Grim Jester

Grim Jester is a medium undead (Challenge Rating 11).

Grim Jester — fantasy monster illustration. Grim Jester is a medium undead (Challenge Rating 11).
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AC: 18

HP: 136

Speed: walk 30 ft.

STR: 14

DEX: 22

CON: 18

INT: 16

WIS: 16

CHA: 20

A skeletal cadaver bedecked in the motley attire of a fool capers about while making jokes that mock mortality.
Amusing Death. When a jester on his deathbed moves an evil death god to laughter, the fool sometimes gains a reprieve. becoming a grim jester, whose pranks serve to entertain the god of death. Their purpose is to bring an end to mortal lives in a gruesome, comic, and absurd manner. As long as such jesters keep the death god amused, their continued unlife is assured.
Grisly Humor. A grim jester’s jokes are not funny to their victims, but they offer a grim finality in combat. A killing joke might be absurd, such as “Here is your final pineapple soul, a parting gift, goodbye.” or sheer braggadocio such as “Your footwork is atrocious, and your spell’s lost its focus, your party’s no match for my hocus-pocus.” Others might be high-flown, such as “Mortal, your time has come, the bell within your skull does ring, ding, dong, dead.” Grim jesters are famous for grim, bitter mockery such as “Your blood on fire, your heart pumps its last, show me now a hero’s last gasp!” or “Odin’s raven has come for you; the Valkyries were busy. You lose, mortal.”
A grim jester’s mockery rarely entertain the living—but gods of death, chained angels, and demons find them quite amusing.
Randomness. Grim jesters often get their hands on wands of wonder and scrolls of chaos magic. Beware the grim jester with a deck of many things—they are quite talented in pulling cards whose magic then applies to foes and spectators.
Undead Nature. A grim jester doesn’t require air, food, drink, or sleep.

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Further reading

Jetpack7 Game Master Series
The Game Master's Book of Random Encounters
Jeff Ashworth · 2020
The Game Master's Book of Traps, Puzzles and Dungeons
Jeff Ashworth · 2022
The Game Master's Book of Legendary Dragons
Aaron Hübrich · 2022
Last updated 7/27/2026·Tags: monster, undead, medium