Harlequin Demon

Medium fiend (demon), chaotic evil

---

Armor Class 18 (Natural Armor)
Hit Points 112 (15d8 + 45)
Speed 50 ft.

---

Str	Dex	Con	Int	Wis	Cha
14 (+2)	20 (+5)	16 (+3)	15 (+2)	12 (+1)	18 (+4)

---

Saving Throws Dex +9, Wis +5, Cha +8
Skills Acrobatics +11, Deception +8, Performance +8, Stealth +9
Damage Resistances cold; bludgeoning, piercing, and slashing from nonmagical attacks
Damage Immunities fire, poison
Condition Immunities charmed, frightened, poisoned
Senses darkvision 120 ft., passive Perception 11
Languages Abyssal, Infernal, Telepathy 120 ft.
Challenge 10 (5,900 XP)

---

TRAITS

• Innate Deception: The Harlequin Demon is a master of illusion and misdirection. It has advantage on Charisma (Deception) checks. Additionally, it can cast the Disguise Self spell at will, without expending a spell slot.
• Improved Evasion: When the Harlequin Demon is subjected to an effect that allows it to make a Dexterity saving throw to take only half damage, it instead takes no damage if it succeeds on the saving throw, and only half damage if it fails.
• Chaotic Agility: The Harlequin Demon can take the Dash or Disengage action as a bonus action on each of its turns.
• Sneak Attack (3d6): The Harlequin Demon deals an additional 3d6 damage when it hits a target with a weapon attack if the target is surprised, or if the demon has advantage on the attack roll.

---

ACTIONS

• Multiattack: The Harlequin Demon makes two attacks with its Anarchic Dagger and one with its Unholy Dagger.
• Anarchic Dagger: Melee Weapon Attack: +9 to hit, reach 5 ft., one target. Hit: 8 (1d6 + 5) piercing damage plus 3 (1d6) chaotic damage. This weapon is considered magical and chaotic for the purposes of overcoming damage resistance.
• Unholy Dagger: Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 7 (1d6 + 4) piercing damage plus 2 (1d6) necrotic damage.
• Harlequin’s Laugh (Recharge 5-6): The demon releases a terrifying, manic laugh that echoes throughout the area. All creatures within 30 feet of it that can hear it must succeed on a DC 16 Wisdom saving throw or become frightened for 1 minute. While frightened, a creature can repeat the saving throw at the end of each of its turns, ending the effect on itself on a success. A creature that succeeds on the saving throw is immune to this effect for 24 hours.
• Dance of Madness (Recharge 5-6): The Harlequin Demon performs an acrobatic, frenzied dance. Each creature within 15 feet of it must make a DC 16 Dexterity saving throw or take 14 (4d6) slashing damage and fall prone. On a successful save, a creature takes half damage and is not knocked prone.

---

SPELLCASTING

The Harlequin Demon is a 9th-level spellcaster. Its spellcasting ability is Charisma (spell save DC 16, +8 to hit with spell attacks). It has the following spells prepared:

• Cantrips (at will): Thaumaturgy, Minor Illusion, Prestidigitation, Eldritch Blast
• 1st level (4 slots): Disguise Self, Charm Person, Hideous Laughter, Color Spray
• 2nd level (3 slots): Mirror Image, Blur, Scare
• 3rd level (3 slots): Counterspell, Fear, Blink
• 4th level (3 slots): Greater Invisibility, Phantasmal Killer
• 5th level (2 slots): Dominate Person, Cloud of Daggers

---

LEGENDARY ACTIONS

The Harlequin Demon can take 3 legendary actions, choosing from the options below. Only one legendary action option can be used at a time and only at the end of another creature’s turn. The Harlequin Demon regains spent legendary actions at the start of its turn.

