The Crooked Man
A Cursed and Trapped Nightmarish Boogeyman
Long ago, this being was once a hobgoblin who fetched things that his master desired. He began to change after stealing a page from the Queen of Crones’ infamous demonic grimoire. The demonic power influenced his mind and body, making him as crooked as his thieving ways. After she discovered his theft, the Queen of Crones cursed and banished him. This “Crooked Curse” mixed in unexpected ways with the abyssal energy within him to create what is now known as the Crooked Man.
The curse placed on him broke the Crooked Man’s body and mind, while also severing the bond between him and his former master. Tortured by this curse, the Crooked Man starves, only able to nourish himself on the nightmares of others. Thus, he uses his powers to spread his curse, seek out prey, and torture the minds of his victims throughout the multiverse. In times of desperate starvation, the Crooked Man is known to kidnap unconscious prey and ration their terror to sustain his strength.
After being mangled by his curse, he was banished to a demiplane prison known as the Crooked Road: an endless, jagged cobblestone path winding through a dark mirror of the fey realm where the forests are twisted into unnatural angles. The demiplane is forever trapped in night, dimly lit only by a crooked moon. The moonlight is dispersed by an eerie haze that never lifts and is accompanied by the glow of fungal growths that line the path. It is here that he is forced to wander, only able to leave when summoned. On rare occasions, planar travelers have found their way onto the Crooked Road. Even more rarely do they return, as mad as a hatter.
The Crooked Man strives to spend as much time as possible free from his prison, opting for prolonged psychological torture over murdering his unfortunate victims. Tormented by endless nightmares of the Crooked Man, he’ll often offer his quarry a chance of respite. This trial consists of the victim traveling the Crooked Road for as long as he deems necessary. Should one manage to do so and retain their sanity, the Crooked Man will release them when he next escapes the Crooked Road as a warlock bound to him. These heralds of his are tasked with spreading the Crooked Man’s curse far and wide, often under the guise of a nursery rhyme.
Illustrated by Rachel Frost
The Crooked Man’s Crooked Curse
“There was a Crooked Man, who walked a crooked mile. He had a crooked mind and wore a crooked smile. His food would turn to ash, his water turned to bile. He’ll come when you’re a slumber, turn your dreams to something vile.
There was a Crooked Man, who walked a crooked mile. To walk his Crooked Road, announce this bleak recital. The gate appears before you, it heralds his arrival. To those who seek his power, complete his crooked trial.
There was a Crooked Man, who walked a crooked mile. To evade his twisted ire, embrace his crooked spiral. If you thought you could escape him, outwit his cunning guile. Beware he lurks behind you, he’s been there for a while.”
I had initially designed the Crooked Man for a high leveled D&D one shot that I was running for the Advancing Heroes Foundation charity that was themed after the fey and fairy tales. I wanted to design a threatening monster for high level play that had a gimmick to it rather than it just being a sack of hit points that the players could beat into submission.
With this being the first monster that I designed for the new 2024 rules update of 5th Edition Dungeons & Dragons, I was initially nervous and had to throw out a lot of what I knew about monster design for the older rules set. I started by gauging the stats and abilities of monsters of a similar Challenge Rating. I compared and contrasted to make sure that they were on a similar power level and continued to do so throughout the design process. This applies to the monsters stats, its hit points, and its average damage output.
Next, I wanted to make it capable of holding its own as a boss monster in high-level D&D combat. This meant that it would need both Legendary Resistances and Legendary Actions. To make it hardier, I gave it the Dream Feast and Magic Resistance Traits along with a few Resistances and Immunities that seemed appropriate for its lore and abilities. Next, to make sure that it couldn’t be taken out from afar without threat, it needed a ranged attack so I gave it its Crooked Bolt action.
At this point, I could focus on making the creature fun and dynamic to use in D&D combat. Its Crooked Step Trait and its Walk A Crooked Mile Reaction lended the monster additional mobility to close distance or reposition itself, while its Spellcasting options gave it some utility and ways to hide should the need arise. Finally I came to the gimmick of the monster; its curse. Without a character uttering its curse, the character may not be able to see the monster but it would also not be able to be targeted by its Crooked Curse Bonus Action, nor would it benefit from its extra damage with every hit it lands.
In gameplay, this monster has been incredibly well received and has been praised for its entertaining and challenging fights. The popularity of the Crooked Man amongst the Lukallion’s Ledger of Legends project has led to it becoming a sort of mascot for the series.