Early references to the grinning Cheshire cat
The allusion to the expression by "Peter Pindar" (John Wolcot) appears in The Edinburgh Magazine (September 1792), where it appears as an extract from "A Pair of Lyric Epistles to Lord Macartney and his Ship":
Yet, if successful, thou wilt be ador'd—/ Lo, like a Cheshire cat our Court will grin!/ How glad to find as many gems on board,/ As will not leave thee room to stick a pin!
Interestingly, a slightly different wording appears in an untitled item in The London Chronicle (August 30, 1792):
This Day was published. Price 1s. 6d. A PAIR of LYRIC EPISTLES to Lord MACARTNEY and his SHIP. BY PERTER PINDAR, Esq.
O, if successful, thou wilt be ador'd! / Wide as a CHESHIRE CAT our COURT will grin, / To find as many Pearls and Gems on board / As will not leave thee room to stick a pin
Another early instance is in a letter from Charles Lamb to Thomas Manning (February 26, 1808):
I made a pun the other day, and palmed it upon Holcroft, who grinned like a Cheshire cat. (Why do cats grin in Cheshire? Because it was once a county palatine, and the cats cannot help laughing whenever they think of it, though I see no great joke in it.)
A county palatine is a district ruled by a noblemen with some degree of autonomy from the crown.
The earliest match in the British Newspaper Archive Collection is from the Kentish Weekly Post or Canterbury Journal (September 5, 1809):
...and having spread his pills in certain magical directions on the parlour floor, he pulled out his square box of sand, formed a horoscope, pronounced several cabalistic words, fetched some deep groans, gave some talismanic knocks on the door, and, finally, distorting his countenance, and grinning like a Cheshire cat, he exclaimed, You are a happy thrice happy man! your house is so swarmd with rats, both young and old, that in a few days you should, together with your family have been devoured outright; but all's well—my art will overcome all!
Also, from "Sketches of English Manners," in the Westmoreland Gazette (March 13, 1819):
For example, when I went out to the library t'other day, there you stood like a stake, staring like a stuck pig, and grinning like a Cheshire cat, instead of having a respectful and composed compearance, and putting your hand to your hat!
And from "Bristol Imports," in the Bristol Mirror (January 22, 1825):
every day making all the wry faces in the world; one day having the mouth and chin drawn up, another grinning like a Cheshire cat. Now this expression won't do for The Lancet. (Here the whole class laughed, in which the lecturer himself heartily joined.)
There are numerous additional matches for the phrase from the first half of the nineteenth century in the British newspaper archives. The first instance to reach Australia is from "The Safety, or Plenipo Pills" in the [Sydney, New South Wales] Australian (March 6, 1835):
So confident indeed were the party of the horse winning the Derby, though others, not in the secret, thought him too fat to go to the distance, that they would not edge one shilling of their money; but, on the contrary, Sam, with his hat agee, and grinning like a Cheshire cat at a piece of cheese, and their other Commission Agent, kept backing him at the short odds of 2 and 3 to 1 up to the time of starting. Well, he won the Derby cleverly; beating Shilelah and a large field ; and the public were told and believed — -and, if we mistake not, still believe — there had not been such a horse foaled since Eclipse.
Back to England, from Matthew Barker, Jem Bunt (1841):
Now it so happened that during this process of beheading [the mastheads of some captured Dutch vessels], one of the jolly tars, a messmate of Bilberry's, espied a curious misshapen monster, that, grinning like a Cheshire cat, adorned the windlass of one of the schuyts.
Two other fairly early books about Englishmen at sea or abroad in the empire—Jack Ariel, Or, Life on Board an Indiaman (1847) and Ten years in India; or, The Life of a Young Officer (1850)—use the phrase, too.
From Punch, or the London Charivari (January–June 1843):
Interesting Extract from the Last Bridgewater Treatise. By Professor Kirby.—Such is now the progress of general knowledge, that the nation is absolutely losing its ancient vulgarisms. No person, however limited his education, would now inquire the precise meaning of the phrase "a brace of shakes." No one, in these days, would observe that his risible friend "grinned like a Cheshire cat:" nor would any person, to express his alacrity, state that he would be with you "in a pig's whisper," or "the twinkling of a bed-post." The most simple child, in those times, would disdain to inquire for either "pigeon's milk" or "strap oil;" and at the same moment would not acknowledge that he was "as silent as a church mouse."
Charles Hervey, "The Habitue's Note-book," in The New Monthly Magazine and Humorist, volume 88 (1850) adds an interesting footnote about the mythology of Cheshire cats pre–Lewis Carroll:
*They say that nothing kills a Cheshire cat.
