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'Cheshire grin' seems to be a phrase derived directly from the famous grinning Cheshire Cat in Alice in Wonderland. The cat was itself based on the well known phrase 'grin like a Cheshire cat'.

So a 'Cheshire grin' is an enormous grin, reminiscent of the Cheshire Cat's.

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What character from Alice in wonderland had an enourmous grin?

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