The Impossible Possibility of The Phantom Tollbooth

“WHY NOT?–

That’s a good reason for almost anything,” explains the gateman at the entrance to Dictionopolis, the mysterious kingdom of words in Norman Juster’s The Phantom Tollbooth. “A bit used, perhaps, but still quite serviceable.”

That used, but still quite serviceable, reason, “why not,” was the one that convinced me to finally read The Phantom Tollbooth. Like its young protagonist, Milo, I had too much time on my hands and nothing I wanted to do with it. And the brightly-covered blue paperback edged in pink, featuring a thinly-sketched boy pondering a dog with a giant clock for a midsection, was lying unread in my room.

I did not like fantasy. It scared me. Not in a Scary Stories to Tell in the Dark kind of way; I actually loved those books and the heebie jeebies they gave me. More in an anything beyond the lines of normal is bad kind of way.

The best illustration of this perplexing discomfort is how terrified and weirded out I was by Peter Gabriel’s “Sledgehammer” music video. Groundbreaking in its use of stop-motion animation and claymation, it contained all sorts of strange: two roast-ready chickens dancing, a portrait of Gabriel’s face made of vibrating pieces of fruit, a claymation version of the singer with sledgehammers for hands.

Even a fantastical title could put me off, and I was a voracious reader. It took me ages to crack open a copy of E.L. Konigsburg’s From the Mixed-Up Files of Mrs. Basil E. Frankweiler, which I loved. Even so, I could barely glance at my friend’s beloved copy of Konigsburg’s Jennifer, Hecate, Macbeth, William McKinley, and Me, as if it were a giant spider in the corner. Too many weird names. I’ve still never read it, though I love and have taught Macbeth.

Only a life-changing upheaval could persuade me to try fantasy, and mine was a doozy.

I didn't buy The Phantom Tollbooth; it was a gift. My friend Lesley and I no longer went to the same school, so I don’t even remember how she learned that I was in the hospital for a severe relapse of inflammatory bowel disease. All I know is that she and her mom brought me The Phantom Tollbooth. I set it aside, too drained for something potentially Peter Gabriel-esque. It was 1992. I was twelve.

Once home, slowly putting back the 30 pounds I had lost on my already small frame, I had a lot of solitary time on my hands. Both of my divorced parents worked, I lived in a neighborhood with no kids my age, and I didn’t have much energy to play, anyway. Books had always been my escape. Any words, really—my parents had given up years ago trying to keep me from reading the condiment labels at the dinner table. So, boredom+dis-ease+disease equaled “WHY NOT?” It was the right alchemical, astrological time for The Phantom Tollbooth.

Given this love of words, it makes sense that my fantasy breakthrough came through a book built upon puns and figurative language taken literally. The Phantom Tollbooth opens when Milo, a perpetually bored child, receives a mysterious package: a DIY purple cardboard tollbooth “FOR USE BY THOSE WHO HAVE NEVER TRAVELED IN LANDS BEYOND.” With a shrug, he figures he has nothing else to do and pays the fare.

His first stop is Expectations, from which he must—you guessed it—go Beyond. Insightful wordplay shapes the quest that Milo undertakes to bring the Princesses of Rhyme and Reason back to the Kingdom of Wisdom. From the scenic Point of View in the Forest of Sight, to the symphony of color that plays the sunrise and sunset into being, to the warring kingdoms of Dictionopolis and Digitopolis, Milo keeps encountering new ways of looking at old things--and seeing something in them he’s never noticed before.

With him throughout the journey are the Humbug, a pretentious yet ultimately kind and helpful insect, and Tock. Tock is the watchdog on the cover, guarding time with all the ferocity appropriate for a guard dog. (He roars with anger when Milo blithely mentions wasting time.)

This magical book filled me with a joy I hadn’t felt since my hospitalization. It was just so fun. As with all great books, moreover, the fun had a profound, purposeful wisdom to impart. After Milo, Tock, and the Humbug have successfully brought Rhyme and Reason home, King Azaz of Dictionopolis and the Mathemagician of Digitopolis tell Milo what they couldn’t say when he was setting off on his quest: that the whole thing was impossible:

“Yes, indeed,” they repeated together; “but if we’d told you then, you might not have gone--and, as you’ve discovered, so many things are possible just as long as you don’t know they’re impossible.”

At that moment in my life, I needed the possibility of the impossible.

I couldn’t imagine that I might, one day, feel better again. My guts had irrevocably changed, and with them my life. The Phantom Tollbooth showed me the weird could be wonderful and full of joy, not just wacky and full of nonsense. As a fellow boy Milo encounters at Point of View points out, “it's all in how you look at things.”

The Phantom Tollbooth helped me look at fantasy differently. It taught me that imagining things beyond the possible was not an act of insanity and abnormality but, rather, of courage and hope. It’s a lesson I’ve never forgotten.

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Hello, I’m Sara!

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