Out of Box Encounters: Oogie’s Lair of Dicey Doom
Using Oogie Boogie in a D&D adventure during October is the perfect way to inject some spooky, playful fun into your campaign. Inspired by The Nightmare Before Christmas, Oogie Boogie 
embodies that mischievous blend of horror and whimsy, making him an ideal villain for a Halloween-themed session. His love for traps, games of chance, and creepy atmosphere gives DMs a chance to challenge players with more than just combat—facing Oogie means navigating deadly puzzles, overcoming terrifying swarms, and dealing with his twisted sense of humor. It’s a way to celebrate the season by putting your players through a thrilling, nightmare-fueled adventure! So now onto another Out of the Box Encounter.
Oogie’s Lair of Dicey Doom
Encounter Level: 5-6
Summary
The party mysteriously awakens in the depths of Oogie Boogie’s lair, kidnapped by his mischievous underlings: Lock, Shock, and Barrel. They must navigate the bizarre and dangerous traps of Oogie’s lair to escape, all while evading or confronting the malevolent boogeyman himself.
Introduction/Hook
As the party settles down for a rest, their sleep is disturbed by strange, cackling laughter. Darkness envelops them, and when they awaken, they find themselves in a dimly lit chamber filled with bizarre decorations, flickering neon lights, and the constant sound of dice rattling. They’re bound in scratchy burlap sacks, and standing before them are three mischievous figures: Lock, Shock, and Barrel, Oogie Boogie’s troublesome henchmen.
Lock grins and says, “Welcome to Oogie’s funhouse! Try to escape if you can… but ol’ Oogie loves a game, so good luck!” With that, they vanish into the shadows, leaving the party to their fate.
Scene Description
The party finds themselves in a large, circular room with dark, damp stone walls and glowing, flickering lights strung overhead. The atmosphere feels like a twisted carnival, with garish decorations, random piles of bones, and strange contraptions that hint at hidden dangers.
Details of the Lair:
- Faint music and dice sounds echo from all directions, giving the area an eerie vibe.
- Doors leading to various chambers are carved with symbols of dice, skulls, and cards, suggesting the lair is full of traps and games.
- Chute-like openings in the ceiling hint that Lock, Shock, and Barrel are always watching, ready to drop something nasty onto the party.
- The entire place smells faintly of mildew, with a dry, dusty undertone, like old fabric or moldy gambling halls.
Encounter Dynamics
The party must escape Oogie Boogie’s lair. Along the way, they’ll face:
- Randomly triggered traps, themed after gambling or carnival games.
- Oogie Boogie’s lair defenses, including swarms of insects and gambling-themed hazards.
- The encounter culminates in a confrontation with Oogie Boogie himself, a creature of shadow and bugs who loves to play with his food.
Escape Mechanics
The lair is laid out like a twisted game show, where the party must solve puzzles and avoid traps to make it to the final chamber. Each chamber has a “game” aspect to it, where the party’s choices affect their fate.
Chamber 1: Dicey Hallway
This long hallway has pressure plates shaped like dice, which can either help or hinder the party.
- Pressure Plate Effect (Roll 2d6):
- On a roll of 2-3, poisonous darts shoot out, dealing 1d6 poison damage to those standing on the plates (DC 14 Dex save to avoid).
- On a roll of 4-5, the ceiling lowers, threatening to crush the party (DC 15 Dex save to avoid 2d8 bludgeoning damage).
- On a roll of 6-8, nothing happens.
- On a roll of 9-10, the party finds a hidden treasure (500 gp worth of gems).
- On a roll of 11-12, a swarm of beetles (stats below) emerges from the walls and attacks.
Chamber 2: The Slot Room
In this chamber, the walls are covered in massive, spinning slot machine reels. To open the next door, a lever must be pulled, but the result could lead to different outcomes.
