The Phantom Tollbooth – A Nostalgic Retrospective


A Time Long Ago

Do you ever long for a time in the distant past? A period in your life when every day was defined by the safe exploration of an unknown world and everything seemed to hold so much wonder. The start of a wintery December when the last leaves were still crisp on the ground. That time in school when your best friend stood up for you in a fight. Or those rainy afternoons when there was nothing good on TV, so you spent them kicking your feet as you laid on your back and read some utterly bizarre book that made nonsense par for course. For me, those afternoons probably would have been spent with the stories of Roald Dahl. I never got into Charlie and the Chocolate Factory, but The Witches was a terrifying and hilarious escapade, and while I always liked James and the Giant Peach, it was the absolute insanity of George’s Marvellous Medicine that truly sucked me in. There was just something about a kid performing cartoonish medical experiments on unfortunate farm animals that appealed to that part of me which craved to see all the rules of the world turned upside down. To be honest though, I wasn’t that big of a reader as a kid, so when I feel pangs of nostalgia for the idea of being lost in a children’s book, I think it’s for a time that never actually was, something which was put into focus for me as an adult when I discovered The Phantom Tollbooth by Norton Juster, a story which seems to have been popular in the United States, but never really made a cultural impact in Ireland, at least when I was a boy. Nevertheless, I think a big reason the book appealed to me now as an adult is because the story, that of a kid named Milo who’s bored with everything, from going to school to playing with his toys, is something I could relate to at any age. Anybody who’s been around kids will know that one of their main pastimes is to complain about being bored, but I kind of think that if we’ve lost that habit as so-called grownups, it’s only because we’ve become complacent with the humdrum nature of existence. You know, when you move into a new house and decide to explore the attic for the first time, you’d probably just think yourself lucky if you found a couple of all old tins of paint you could use to spruce up the shed, rather, than say, ask yourself if maybe there’s a treasure map up there that will set you on the path to an incredible adventure. When you read a book like The Phantom Tollbooth though, it allows you to remember what these whimsical daydreams were like, and even invites you to indulge in one as you journey with Milo to a surprisingly unique fantastical land.

The Story

Like most good children’s books, the plot of The Phantom Tollbooth is as clever as it is bonkers.

At the start of the story, Milo is having a typically mundane day when he receives a package that includes a turnpike tollbooth, which when passed through will take him to a magical world, a map of that world, as well as a book of rules and traffic regulations that must be followed at all times. As it so happens, Milo has a small electric car he’s able to drive and so, with a shrug of his shoulders and a comment about how there’s nothing else to do, he promptly sets off, heedless of whatever dangers lay ahead. Once he passes through the strange portal, it isn’t long before he starts to meet some strange characters and even make a couple of friends. The first person he crosses paths with is called the Whether Man, a typically frantic character who certainly can’t tell you anything about the weather, but rather, considers it his job to move people along whether they like it or not. Rushed on with little sympathy, Milo finds himself lost in a land known as the Doldrums. Luckily enough, a character called the Watchdog shows up who barks at him, offended to witness a boy killing time, and insists if Milo wants to get anywhere he’ll have to do some thinking. So Milo does think; of birds and fish and what he had for breakfast and words that start with J. Sure enough, with this little discovery of internal magic, Milo’s car engine buzzes to life, and off the Watchdog and he go to Dictionopolis, a city where the pun really gets started. There, we meet a Spelling Bee, who, you guessed it, is a bee that has the somewhat annoying habit of spelling everything that’s said. The Humbug, another character based on an old-fashioned phrase, is an uppidity insect who isn’t easily impressed by anything on the journey he’s about to join. Nevertheless, when he accompanies Milo and the Watchdog on their zigzagging trip, he provides an ample amount of curmudgeonly humour as they realise if they want anything in this crazy world to make sense, they’re going to have to fight for the return of Rhyme and Reason, a pair of princesses who helped to maintain peaceful relations between Dictionopolis and it’s mathematical counterpart, Digitopolis, where Milo learns the impressive fact that if a beaver two feet long with a tail a foot and a half long can build a dam twelve feet high and six feet wide in two days, all you would need to build human-sized Dam is a beaver sixty-eight feet long with a fifty-one-foot tail.

