The Book that Boredom Wrote

Can we read? No. 104: From guest writer Dana Gaskin Wenig

Once a month between March and October 2023, Dana Gaskin Wenig will take my place in your inbox and share her own extensive knowledge of, experience with, insight into, and love of children’s literature.

Here’s her offering for May — enjoy!

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The Phantom Tollbooth by Norton Juster, illustrated by Jules Feiffer, is about a boy named Milo who “regarded the process of seeking knowledge as the greatest waste of time of all.” Milo returns home from school one day to settle into “another long afternoon,” being bored, bored, bored by the toys and books and games in his room, when he notices a very large package with his name on it. Inside, Milo finds a tollbooth complete with signs, coins, a map, and a book of “rules and regulations.” Milo already has a small car (cars for kids were popular even then), so he is fully prepared to use the tollbooth which turns out to be the portal through which Milo enters the Lands Beyond.

Once in the Lands Beyond, reality flips on its head. Of the three signs that came with the tollbooth, the last, “Have your destination in mind,” gets Milo’s little car going, but once he gets beyond expectations, he quickly finds himself in the Doldrums. Thinking is illegal here, and “laughter is frowned upon and smiling is only permitted on alternate Thursdays.” No one does anything at all. Milo is really stuck until help arrives. This is the beginning of a hilarious and mind-expanding road trip that will take Milo and friends he meets along the way on a long journey through fabulous, thought-provoking, and curious places where Milo will discover what’s really important and find what he’s been missing all along. I’m not a spoiler, so I’m not going to give a lot of detail — you’ll just have to get the book.

Published in 1961, The Phantom Tollbooth is a quintessentially American story written at a time when most of the great fantasies for children were written by British authors: Kenneth Grahame, Lewis Carroll, Mary Norton, C.S. Lewis. In discussing how he wrote the book in the documentary about the process (available here), Juster says:

When I started writing The Phantom Tollbooth, I realized that what I had to do was get Milo to a place where the world is really upside down. Alice goes down a rabbit hole, in The Lion the Witch and the Wardrobe they go through the back of the wardrobe. It’s something that when you pass through it’s very sharp and you know you’re someplace different. And I remembered because when I was a kid we drove lots of places, and there was always great anticipation. Always feeling it was a bit of an adventure when we went through a tollbooth. And I started playing with that.

Published in 1961, the book could not have been written without the benefit of procrastination. It is the result of a collaboration between Juster, an architect, and Jules Fieffer, an illustrator, young men early in their careers. Juster was an accidental children’s book author — he was an architect like his father and older brother — but he had received a grant from the Ford Foundation to write a book for children on urban perception. After two months of pacing the floor avoiding writing the book he was supposed to write, Juster went out of town and took himself for long walks on the beach where he had time to muse. He remembered a far-reaching conversation he’d had recently with a small boy who had asked him what the biggest number in the world was (which quickly became a delightful conversation about infinity). This meeting of the minds brought Juster memories of himself as a child, how much he disliked school (I’m sure all children feel like this sometimes), his special difficulty with math, and memories of his father’s singular love of wordplay.

School was especially difficult for Juster, in part because he had a neurological condition called synesthesia, shared by about one out of three hundred people. (Famous synesthetes include Marilyn Monroe, author Vladimir Nabokov, Beyoncé, physicist Richard Feynman, and musicians Pharrell Williams and Frank Ocean.) For Juster, this condition made learning math virtually impossible until he incorporated his experience of numbers being associated with specific colors and started doing his math problems with colored pencils. In this way, he managed to engage in conventional education.

As a former bookseller, it has been my sincere pleasure to pull a copy of The Phantom Tollbooth off the shelf and hand it to prospective buyers. I know I’m introducing readers to puns and wordplay, the power of words, a philosophical ode to the freedom to learn in whatever way works best. John Holt, American critic of public education and homeschooling/unschooling advocate, said, “We can best help children learn, not by deciding what we think they should learn and thinking of ingenious ways to teach it to them, but by making the world, as far as we can, accessible to them, paying serious attention to what they do, answering their questions — if they have any — and helping them explore the things they are most interested in.” I believe Juster and Feiffer were united in this viewpoint of education in life and in their creative collaboration. As Jules Feiffer said, “The road means freedom.”

Other classics published that same year include Where the Red Fern Grows by Wilson Rawls, The Incredible Journey by Sheila Burnford, and Roald Dahl’s James and the Giant Peach, but for me, The Phantom Tollbooth stands out. Feiffer’s line drawings are lively, evocative, and humorous — no surprise from a man who became a highly accomplished American cartoonist, playwright, book author, illustrator and art instructor, and who was a widely-read satirist. As both men tell it, they met taking out the trash behind the apartment building they both lived in in Brooklyn Heights, New York. Later they were roommates and Juster did all the cooking (they joke that Feiffer didn’t eat if he didn’t draw).

Milo, Tock, and the Humbug

At that time, and even now, children’s book authors write books, and publishers choose the illustrator. Luckily for us, this book was created as a collaboration between two men who clearly enjoyed each other, appreciated the other’s contributions, and weren’t afraid to engage in jovial banter about literally everything. In this vein, Juster was insistent on a map of the Lands Beyond for the endpapers of his book like the beautiful maps by Pauline Baynes that serve as endpapers in Tolkein’s The Lord of the Rings trilogy and E. H. Shepard’s endpaper map in Kenneth Grahame’s The Wind in the Willows. But Jules Feiffer wouldn’t do maps. Juster ended up drawing the map himself and Feiffer went over it to give it the now-famous Feiffer line.

This is not a book to speed through with your child — it’s likely to bring up the big questions. You may even have to pull out a dictionary. In-depth conversations may ensue. But what conversations they will be! Each time I read this book I pick up something new, some new bit of wordplay, a concept I wasn’t ready for last time I read it. Something else I learned watching the documentary about this book: Dr. Seuss’s The Cat in the Hat was written with a very small vocabulary (100 easy-to-read words) so that American children wouldn’t be left behind during the Cold War. By contrast, Juster wrote the The Phantom Tollbooth while referring to pages and pages of notes on wordplay and puns that he had collected throughout his life, some from his father. He had no thoughts of keeping it simple. He wrote the book he wished for as a child, and he respected his reader (child or adult) deeply enough to use the full power of his mind and heart (and his dictionary and thesaurus) to say what he meant rather than trying to clothe a message in an adventure story.

I love this book, I respect Norton Juster and Jules Feiffer, and I’m delighted to know the story of how they met. You may even want to get The Annotated Phantom Tollbooth, annotations by Leonard S. Marcus (2011). It’s got a lot of fun information in it. All this only increases my appreciation for the book and reinforces my recommendation that you get a copy and enjoy it with as many people you can. You can thank me later.

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Dana Gaskin Wenig is a writer, writing teacher, and former bookseller. She lives in the Seattle area.