Notes and Queries (July 17, 1852, includes this brief response and follow-up query from Juvenis to an earlier query about it origin:
Grinning like a Cheshire Cat (Vol. v., p. 402). —The form in which I have heard this expression is "Grinning like a Cheshire cat chewing gravel." Are the last two words merely the addition of some enterprising genius, or are they part of the original simile?
W. M. Thackeray, The Newcomes: Memoirs of a Most Respectable Family (1855) has this instance:
For her own part, Rosey is pleased with every thing in nature. Does she love music? O, yes. Bellini and Donizetti? O, yes. Dancing? they had no dancing at Grandmamma's, but she adores dancing, and Mr. Clive dances very well, indeed. (A smile from Miss Ethel at this admission). Does she like the country? O, she is so happy in the country! London? London is delightful, and so is the sea-side. She does not know really hat she likes best, London or the country, for mamma is not near her to decide, being engaged to Sir Brian, who is laying down the law to her, and smiling, smiling with all her might. In fact, Mr. Newcome says to Mr. Pendennis in his droll, humorous way, " That woman grins like a Cheshire cat." Who was the naturalist who first discovered that peculiarity of the cats in Cheshire!
[Manchester] City News Notes and Queries (1878) includes this interesting note from a former resident of Cheshire, published on August 3, 1878):
GRINNING LIKE A CHESHIRE CAT.—Perhaps some of your readers, whether naturalists or not, may be able to shed some light upon this saying. I have lived in Cheshire, but have only heard the saying since I came to Lancashire.
Similarly John Harland & Thomas Wilkinson, Lancashire Legends, Traditions, Pageants, Sports, &c. lists "Grinning like a Cheshire cat chewing gravel" under the subheading "Lancashire sayings."
Early references to the grinning chessy cat
No one talks much about chessy cats these days, but Google Books matches from U.S. sources for that alternative to Cheshire cat are more frequent than matches for Cheshire cat in the period before Lewis Carroll's Cheshire cat arrived on the literary scene (in 1865). The earliest instance that a Google Books search finds is from Thomas Halliburton, The Clockmaker: The Sayings and Doings of Samuel Slick of Slickville (1837):
Well they were gathered there according to orders, they looked streaked enough you may depend, thinkin they were going to get it all round, and the wenches they fell to a cryin, wringin their hands , and boo-hooing like mad. Lavender was there with his cowskin, grinnin like a chessy cat, and crackin it about, ready for business.
From Joseph Neal, Charcoal Sketches; or, Scenes in a Metropolis (1838):
"Never mind," said Ripton, as he was conducted from the office, "everything goes round in this world. Perhaps I'll be stuck up some day on a bench to ladle out law to the loafers. Who knows? Then let me have a holt of some of the chaps that made Miamensin. I'd ladle out the law to 'em so hot, they'd not send their plates for more soup in a hurry. I'd have a whole bucketful of catnip tea alongside, and the way they'd ketch thirty days, and thirty days a top of that, would make 'em grin like chessy cats. First I'd bag all the Charleys, and then I'd bag all the mayors, and sew 'em up."
From Thomas Halliburton, The Clockmaker: Sayings and Doings of Samuel Slick of Slickville in Bentley's Miscellany (1840):
Snowball, says I, have you seen any thing of the Major? where on earth is he? I'm waitin' for him to settle the bill.—Massa hab to wait den one berry long time, sar: de last iseter, sar, he always fix Major's flint, sar, and make him cut his stick. You won't see him no more, sar; and he grinned from ear to ear like a chessy-cat. De bill is four dollar, massa, and a quarter-dollar for Snowball—
From Geoge Lippard, Paul Ardenheim, the Monk of Wissahikon (1848):
Betsy was a widow; Betsy had no care; Betsy had teeth like pearls; therefore Betsy laughed.
Don't mindt te gal, Dominie," exclaimed Jake, " It's her way. Always grinnin' like a chessy-cat."
From "The Bunkum Flagstaff and Independent Echo," in The Knickerbocker (October 1849):
We suppose you never seen a colored man's countenance so brighten up. A load seemed to be taken from his stomack to once-t. First he grinned like a chessy cat, and then laughed right eöut. 'Lyin', says the old gennelman. "Is that all? why missy, says he, lookin' at our wife, they will do that!"
Several other examples from 1849 and 1850 come from U.S. sources as do others over the second half of the 1800s. A search of the British Newspaper Archive, however, finds only three matches for "chessy cat" through the year 1892, all of them in stories imported from the United States. This should put to rest a theory floated in American Notes and Queries (November 9, 1889) that chessy cat may have been the original wording and Cheshire cat the variant:
Cheshire Cat.—This animal, familiar by name to all readers of "Alice in Wonderland," has found a place in the "Century Dictionary" under CAT. Fifty years ago, in New England, we used to hear that expression, "Grinning like a Chessy cat." Now, the town of Chertsey, on the Thames, is vulgarly called Chessy; and the question arises whether the ringent feline did not originally belong to Chertsey rather than to Cheshire.
