Cheshire Cat

Medium Fey, Chaotic Neutral

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Armor Class 17 (natural armor)
Hit Points 136 (16d8 + 64)
Speed 40 ft., climb 30 ft.

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STR	DEX	CON	INT	WIS	CHA
14 (+2)	20 (+5)	18 (+4)	16 (+3)	17 (+3)	20 (+5)

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Saving Throws Dex +9, Wis +7, Cha +9
Skills Perception +7, Stealth +13, Insight +7, Deception +9
Damage Resistances Psychic; bludgeoning, piercing, and slashing from nonmagical attacks
Damage Immunities Charm, Fear
Condition Immunities Charmed, Frightened, Grappled, Restrained
Senses Darkvision 120 ft., passive Perception 17
Languages Common, Sylvan, telepathy 120 ft.
Challenge 10 (5,900 XP) Proficiency Bonus +4

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Innate Spellcasting (Fey Magic)

The Cheshire Cat’s innate spellcasting ability is Charisma (spell save DC 17). It can innately cast the following spells, requiring no components:

• At will: Minor Illusion, Invisibility, Mage Hand, Prestidigitation
• 3/day each: Mirror Image, Blur, Misty Step, Confusion
• 1/day each: Phantasmal Killer, Greater Invisibility, Mislead

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Traits

Grin Without a Cat (Recharge 5–6).
As a bonus action, the Cheshire Cat disappears entirely, leaving behind only its iconic grin for 1 minute or until it chooses to end the effect (no action required). While active:

• The Cheshire Cat is invisible and cannot be targeted unless seen by true sight or similar magic.
• Creatures that start their turn within 30 feet of the grin must succeed on a DC 17 Wisdom saving throw or become frightened until the start of their next turn.
• The grin can be moved up to 30 feet as a bonus action.

Vanishing Step.
When the Cheshire Cat takes damage, it can use its reaction to teleport up to 30 feet to an unoccupied space it can see and become invisible until the start of its next turn.

Otherworldly Agility.
The Cheshire Cat can take the Disengage or Hide action as a bonus action on each of its turns.

Reality-Bending Presence.
Creatures within 60 feet of the Cheshire Cat have disadvantage on Intelligence, Wisdom, and Charisma saving throws, unless they are immune to being charmed.

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Actions

Multiattack.
The Cheshire Cat makes two Claw attacks or uses Mesmeric Whispers and one Claw attack.

Claw. Melee Weapon Attack: +9 to hit, reach 5 ft., one target.
Hit: 13 (2d6 + 6) slashing damage plus 7 (2d6) psychic damage.

Mesmeric Whispers (Recharge 4–6).
The Cheshire Cat whispers maddening truths. Up to 3 creatures within 60 feet must make a DC 17 Charisma saving throw. On a failure, they are affected by Confusion for 1 minute. Affected creatures may repeat the saving throw at the end of each of their turns, ending the effect on a success.

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Legendary Actions

The Cheshire Cat can take 2 legendary actions, choosing from the options below. Only one action can be used at a time, and only at the end of another creature’s turn. It regains spent actions at the start of its turn.

• Flicker. The Cat teleports up to 20 feet and becomes invisible until the start of its next turn.
• Whisper. One creature the Cat can see within 60 feet must succeed on a DC 17 Wisdom saving throw or have disadvantage on its next attack roll or saving throw.
• Illusory Clone (Costs 2 Actions). The Cat creates an illusory duplicate that lasts until the start of its next turn. The next attack against the Cat has a 50% chance of hitting the illusion instead.

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Lair Actions (Optional)

If encountered in its home domain—a dreamlike glade or the fringes of the Feywild—the Cheshire Cat can use lair actions on initiative count 20 (losing initiative ties):

• Warping Grin. A floating smile appears in a space the Cat can see. Creatures within 15 feet of it must succeed on a DC 15 Wisdom saving throw or be charmed until the next round.
• Flipped Perspective. Terrain in a 30-foot radius becomes inverted and illusory for 1 minute. It counts as difficult terrain, and creatures have disadvantage on attack rolls while inside.
• Echoing Laughter. Maddening laughter erupts. Each creature of the Cat’s choice within 60 feet must make a DC 15 Intelligence saving throw or lose concentration on any active spell.

