Death Jester (5e Creature)
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Medium humanoid (any race), any evil alignment
Saving Throws Dex +9, Con +6, Int +7
Evasion. If the jester is subjected to an effect that allows it to make a Dexterity saving throw to take only half damage, the jester instead takes no damage if it succeeds on the saving throw, and only half damage if it fails.
Sneak Attack. Once per turn, the jester deals an extra 21 (6d6) damage when it hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 feet of an ally of the assassin that isn't incapacitated and the assassin doesn't have disadvantage on the attack roll.
Spellcasting. The jester is a 7th-level spellcaster. Its spellcasting ability is Intelligence (spell save DC 15, +7 to hit with spell attacks). The jester has the following wizard spells prepared, requiring no material components:
Cantrips (at will): dancing lights, mage hand, minor illusion
Multiattack. The jester makes three attacks.
Scimitar. Melee Weapon Attack: +9 to hit, reach 5 ft., one target. Hit: 8 (1d6 + 5) slashing damage, and the target must make a DC 15 Constitution saving throw, taking 24 (7d6) poison damage on a failed save, or half as much damage on a successful one.
Dagger. Melee or Ranged Weapon Attack: +9 to hit, reach 5 ft. or range 20/60 ft., one target. Hit: 7 (1d4 + 5) piercing damage, and the target must make a DC 15 Constitution saving throw, taking 24 (7d6) poison damage on a failed save, or half as much damage on a successful one.
Parry. The jester adds 4 to its AC against one melee attack that would hit it. To do so, the jester must see the attacker and be wielding a melee weapon.
"Death jesters." "Blade harlequins." "Jacks of knives." Known by many names, they are nonetheless extremely deadly assassins, as not only are they paragons of combat but they also excel at illusion magic and any other school of magic that supports their deadly art. They are famous for dressing flamboyantly and speaking in a thespian manner like that of riddlers and tricksters, especially in a nasally and pompous voice. Their attire is utterly flamboyant and it would seem for all their bright and garish colors, especially with the outlandish bells and masks that decorate their accoutrement they would be easily given away but no, they are extremely stealthy and extremely deadly. In combat they jump, joke, drink, dance and sing all the while disemboweling and decapitating innocents. Though these enemies might seem almost comedic, survivors speak of these mad jesters performing unspeakable acts to survivors all the while laughing manically. Generally, these malicious tricksters are followed by an entourage of assassins but sometimes they work together in deadly troupes of death jesters.