From Pennywise to the Joker, to the Killer Klowns from Outer Space, the scary clown trope has been the architect of nightmares for generations of children.

Sure, a lot of this fear comes from explicit attempts by media to make a seemingly childish thing scary. But sometimes there’s just something about a clown’s makeup, or perhaps having just a bit too long of an offstage conversation with a stand-up comic, that instills us with the sense of something sinister behind telling jokes.

It’s from this feeling of dread that Kobold Press’s Tome of Beasts 1 draws forth the grim jester.

• Jokes That Kill: The Lore Behind the Grim Jester
• Tricks Up The Grim Jester’s Sleeve
• Punching Up Your Games with the Grim Jester

Jokes That Kill: The Lore Behind the Grim Jester

There’s an important distinction in the history of clowning to be made here. Modern circus clowns largely evolved from the commedia dell’arte harlequin, and are theatrical performers whose intent is to entertain and delight the masses. A jester, on the other hand, was typically a member of a noble or even royal court. Their audience was usually much more limited. While claims can be made on their ability to exert some political influence in the process, ultimately the jester served at the pleasure of powerful leaders, and their careers, and sometimes even their lives, depended on keeping their masters happy.

The grim jester takes that relationship to a darker and more desperate level. They’re jesters who, upon their deaths, managed to crack a smile on the face of an evil death god. Their boon for this feat is to be granted the gift of undeath as a skeletal maker of japes. To prolong their undead existence, they must kill mortals in new and more comical ways. Essentially, every grim jester is a prop comic but instead of a box full of watermelons to smash, their proverbial hammer must fall on mortal lives.

Tricks Up The Grim Jester’s Sleeve

Artist: Bryan Syme

The grim jester has a few different and potentially devastating tricks in its bag, which earns it a CR 11. Here are a few of the grim jester’s abilities that we find particularly clever.

Killing Joke

This takes Tasha’s Hideous Laughter to macabre new heights. On each of its turns, in addition to attacking with its necrotic claws, the grim jester can tell a nihilistic joke to one creature it can see within 60 feet. If the creature fails on a DC 17 Wisdom saving throw, it falls prone and is incapacitated by laughter for 1 minute.

What makes this action even more terrifying is that for every turn the incapacitated creature fails their save, they take 4d6 necrotic damage. And if the creature fails the initial save by more than 5, they are immediately reduced to 0 hp. Meaning you can easily laugh yourself to death saves.

Joker’s Shuffle

A particularly creepy power, the grim jester can use a bonus action to secretly exchange locations with a Medium or smaller creature it can see within 60 feet of it. A magical illusion then makes the grim jester and its target look and sound like each other. Unless another creature uses an action and succeeds on a DC 19 Intelligence (Investigation) check to inspect the two creatures, they won’t be able to discern the illusion.

Props

Grim jesters are fans of using props in their comedy. They are always in search of new and interesting ways to make their death god masters laugh. Dungeon Masters who want to up the challenge of their grim jester encounters are encouraged to arm them with items like a Wand of Wonder, or, if you’re feeling particularly malicious, a Deck of Many Things. Tome of Beasts 1 implies a degree of power or manipulation over the Deck of Many Things, so a DM could stack the deck with some of the more destructive cards for the moments when the grim jester makes its draws.

Telepathy

A trait you might miss at first glance of the grim jester’s stats is that it can utilize telepathy from up to 120 feet. While it doesn’t have any specific attacks that capitalize on this power, it does open up some fun and creepy roleplay opportunities for adventuring parties that are closing in on one, or have one closing in on them. Hearing bleak attempts at humor echoing in their minds, or the distant unsettling sounds of laughter, are some ways this could set a chilling tone.

Last Laugh

The purpose of a grim jester’s existence is to make their masters laugh, and that extends to their defeat in battle. The same death gods who created them will not be satisfied with a grim jester’s destruction that doesn’t amuse them. An adventuring party may think they’ve defeated a grim jester only to have it resurrect 1d20 days later, ready to mount an encore performance. This is a particularly fun detail because it requires the party to also find a way to amuse an evil death god if they wish to permanently defeat its servant.

Punching Up Your Games with the Grim Jester

The grim jester is a pretty legitimate threat, but how can you best use their japes in your game?

Fetch Quest Gatekeeper

Because of the grim jester’s love of chaotic magic items, adventurers might be likely to stumble upon this monster while they’re in search of one. A grim jester could make for a fun encounter to face down when securing your Wand of Wonder, Deck of Many Things, or other such items.

Ongoing Nuisance

There’s something to be said for having a recurring nemesis throughout a campaign that isn’t the big bad of the whole story. A grim jester could just be a thorn in your side that keeps coming back when you least expect and most dread it.

I Thought We Killed a Regular Clown

Sometimes it’s just fun to lean into a trope. If the party is attending a town where a street festival, circus, or carnival is happening, a grim jester who has fiendishly replaced a performer could be a frightening conflict. This is especially true if there are civilians around for it to swap places with using its Joker’s Shuffle ability.

Minions for a Bigger Enemy

Since grim jesters are created by evil death gods for their own amusement, it does beg the question of which god created the one you fought? And when, how, why, and, of course, what are they going to do when a group of heroes finally destroys one of their creations?

Riff Away

There’s a reason Batman stories always end up coming back to the Joker. There’s just something about the creepiness of an evil clown that serves a dark sense of humor that lends itself to some fun stories.

Grim jesters from Kobold Press’s Tome of Beasts 1 are just one of the many monsters that put new and interesting spins on well-known ideas or threats. How do you think you might use one in your adventures?

Riley Silverman (@rileyjsilverman) is a contributing writer to D&D Beyond, Nerdist, and SYFY Wire. She DMs the Theros-set Dice Ex Machina for the Saving Throw Show, and has been a player on the Wizards of the Coast-sponsored The Broken Pact. Riley also played as Braga in the official tabletop adaptation of the Rat Queens comic for HyperRPG, and currently plays as The Doctor on the Doctor Who RPG podcast The Game of Rassilon. She currently lives in Los Angeles.