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11 Whimsical Facts About The Phantom Tollbooth

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Norton Juster’s 1961 tale of a bored boy who travels to a magical land is more than it seems—as its plot enchants, The Phantom Tollbooth also manages to illustrate the joys of learning. The story behind the book's creation is just as fascinating, so we’ve compiled some fun facts for your next journey through the Kingdom of Wisdom.

1. The Phantom Tollbooth is a product of Juster’s procrastination.

After serving three years in the Navy, Juster returned to his hometown of Brooklyn to work as an architect. He received a $5,000 grant from the Ford Foundation to write a children’s book about cities, but overwhelmed by the amount of research it required, decided to take a vacation. Upon returning, Juster’s guilt over his lack of progress on the city book led him to start writing snippets of stories about a little boy named Milo—who happened to be quite similar to a young Juster. As Juster told NPR, “In order to stop thinking about cities, I had to start thinking about something else.”

2. Juster’s childhood synesthesia shaped the book.

Synesthesia is the condition in which one type of stimulation evokes the sensation of another. It causes the afflicted to inexplicably associate a sound with a specific color, or perhaps a word with a color—the condition manifests differently in each synesthete.

Juster’s synesthesia caused him to associate numbers with colors, and similarly, words and images. Although he eventually grew out of it, the visual blurring of senses is evident in his writing. Juster once noted, “When I start to write I have to create visually, no matter how abstract, no matter how undefined. … It’s not only that I would have been a different writer had I not had that very developed visual sense, I don’t think I would have been a writer at all.”

3. Despite the similarities, Juster wasn't inspired by Alice in Wonderland.

It’s easy to draw comparisons between the Kingdom of Wisdom and fantastical worlds like Narnia, the Emerald City, or Wonderland. Lewis Carroll’s protagonist Alice is, like Milo, a bored child frustrated with reality; later, they both discover new worlds where “things aren’t always what they seem.” However, Juster’s inspiration came from a different source. The Phantom Tollbooth was heavily influenced by Juster’s father’s love of puns and wordplay, and further shaped by a childhood spent listening to the radio and imagining what could be.

4. A “boy who asked too many questions” inspired Milo.

While struggling with his book on cities, Juster had an interesting encounter with a young boy who asked him, “What is the biggest number there is?” The always-clever Juster replied, “Tell me what you think is the biggest number there is,” and then repeatedly told the boy to add one to that number, leading to a discussion about infinity. Thus, the “boy who asked too many questions” was born.

5. Milo’s watchdog had radio roots.

The character Tock was based on Jim Fairfield from Jack Armstrong, the All-American Boy, a popular radio show during Juster’s childhood. Tock, the “watchdog,” befriends Milo early in the book and accompanies him on his adventures. Jack Armstrong’s “Uncle Jim” was not a canine, but he did share Tock’s wisdom, courage, and adventurous spirit.

6. The iconic illustrations are the product of a lucky coincidence.

Jules Feiffer, a cartoonist who lived in the same apartment building as Juster, would often hear the author pacing in his apartment as he was working on Tollbooth. Curious, Feiffer asked to see some of Juster’s manuscripts, and soon found himself illustrating scenes from the book. Feiffer sketched his original drawings on flimsy pieces of tracing paper, most of which have now been lost or damaged. Feiffer later remarked, “Had Norton told me he was writing a classic, I would have done the drawings on nicer paper.”

7. Juster and Feiffer fell into a (mostly) playful power struggle.

Juster did most of the cooking for the pair and later joked that if Feiffer wanted to eat, he had to draw. The two got into it constantly: Juster frequently described scenes that were impossible to draw, and Feiffer responded by drawing things the way he wanted. Feiffer, for example, wasn’t good at drawing horses, so he drew the armies of wisdom riding in on cats instead. Despite their creative differences, the two remain good friends today.

8. It was supposed to be a flop …

As Juster told The New Yorker in 2011, the initial sales projections for his collaboration with Feiffer weren’t great. “Everyone said this is not a children’s book, the vocabulary is much too difficult, the wordplay and the punning they will never understand, and anyway fantasy is bad for children because it disorients them.”

9. But The New Yorker saved the day.

A glowing review from The New Yorker critic Emily Maxwell paved the way for the book's success. Maxwell adored it, comparing its themes to John Bunyan’s 17th century classic The Pilgrim’s Progress. She wrote, “As ‘Pilgrim’s Progress’ is concerned with the awakening of the sluggardly spirit, ‘The Phantom Tollbooth’ is concerned with the awakening of the lazy mind.”

10. Juster spent most of his career as an architect, not an author.

Although The Phantom Tollbooth became a classic, Juster wrote only a few more books (the most famous of which is The Dot and the Line: A Romance in Lower Mathematics). Instead, he spent most of his working life as an architect. Juster served as a professor of architecture and environmental design at Hampshire College for more than 20 years and even co-founded a small architectural firm in 1970.

11. Juster wanted to demonstrate that learning is a “world we enter.”

In a 2011 installment of NPR’s All Things Considered, Juster shared his motivation for writing the book:

The prevailing wisdom of the time held that learning should be more accessible and less discouraging. The aim was that no child would ever have to confront anything that he or she didn't already know. But my feeling is that there is no such thing as a difficult word. There are only words you don't know yet—the kind of liberating words that Milo encounters on his adventure.

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