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    Headhunting Beast 

Headhunting Beast / Wicked Dragon Hunter Vorpal

The starter boss of the game, a horrifically mutated rabbit.
  • Degraded Boss: More Headhunting Beasts can be found as a standard enemy in the Chaos Dungeon.
  • The Dragonslayer: Its form as Vorpal adds the "Wicked Dragon Hunter" title. This is in reference to its past as the one who slew Jabberwock.
  • Expy: Directly based off Ludwig from Bloodborne, who both started off as rabid beasts that crawl on all fours before remembering a bit of their former heroism, making them take up their sword and shift to standing, even if hunched, once more.
  • Hair-Raising Hare: It's a rabbit, one that has a twisted form with elongated limbs on all fours, stretched mouth, googly eyes, and fangs not just in its mouth but sprouting from all over its body.
  • Hero of Another Story: In the distant past, it killed Jabberwock and led the Rabbits to safety.
  • Off With The Head: It's in the name as Vorpal.

    Beast of Distraction 

Beast of Distraction / Uggug

The boss of Lutwidge Town. A monstrous, thorn-covered creature.
  • Degraded Boss: More Beasts of Distraction can be found as a Depths 2 enemy in the Chaos Dungeon.
  • Expy: Based off Ugug from Carroll's Sylvie and Bruno.
  • Was Once a Man: Supplemental materials in the Mental Ward reveal this, having been a man who fell of a bridge but later grew thorns from the Lake God.

    Edith 

Great Grey Eagle Edith

The boss of the Mental Ward. Edith Liddell, twisted into an inhuman and monstrous form.
  • A Day in the Limelight: Never appears in the game proper, but we see more of her in the "Isolation Room's Neighbor" movie in Queensland and the Liddell House in Winterbell.
  • Dual Boss: With Jack the Ripper in Chaos Dungeon.
  • Ill Girl: The Liddell Family section reveals her to be this.
  • Star-Crossed Lovers: Her Soul and the Chaos Dungeon description of the Jack & Edith boss fight reveals that she was in love with Prince Leopold, but he had to abandon her.
Love surpassing barriers, between a student and a prince. They slipped away from the country for a night, and then another, in a never-ending escape drama. Even so, knowing what awaits them, the two go to meet the tragic end. "Ahh, please do not cry. Forget about me, leave me in the past. You need to go straight to your home. Hurry, before the soldiers come..." "No. I'd hate to, my prince. Have you not promised to take me outside? Is it wrong for a man and a woman who love each other to be together?" "Ahh, God. Please, if you exist...I beg you. Guide us to a paradise for only the two of us, with no one to bother." The ephemeral prayer of the little girl reached a god who didn't understand love and was selfishly consumed.
  • Tragic Monster: A deeply sweet and innocent girl turned into a Demonbeast.
  • Turns Red: Kill Jack first in the Chaos Dungeon boss fight and she will go berserk.

Three Nightmares of Wonderland

    The Nightmares in general 
  • Optional Boss: Played with. In gameplay, there is no ending where they are required to die, so you're free to make Covenants with them if you don't wish to fight them, and the only reason you'd want to fight Bandersnatch and Jubjub is because the former is blocking a road and would have forced you to make a detour, and you can only make a Covenant with her by defeating her in battle anyway, while the latter will kill every NPC in the game if you don't deal with her by the time progress reaches stage 10. Subverted in End F and End G, however, where they will ambush you and you're forced to fight all three of them. And since End G is a requirement for End H, you'll have to face them at least once.
  • Suspiciously Similar Substitute: In gameplay and lore, they're functionally similar to the Demonic Princesses of I whom you can choose to make Covenants with, kill or imprison them.

    Bandersnatch 

Frumious Bandersnatch

The boss of the Fuming Forest. A furious creature returning from BLACKSOULS.
  • Cute Monster Girl: In contrast to her monstrous self in I, here she's a cute girl with the beastly parts of her first form.
  • Dumb Muscle: Though Dumb Is Good.
  • Fiery Redhead: Has a mane of red that matches her impulsive tempers.
  • Leeroy Jenkins: Her Establishing Character Moment has her bursting out of her cave and roaring fiercely that she'll destroy the intruding protagonist... before charging off the cliff and falling to her death, leading to a Victory Achieved screen.
  • Token Good Teammate: Though she's a dangerous boss and one of the Nightmares of Wonderland, she's not in the least malicious in the way that Jubjub and Jabberwock are. Even her soul refers to her as a "shadow of innocence".
  • Undying Loyalty: To the original first Alice from I.

