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A Book for All Life’s Seasons

The Phantom Tollbooth is much more than a children’s book.

Daniel Ross Goodman

Norton Juster, author of the beloved children’s book The Phantom Tollbooth, died this past March at his home in Northampton, Massachusetts, at the age of ninety-one. Juster first published The Phantom Tollbooth in 1961. It is an enchanting story about Milo, a frequently bored young boy, who is one day given a magical tollbooth that takes him on a rollicking series of adventures in a far-off fantasy world. Combined with Pulitzer Prize-winning cartoonist Jules Feiffer’s simple black-and-white illustrations, the book became an instant hit. It has sold almost five million copies, has been adapted into a stage play and animated film, and has been anthologized in HarperCollins’ Essential Modern Classics series.

The Brooklyn-born Juster, whose primary background was in architecture, not literature, would go on to write several other children’s books, none of which attained anywhere near the sustained acclaim enjoyed by The Phantom Tollbooth. What accounts for the book’s enduring, near-universal appeal?

First, perhaps most important, the book tells a fun, exciting story in simple, engaging prose—much of which is remarkably funny, even sixty years later. More, the book tells its story not just in words but also in pictures. Feiffer’s fun, evocative sketches add just the right touch of visual whimsy to a story about a boy learning how to appreciate the oddities, caprices, and wonders of the world.

We have grown accustomed to thinking that pictures are OK in children’s books, but that it is “childish” and intellectually regressive for an adult to read illustrated books. The fact that The Phantom Tollbooth is a book for readers of all ages, not only children, shows that nothing could be further from the case. So does Dante’s Divine Comedy (1472), the text that more than any other is, as we shall see, the primary influence on The Phantom Tollbooth.

No one would mistake The Divine Comedy, which portrays the most gruesome tortures of sinners in hell and includes discourses on undoubtedly adult topics like theology and politics, as a children’s book. Artists including Sandro Botticelli, William Blake, and Salvador Dalí have illustrated The Divine Comedy. The most popular version is probably the edition with haunting black-and-white drawings by Gustave Doré, which accompany nearly every canto. Doré’s illustrations demonstrate that when skillful visuals are paired with magnificent writing, the result is something even more than what can be achieved through words or pictures alone.

Similarly, Feiffer’s illustrations are a perfect match for Juster’s words. Serious art and serious literature need not be segregated from one another. On the contrary, they are better together than apart (as C.G. Jung’s illustrations to his own Red Book and Black Books and Enrico Mazzanti’s illustrations to the first edition of Carlo Collodi’s Pinnochio (1883) demonstrate as well).


The second point about The Phantom Tollbooth is that it is not just a children’s book: It is serious literature, deeply grounded in centuries of “hero’s journey” adventure tales. Alice’s Adventures in Wonderland (1865) is the most thematically and stylistically similar immediate precursor to The Phantom Tollbooth, with its incessant wordplay and its plot centered on a bored young child going down a rabbit hole, like Milo’s magic tollbooth, and there encountering a series of eccentric characters and an adventure in a peculiar fantasy realm. The genre also includes The Wizard of Oz (1939); The Lion, the Witch, and the Wardrobe (1950); Pilgrim’s Progress (1678); Gulliver’s Travels (1726); and, of course, The Divine Comedy.

As with Dante’s protagonist, Dante the pilgrim, Milo is lost when we first meet him, a boy “who didn’t know what to do with himself.” (Feiffer’s first illustration in the book, of a bewildered Milo shrouded in shadows, is remarkably similar to Doré’s first illustration depicting Dante “astray in the Dusky Wood.”) Like Dante the pilgrim, Milo sets out on an adventure through a fantasy realm, beginning in awful places—the dreaded Doldrums, much like Dante’s inferno and ante-inferno—and ending with him in the Heavenly locale. Both are accompanied on their journeys by loyal, resourceful guides, Virgil for Dante and Tock for Milo; both are moved through the unpleasant parts of the journey by the promise that virtuous women, Beatrice for Dante and the princesses Rhyme and Reason for Milo, await them in the ethereal abode above.

In The Divine Comedy, sinners condemned to hell are punished in a “contrapasso” (corresponding) manner. Those who sinned through the passions of lust are doomed to be battered by gale-force winds. Those who were mired in gluttony are doomed to spend their afterlives mired in filth. Those who stood for nothing are condemned to chase banners that stand for nothing.

