Milo - A boy (can be played by a girl) who is uninterested in everything around him but is pulled from his boredom when his dresser magically transforms into The Tollbooth. Starring role that requires a very large commitment outside of rehearsals. Multiple solos and lots of lines. Remains onstage for most of the performance.
Demons - The Demons are evil characters who try to keep Milo from doing what he wants to do. Demons have speaking parts and group singing.
The Tollbooth - Instructs Milo on how to begin his travels. Has a couple of lines and sings an entire song alone. May be able to take on other roles in the play as well.
Whether Man - Eccentric individual not to be confused with a weather man! Speaking parts and a short solo.
Narrators - Non singing parts that require focus and good public speaking skills.
Lethargians - Slow motion, unmotivated, incredibly lackadaisical beings. Speaking parts and group singing.
Tock - Extremely energetic, lovable dog. Must be very physical, crawling and sliding across the floor. Large speaking role. Group singing and very short solo. This role is good for a confident actor who can memorize lots of lines but does not feel comfortable with a large singing role.
Azaz - The King of Words who does not want to work with his brother, the Mathemagician. Large speaking role and a few vocal solos required.
Mathemagician - The King of Numbers who does not want to work with his brother, Azaz. Large speaking role and a few vocal solos required.
Rhyme and Reason - The princesses banished to the Castle in the Air. Speaking parts and group singing or option for solo.
Guard, Page, Advisors, and Lackeys - Subjects of the Royal Kingdom. All non singing roles and may be able to take on other roles in the play.
Miners - Subjects of Digitopolis. Acting should be very silly! Speaking parts and group singing with optional solos.