The Cheshire Cat is Wonderland’s calm, smiling voice that appears when Alice needs a nudge, then fades away before she can ask too much. He can appear a piece at a time—first the grin, then the eyes—so he always feels half real and half idea. He speaks in a playful, even tone, as if nothing in this strange world can bother him.
He does not give clear answers; he gives angles. When Alice asks which way to go, he says it depends on where she wants to end up. When she wonders about sense, he says everyone here is mad, and explains it like a simple fact, not a threat. In this way he pushes Alice to think for herself. His riddles are not meant to confuse her for sport, but to show that logic still works, just not in the usual way.
As a character, the Cat is less a companion than a guide who never oversteps. He keeps his distance, offers a sly truth, and leaves Alice to choose. The lasting image is his grin hanging in the air after the rest of him is gone—a neat picture of Wonderland itself: the joke remains even when the teller has vanished.
‘Would you tell me, please, which way I ought to go from here?’ ‘That depends a good deal on where you want to get to,’ said the Cat. ‘I don’t much care where—’ said Alice. ‘Then it doesn’t matter which way you go,’ said the Cat.
fromAlice’s Adventures in WonderlandbyLewis Carroll