Musings on The Phantom Tollbooth

Boredom Meets the Imaginative

I first picked up the Phantom Tollbooth when I was in fifth grade. To say that it made an impression on me is an understatement. I became captivated by these strange yet all-to-familiar characters, identified deeply with Milo, and found myself sucked into this enchanted land following our protagonist and his supporting cast on their gallant quest. I have since ready the book about four or five times since–the book seeming always to find me serrindipitously exactly when I need to re-read it. This last time, of course, was no exception. When I was perusing a book store I found a copy glaring at me, and my childhood instantly came rushing back in one timeless moment. It is a feeling of powerful emotion. A mixture of nostalgia, longing, and gratitude. And yet, simultaneously, the feeling equally eludes description. If you’re unfamiliar with the story by Norton Juster, and the scrawling enigmatic illustrations by Jules Feiffer that accompany the narrative, I will offer a quick summary by highlighting some of my favorite and most clever parts of the book. Thereupon, I shall share a few thoughts of mine on the magic that is the Phantom Tollbooth.


Juster is a master at igniting the imagination in the reader while seamlessly weaving play-on-words and double entendres in a jocular narrative in order to ease us into hard-hitting, profound, and challenging truths. Each chapter recounts a different character in a new place that Milo and his friends meet. By the end of each chapter, through absurdity and wit, a new life lesson is learned or insight gained. In the doldrums, for example, no one is aloud to think, and one must lazily float along throughout each day, perchance wasting their life away for no good reason at all (Remember, there can be no reason with the absence of Reason from the kingdom). In Dictionopolis, Milo encounters the use of synonyms in a superfluous way. “I never knew words could be so confusing,” Milo said to Tock as he bent down to scratch the dog’s ear. “Only when you use a lot to say a little,” answered Tock.” One thinks of Plato’s warnings against the sharp rhetoric of the Sophists, or the cunning silver tongue of modern politicians.

“Juster is a master at igniting the imagination in the reader while seamlessly weaving play-on-words and double entendres in a jocular narrative…”

At the royal banquet in Chapter 7, we see the importance of modesty and temperance, especially when it comes to eating too much. The more Milo and his friends ate, the hungrier they got. For when you are not eating you are slowly getting full! After the feast, all of them reason they probably should not have eaten so much. In Chapter 9, they meet Alec, a boy who grows from his feet downward towards the ground. The story, I believe, leaves a powerful truth that everyone’s perspective is different. How important is it to be able to see things from the other side? In Chapters 10 and 11, we see Milo being taught how important it is to appreciate your surroundings and nature, and also the wonderful and dynamic importance of sound, music, and color.

One of my favorite puns is when they get stuck on the island called “Conclusions.” You guessed it, the only way to get there is to jump. Unfortunately, for our heroes, it’s very easy to get there, but all the more difficult to get off. In this, we can see Juster teaching us the importance of reserving judgment until all the facts are in, being moderate in temperament, allowing for a diversity of opinions and perspectives, and to make conclusions confidently but cautiously. In fact, the best way to arrive at the island of Conclusions is to not jump, but rather to swim there through the “Sea of Knowledge.” The lesson is clear: hard work and careful examination through knowledge is the proper way to formulate a conclusion.

As the heroes near their destination, they approach the Foothills of Confusion, where dirty birds, who flew far away from their homeland called “context”, confuse Milo and his party with homophones and nonsense. The smooth talking elegant man, the Trivium, steals their time by making them work endless, dead-end, but facile, tasks. Juster here is warning us against being a “yes-man” and exhorting us to not get caught in the 9-5 rat race of life. Finally, after saving Rhyme and Reason, our heroes flee in haste in an attempt to return back to the kingdom. Nevertheless, they are chased by a cunning panoply of demons such as The Over-bearing Know it All, Gross Exaggeration and the Threadbare Excuse. Eventually, Milo, Tock, and the Humbug return Rhyme and Reason to the cities and the kingdom is reunited and restored once again. For himself, Milo returns back to his room via his phantom tollbooth with a renewed enthusiasm for life, an appreciation again for numbers and words, and a curiosity and lust for living that hitherto had laid dormant in his youth. All of this, and he realized that he had only been gone for one hour!

“His thoughts darted eagerly about as everything looked new–and worth trying. Well, I would like to make another trip,’ he said, jumping to his feet; ‘but I really don’t know when I’ll have the time. There’s just so much to do right here.”

Final Thoughts

At its heart, The Phantom Tollbooth is a clarion call to all generations to never lose the enchantment of the world; the magic of curiosity, and the illustrious wonder of exploration. Juster reminds us to say what you mean and mean what you say, and to be accountable for our actions whether good or bad. The narrative has all of the good of Carroll’s Alice in Wonderland, a mixing of Thoreau’s transcendentalism, coupled with a little bit of Platonic and Aristotelian foundation. While the book shall return to the shelf for now, it will call out again, at just the right time, when the reader needs to hear its message the most. As Milo concluded quite apropos, “Whenever you learn something new, the whole world becomes that much richer.” May we all strive to experience the richness of the world while we still can.

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