are blown wide open and pushed to their limits. But that doesn't make that warped image we see in the mirror any less real.

    Questions About Versions of Reality

    1. What seems more real to you: Milo's apartment in the city, or the places he encounters in the Lands Beyond?
    2. Which is your favorite place in the Lands Beyond? Your least favorite?     
    3. Is all this happening in Milo's head? If it is, does that make it any less real?
    4. Do you think the future imaginative adventures that Milo will have will see just as real as the one in the novel?

    Chew on This

    Even though they're imaginary, the different places in the Lands Beyond are described so vividly that they seem just as real as actual landscapes.

    The different facts Milo learns in the Lands Beyond aren't that different from the facts he might learn in school. It's <em>how</em> he learns them that make that realm so much more appealing than his own.

  • Exploration

    In <em>The Phantom Tollbooth</em>, it takes a ton of courage for Milo to get in his little car and pass through the Phantom Tollbooth. He knows he's going someplace he's never been to or even heard of before, but this doesn't faze him at all. And once he gets into the Lands Beyond, he faces each new part of it with a pure heart and a clear interest. Our guy is the ultimate explorer. He wants to know more about these unrealistic places, no matter what dangers he might face. He's more interested in each of them than he ever was in the geography or history of "real" places he learned about in school, which begs the question: what is it about the Lands Beyond that has normally-bored Milo itching to see more?

    Questions About Exploration

    1. Why is Knowledge represented as a Sea in the Lands Beyond? What do you think it would be like to sail on it or swim in it?
    2. If you were going to add your own land to the Lands Beyond, what would it be? What adventures would Milo have there? What lessons would he learn?         
    3. Is map-reading a valued skill in <em>The Phantom Tollbooth</em>? Or is it better to wander aimlessly and just go with the flow?           
    4. Which of the book's characters would you choose as your sidekick if you were departing on a quest of your own?
    5. Do you think Milo is brave or foolhardy? Would you have gone so willingly on this adventure in the Lands Beyond? Or would you rather have stayed in the safety of your room?

    Chew on This

    While the kingdoms of Dictionopolis and Digitopolis are interesting and entertaining, the majority of <em>The Phantom Tollbooth's</em> action takes place not in the Kingdom of Wisdom but in the Mountains of Ignorance, because that's where the characters need to do the most exploring (and learning).

    If Milo had examined the map that arrived with the tollbooth more carefully, he might not have gone on his journey in the first place.