    Jubjub 

Mad Bird Jubjub

The boss of the Sickening Clock Tower. An insane, bloodthirsty creature who delights in madness.
Sister Alice: "...Plase don't misundertand... I don't care what happens to you. My leading principle is selfishness, always. Ahh! DAMMIT!! ...Who the fuck is your little sister!! This chocolate cake!! C'mon be gone already! Get out of my sight, my memory, my heart!"
  • My Rules Are Not Your Rules: Unlike the player's version of the Madness status effect, Jubjub's version does not drastically reduce HP every turn on top of no having any reduction to the damage buffs it grants.
  • Nipple and Dimed: Despite never wearing clothes, her nipples are only shown in sex scenes.
  • Token Evil Teammate: In a way. Compared to Jabberwock, who is a Retired Monster who won't start any fights on her own unless the protagonist does and Bandersnatch, who's Dumb Is Good Dumb Muscle, Jubjub is outright malevolent and will kill every NPC in the game if the protagonist doesn't stop her first.
  • Token Good Teammate: Ending H reveals her to be this, turning against Jabberwock and Bandersnatch to aid the protagonist.

    Jabberwock 

Corpse Dragon Jabberwock

One of the Three Nightmares, and the only one to not be initially hostile. An evil dragon who was once slain by a hero, though she is now an easygoing dragon girl in the present.
  • Affably Evil: Very much so.
  • Ambiguously Bi: In the dungeon she locks Grimm in after a failed rape attempt, there are other cells marked for Alice, Red Hood, and Mary Sue.
  • Bullying a Dragon: Literally. If the player attempts to rape her, not only will you then immediately have to fight her but if you lose Jabberwock will reverse the situation on you.
  • Dracolich: A Cute Monster Girl variant.
  • Eldritch Abomination: As much as all the girls in the game are, Jabberwock is a particular example, openly turning into her Great One form and using her powers in Ending F/G.
  • Evil Matriarch: Often talks about raising children, and offers to be the protagonist's mother in one scene.
  • I Love the Dead: She's a corpse, which is brought up repeatedly in her sex scenes.
  • Nightmare Fetishist: In Ending F/G, her Motive Rant reveals that her greatest desire is to see souls blacken completely as people fall into utter despair.
  • Retired Monster: First encountered as this. If fought as soon as you see her and in the scene after a failed Attempted Rape, she'll say that she liked to be retired, but if they want an evil dragon, she'll give them one. Though once you're further in the game...
  • Terms of Endangerment: Regularly engages in these, particularly with Vernai, who she calls Ver-ver.
  • The Man Behind the Man: Claims to have been this to Mary Sue in Ending F/G.

Chaos Dungeon / Chess World Shatranj

    Ravenous Mimic 

Ravenous Mimic

Very rarely, what appears to be a mess of treasure chests is actually a mass of mimics.


  • Acid Attack: Spits out acid to reduce the player's HP, ATK and DEF.
  • Body of Bodies: The Ravenous Mimic is actually composed of a good amount of mimics.
  • Chest Monster: A whole bunch of them cobbled together.
  • King Mook: A boss version of the various Mimics found throughout the series.
  • My Rules Are Not Your Rules: Unlike other enemies in the Chaos Dungeon, dying to it will have it steal your souls with no way of getting them back.
  • You Will Not Evade Me: Erupts with vomit at the start of the fight, reducing both speed and evasion for the player.

    Trash-Eater Grasshopper 

Trash-Eater Grasshopper

"The hard-working ants? Will they work until they die?" So ridiculed the lazy grasshopper who only cared for songs and dances. But with the death by winter's cold coming, he finally had to spread his wings in search of food. Songs and dances are of no use in the world of nature. With no proper food to be found in the freezing cold, the grasshopper trembled and wept, but continued to eat corpses, mud, feces, rotten fruits... When the spring came and the ants came out, a huge shadow fell upon them. With snow and blood on its face and feelers, the shadow whispered: "FOOD, hand over. FOOD, hand over. ALL, hand over. FEED me."
Trash-Eater Grasshopper Chaos Dungeon description.

One of the potential bosses that can be found in the Chaos Dungeon


    Wolf in Grandma's Clothing 

Wolf in Grandma's Clothing / Cunning Wolf

"Oh, grandmother, what big ears you have." "The better to hear you with, my child." "But, grandmother, what big eyes you have." "The better to see you with, my dear." "Oh, grandmother...what a terrible big mouth you have." "The better to eat you with, my dear!!!" Her entrails torn by sharp claws, her body ripped apart and devoured, Red Hood finally reunited with her beloved Granny as Wolf's feces, or so the story goes. And they all lived happily ever after... ......hmmm, NO! Such a trite, vulgar ending is no fun at all! This is my very special maiden work. Red Hood will be playing a bigger part and heroically kick the bucket♪
Wolf in Grandma's Clothing Chaos Dungeon description

One of the potential bosses that can be found in the Chaos Dungeon, originally intended to bring the death of Red Hood... until an Outer One had other ideas.


