This is the first in a series of literary cat shout-outs I’ll be doing here, because we love cats here at The Book Broad (me. I love cats.), and there are a lot of wonderful fictional ones. And who better to start with than the OG:

A cat so famous he transcends his source material, the Cheshire Cat is known for his disappearing body and mischievous grin—the latter a representation of how all cats feel on the inside when they get one over on us, I would imagine.

Per Wikipedia, a possible origin of the phrase “grinning like a Cheshire Cat” is one favored by the people of Cheshire, a county in England that has a lot of dairy farms; hence the cat’s grin because of the abundance of milk and cream.

I’d also connect Cheshire’s smile to the “cat that ate the canary” idiom that means to look very smug and self-satisfied about something (naughty) you’ve done.

He debuted in the 1865 novel Alice’s Adventures in Wonderland by Lewis Carroll, which included illustrations by John Tenniel, and he’s made appearances in the 1951 Disney animated adaptation, Tim Burton’s 2010 live-action remake, and Burton’s Through the Looking Glass in 2016—not to mention countless other Alice adaptations, including television, video games, and comic books.

Cheshire first meets Alice at the Duchess’s house, and later he’s found in the branches of a tree, where he engages her in confusing conversation, raising philosophical points that sometimes annoy or perplex her. But in the end, when the Queen of Hearts sentences her to death, he has her back by creating a diversion with his floating head.

To be fair, he framed Alice for the prank that put her on trial for execution in the first place—make of that what you will.

He may be a little mad, but he knows something we don’t, and his biggest trick might be hiding the fact that he’s the sanest one of all.

“And how do you know that you’re mad?”

“To begin with,” said the Cat, “a dog’s not mad. You grant that?”

“I suppose so,” said Alice.

“Well then,” the Cat went on, “you see, a dog growls when it’s angry, and wags its tail when it’s pleased. Now I growl when I’m pleased, and wag my tail when I’m angry. Therefore I’m mad.”

―Lewis Carroll, Alice’s Adventures in Wonderland