- Slot Machine (Roll 1d6):
- 1: The room fills with an illusory gold rush, but characters must make a DC 15 Intelligence (Investigation) check to realize it’s fake. Those who fail are charmed and lose their next turn.
- 2-3: A trapdoor opens, dropping the party into a pit filled with sharp bones (DC 14 Dex save or take 2d6 piercing damage).
- 4-5: A riddle appears on the wall. Solving it opens the door to the next chamber (DC 14 Intelligence check).
- 6: The door opens automatically and 2d8 giant bugs (centipedes) crawl out of the walls to attack the party.
Chamber 3: Oogie’s Den
The final room is Oogie Boogie’s lair itself—a giant, dark chamber filled with glowing dice, cards, and piles of bones. Oogie waits in the center, seated on a throne made of twisted metal, gambling tokens, and cobwebs.
Oogie Boogie’s Tactics
Oogie Boogie loves to toy with his victims. He opens the encounter by casting illusions or setting off traps while laughing and taunting the party. If threatened, he releases insect swarms or throws dice imbued with magic (as ranged attacks). He will fight to the death but uses trickery and fear to keep the party on edge.
Stat Block: Oogie Boogie
Oogie Boogie is a hulking figure made from burlap and filled with insects. His body is almost impossible to damage unless it’s torn open.
Large Fey (Nightmare Spirit), Chaotic Evil
- Armor Class: 15 (natural armor)
- Hit Points: 104 (11d10+44)
- Speed: 30 ft.
| STR | DEX | CON | INT | WIS | CHA |
|---|---|---|---|---|---|
| 19 (+4) | 16 (+3) | 18 (+4) | 14 (+2) | 12 (+1) | 18 (+4) |
- Saving Throws: Dex +6, Con +7
- Skills: Deception +7, Intimidation +7, Stealth +6
- Damage Resistances: Poison; Bludgeoning, Piercing, and Slashing from Nonmagical Attacks
- Condition Immunities: Charmed, Frightened
- Senses: Darkvision 60 ft., Passive Perception 11
- Languages: Common, Infernal
- Challenge: 6 (2,300 XP)
Insect Swarm Form (Recharge 5-6): As a bonus action, Oogie can unravel into a swarm of insects. While in this form, he gains the effects of swarm of insects (spiders) and is immune to nonmagical damage. He can reform into his normal shape after 1 minute.
Fearsome Dice (3/Day): Oogie can throw enchanted dice at a target within 60 feet. The target must succeed on a DC 15 Wisdom saving throw or be frightened for 1 minute. While frightened, the creature takes 1d10 psychic damage at the start of its turn.
Trap Master: Oogie can trigger any trap within 30 feet as a bonus action.
Actions
Multiattack. Oogie makes two attacks with his burlap fists.
Burlap Fist. Melee Weapon Attack: +7 to hit, reach 10 ft., one target. Hit: 13 (2d8 + 4) bludgeoning damage.
Insect Swarm (Recharge 6). Oogie releases a swarm of biting insects in a 15-foot cone. Each creature in the area must make a DC 14 Dexterity saving throw, taking 24 (7d6) piercing damage on a failed save, or half as much on a successful one.
Aftermath
If Oogie is defeated, his body disintegrates into a pile of scattered bugs. His lair remains dangerous, and the party may find clues about Oogie’s underworld connections or magical dice that could lead to future encounters with more twisted, nightmarish fey. The party earns 1,000 gold worth of valuables, some of which may be cursed or haunted (at the DM’s discretion).
Lock, Shock, and Barrel may attempt to ambush the party during their escape or remain a threat in the future, plotting to revive their fallen master.
This encounter brings a creepy, whimsical challenge to your campaign, blending mischief, puzzles, and horror. Oogie Boogie’s lair is a living nightmare—a perfect Halloween-themed escape for adventurers who think they can beat the odds! So add this into your next D&D Session to have Oogie Boogie sing, dance and horrify your players.
Thanks for reading. Until Next Time, Stay Nerdy!
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