Harold and the Purple Crayon by Crockett Johnson is a classic.
The Salamander Room by Anne Mazer, illustrated by Steven Johnson and Lou Fancher, is one of my favorites.
Both books go "meta" as they explore an inevitable interest for illustrators and writers: the act of creation. I would argue that all artists are drawn to exploring this idea at some point. In other words, all of us, no matter what are abilities, are at some point drawn to a story or illustration that breaks the third or fourth wall to explore what makes creation work.
The concept can be taken too far. Gatiss's scripts for BBC Sherlock are fascinating since they explore the legend of Sherlock as much as they tell a story. But after one episode, the viewer (me) wants story, not more literary exegesis. Similar to characters addressing the camera, a little goes a very long way. Even the relatively benign narrators of nineteenth century literature--the ones who break "character" and speak directly to the reader--can get in the way.
Still, when lovingly done, the exploration of the question, "How does art come about?" can be fascinating.
Harold and the Purple Crayon is classic, in part because Crockett Johnson never breaks out of Harold's meta-world. Harold draws himself into bed. In comparison, at the end of Aaron Becker's Journey--in which a young girl uses a red crayon--the girl returns to the "real" world and finds a friend.
The Salamander Room is the most self-contained of the books. The boy imagines the room in response to questions from his mother as he goes to bed. He paints for himself a forest world. There's no embedded lesson. No returning to or, for that matter, leaving of reality. The boy is allowed to imagine a new world in the way that children do.
When I was a child, I imagined living in a huge tree, much like the boy in My Side of the Mountain (Jean Craighead George) except my desire was far less pragmatic. I had no intention of capturing and cooking my food. I also wasn't thinking, "I'm going to go do that some day." I was letting my imagination roam.That is The Salamander Room.
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