In the same way, characters in The Phantom Tollbooth who commit certain types of errors or behave in certain inadvisable ways are sent to places that correspond to their behaviors. Thus, when Milo, early in his adventures, lapses into inattentiveness and indifference, he winds up in the doldrums—literally. He’s made to visit a place called the Doldrums, where small, lethargic creatures sit around all day with no aims or ambitions and no drive to accomplish anything.

When Milo asks about the place, one of the Lethargians, the creatures who live there, tells him, “That’s why you’re here. You weren’t thinking, and you weren’t paying attention. People who don’t pay attention often get stuck in the Doldrums.” Milo then asks what you can do in the Doldrums. The Lethargians, in a line that sounds like a particularly good Seinfeld bit, tell him, “Anything as long as it’s nothing, and everything as long as it isn’t anything.”

In another part of the journey, when Milo, Tock, and a foolish traveling companion named “the Humbug” make some silly assumptions, they end up on Conclusions, a small, rocky island crowded with people who have committed the same intellectual sin. Milo asks an inhabitant how he, Tock, and the Humbug got there. The man answers, “You jumped, of course. That’s the way most everyone gets here.… Every time you decide something without having a good reason, you jump to Conclusions whether you like it or not. It’s such an easy trip to make that I’ve been here hundreds of times.”


Like The Divine Comedy, The Phantom Tollbooth is concerned with virtue. Destructive inclinations and unethical qualities—Hate, Malice, insincerity, triviality—are personified as demons like the Terrible Trivium, the “demon of petty tasks and worthless jobs,” and the Overbearing Know-it-all, “a dismal demon” who is “mostly mouth” and is “ready at a moment’s notice to offer misinformation on any subject.” Aesthetic and intellectual virtues like Rhyme and Reason are personified as princesses.

This brings us to the third and final point about The Phantom Tollbooth: Few popular books in the past hundred years have been so interested in promoting goodness and wisdom and cultivating constructive character traits. Tock, Milo’s Virgil—his companion on the journey from the Doldrums to the Castle in the Air—has the head and legs of a dog and the body of a ticking clock. His purpose is to remind everyone about the importance of using time wisely. When he first meets Milo in the Doldrums, Tock asks what Milo is doing there. “Just killing time,” Milo answers. “KILLING TIME!”, Tock roars. “It’s bad enough wasting time without killing it.” (One can only imagine what poor Tock would make of TikTok.)

The princesses Rhyme and Reason tell Milo about the importance of learning: “Whenever you learn something new, the whole world becomes that much richer.” More broadly, just about everyone and everything Milo meets teach him about thinking. As Tock tells him about escaping the Doldrums, “[S]ince you got here by not thinking, … in order to get out, you must start thinking.”

Yet The Phantom Tollbooth’s greatest gift to us is the reminder that our own minds are an even greater gift. Along with wasting time—or, even worse, “killing” it—there is no greater sin, against others and ourselves, than not using our minds. Milo discovers that it can be quite hard to really think because, as he discovers, we’re so unaccustomed to it. In our screen-surrounded society, real thinking is almost impossible unless we actively distance ourselves from the distractions that threaten to drown us every day. Milo learns “how much could be accomplished with just a little thought.”

The Phantom Tollbooth shows us that the greatest rewards in life come from using our minds, not shutting them off. Our own wondrous minds and inexhaustible imaginations are far richer and grander than anything we can possibly come across on our phones, Netflix, or Amazon. But to keep this in mind, we also need to keep a childlike sense of wonder and imagination alive in us. As Juster said in a 2012 interview, “You have to retain … a good piece of the way you thought as a child.… If you lose all of that, that’s where the deadliness comes from.… The most important thing you can do is notice.”

There’s no better way of doing that than to reread The Phantom Tollbooth, especially when we need a reminder of what Milo realizes after his trip—that because of our capacious intellect and infinite imagination, “There’s just so much to do right here.”

Daniel Ross Goodman is a rabbi, writer, and scholar. He is author of Somewhere Over the Rainbow: Wonder and Religion in American Cinema (2020) and the novel A Single Life (2020).

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