WARNING

What follows are dark and twisted parodies of these characters. If you came here looking for a happy, honey-loving, bear and his friendly companions, you will be dissatisfied.

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The Hundred Acre Wood hides many secrets, both wondrous and dark. Far beneath the elms and idyllic glades dwell terrible horrors from places where no mortal dare tread. Without the guidance of Christopher Robin and with the promise of sweet smelling honey drawing him closer, one night Winnie the Pooh waddled his way into the abode of a creature which must not be named. In exchange for a pot that never runs out of the delicious golden sugary syrup the bear craves so badly, he traded his soul and pledged service to a new master. Now he spends his days endlessly consuming, only stopping when suddenly the jar goes empty—refusing to fill again until whatever new desire the foul thing that controls him has is met.

(Illustration by CoffeeHouseArtist on DeviantArt)

Winnie the Pooh

Small monstrosity, chaotic evil
Armor Class 17 (natural armor)
Hit Points 142 (15d6+90)
Speed 30 ft., climb 20 ft.

STR	DEX	CON	INT	WIS	CHA
18 (+4)	9 (–1)	22 (+6)	8 (–1)	9 (–1)	19 (+4)

Saving Throws Wis +3
Skills Athletics +8, Perception +7, Performance +12
Damage Vulnerabilities fire
Damage Resistances force, necrotic, thunder; bludgeoning; slashing from weapons that are not magical or made of silver
Damage Immunities poison
Condition Immunities poisoned
Senses darkvision 120 ft. (sees through magical darkness), passive Perception 17
Languages Common
Challenge 9 (5,000 XP)

Dark One’s Blessing. When Winnie the Pooh reduces a hostile creature to 0 hit points, he gains 13 temporary hit points.

Dark One’s Own Luck (1/Short Rest). When Winnie the Pooh makes an ability check or a saving throw, he can choose to add d10 to the roll. 

Eldritch Invocation: Bewitching Whispers (1/Long Rest). Winnie the Pooh casts compulsion using a warlock spell slot.

Fiendish Resilience. Winnie the Pooh can change his resistance to slashing from weapons that are not magical or made of silver to piercing from weapons that are not magical or made of silver whenever he finishes a short or long rest.

Keen Smell. Winnie the Pooh has advantage on Wisdom (Perception) checks that rely on smell.

Mystic Arcanum (1/Long Rest). Winnie the pool can cast mass suggestion once without expending a spell slot. 

Pact of the Chain. Winnie the Pooh can cast find familiar as a ritual to summon a quasit named Piglet. When Winnie the Pooh takes the Attack action, he can forgo one of his own attacks to allow Piglet to make one attack with its reaction.

Pact Magic (Recharge on Short Rest). Winnie the Pooh is an 11th-level spellcaster and his spellcasting ability is Charisma (spell save DC 16; +8 to hit with spell attacks). He knows the following warlock spells:

Cantrips: chill touch, eldritch blast, mage hand, poison spray
5th-level (3 slots): blight, command, contact other plane, darkness, expeditious retreat, fireball, hallow, hellish rebuke, scorching ray, suggestion, vampiric touch

 

ACTIONS

Claw. Melee Weapon Attack: +8 to hit, reach 5 ft., one target. Hit: 7 (1d6+4) slashing damage.

Eldritch Blast. Ranged Weapon Attack: +8 to hit, range 300 ft., three beams at up to three targets. Hit: 9 (1d10+4) force damage and the creature is pushed 10 feet away from Winnie the Pooh in a straight line.

 

 

Tigger went looking for Christopher Robin when his cherished friend left the Hundred Acre Wood—unfortunately the world found the stuffed tiger first, teaching him lesson after lesson in cruelty and disappointment. Tigger rolled with the punches for a while but as the years dragged on his spirit diminished, his heart hardened, and scars accrued until finally he became a downright mean bastard. Now the hard-bitten tiger’s pep has been replaced by cynicism and a burning urge to dish out some of the pain he’s suffered in his travels, leading him to strike first and ask questions if anyone has enough of a jaw left to answer.

 

(FANTASTIC illustration by Dan Luvisi)

Tigger

Small monstrosity, chaotic neutral
Armor Class 16
Hit Points 75 (10d6+40)
Speed 50 ft.

STR	DEX	CON	INT	WIS	CHA
19 (+4)	22 (+6)	18 (+4)	9 (–1)	8 (–1)	13 (+1)

Skills Acrobatics +12, Perception +5, Stealth +9
Damage Vulnerabilities fire
Damage Resistances force, thunder; bludgeoning
Senses passive Perception 15
Languages Common
Challenge 8 (3,900 XP)

Bounding Charge. If Tigger moves at least 15 feet straight toward a target and then hits it with a slam attack on the same turn, the target takes an extra 7 (2d6) bludgeoning damage. If the target is a creature, it must succeed on a DC 15 Strength saving throw or be knocked prone.

Brave. Tigger has advantage on saving throws against being frightened.

Disruptive Strikes. A creature hit by Tigger’s opportunity attack reduces its speed to 0 until the beginning of the next round and disengaging from him still provokes opportunity attacks. 

Energized. Tigger has advantage on saving throws against exhaustion.

Keen Smell. Tigger has advantage on Wisdom (Perception) checks that rely on smell.

Mobile. Tigger can Dash through difficult terrain without requiring additional movement. Whenever he makes an attack against a creature, until the end of his turn Tigger doesn’t provoke opportunity attacks from that creature.

Monstrous Momentum. For every 15 feet he moves on its turn, Tigger gains a +1 bonus (maximum +3) to Dexterity saving throws, melee attack rolls, and melee damage rolls until the start of his next turn.

Pounce. If Tigger moves at least 20 feet straight toward a creature and then hits it with a slam attack on the same turn, that target must succeed on a DC 15 Strength saving throw or be knocked prone. If the target is prone, Tigger can make one slam attack against it as a bonus action.

Tigger Tumbling (Recharge 5–6). Tigger can use his bonus action to flip, roll, and tumble his way through combat, making a Dexterity (Acrobatics) check. Until the start of his next turn, Tigger replaces his armor class with the result.

 

ACTIONS

Multiattack. Tigger attacks three times with his slam.

Slam. Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 6 (1d4+4) bludgeoning damage.

 

REACTIONS

Opportunist. Tigger can use his reaction to make a melee weapon attack against a creature within 5 feet when it makes an attack against a target other than him.

Slow Fall. Tigger can use his reaction when he falls to reduce any falling damage he takes by 50.