On ‘The Phantom Tollbooth’

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Milo approaching the tollbooth in his bedroom; illustration by Jules Feiffer from Norton Juster’s The Phantom Tollbooth

When I was a boy I read, in a biography of Daniel Boone, or of Daniel Beard, that young Dan (whichever of the two it may have been—or maybe it was young George Washington) had so loved some book, had felt his heart and mind inscribed so deeply in its every line, that he had pricked his fingertip with a knife and, using a pen nib and his blood for ink, penned his name on the flyleaf. At once, reading that, I knew two things: (1) I must at once undertake the same procedure and (2) only one, among all the books I adored and treasured, was worthy of such tribute: The Phantom Tollbooth. At that point I had read it at least five or six times.*

First published in 1961, The Phantom Tollbooth describes the comical-epic journey of Milo, a rather etiolated young fellow awash in grade school ennui who, one day, under mysterious circumstances, finds himself in receipt of a package containing the eponymous tollbooth. Mildly curious—a strong emotion for mild Milo—he climbs into his battery-powered toy car and rolls through the tollbooth, duly paying his fare, and finds himself on the outermost outskirts of the Kingdom of Wisdom. Milo’s journey, at first undertaken with a shrug, transforms itself into a quest, one that takes him from Expecta- tions, through Dictionopolis, Digitopolis, and the Mountains of Ignorance, to the Castle in the Air, where a pair of princesses, Rhyme and Reason, languish in captivity. Clearly the geography and topography of the Kingdom of Wisdom, like the plot of the novel, emit a powerful whiff of the allegorical; yet somehow, through the wit and artistry and recursive playfulness of its author, Norton Juster, The Phantom Tollbooth manages to surmount the insurmountable obstacle that allegory ordinarily presents to pleasure.

The book appeared in my life as mysteriously as the titular tollbooth itself, brought to our house one night as a gift for me by some old friend of my father’s whom I had never met before, and never saw again. Maybe all wondrous books appear in our lives the way Milo’s tollbooth appears, an inexplicable gift, cast up by some curious chance that comes to feel, after we have finished and fallen in love with the book, like the workings of a secret purpose. Of all the enchantments of beloved books the most mysterious—the most phantasmal—is the way they always seem to come our way precisely when we need them.

This was, I’m guessing, somewhere around 1971 (as long ago now as the days of zeppelins, iron lungs, and Orphan Annie were to me then, at eight years old). I was not as discontented with or disappointed by life as Milo (not yet), and I can remember feeling a faint initial disapproval of the book’s mopey young protagonist the first time I …

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  1. *

    This essay is drawn from Michael Chabon’s introduction to a fiftieth- anniversary edition of The Phantom Tollbooth that will be published by Knopf in October.