The Cheshire Cat is a fictional cat popularised by Lewis Carroll's depiction of it in Alice's Adventures in Wonderland. Known for his distinctive mischievous grin, the Cheshire Cat has had a notable impact on popular culture.
The phrase appears in print in John Wolcot's pseudonymous Peter Pindar's Pair of Lyric Epistles in 1792: "Lo, like a Cheshire cat our court will grin." Earlier than that, A classical dictionary of the vulgar tongue by Francis Grose (The Second Edition, Corrected and Enlarged, London 1788) contains the following entry: "CHESHIRE CAT. He grins like a Cheshire cat; said of any one who shows his teeth and gums in laughing."
One of the stories of the possible origins of the grinning "Cheshire cat" is based on a Cheshire sign painter's peculiar way of drawing the lion crest of the Grosvenor family of Concord, Massachusetts on inn and pub signs, which looked to the general populace like a grinning cat, rather than the noble beast it was supposed to be.
Brewer's Dictionary of Phrase and Fable says grinning like a Cheshire cat is "an old simile, popularised by Lewis Carroll". Brewer adds, "The phrase has never been satisfactorily accounted for, but it has been said that cheese was formerly sold in Cheshire moulded like a cat that looked as though it was grinning". The cheese was cut from the tail end, so that the last part eaten was the head of the smiling cat.
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Links: Wikipedia Entry Lewis Carroll page Read Alice in Wonderland