The Books That Made Us: The Phantom Tollbooth

The Phantom Tollbooth's 1961 cover image by Jules Feiffer.

Whenever I am in the company of any person on the planet, and I mention that I mostly write for young people, that person without fail will offer up, unsolicited, their favorite book from childhood. Usually their face will light up. They can remember details. They say things that make me think that, somehow, that book helped form them, either by boosting their thoughts, or mirroring exactly some truth about them at the time. Maybe it expanded their world view. They talk about “that book” as if it were a friend.

Continuing with our series on the books that made us, we pay tribute to The Phantom Tollbooth on the occasion of its 50th anniversary. To accompany Chelsey Philpot's essay, "Puns, Games, and Mathemagic," we asked a few writers to tell us about their first experiences with the Norton Juster classic. — Cecil Castellucci, Section Editor, Young Adult Fiction

Aimee Bender

The Phantom Tollbooth made jokes I could understand and thought were really funny. The world’s longest number? Was a certain length. A man could actually jump to conclusions! A square meal was made of squares. Words, words, words: this writer knew about words and idioms and both loved them and felt their limitations and celebrated all of it.

Norton Juster’s book, with the lightest of touches, is filled with concepts, with the act of making literal what we say and mean. It was the first book I’d ever read like this, riddled with funny abstractions made into affecting characters and stories — princesses named Rhyme and Reason, a place called The Doldrums that made everything slow down to a terrible pace, a musician who could paint the sky with colors. I keep meaning to go to the other room to consult the book to verify these scenes but they are all so clear and sharp in my memory — I read this book over and over as a kid, relishing its humor and freshness every time, and it introduced me to a new way of writing.

Without ever stepping out of the quest, or losing sight of Milo, or Tock, or the human yearning behind all the adventures, Juster was saying something to us about language and meaning. He’s an architect — there is something structural and tangible about his manner of storytelling — but the fact that The Phantom Tollbooth has depth and isn’t just fun wordplay is nothing short of amazing. There’s really no other children’s book quite like this.

When, in college, I found The Dot and the Line, a conceptual love story also by the same author with a similar playfulness and heart and joyous exploration of abstraction, I was outrageously charmed all over again.

Jenny Hendrix

It was in second grade that I decided to be a writer, which also happened to be the year my teacher read The Phantom Tollbooth in class. I can’t help but believe that these are connected, that the emergent symptoms of what would become my chronic infatuation with language were somehow picked up during this sojourn in Norton Juster’s joyously allegorical world.

It would in any case be safe to say that it was Juster (or perhaps Milo, his rather torpid hero) who diagnosed me. His words — enlivened, electrified, transmogrified into pun — made obvious and specific what I’d only guessed about language in general. Names alone were enough to send the imagination reeling: the Whether Man, Officer Short Shrift, Dr. Kakofonous A. Dischord, the Terrible Trivium, Faintly Macabre, the Dyne, the Dodecahedron. The Tollbooth proved that words could have the qualities of characters; that they could be real places I could go, enter into and explore; that metaphors could be tangible; that objects had synesthetic qualities as true as those I could see. Words — like the absurdly literal “square meals” served by Digitopolis’s King Azaz — were themselves accessible to taste, touch and smell.

At the end of the year, my teacher gave me her copy of the book. She had marked a passage for me at the end:

Outside the window, there was so much to see, and hear, and touch — walks to take, hills to climb, caterpillars to watch as they strolled through the garden. There were voices to hear and conversations to listen to in wonder, and the special smell of each day. And, in the very room in which he sat, there were books that could take you anywhere, and things to invent, and make, and build, and break, and all the puzzle and excitement of everything he didn’t know — music to play, songs to sing, and worlds to imagine and then someday make real.

I still treasure this as, among other things, an artifact of what the world promised to an eight-year-old at the start of a love affair with the written word: it was a place that I recognized, but at the same time one somehow strange and mysterious and new. The Tollbooth’s world was the writer’s world, the world as it might be, but never quite is. Which is why, I imagine, we keep trying get there.

Jonathan Auxier

Norton Juster knows what all the best teachers know: children rise or sink with the expectations placed upon them. When I read Tollbooth for the first time, I was overwhelmed by all the wordplay and punning, but I was also enthralled by the fact that this author expected me to keep up. There is no higher respect that a children's writer can pay his young readers. Needless to say, I rose to his challenge; The Phantom Tollbooth was the first book that forced me to keep a dictionary at my side (a reading habit that continues to this day).

Critics have made much over the similarities between Tollbooth and Alice in Wonderland, but for me, Juster’s virtuoso wit hearkens to an earlier era. Reading Tollbooth, I see shades of Jonathan Swift and Samuel Johnson. Unlike those 18th century showoffs, however, Juster never lets his own ego overrun the story. He cedes the spotlight to Milo, which gives his book an immersive quality that his predecessors never attained.

At its core, Tollbooth is a lesson on making light play of heavy work. It urges readers to spot cracks in the façade of serious things like language and numbers. (Consider how Juster builds his fantastical characters and places on the foundation of schoolhouse vocabulary: the Spelling Bee, Dictionopolis, etc.) This is more than simple mockery: it is a master class in enchanted thinking.

I can still remember the feeling I had when I finished reading Tollbooth for the first time. The book ignited a sense of wonder at the world of learning that I had previously thought dull. Just like Milo, I suddenly understood that the only difference between boredom and adventure is a want of imagination. What greater lesson could there be?

Sally Nemeth

In 1968, I’m sure there were things I wanted desperately for Christmas, but I don’t remember what they were or if I received them. What I did get was a copy of The Phantom Tollbooth, a copy I still treasure.

Milo’s journey, with the faithful watchdog Tock and the grumbling Humbug, was irresistible to me, if inconceivable. I was, if anything, an over-scheduled child. The thought that any kid was so bored he didn’t know what to do with himself was new to me. That this same child had this great adventure dumped in his lap made me jealous. But Norton Juster swept me up and took me along on Milo’s ride, aided and abetted by the genius of Jules Feiffer.

I felt grateful to be a part of Milo’s quest, clever for sussing out double meanings, and colossally let down when the rescue of Rhyme and Reason made no difference in the Kingdom of Wisdom. But of course the rescue was never the point. As Milo and I realized in the end, his was a journey of self-discovery where real adventure lay right outside the front door.

As I grew up I revisited the book, and each time found in it different things that spoke to me. I gave it to friends on milestone birthdays and lent it to new boyfriends as sort of an acid test. If a guy loved the book as much as I did, we were simpatico.

A couple years after the great love of my early twenties and I had broken up, I opened my copy of The Phantom Tollbooth to find his bookmark: a retired catalogue card from our college library. On it, he’d written this quote from the Mathemagician: “You’ll find that the only thing you can do easily is be wrong, and that’s hardly worth the effort.”

To this day, it’s the best apology I’ve ever received, and it remains between the pages of my beloved, tattered copy.