The story starts off with a young boy staying up late drawing pictures of a boy named Simon being chased by a large and scary monster. But then, the boy falls asleep before he can complete the drawing. Within a few minutes, a pair of pens and an ink bottle come to life and meet up with Simon in the drawing. Unfortunately, Simon, the pens and the ink bottle ended up being chased by the large monster throughout the book, and the whole story comes to a surprising conclusion.
Simon's Book provides examples of:
- Adorkable: Simon and his companions, the ink bottle and the pens.
- Animate Inanimate Object: The pens and ink bottle that suddenly came to life in the middle of the night.
- Dark Is Not Evil: The monster that chases Simon and his friends is pretty scary, but it turns out to be friendly at the end.
- Gentle Giant: At first, the monster was pretty frightening as it chased Simon and his friends throughout the book, however, when the monster turns out to be friendly, it becomes friends with Simon, the pens and the ink bottle..
- Grotesque Gallery: The two pens and the ink bottle that suddenly come to life and the monster (who looks like a large warthog) that chases Simon and his friends throughout the book.
- Knight of Cerebus: Subverted with the warthog monster. When the warthog monster first shows up, the story becomes darker and more intense as the monster starts chasing Simon and his friends throughout the book. However, when it turns out that the monster is actually friendly, the story becomes sweet and heartwarming.
- Mind Screw: So, the pens and the ink bottle suddenly come to life in the middle of the night and they save Simon from the monster. However, the ending implied that it was the pens and the ink bottle that finished the story that the young boy was trying to finish. WHAT?
- Mood Whiplash: The book started off as being extremely intense, especially when the monster started chasing Simon and his friends, but when the monster reveals himself to be friendly, the mood of the story turns sweet and heartwarming.
- Oh, Crap!: The expressions that Simon, the pens and ink bottle all showed when the monster showed up.
- Ragtag Bunch of Misfits: Simon and his friends. Simon is a human boy who befriends two ink pens and an ink bottle. They also become friends with a giant warthog monster at the end!
- Surreal Horror: A drawing of a monster coming to life in the middle of the night and then chasing a young boy and his friends is something that would come straight out of a bizarre dream.