Milo mopes in black ink sketches, until he assembles a tollbooth and drives through. He jumps to the island of Conclusions. But brothers King Azaz of Dictionopolis and the Mathemagician of Digitopolis war over words and numbers. Joined by ticking watchdog Tock and adult-size Humbug, Milo rescues the Princesses of Rhyme and Reason, and learns to enjoy life.

Oh how I wished I had read this book when I was younger! (perhaps not young you understand, just younger). What have I been missing? I heard about this book several times on book related podcasts, such as NPR and it was only whilst I was doing a trawl through the local children's department for Christmas presents that I saw the 50th anniversary edition out on a table. Well, the child I was buying for never got it (he'll live), and it was slipped onto my TBR shelf.

The Wikipedia page is here. I also found several reviews of the book (I wont talk about the film as I currently dont intend to see it), one from the UK in the form of The Guardian newspaper and one from Michael Chabon, writing in the New York Review of Books.

Essentially Milo starts the book as a child who does no independent thinking, dreaming, learning, abandons his toys almost immediately after getting them, and generally wastes his childhood doing not much. He returns home one day to find a gift in his bedroom. After building what turns out to be a toy tollbooth, he drives his little car through and into another world, called Wisdom.

The world is made up of several different cities - Dictionopolis (the city of words) and Digitopolis (the city of numbers), and things have never been right since the Princess Rhyme and Princess Reason were banished to the City in the Air. Milo, with Tock the (watch)dog, and Humbug, are sent to rescue the two Princesses and so travel across the land.

Along the way, the three of them encounter various different characters including: Faintly Macbre, the Not-So-Wicked Which. who regulated all words used in public, but became so stingy with them that people became afraid to talk at all; Dr. Kakofonous A. Dischord, a scientist who enjoys creating unpleasant sounds, and curing pleasant sounds; The Soundkeeper, who loves silence, rules the Valley of Sound - her vaults keep all the sounds ever made in history; Alec Bings, a boy of Milo's age and weight who sees through things - he grows downwards from a fixed point in the air until he reaches the ground, unlike Milo, who grows upwards from the ground.

The book is written in such a way that it can take a while to realise you're being taught a little truth (e.g. that if jump to Conclusions, it's not a pretty place and it's tiring work to get away from it). He rescues the Princesses - who were after all, simply McGuffins - and returns home. He is sad to see that the Tollbooth has disappeared - only to realise that he no longer needs it as he has so many new worlds to explore without it!

Few books are so full of ideas, ideas well told by fitting them into interesting stories. ( )

An irreverent and funny adventure reminiscent of the OZ series by Baum.

Milo is a bored little boy who discovers a mysterious tollbooth in his room one day. He decides to drive his toy car through it because he couldn't think of anything better to do and he ends up in a fantastical world and undertakes a journey to bring peace back to the people he meets.

I never read this book as a kid. I don't know why because I have heard of it. I don't know if the author was influenced by Baum's OZ series, but it wouldn't surprise me to find out that he was. There is the same kind of humor and literalness in the naming of the characters that Milo meets.

There are morals scattered throughout which reminded me of Aesop's Fables. Overall, I think it's a wonderful book full of puns and double meanings. ( )

I probably read this way too late in life, so it didn’t quite grab me. It’s very Alice in Wonderland/Wizard of Oz. But the last page or so was beautiful. ( )

A classic kid’s book, that the kid and I just read together. So many puns and so much delight!‬ ( )