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Roleplaying the Cheshire Cat

• Voice: Silky, eerie, always amused
• Mannerisms: Vanishes mid-sentence, appears upside down, speaks in paradoxes
• Motivation: Seeks amusement, mischief, and the unraveling of rigid logic
• Behavior: May offer riddles, misleading advice, or moments of unsettling insight

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D&D 5E Epic Monsters: Cheshire Cat

D&D 5E – Epic Monsters: Cheshire Cat | EN World | Dungeons & Dragons | Tabletop Roleplaying Games

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The Cheshire Cat, widely known for its mischievous grin, was popularized by Lewis Carroll in Alice’s Adventures in Wonderland (1865). Though closely tied to Alice’s world, the idea of the grinning cat predates the novel and has become deeply embedded in broader popular culture. The cat’s most iconic trait—vanishing until only its smile remains—has since become a metaphor for the surreal and absurd.

The phrase “grinning like a Cheshire Cat” was in use in England well before Carroll’s time. One theory connects it to the county of Cheshire, famed for its dairy farms. A well-fed, cream-filled cat would certainly have reason to grin. According to Brewer’s Dictionary of Phrase and Fable, cheese was once molded in the shape of a grinning cat, with people eating from tail to head—leaving the grin for last.

Another theory points to the pub signs and inns of Cheshire and nearby Charlton, many of which featured cats, lions, or tigers on their crests. A 1788 entry in Francis Grose’s Classical Dictionary of the Vulgar Tongue defines a “Cheshire Cat” as someone who “shows his teeth and gums in laughing.” Literary references followed in the decades before Alice, including works by Jon Wolcot (1792) and William Thackeray (1854), both using the phrase in similar fashion.

The most plausible origin may simply be a blend of these ideas: dairy-rich Cheshire and the old phrase “like the cat that got the cream.” The disappearing act, however, may have deeper roots. In the Middle Ages, Cheshire enjoyed unusual legal independence. Royal sheriffs couldn’t pursue fugitives into the county—an escape worthy of a sly grin. Add in that “caitiff” once meant “villain” and that “cat” could imply “clever fellow,” and the symbolic Cheshire Cat begins to take shape.

For most readers outside the UK, Carroll’s version is the first real encounter with the character. The Cheshire Cat in Alice is part trickster, part philosopher—appearing and disappearing at will, questioning reality and identity, and never quite answering directly.

Several other theories about the character’s origins persist. Carroll, a mathematician, would likely have known the term catenary—the curve a hanging chain forms, visually similar to a wide grin. There’s also a cat-like carving on St. Wilfrid’s Church in Grappenhall, near Carroll’s birthplace in Cheshire. Lastly, some suggest the British Shorthair, a breed said to smile when flustered, may have inspired the look.

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.

The Cheshire Cat

Medium Fey (Incorporeal, Extraplanar)
Hit Dice: 9d6+27 (58 hp)
Initiative: +7
Speed: 40 ft. (8 squares), climb 20 ft.
Armor Class: 20 (+3 Dex, +4 deflection, +3 natural), touch 17, flat-footed 17
Base Attack/Grapple: +4 / —
Attack: Incorporeal touch +7 melee (1d6 Wisdom drain)
Full Attack: Incorporeal touch +7 melee (1d6 Wisdom drain)
Space/Reach: 5 ft. / 5 ft.
Special Attacks: Spell-like abilities, mesmeric grin, reality slip
Special Qualities: Blindsight 60 ft., damage reduction 10/cold iron, fast healing 5, fey mind, invisibility, spell resistance 21

