The Smiling Man

medium fey (corrupted fey), chaotic evil

Challenge 8.0 (3,900 XP)

STR
14 (+2)
DEX
20 (+5)
CON
16 (+3)
INT
18 (+4)
WIS
15 (+2)
CHA
22 (+6)

Proficiencies & Senses

Saving Throws Dexterity, Charisma
Skills
Arcana +7, Insight +5, Stealth +8, Deception +9, Acrobatics +8, Perception +5, Intimidation +9, Investigation +7
Senses
darkvision 60 ft.
Shadow Step 30 ft. (Can teleport from one shadow to another within 30 feet.)
passive Perception 15

Characteristics

Damage Vulnerabilities
radiant
Damage Resistances
Damage Immunities
Condition Immunities
charmed, frightened
Languages Sylvan, Common, can mimic any language they have heard.

Traits

Shadow Veil

The Smiling Man can meld into shadows, becoming invisible in dim light or darkness.

Mimicry

The Smiling Man can imitate the sounds and speech of others it has heard. Each creature that hears the sounds can tell they are imitations with a successful DC 15 Wisdom (Insight) check.

Dark Fey Magic

The Smiling Man can cast spells. It has a spellcasting ability of Charisma (spell save DC 17).

Actions

Multiattack

The Smiling Man makes three Shadow Blade attacks or casts two spells.

Shadow Blade

Weapon Attack: +10 to hit, reach 5 ft., one target. Hit: 1d8 + 5 psychic damage.

Memory Drain

The Smiling Man targets one creature it has entered the shadow of. The target must succeed on a DC 17 Wisdom saving throw or it loses 1d4+1 skill levels from its skills for 24 hours. The Smiling Man gains proficiency in that skill for one hour.

Reactions

Fey Escape

When the Smiling Man takes damage, it can use its reaction to teleport to the nearest shadow.

Combat Behavior

Tactics


• Use stealth to ambush targets from shadows.
• Mimic voices to lure prey into traps or danger.
• Utilize Memory Drain to weaken foes before attacking.

Combat Style

Uses deception and psychological warfare in combat. Prefers to attack from shadows and retreat when discovered.

Morale

The Smiling Man flees when severely injured or if outnumbered, preferring to strike again another day.

Monster Description

The Smiling Man is a twisted remnant of what once was a joyous fey spirit. Many years ago, it thrived in the bright, vibrant landscapes of the Feywild, reveling in games and laughter. However, due to unknown dark sources—perhaps the influence of an ancient curse or malign fey magic—this entity became a harbinger of dread. It now wanders the shadows, luring those who venture too close with an alluring smile and promises of forgotten memories. The Smiling Man is no longer the friendly fey that once brought joy but a creature that thrives on the despair of others, using its charm to snare unwary adventurers and steal their essence.

Monster behavior

The Smiling Man employs cunning tactics to isolate its prey. Initially, it will use its mimicry to imitate enticing sounds—perhaps the laughter of children or the distant echo of music—to draw adventurers into its domain. Once entangled within its web of shadows, the creature reveals its darker intentions by utilizing its shadow abilities to strike from ambush and drain the memories of those it captures. This monster revels in psychological warfare, often whispering stolen memories back into the ears of its victims to confuse and terrify them. If threatened, it uses its fey escape to distance itself from combat, only to ambush again when the moment is right. The Smiling Man is best encountered in pairs or small packs, where their ability to mimic adds to the chaos of battle.

Ecology

The Smiling Man plays an unsettling role in the fey ecology, now residing at the fringes of the Feywild. It exists in a tragic balance between creation and destruction, preying on both mortals and benevolent fey. Their ability to drain memories and skills not only impacts the individuals intimately but further contributes to the decay of the lands they inhabit, creating an atmosphere thick with dark magic. Through its corrupting presence, the Smiling Man embodies the feywild's duality of beauty and horror, reminding those who wander too close of the loss of innocence and the heavy price of dark power.

History

The origin of the Smiling Man is steeped in tragedy and corruption. Originally a jester from the Feywild Court, it thrived on creating joy and laughter. However, after an ancient curse was unleashed by a rival of the Court, several fey were transformed into grotesque shadows of their former selves. The Smiling Man emerged from this chaos, a once-happy spirit now marred by despair and darkness. Over centuries, its power grew as it became a master of manipulating shadow and memory. Now, it exists as a specter of horror, haunting the edges of reality, seeking vengeance against its kin and feasting on the essence of the unsuspecting. Legends tell of brave adventurers who attempted to banish it, only to be consumed by its insatiable hunger for memories.

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