• Mimicry (Costs 1 Action): The demon imitates sounds it has heard, such as voices or other noises, to confuse or distract its enemies. All creatures within 60 feet that can hear it must succeed on a DC 16 Wisdom saving throw or have disadvantage on their next attack roll or saving throw until the end of the demon’s next turn.
• Tumble (Costs 1 Action): The demon can use its acrobatic abilities to move through enemy spaces without provoking opportunity attacks. The demon can move through any number of spaces occupied by enemies, but the movement must be at least 10 feet.
• Feint (Costs 2 Actions): The demon feints with one of its daggers, attempting to confuse its target. One creature within 5 feet of the Harlequin Demon must succeed on a DC 16 Wisdom saving throw or grant the demon advantage on its next attack roll against that creature before the end of the demon’s turn.

---

REACTIONS

• Parry: The Harlequin Demon adds 2 to its AC against one melee attack that would hit it. To do so, the demon must be wielding a melee weapon.

---

LAIR ACTIONS

If encountered in its lair (a twisted, labyrinthine theater or chaotic circus environment), the Harlequin Demon can take lair actions. On initiative count 20 (losing initiative ties), it can take one of the following lair actions:

• Illusionary Spectacles: The Harlequin Demon casts Mirror Image on itself, creating illusory duplicates that confuse enemies.
• Chaotic Stage: The environment warps and shifts, causing all creatures within 30 feet of the Harlequin Demon to make a DC 16 Wisdom saving throw or be momentarily stunned for 1 round, as the ground beneath them becomes slippery or unnaturally difficult.
• Summon Minions: The Harlequin Demon can summon 1d4 Dretch (chaotic evil) or 1 Quasit (chaotic evil) to fight alongside it for 1 minute, after which the creatures disappear back into the Abyss. These summoned demons are aligned with the Harlequin Demon’s chaotic nature and will attack anyone in their path, wreaking havoc and confusion.

---

The Harlequin Demon excels at creating chaotic, unpredictable battles. Using its agility, illusions, and psychological manipulation, it’s a creature that delights in dismantling its foes, both physically and emotionally, while sowing confusion and fear wherever it goes.

---

TACTICS AND COMBAT STRATEGY

The Harlequin Demon fights with an unsettling blend of acrobatic flair and vicious cunning. In battle, it targets the most lawful or pious-looking opponent, using its agility to avoid blows and set up sneak attacks with its daggers. The demon relies on its Chaotic Agility and Dance of Madness to keep enemies disoriented and off balance. If the situation calls for it, the demon will use Harlequin’s Laugh to instill fear, making opponents hesitate in their attacks.

In addition, the Harlequin Demon will often use its Legendary Actions to control the battlefield, moving fluidly through the space to avoid being cornered. Its Mimicry ability is used to sow confusion, causing its enemies to second-guess their moves, while Feint allows it to disarm and outsmart foes who might think they can predict its next move.

Should the battle turn against it, the Harlequin Demon is not above fleeing via Greater Invisibility or Blink, and will regroup using its spells to harry its enemies from afar before re-engaging when the time is right.

Harlequin Demon

Having executed a perfect series of back flips, the harlequin comes to a rest before you, dressed in red and black diamonds, its face white with painted black tears dripping down its cheeks. Something is clearly wrong, though, for the clown has pools of darkness for eyes, the tears are real, dripping down its cheeks in mirth. In fact, the bodysuit seems to be its actual skin. As you recoil in horror, the Harlequin Demon draws two daggers from the air and throws its head back in raucous laughter.

Originally from The Book of Fiends
Designed By Aaron Loeb, Erik Mona, Chris Pramas, and Robert J. Schwalb

Harlequin Demons are the children of Ipos, the demon Lord of Masques. Most of these demons function as entertainment for the lords of the Abyss. They also serve as spies and assassins, secretly killing rivals, and weaving dangerous intrigues capable of toppling even the most powerful of lords. A few harlequins make their way to the Material Plane, where they perform in many of the same capacities as they do in the Abyss. Through their illusions and skills in deception, they present a façade nearly impenetrable by mortal eyes.