On the subject of chessy cats, L.J. Vance of New York city sent the following note to American Notes and Queries (November 18, 1889):
Last summer while spending a few days' vacation in Central New York, I heard a current expression, which, at first blush, I regarded as a local usage. Thus, when any person smiled in a particularly annoying or provoking manner, he or she was said to "grin like a Chessy (pronounced often Jessy) cat." I have since found that the phrase comes of Good old English origin, namely, "he grinned like a Cheshire cat?" But why like a Cheshire cat?
Theories of how the expression arose
Stepping through the history of theories about what the phrase means, we have first this reply by T.D. to a query about its origin in Notes and Queries (November 16, 1850, page 412):
Cheshire Cat (Vol. ii., p. 377).—A correspondent, T. E. L. P. B. T., asks the explanation of the phrase "grinning like a Cheshire cat." Some years since Cheshire cheeses were sold in this town moulded into the shape of a cat, bristles being inserted to represent the whiskers. This may possibly have originated the saying.
Next, a reply by H. to the same earlier query, in Notes and Queries (April 24, 1851, page 402):
Grinning like a Cheshire Cat (Vol ii., pp. 377, 412.). In one of your early numbers I have seen some Queries respecting the phrase "Grinning like a Cheshire Cat." I remember to have heard many years ago, that it owes it origin to the unhappy attempts of a sign painter of that county to represent a lion rampant, which was the crest of an influential family, on the sign-boards of many of the inns. The resemblance of these lions to cats caused them to be generally called by the more ignoble name. A similar case is to be found in the village of Charlton, between Pewsey and Devizes, Wiltshire. A public-house, by the road side, is commonly known by the name of The Cat at Charlton. The sign of the house was originally a lion or tiger or some such animal, the crest of Sir Edward Poore."
From Egerton Leigh, A Glossary of Words Used in the Dialect of Cheshire (1877):
CHESHIRE CAT, s.—"To grin like a Cheshire cat" is a very old saying, and like many old sayings, the origin is doubtful. Another version is "to grin like a Cheshire cat chewing gravel:" In the Dictionary of Modern Slang is the following: "'To grin like a Cheshire cat' is to display the teeth and gums whilst laughing (à la Tim Bobbin)." Another hardly satisfactory explanation has been given of the saying, "that Cheshire is a οξιμορων γελασασα, "Death grinned horribly a ghastly smile." Still another amplified version is "to grin like a Cheshire cat eating cheese." This may be supposed to produce a smile of satisfaction rather than a grin of disgust.
From Alfred Rimmer, Our Old Country Towns (1881):
The extinct, or nearly extinct, wild animals, such as the badger and wild-cat, lingered here [on the peninsula of Cheshire that lies between the Mersey and the Dee] longer than in other parts, and some years since a veritable specimen of the latter was shot on Peckforton Moss by a friend of the writer's. It was much heavier than any domestic cat, and some naturalists say that the wild-cat was of a different species. The face and mouth were very wide, and so ferocious did they look when disturbed, that it was easy to see why to "grin like a Cheshire cat" is yet a common proverb in the north of England.
One need not go far to account for a Cheshire cat grinning. A cat's paradise must naturally be placed in a county like Cheshire, flowing with milk.
From a reply by Alfred Burton in Cheshire Notes and Queries (February 11, 1882):
The origin of many of our common sayings is so obscure that we can do little more than guess at it; but it is more easy to give their variations. In my note-book I have the saying, "Grinning like a Cheshire cat when it smells cheese;" but why a cat, and a Cheshire one above all others, should grin when it smells cheese, I am unable to conjecture, except that it is conscious of the good thing in prospect. ... Another version is "To grin like a Cheshire cat chewing gravel," a feat which I have not found recorded in any work on natural history, and must be a rara avis.
From Robert Holland, A Glossary of Words Used in the County of Chester (1886):
The origin of the saying is unknown, though various conjectures, more or less fanciful have been hazarded. ... It is possible, however, that the arms of the Earls of Chester, namely a wolf's head, may have suggested the phrase; for I am bound to say that in the engraving of the coat of arms of Hugh Lupus, as given by Sir Peter Leycester, the wolf's head might very well be mistaken for that of a cat; while the grin is unmistakeable.
The 1792 poem by Peter Pindat remains the earliest authenticated print occurrence for "grin like a Cheshire cat," although various sources form the following century insist that the expression is much older than that—and the fact that Charles Lamb in 1808 speculates about why cats in Cheshire smile—rather than why Peter Pindar thinks they do—strengthens the impression that the saying is quite old.