Suffice it to say, the whole thing follows a story structure that might have been put together by a child, you know, ‘This happened then this happened then this happened…’ And there’s practically an exhausting amount of wordplay and number tricks that can act as kindling for a kid’s imagination. But there’s also a series of absolutely surreal moments that would have fit quite quite well into a Salvador Dali and Walt Disney collaboration, such as when Milo becomes the conductor of an orchestra whose musical instruments imbue the world with colour, that is of course until Milo loses control of the musicians and what was going to be a beautiful painting at sunrise turns the entire universe into a discordant muddy brown.

All in all, the book is so dense with ideas and double-meanings that I think any child who tries to tackle it would want to be of a pretty high reading level, but that in itself is a hint as to how it’s probably best enjoyed. By that I mean, it’s an ideal experience when read as a bedtime story. There’s so many clever asides, so many characters and silly references packed into each and every line that it’s the perfect way for an adult to inspire a sense of mischievousness in a lot of stuff like reading and mathematics that at one stage or another will have probably bored their child. Even so, whether it’s a trip you’re taking with your kid, or one they’re able to take alone, it’s not short on the most important elements any adventure should have. That is, each chapter contains a tantalising mystery as to what’s around the next corner, there’s an awesome a map to help Milo and the reader find their way, and, most importantly, there’s a dog who it doesn’t take long to think of as both a vigilant protector and a loyal best friend. 

Then and Now

I think at this point it’s fair to say, you probably get why The Phantom Tollbooth is a great book for a younger reader, but given that I never actually read the book when I was a kid myself, it is a bit curious that it conjures up so much nostalgia for me.I suppose a part of it is because whatever age you’re at, it’s important to let a little chaos into your life when your day to day routine becomes too structured. The older you get the more things fall into this predictable pattern and, frankly speaking, the less you look at the world around you and gawk at it in awe. On top of that, nostalgia itself has become such a commodity in popular culture that for the most part the sensation has been kind of sucked dry from me. For instance, I quite liked Star Wars when I was a kid. I inherited a Millenium Falcon toy from my older brothers, and even before I saw the movie, I can remember what it felt like to land the thing in the needles of our Christmas tree and bounce the Han Solo figure from branch to branch like he was hopping around some pine scented moon. Well, that’s a feeling that Hollywood has obviously dug up and trotted about like some harlet zombie a fair few times now. I’ve lost count of how many Star Wars movies have been released in the past few years and with each one it becomes harder and harder not to see the corporate hands milking the nostalgia juice dry. I gather people feel much the same about Disney’s live-action remakes of their animated classics, and the less said about the Jurassic Park reboot the better. Untouched by all that though is this delightful little experience; The Phantom Tollbooth, a book that reminds you that the ultimate point of existence isn’t to save the world. That not every journey has to include the perils of life and death. And that really, some of the purest joys in life come from the simple realisation that the biggest number imaginable is always one more bigger than you can think of and that if you jump to many conclusions you’ll probably end up somewhere you don’t belong. I suppose I could get a little pretentious and point out how a lot of these silly ideas have the grains of genius in them, to the extent that the nearest comparison I can think to draw in the field of more mature fiction is the work of Jorges Luis Borges, who wrote these kind of surreal kafkaesque stories about infinite libraries and such. Because really, the biggest difference between Borges and Norton Juster that I can think of is that the former tried to get a nod of the head from the world of academics, while the latter preferred to nudge a giggle out of a child.

Media Source List – Music And Movies Used In Video

Lullabye by Aaron Kenny
Hulu Ukulele by
Chris Haugen
Majesty by
Spazz Cardigan

The NeverEnding Story (1984)
Wallace & Gromit: The Curse of the Were-Rabbit (2005)
The Phantom Tollbooth (1970)
Kindergarten Cop (1990)
The Invisible Man (2020)
The Goonies (1985)
Destino (2003)
Fantasia (1940)
The Tree of Life (2011)
Matinee (1993)
Beauty and the Beast (2017)
Interstellar (2014)


Simon Fay

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