A Harlequin Demon’s strength originates from its abilities to entertain. They specialize in the lewd, blasphemous and grave. They regularly place the gods in scandalous positions so outrageous they can elicit laughs from even the pious. It is the capitalization on the unexpected, the turn of the proper word and the nasty streak that gives them power over mortals, planting the seeds of doubt in their ethical conscious regarding their faith in the gods and placing them on the first steps to damnation.

Harlequin Demons, though rather intelligent, find humor in everything. Coupled with their passion to entertain, they are capricious tools at best. However, all harlequins hate lawful good individuals above all else. When they encounter an opponent of that alignment, they focus their attacks against them almost to the exclusion of all else. Harlequins speak Common, Abyssal and Infernal.

---

Harlequin Demon
Medium outsider (Chaotic, Demon, Evil, Extraplanar)
Hit Dice	9d8+18 (58 hp)
Initiative	+7
Speed	50 ft. (10 squares)
Armor Class	22 (+7 Dexterity, +5 natural), touch 17, flatfooted 15
Base Attack/Grapple	+9/+10
Attack	+1 anarchic dagger +17 melee (1d4+2)
Full Attack	+1 anarchic dagger +15/+10 melee (1d4+2), +1 unholy dagger+15 melee (1d4+1)
Space/Reach	5 ft./5 ft.
Special Attacks	Sneak attack +3d6, spells, summon
Special Qualities	Damage reduction 10/good, demon traits, immunity to mind-affecting spells and effects, improved evasion, Spell Resistance 24
Saves	Fort +8, Ref +13, Will +6
Abilities	Strength 12, Dexterity 24, Constitution 14, Intelligence 13, Wisdom 11, Charisma 17
Skills	Balance +21, Bluff +15, Climb +13, Diplomacy +5, Disguise +3 (+5 acting), Hide +19, Intimidate +5, Jump +23, move silently +19, Perform (comedy) +15, Sleight of Hand +21, Tumble +29
Feats	Dodge B, Improved Feint B , Mobility, Spring Attack, Two-weaponfighting B , Weapon Finesse
Environment	The Abyss
Organization	Solitary, Harlequinade (2-6)
Challenge Rating	13
Treasure	Standard
Alignment	Always chaotic evil
Advancement	10-27 HD (Medium)
Level Adjustment	–

Combat

Harlequins are fast and dangerous in combat, able to blend spells with martial prowess. Harlequins will quickly survey a battlefield, looking for lawful and good opponents. They Tumble through occupied squares as if no opponent stood there, weaving and dodging through defenses to get in a position to cut apart their hated opponents. Harlequin attacks are considered both chaotic and evil for purposes of overcoming damage reduction.

Knives: Each harlequin uses two special daggers created in the darkest forges by master craftsmen and wizards. In the hands of a non-harlequin,the dagger carries a powerful curse. They confer a negative level to any character holding them regardless of alignment. Good-aligned wielders gain a random disease once/week they retain the item beginning on the first day they hold it.

Sneak Attack: Harlequins sneak attack as 5th-level rogues.

Spells: Harlequins cast spells as 9th-level sorcerers.

Typical Sorcerer Spells Known (6/7/7/5; save DC 13 + spell level):

• 0 – acid splash, daze, detect magic, flare, ghost sound, message, read magic, touch of fatigue;
• 1st – burning hands, charm person, color spray, jump, shield;
• 2nd – blur, invisibility, mirror image, scare;
• 3rd – blink, displacement, haste;
• 4th – confusion, rainbow pattern.

Summon (Sp): Once per day, a harlequin may attempt to summon 1d6 schir,1d3 babaus, one glabrezu or another harlequin with a 50% chance for success. This ability is the equivalent of an 8th-level spell.

Skills: Harlequins gain a +8 racial bonus to Jump and Tumble checks.