The expression seems almost certainly to have originated in England (although not necessarily in Cheshire, as early recorded discussions of the term more often identify Lancashire as the place where country folk used it idiomatically. It soon (by 1838) popped up in the United States, as well, although more commonly in the form chessy cat than Cheshire cat. It is certainly possible that it came over from England in the eighteenth century as Cheshire cat and mutated into chessy cat at some point owing to isolation of the expression in parts of colonies.
Lewis Carroll's Cheshire cat character is Alice in Wonderland (1865) soon became the dominant reference point for the behavior of the magical grinning felines, even when the terminology remained distinct. Thus, for example, a pontificating character in "A reminiscence of Browning," in The Occident (1889) offers this discourse:
Mr. Delsarto hurriedly turned to the notes—"Ah! here the editor says Alice typifies the soul of man, or the evolution of nature and the way the Cheshire Cats' grin comes and goes is a proof of the immortality of the soul. I see he refers to the re-appearances of the Holy Grail, but I hardly thought it worth while to look up so trivial a reference. You remember the Chessy Cat began to vanish at the end of its tail and the grin vanished last of all. Well I think that is a symbol of the final triumph of good over evil—like the rainbow. It makes me think of 'Her Sweet smile haunts me still.'"
suggesting (if nothing else) that Americans had no trouble shifting back and forth between Carroll's Cheshire cat and their more familiar chessy cat.
None of the explanations for how the expression came into being is particularly persuasive. One possibility is that the word Cheshire is a local-color stand-in for a different adjective, such as angry. A very popular nineteenth-century guide to zoology was that passed through many editions under many titles and several credited authors (including Oliver Goldsmith, Thomas Smith, F.L. Pearce, and William Bingley) between 1803 and 1879 includes a passage about the sea otter. From William Bingley, Animal Biography, Or, Authentic Anecdotes of the Lives, Manners, and Economy, of the Animal Creation volume 1 (1803):
They make no resistance, but, when attacked, endeavour to save themselves by flight: when, however, they are closely pressed, and can see no means of escape, they scold and grin like an angry Cat. On receiving a blow, they immediately lie on their side, draw up their hind legs together, cover their eyes with their fore paws, and thus make ready to die.
So it may be that the original Cheshire cat grinned not because it was feeling jovial but because it was angry. A Cheshire cat might thus be the feline equivalent of a junkyard dog. This interpretation would explain the extended form "grin like a Cheshire cat chewing gravel"—a grin that may well be one of fury. On the other hand, the fairly early emergence of the very different form "grin like a Cheshire cat eating [or smelling] cheese" suggests that folk opinion about why the cat was grinning diverged long ago.
Update (February 13, 2022)
Belatedly following up on user65692's comment above noting an occurrence in Francis Grose, A Classical Dictionary of the Vulgar Tongue, second edition (1788), I checked that reference work and found this entry:
CHESHIRE CAT. He grins like a Cheshire cat ; said of any one who shews his teeth and gums in laughing.
This entry suggests that the expression "He grins like a Cheshire cat" was a commonplace among what Grose calls "the great vulgar." Nevertheless, the entry for "Cheshire cat" does not appear in the first edition of Grose's dictionary (1785), so it remains unclear whether the expression "grin like a Cheshire cat" was omitted by oversight or because it arose in the 1780s and had not come to Grose's attention in 1785.
Another early occurrence of the expression appears in anonymous, The Observant Pedestrian; Or, Traits of the Heart (1795):
I should like to see the boy," said I, "and hear his own story."
"Oh, I makes him fag I promise you, you'll see him come in with your supper, I keep his heels from swelling, and yet he is always happy, and hard at it from morn to night, grinning like a Cheshire cat."
And another appears in Miss Hutchinson, Exhibitions of the Heart ; A Novel, volume 2 (1799):
From the ball-room, Lady Beaufort's attention was called to the card-tables by young Sinclair—"For God's sake, Lady Beaufort," whispered Sinclair, "come with me : I've been ready to die with laughter at Mrs. Farrinton.—You know she is passionately fond of foreigners; and although she can hardly speak a word of French, she is always the first to intrude herself among them : to-night she is in her glory: dem'me, the old lady is grinning like a Cheshire cat; she has got no less than three French chevaliers at her table : do pray come, you will be much amused."
These early instances suggest that "grin like a Cheshire cat" was used by members of very different social classes in England from an early date—from the coarse innkeeper in the anonymous 1795 travelogue (or quasi-travelogue) to the upper-class acquaintance of Lady Beaufort in Miss Hutchinson's 1799 novel.
Still the earliest confirmed instance of the expression in print is in the second edition of Grose's Classical Dictionary of the Vulgar Tongue (1788), which treats it as a popular simile.