Books That Made Us: The Phantom Tollbooth

By Chelsey PhilpotNovember 17, 2011

Books That Made Us: The Phantom Tollbooth
Puns, Games, and Mathemagic

IN AN AUGUST 2004 ARTICLE for the New York Times entitled "Why Teachers Love Depressing Books," writer and critic Laura Miller wrote, "I decided that there were two types of children's books: call it Little Women versus Phantom Tollbooth. The first type was usually foisted on you by nostalgic grown-ups. These were books populated by snivelers and goody-two-shoes ... The people in the other kind of book, however, were entirely different. They had adventures." 

This October marked the 50th anniversary of Norton Juster's story about a little boy named Milo, who is rescued from disenchantment by a magic tollbooth that transports him in his little car to the kingdom of Wisdom. There he meets Azaz the Unabridged, king of Dictionopolis, and the Mathemagician, ruler of Digitopolis, who charge him with the daunting task of rescuing the exiled Princesses Rhyme and Reason. Milo, a child who "didn't know what to do with himself — not just sometimes, but always," rises to the challenge, aided by his friends, the Watchdog Tock (who literally has a clock in his side) and the foolish, beetle-like Humbug. With buoyant, humorous drawings from artist Jules Feiffer, The Phantom Tollbooth is the kind of book you want to start over as soon as you finish.

Tollbooth  didn't win the big one (the John Newbery Medal), but it is a "classic" nonetheless. Critics have compared it to works as varied as John Bunyan's Pilgrim's Progress, Jonathan Swift'sGulliver's Travels, Kenneth Grahame's Wind in the Willows, and Lewis Carroll's Alice stories. In November 1962, the Times Literary Supplement said: "The Phantom Tollbooth is something every adult seems sure will turn into a modern Alice." 

As a child, I dutifully read Louisa May Alcott's Little Women, Johanna Spyri's Heidi, and other books in the "snivelers and goody-two-shoes" tradition. But Tollbooth, I raced through. Reading it as an adult is both the same and different; a contradiction Canby, a character who is both graceful and clumsy as can be, would likely appreciate. I still laugh at all the same parts, like when the Whether Man says, "If you happen to find my way, please return it." I still wish I had a dog like Tock the Watchdog, and I completely relate to Milo's initial malaise. When we are young we hate seemingly meaningless rituals (dentist appointments, standardized tests), and only because we are forced to do accept the banality and boredom of routines, commutes, and filling out tax forms as adults.

The first time I read The Phantom Tollbooth I wanted to be friends with Milo so he would give me a ride in his electric automobile, but if I were to meet him today, I would pat him on the back and say, "Kid, I'd tell you the ennui disappears, but that would be a lie." Adults not only take short trips to the "Doldrums," they make entire vacations out of existential despair. The adventure in Tollbooth doesn't change; it's the meaning we find in it that evolves.

Some critics wondered if this quirky tome was best suited to gifted children or adults. Library Journal was one of those hesitant publications, writing in January 1962: "The ironies, the subtle play on words will be completely lost on all but the most precocious children. Definitely for the sophisticated, special reader. Only the large libraries can afford to experiment with it." Feiffer, naturally, disagreed, saying in an interview in the October 2011 School Library Journal that "the most important responses I got were from kids who had some learning disability that they had to get past, and they did perfectly well with the story." 

Regardless of whether the reader is a wunderkind or a reluctant student, the book lingers long after turning the final page. As novelist Michael Chabon wrote in an April 2011 blog post for the New York Review of Books about traveling with Milo as a young reader: "While you were there, everything seemed fraught and new and notable and when you returned, even if you didn't suffer from Milovian ennui, the 'real world' seemed deeper, richer, at once explained and, paradoxically, more mysterious than ever." A classic indeed.

How Tollbooth came into existence is as legendary as the Princesses Rhyme and Reason's expulsion from Wisdom. The tale starts when Juster, a young architect, won a fellowship to pen a book for children about urban planning, and subsequently became more interested in a very different kind of narrative. He paced the floors of his Brooklyn apartment, pounding out his ideas, while his neighbor below, Feiffer, a cartoonist for the Village Voice, drew. How they met, perhaps while Juster was taking out the trash, or Feiffer was looking for a free meal, is not important. What matters is that they met and became fast friends, bonding over adolescent pranks and eventually sharing a house; and, as Juster would write, Feiffer would sketch. Feiffer's girlfriend at the time was able to get Tollbooth to an editor with enough pull to get their unusual book published. Thus, a writer who described his childhood self as a "funny, introverted, introspective kind of kid," and an illustrator who was famous for his satirical comic strip, created what Maurice Sendak declared a "masterpiece."

In the introduction to the 35th anniversary edition, Sendak wrote, "The Phantom Tollbooth leaps, soars, and abounds in right notes all over the place." This fall's 50th anniversary brings with it a new edition with an introduction from Chabon (his blog post was a teaser for the longer essay) and a delightful annotated edition researched by children's literature scholar Leonard Marcus. 