Saves: Fort +6, Ref +9, Will +10
Abilities: Str —, Dex 17, Con 16, Int 16, Wis 15, Cha 22
Skills: Bluff +18, Hide +20, Listen +14, Move Silently +18, Sense Motive +14, Spot +14, Tumble +14, Use Magic Device +16
Feats: Ability Focus (Mesmeric Grin), Combat Reflexes, Improved Initiative
Environment: Any fey-touched or dreamlike woodland (often the Feywild)
Organization: Solitary or part of a fey court
Challenge Rating: 9
Treasure: Standard
Alignment: Chaotic Neutral
Advancement: 10–13 HD (Medium); 14–18 HD (Large)
Level Adjustment: —

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Description

Floating among twisted branches, a ghostly feline figure materializes briefly—striped fur, glowing golden eyes, and a grin that hangs in the air long after the rest has vanished. The Cheshire Cat is a legend among fey and mortals alike: a trickster, philosopher, and riddle-slinger that haunts the boundaries of reality.

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Combat

The Cheshire Cat avoids direct confrontation, preferring to confuse and scatter its foes with illusions, mind magic, and maddening dialogue. It harasses enemies from concealment, retreating or vanishing when threatened.

It often begins an encounter invisible, whispering riddles or laughing softly. If combat breaks out, it uses confusion spells and its mesmeric grin to disrupt concentration and weaken resolve, only attacking directly when its safety is assured.

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Spell-Like Abilities (Sp):

Caster level 9th. Save DCs are Charisma-based.

• At will – Greater invisibility, minor image, silent image, ghost sound, prestidigitation
• 3/day – Dimension door, mirror image, blur, confusion (DC 19)
• 1/day – Phantasmal killer (DC 20), mislead, dominate person (DC 21)

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Mesmeric Grin (Su):

As a standard action, the Cheshire Cat may fix its disembodied grin and gaze on a single creature within 30 feet. The target must succeed on a DC 21 Will save or become fascinated for 1d4 rounds. While fascinated, the creature takes a –4 penalty on Will saves against illusion and enchantment effects.

Once per day, the Cheshire Cat may instead use this ability to confuse the target (as the confusion spell) for 2d4 rounds.

This is a mind-affecting, compulsion, gaze-like effect. The save DC is Charisma-based and includes the bonus from Ability Focus.

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Reality Slip (Su):

Three times per day, the Cheshire Cat may become incorporeal for 1 minute as a free action. While incorporeal, it gains the incorporeal subtype (including immunity to nonmagical weapons and the ability to move through solid objects) and its melee attacks deal 1d6 Wisdom drain instead of physical damage (Will negates, DC 20). The save DC is Charisma-based.

Once during each use of reality slip, it may cast dimension door as a swift action.

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Fey Mind (Ex):

The Cheshire Cat is immune to confusion, fear, and madness effects. It also gains a +4 racial bonus on saving throws against all mind-affecting spells and abilities.

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Invisibility (Su):

The Cheshire Cat can become invisible at will (as greater invisibility) as a swift action. It may choose to leave its grin visible for aesthetic or psychological effect, but this has no mechanical impact.

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Tactics

Before Combat:
Observes targets invisibly, testing them with whispers or illusions.

During Combat:

• Round 1: Confusion or mirror image
• Round 2: Mesmeric grin or phantasmal killer
• Round 3+: Uses reality slip, dimension door, or greater invisibility to stay mobile. Targets isolated or weak-willed foes.
• If threatened: Retreats using dimension door, then reappears elsewhere for more mischief.

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Lore

Knowledge (Arcana or Nature)

• DC 20: “A fading grin in the forest? That’s the Cheshire Cat—a fey creature known to play tricks and warp minds.”
• DC 25: “It can vanish at will, turn you inside out with riddles, and charm your soul into smiling while it steals your thoughts.”
• DC 30: “Its grin is more than a face—it’s a spell, a trap. The Cat slips between worlds. If you see it, it probably wants something from you—or already has it.”

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Adventure Hooks

• Stolen Memories: A character wakes up without a memory—only a whisper of laughter and a floating grin remain.
• The Smiling Woods: Travelers vanish in a forest where toothy smiles appear on trees and rocks.
• A Fey Bargain: The Cat appears with information the party needs—but demands the answer to a riddle they won’t understand until it’s too late.