#21 The Phantom Tollbooth by Norton Juster (1961)
80 points

It was the very first time that I couldn’t put a book down. I was pretty young, and I read it all in one sitting — I was shocked at myself afterward. Those puns! That wordplay! It meant there were other people in the world with brains that worked like mine. – Aaron Zenz

I do love my wit and puns, so another natural. I can still quote parts of this, and revisit it when I can. – Kyle Wheeler

Funny, punny and filled with adventure. Most kids see a bit of themselves in Milo… for better or worse. – Stacy Dillon

It’s not often that Jules Feiffer’s illustrations take a distinct back seat to the text of the book he’s drawing for, but this is most definitely one of those times. – Hotspur Closser

This was the most shocking change from the last time I conducted this poll (thus far). The Phantom T (as Schmidt on The New Girl calls it) was in the top ten last time around (coming it at #10). We’ve recently seen its 50th anniversary celebration, with a lovely new annotated edition out there for one and all to see. So why the seemingly strange drop in popularity? The funny thing is that it actually showed up on a massive number of people’s lists. Yet only two people named it their number one favorite with most making it #9 or #10. That’s the way this poll works, folks. It seems that while most people enjoy Juster’s classic, few were willing to give it the attention it deserved. And so here we are with a book that has dropped eleven places, but keeps hanging on.

The synopsis from the publisher reads, “For Milo, everything’s a bore. When a mysterious tollbooth appears in his room, he drives through only because he’s got nothing better to do. But on the other side, things seem different. Milo visits the island of Conclusions (you get there by jumping), learns about time from a ticking watchdog named Tock, and goes up against the dastardly Discord and Dynne. By the time Milo and Tock set off toward the Mountains of Ignorance to rescue the twin Princesses Rhyme and Reason, Milo realizes something astonishing. Life is far from dull. In fact, it’s exciting beyond his wildest dreams…”

Let us play that old game of how-it-came-to-be.  The skinny comes via 100 Best Books for Children by Anita Silvey.  According to her, “An architect who wrote for relaxation from arduous planning projects, Norton Juster had received a grant from the Ford Foundation to create a book for children about how people experience cities.  In 1959, to avoid writing this book, he began working on a short story – one that took on a life of its own.  Juster viewed The Phantom Tollbooth as a way to procrastinate from his real responsibilities.”  Turns out, he was buds with Jules Feiffer who hadn’t really done much with children’s literature at that point.  As a recent Publishers Weekly article put it, “Fifty years ago, Norton Juster was pacing his second-floor apartment in Brooklyn Heights, unsure that the manuscript he was working on—his first—would ever be published, much less become a classic of children’s literature. His roommate was his first reader, who also voluntarily sketched some pictures to go with Juster’s story.  The roommate was Jules Feiffer. The manuscript was The Phantom Tollbooth.”

The book has since gone on to sell 3.3 million copies.

In terms of the sheer number of puns in this book, Juster once explained in an interview with Salon where they may have come from.  “My father was a punster. …  he’d say something and I’d groan. There’s no way you can deal with that a