Annotated editions are to book lovers what food festivals are to foodies: feasts where they can gorge themselves until buttons start popping. Marcus's annotations range from the playful and amusing to the erudite and insightful. In one note he discusses how the tradition of clicking drinking glasses came to be, and the next he examines the psychological benefits of daydreaming. Marcus's language is delectable and he makes thought-provoking comparisons, finding commonalities between Tollbooth and E. B. White's Charlotte's Web, Jack Kerouac's On the Road (does that make Milo Dean Moriarty and Tock Sal Paradise?), and Ralph Waldo Emerson's essays. The annotated edition will be cherished by nostalgic adults and inquisitive children alike.

Tollbooth  is also for the crowd that loves numbers and words; or at least they will be much more likely to appreciate them both by the end. Milo learns about infinity by trying to climb a set of stairs to that unreachable number. At the top of the stairs is "a dreadfully poor place," where "they can never manage to make ends meet." He doesn't get there, of course, but he does meet a .58-size child who is part of an average household of 2.58 children. 

Juster's delight in the possibilities of words makes Tollbooth read like a love letter to the English language. In conversation with Marcus for the scholar's book Funny Business: Conversations with Writers of Comedy, Juster reflected, "As a kid I would say a word and repeat it and repeat it and repeat it until it had no meaning and was just a series of sounds. It seemed magical to me." Indeed, the language of Tollbooth is "magical." Some of the words are just fun to say (dillydally, superfluous, exquisite) and are light and fluffy as they roll across the tongue, while others are fantastic to ponder (macabre, quagmire, flabbergasted) and look important and heavy as if they were paperweights holding down the pages. 

The Phantom Tollbooth  also asks readers to embrace puns. For example, the "Senses Taker" helps people "find what they're not looking for." Puns are used as barbs by Shakespeare, the Marx brothers, and hip-hop artists. They are the zingers of satire and poetry. I agree with Chabon when he writes, "I can't see how anybody who claims to love language can fail to marvel at the beautiful slipperiness of meaning that puns, like aquarium nets, momentarily catch and bring shimmering to the surface." Puns are jokes that make you work for the "aha!" moment. You're left to figure out the punch line on your own and it's all the funnier for the thought it requires.

While my appreciation for a good pun is one of the elements of Tollbooth that has not changed, what has evolved for me — as I am no longer a child in rural New England, but an editor working in New York City — is Juster's examination of urban landscapes and modernity. When Milo and Tock stumble upon an invisible city, their guide, an airborn boy named Alec, explains that while the city was once beautiful, "No one paid any attention to how things looked, and as they moved faster and faster everything grew uglier and dirtier ... Because nobody cared, the city slowly began to disappear." Marcus calls the phenomena of the neglected city Juster's "critique of the depersonalization of modern city life."

And there is much more than a consideration of urban environments: Tollbooth dissects modernity as a whole. Sendak writes, "The book treats, in fantastical terms, the dread problems of excessive specialization, lack of communication, conformity, cupidity, and all the other alarming ills of our time. Things have gone from bad to worse to ugly. The dumbing down of America is proceeding apace. Juster's allegorical monsters have all become too real." What would he have to say now that Google and Facebook have become verbs and cell phones rest at the hips like cowboys' holstered guns? Juster's "monsters" seem especially real in the current political climate where presidential hopefuls' squabbling and finger pointing echo the ridiculousness of King Azaz the Unabridged and the Mathemagician fighting over the superiority of words or numbers. One of the wonders of Tollbooth is that many of its insights remain pertinent. Fifty years later, cities are still alienating, adults still act foolishly, and Rhyme and Reason still seem banished.

Will the generations of children who do not know a time before E-Z passes love The Phantom Tollbooth with the same devotion? When I read the classic I was fascinated by Milo's toys, and that he got to walk home from school by himself, but kids who have Wii and cell phones might not be similarly impressed. A December 1961 review in the Atlantic Monthly declared, "This unusual fantasy, besides being very amusing, has a quality that will quicken young minds and encourage readers to pursue pleasures that do not depend on artificial stimulation." That such an insight stands to be as true now as it was then, gives me hope. Because Tollbooth is rich with puns, allegory, and social commentary, it's easy to forget that at heart it's a fantastic adventure story. After each reading, whether as a child or as an adult, the everyday seems a little fuller of possibilities. When Milo realizes that, "there was so much to see, and hear, and touch" outside his window, and, "things to invent, and make, and build, and break, and all the puzzle and excitement of everything he didn't know," right there in his room, readers too will find their sense of wonder renewed. Like other classic children's tales, The Phantom Tollbooth leaves you with the sensation that the best adventures happen when you least expect a magic rabbit hole, a transporting tornado, an enchanted wardrobe, or a phantom tollbooth.

LARB Contributor

Chelsey Philpot is a writer and a book reviews editor at School Library Journal.



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