Many a name has been given to this creature, from our very own stingy jack to jack o lantern all giving many stories around this pumpkin-headed monster. Some say he was once a man who tricked the devil but was tricked himself into becoming this form some say he was a devoted father who turned to the ultimate depravity once his daughter was killed. The truth is unknown but what is, is that the Laughing Jack comes from the lower planes when the spirits are most abundant on the material plane where he gathers their souls in his pumpkin-like pail that he uses to facilitate his head, cackling madly while he does so. Woe be to those who encounter him and luck be to those who try and stop him.

Laughing Jack's tend to dwell and return to the area they most frequented during life (such as a bar where they drunk the most etc) They only tend to appear on nights when the lower plains press against the barriers between planes the most (such as seasonal equinox's etc) Where the Laughing Jack  can extend the most control over spirits that wander the night.

Lair Actions

On initiative count 20 (losing initiative ties), the Laughing Jack takes a lair action to cause one of the following effects; the Laughing Jack can’t use the same effect two rounds in a row:

• Summon 1d4 + 1 Scarecrows
• Obscure a 10ft cube of space with darkness
• Each creature of the Laughing jacks choice that is within 30 feet of the Laughing Jack and aware of it must succeed on a DC 14 Wisdom saving throw or become frightened for 2 rounds. A creature can repeat the saving throw at the end of each of its turns, ending the effect on itself on a success.

Regional Effects

The region containing a legendary Laughing Jack’s lair is enthralled to the whims of the Laughing Jack, which creates one or more of the following effects:

• People withing 1 mile of the lair are prone to fits of maniacal laughter prompting disadvantage on stealth. 
• Spirits are more likely to be drawn to the location of the lair will-o-the-wisps, spectres, ghosts, and various forms of undead can be spotted within a mile of the lair.
• Those who die within 1 mile of the Laughing Jacks Lair are bound to the Laughing Jacks will and can be turned into a scarecrow/undead form.

If the Laughing Jack dies, these effects fade over the course of 1 day.