  • The Big Bad Wolf: The wolf himself appears as a optional boss.
  • Desperation Attack: If the wolf's health reaches critical levels as the Cunning Wolf, he'll gain a much more powerful attack that has a chance to stun.
  • Paper-Thin Disguise: If the in-game battle sprite is of any indication, the way he tries to disguise itself as Red Hood's grandma is pretty terrible, to the point where it's even reflected in gameplay: his Fake Cough and Granny's Fail skills having the former skill involve him both literally and figuratively dodge, while the latter skill has him trying to hide his ears and tail.
  • Shed Armor, Gain Speed: Well, clothes in this case: if he vomits the Granny, he'll become much more aggressive and become faster, but if he devours the Granny once more, he'll become slower and more defensive. This happens every five turns.
  • invokedWhat Could Have Been: In-universe, he was supposed to devour Red Riding Hood at the end of the twisted fairy tale involving her, but a certain Outer God decided it was way too cliché and had something more terrible for her.
  • Wolf in Sheep's Clothing: In this case Granny's clothing. That being said, he sometimes loses it when he vomits the Granny.

    The Three Little Pigs 

The Three Little Pigs

To Little Pigs' houses a pyromaniac came. The straw house burned down. The wood house burned down. How terrible, how terrible. But it's alright! The youngest made a brick house, a house that won't burn! Yaay, yaay, hurrah, hurray. ....Uh, oh? What's wrong? Isn't it hot? Ouch-ouch-ouch, ouch-ouch-ouch. The floor is hot, it's hard to stand. Hot, hot, hot, hot. The door is melting, it won't open. Hot, hot, hot, hot, hot. Papa, save us, get us out. Hot-hot-hot-hothothothothothothothothothothothothot
The Three Little Pigs Chaos Dungeon description

One of the potential bosses that can be found in the Chaos Dungeon.


  • Adaptational Badass: Assuming the wolf and the pyromaniac are the same, apparently the wolf managed to become a firebreather, allowing him to cook the Three Little Pigs by turning the brick house into an impromptu oven with his fire.
  • Ascended Extra: The Three Little Pigs were originally found in the Behemoth Ranch in I as corpses when the Behemoth escaped and devoured them. In II, they can be found in the Chaos Dungeon as optional bosses.
  • Cooked to Death: How they all die at the end of their twisted fairy tale.
  • Didn't Think This Through: Brick houses were not designed to withstand fires, as the Three Little Pigs found out the hard way.
  • Healing Boss: Can sometimes prey to recover their own HP.
  • Turns Red: The Three Little Pigs will become more aggressive if their HP reaches a certain threshold, and will begin charging attacks and sending excrement against the player.

    Frankenstein's Monster 

Frankenstein's Monster

In a certain land, lived the ugliest man in the world. When he would visit towns, all would call him a 'monster' and throw stones at him. With no one who loved him, it wasn't rare for him to be driven far away from the people. And yet such a man found someone he loved. In a cruel asymmetry, he fell in love at first sight with a lovely, beautiful woman. So beautiful she was that her smile was like a blooming flower. She was surrounded by a flower field from the time they met. She would always kindly welcome the ugly man, and they spent every day having pleasant talks. The problem was, she was 'blind'. The man's face was horrible, and his head was to match. But even a fool he was, he knew what future awaited him. If she saw 'how he really looks', she would reject him. Even so, the man couldn't bring himself to run away. The man resolved himself, confessed his appearance, and confessed his love. Hearing him, the woman was silent for a while, and then quietly opened her 'eyes'. No eyes were there, only rows of uneven teeth. Her neck twisted and tore, and her head fell onto the flower bed... "I'm glad. I've been searching for a new spouse myself."
Frankenstein's Monster Chaos Dungeon description

One of the potential bosses that can be found in the Chaos Dungeon.


  • Body Horror: Good lord, his sprite shows a bizarre mishmash of human flesh.
  • Frankenstein's Monster: The "Monster" being in question an abnormal mass of flesh.
  • Mind Screw: Who was the spouse mentioned in the Chaos Dungeon description? Was it someone equally monstrous as him, or was it some kind of parasite? Not helping matters is that the description mentions the monster met the spouse in a flower field, making it even harder to discern what she is.
  • Non-Malicious Monster: The only reason why you fight it is because of the very fact that he is a optional boss. Otherwise, not depleting any of his health will cause him to sob and look for his spouse.
  • Turns Red: After reaching near-death, he will restore his own health only once and become a lot stronger.

    Bluebird of Unhappiness 

Bluebird of Unhappiness

Tragedy's blessing be on the characters. Turn to fuel for the joy of great Mary Sue.
Bluebird of Unhappiness Chaos Dungeon description

Mytyl and Tyltyl, one of the potential bosses that can be found in the Chaos Dungeon.


  • Chekhov's Gunman: Initially, they appears to a boss with no kind of lore whatsoever compared to the other Chaos Dungeon bosses, but in DLC 3 during the Visual Novel sequence, it's revealed that they were the ones who gave Mary Sue the idea to abduct Lewis Carroll's soul to form Grimm.
  • Meaningful Name: The name is a deliberate corruption of the Bluebird of Happiness, and they helped perpetuate one of the biggest tragedies for Mary Sue's pleasure.
  • Minor Major Character: They gave Mary Sue the idea to steal Lewis Carroll's soul, but other than that, they appear as a optional boss fight in the Chaos Dungeon.

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