Milo is the main protagonist of The Phantom Tollbooth.
In the beginning of the book, Milo is characterised by his apathy. He is very bored and polite and has an closed mind, traits which are not revealed until his adventures in the Lands Beyond. Milo later realizes all of the greatness in the world and his personality improves. Milo can be tricked easily. One example was when he was in the Doldrums.
Tock was the closest friend Milo had in Wisdom. The Watchdog acted as a personal protector and mentor.
When Tock was killed by the Demons of Ignorance, Milo expressed much sadness sobbing over Tock. When Tock was revived, Milo was glad to see his friend alive.
Though the Humbug is not naturally friendly, Milo becomes attached to him throughout his travels as well.
The Whether Man
Milo met The Whether Man when he entered the new world. At first, he thought he was the weather man, but quickly found out he was the whether man. The whether man told Milo where to go in order to get to Dictionopolis.
When Milo first met Officer Short-Shrift, he found himself accused of many things like driving to fast (When he isn't even moving) and then when he protested against this, Short-Shrift then accused him of not moving.
At the ending when Rhyme and Reason were rescued, Short-Shrift had a new personality, seemingly being on good terms with Milo.
When in the Doldrums, Milo encountered the Lethargians who were small lazy creatures who did nothing all day but waste their time. Milo found the Lethargians' way of living ridiculous and concluded that they didn't want to get anything done which was exactly the way the Lethargians wanted it. During their time together, the Lethargians would snap at Milo for thinking, laughing and questioning their ways of living.
Milo, already being a boy bored with everything, decides to stay awhile with the Lethargians until Tock arrives scaring away the Lethargians and convinces Milo to start thinking.
In the movie, Milo was manipulated by the Lethargians (Who were portrayed as mischievous creatures in the movie) into staying with them by singing him to sleep and soon proceeded to join them by singing and falling asleep with them unaware of their intentions as they engulfed his car. Luckily, Tock arrived to save Milo and convinced him that the Lethargians didn't want him to think, eat or breathe. Realizing his error, Milo soon escaped the Doldrums with help from Tock.
During their encounter, Milo showed some politeness towards the Lethargians such as shaking one of their hands when first meeting them, holding one up as it nearly melted to the floor of his car and even showed some kindness towards them by tucking one to sleep with his shoulder though he was blissfully unaware of the Lethargians' true nature at the time.
- In the film, he has his own theme song.
- Milo lives in San Francisco, California, due to the fact he rode home from school on a trolley.