Peter Sagal, host of NPR's uproarious Wait, Wait, Don't Tell Me!, wrote a fine essay in the Chicago Tribune about reading The Phantom Tollbooth to his daughters. Such was his early love for the book that he would have named each of those female children Milo if not for the little matter of a missing Y chromosome.
The girls enjoyed the book, but Sagal found rereading it painful:
...moments I had treasured from the book down through the decades now seemed like cheap gags. The first place he arrives is a stop in the road called "Expectations." Thus, every place he goes after that is "beyond Expectations." Get it? At one point the characters make statements unsupported by facts and suddenly fly through the air to an island called "Conclusions." They jump to Conclusions. See?I suspect that Sagal would have writhed just as much if he'd gotten a look at himself at the age when he first read and loved The Phantom Tollbooth. And even more if he'd been able to see into his mind at that point. I know I would have. "Self-satisfied intellectual humor" seemed like an apogee to aspire to.
Milo's friends on his quest, whom I had once thought of as my own friends, were simple archetypes who showed up, made their speeches and vanished. Where as a child I had seen mystery and wonder, as an adult I saw smug, self-satisfied intellectual humor. . . .
But I should stress, again, that while I was sitting in our beat-up glider chair reading the book, silently, motionlessly writhing as my childhood collapsed around my ears, my kids were having a fine old time.
The Tollbooth seems expertly calibrated for kids breaking into the realm of abstract thought. The puns and archetypes that Sagal now finds so facile are almost all based on abstractions like "Expectations" and "Conclusions." The book's treatment of them isn't very deep, to be sure. But it's many miles wide: it takes young readers on a whirlwind tour of the new possibilities of their minds, their language, their logic and mathematics. If you read the Tollbooth at the right age, its jokes are funny because they come at you for the first time, and because they represent the delight of discovering a new way to play with the world.
Now when I say "expertly calibrated for kids," I mean not calibrated at all, by someone who never claimed to be an expert and wasn't thinking of kids. As Juster told an interviewer at Powells.com, "There was no audience but me." Eventually he was also writing for his neighbor Jules Feiffer, who had gotten the assignment of illustrating this strange book. (Similar remarks from Juster at AbsoluteWrite.com.) The Tollbooth had to come from outside the children's lit field. It's not about vivid characters or a plausible world or a tight plot. It's about exploring something more, beyond Expectations.
I think everyone should read The Phantom Tollbooth once. Life won't be the same. Rereading many years later--well, that might indeed be painful.