D&D 5E Epic Monsters: Cheshire Cat

We all know the grin of today’s entry in Epic Monsters, but there is much about this mysterious creature that will surprise you—like how its first appearance was not in Alice’s Adventures in Wonderland. Are you intrigued? Good because I think it’d like that. Click onward for the Cheshire Cat!

Cheshire Cat DnD5e BANNER.jpg


A quick note: Thank you to everyone who pledged to or shared the Mythological Figures & Maleficent Monsters Kickstarter. We are all crazy happy about how well the project went and can’t wait to see folks get their copies of the book. You are great human beings!

British readers of the column: this won’t be quite as fun for you as you might already know that “grinning like a Cheshire Cat” has been a phrase in your soggy lands for some time before 1865. First off there’s a county in England called Cheshire that’s long been known for its dairy farms, and a happy milk-and-cream-filled cat is a grinning cat! If we’re believing Brewer’s Dictionary, "it has been said that cheese was formerly sold in Cheshire moulded like a cat that looked as though it was grinning," and the practice of eating started at the tail and ended with its smiling head.

However, public-houses and inns in Cheshire (and the village of Charlton) might have spawned it, being associated with cats for various reasons (either by their name like “The Cat at Charlton” or a degraded lion crest or tiger crest of an associated family). Looking back to the 1788 work by Francis Grose, A Classical Dictionary of the Vulgar Tongue, Second, Corrected, and Enlarged Edition, you can find an entry for Cheshire cat: “He grins like a Cheshire cat; said of any one who shows his teeth and gums in laughing.” Four years later in Jon Wolcot’s Peter Pindar’s Pair of Lyric Epistles again we get another literary reference: "Lo, like a Cheshire cat our court will grin." A decade before Carrol’s big work comes out, in William Thackeray’s The Newcomes, again we get a third literary reference: "That woman grins like a Cheshire cat."

In my opinion the most likely source of these references is rooted in the first suggestion and the (apparently widely used) phrase “grinning like a cat that got the cream” and the association with Cheshire County where dairy production in England has been central for a very long, long time. But what about the disappearing part? Hop in that time machine folks because we’re winding it way, way back, all the way to the 11th and 12th century where Cheshire received special borderland laws and notable independence from the crown for centuries. King’s Sheriffs chasing after criminals could not pursue them into Cheshire—which would certainly bring a grin to any thief’s face, and give us some due for this character’s disappearing act. Throw in that ancient languages show that ‘caitiff’ meant ‘cowardly or base villain; mean despicable fellow’, and that ‘cat’ meant ‘sharp fellow’ and it’s starting to congeal.

For everyone not in the United Kingdom, our first introduction to this concept and character came in Lewis Carroll’s Alice’s Adventures in Wonderland. The creature—cheerleader, philosopher, weirdo—stalks after the book’s young lady protagonist, quizzing her in odd ways as it disappears and reappears in different places. Where the novel’s character’s origins lay is murky. During Carroll’s time there was a professor at Oxford named Edward Pusey, known as the Patristic Caternay. Speaking of caternay, Carrol was a mathematician and must have known about the word’s alternate definition: the curve of a horizontally-suspended chain and same shape as a grin. Turning back onto the church again, a curious cat statue on the tower of St. Wilfrid’s Church less than 5 miles from where Lewis was born in Cheshire County (which he would’ve seen plenty with his father, Reverend Charles Dodgson, the Rector of Croft and Archdeacon of omg I’m bored with it already he was way into the church jfc). The final possibility we’re going to consider here is that it’s got to do with a breed of cat known as the British Shorthair that’s said to, when embarrassed, react by putting on a “Cheshire cat smile”.

Design Notes: Obviously this statblock began with a cat’s but it’s gone so very far from there. Staged Invisibility is what most people know the Cheshire Cat for and I think the trait I’ve whipped up for that is appropriate, however I endeavor to always keep entries in Epic Monsters interesting so I’ve woven in some other fun tidbits—short teleports with misty step, some detect thoughts to pester people, confusion because it seems right, and hellish rebuke is just so obviously made for felines. Magic Resistance and some limited general defenses (immunities and resistance to psychic damage) round things out for a surprisingly robust little monster. With that let’s take a look at the numbers! The DMG came in real low here at 2.5625 while the Blog of Holding hit a higher note at 4.2, averaging out all together to not quite halfway above 3. A fine monster to throw at some low level adventurers that won’t quickly become a corpse without some fun roleplay first!

Cheshire Cat
Tiny fey, chaotic neutral
Armor Class 14
Hit Points 36 (8d4+16)
Speed 40 ft., climb 30 ft.

STR
DEX
CON
INT
WIS
CHA
3 (–4)​
19 (+4)​
14 (+2)​
15 (+2)​
12 (+1)​
16 (+3)​

Saving Throws Dex +6, Wis +4, Cha +5
Skills Deception +7, Insight +3, Perception +3, Stealth +6
Damage Resistances psychic
Condition Immunities charmed, frightened
Senses darkvision 120 ft., passive Perception 13
Languages English, Sylvan
Challenge 3 (700 XP)

Innate Spellcasting. The Cheshire Cat’s innate spellcasting ability is Charisma (spell save DC 13). The Cheshire Cat can innately cast the following spells, requiring no material components:
At will: misty step, vicious mockery
3/day each: confusion, detect thoughts, hellish rebuke
Keen Smell. The Cheshire Cat has advantage on Wisdom (Perception) checks that rely on smell.

Magic Resistance. The Cheshire Cat has advantage on saving throws against spells and other magical effects.

Staged Invisibility. The Cheshire Cat uses an action to magically turn invisible, but it does so gradually. Before the end of its turn the Cheshire Cat’s body and any equipment it is carrying or wearing disappear, giving it +2 to AC. At the start of its next turn everything but the Cheshire Cat’s grin disappears, increasing its bonus to AC to +5. Finally at the start of the following turn the Cheshire Cat is completely invisible (no AC bonus). When it is fully invisible, the Cheshire Cat’s invisibility lasts until it attacks or its concentration ends (as if concentrating on a spell).


ACTIONS
Claws. Melee Weapon Attack: +0 to hit, reach 5 ft., one target. Hit: 1 slashing damage.
 

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Mike Myler

Mike Myler

Rafael Martin

Adventurer
Another great contribution to epic creatures, but if you are including the Chesire Cat, what about The Mad Hatter? I did a search on here and could not find it. If you have written up that character (who was played quite well by Johnny Depp) then please show it here. Otherwise, please write up the character ASAP!!!!
1596469222606.png
 

Mike Myler

Have you been to LevelUp5E.com yet?
Another great contribution to epic creatures, but if you are including the Chesire Cat, what about The Mad Hatter? I did a search on here and could not find it. If you have written up that character (who was played quite well by Johnny Depp) then please show it here. Otherwise, please write up the character ASAP!!!!
checks list
I think I need to do some preliminary work to make sure there's enough to bite into for it, but he's on the list until then. :)
 



Thirteenspades

Great Wyrm
We all know the grin of today’s entry in Epic Monsters, but there is much about this mysterious creature that will surprise you—like how its first appearance was not in Alice’s Adventures in Wonderland. Are you intrigued? Good because I think it’d like that. Click onward for the Cheshire Cat!
Is Epic Monsters for monsters from epics or monsters that are epic?
 


Mike Myler

Have you been to LevelUp5E.com yet?
Is Epic Monsters for monsters from epics or monsters that are epic?
It's really part of the Mythological Figures column (which runs the gamut from historical to legendary to literary), but we call it something different because the essential design rules are different (as you can see, CC here has no class levels and is built purely as a monster).
 



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