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"I was old before this world was even born. I watched my brothers rule for a thousand years until little worms like you overcame them. But I am not my brothers. I am older than they are, greater. I have devoured stars and shattered worlds. I have sired whole races, populated entire planes, and then hunted them to extinction for my amusement."

"I don't give a good fuck what you know, or don't know, but I'm gonna torture you anyway, regardless. Not to get information. It's amusing, to me, to torture a cop. You can say anything you want, but I've heard it all before. All you can do is pray for a quick death... which you ain't gonna get."

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"You just barely got that. Too bad, I was hoping I could laugh at your failure."
Solaris Paradox, BrainScratch Commentaries

"I *am* the supreme leader of evil, so it's obvious my personality would be twisted. The more you suffer, the more I enjoy it. There are people in this world who spread grief and misery for no reason than the thrill of it! And I'm one of those people. Nothing pleases me more than inflicting pain on others!"
Kokichi Oma, New Danganronpa V3

General: Now hold still. If I do it wrong, it will hurt a little.
Prisoner: What if you do it right?
General: Then it will hurt a lot.
General Mikhail Bardachenko, Hitman 2: Silent Assassin

"Scream, weakling! I want to hear your suffering!"

"Everything I told you is a lie. This isn't happening to you for a reason...well, one reason. I enjoy it."

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It takes quite a bit to be considered "cruel" by the Giovanni, but the Rosselini managed it. More than one Giovanni secretly suspected that the reason the Rosselini wound up serving Giovanni (and not the other way around) was philosophical more than tactical: the Giovanni pursue necromancy for the power to exalt the family; the Rosselini do it because they simply like it.
Vampire: The Masquerade - Clanbook: Giovanni (Revised)

Bayonetta: "Oh, I almost forgot. There's another reason I'm letting [Gomorrah] devour you. I really like to watch. I enjoy seeing your face distort with pain.
Beloved: (As Gomorrah bites down on him, causing him to crack) "Transform the world to how it should be...!"
Bayonetta: That's more like it. I'm all hot and bothered. (chuckles) So exciting.
Bayonetta, Bayonetta: Bloody Fate

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"You know, you're not nearly so ugly when you're screaming."
Bayonetta after defeating Fortituido, Bayonetta

"Let me hear your sweet scream..."
Juri Han, Street Fighter V

"A weak life that can't do anything is no different from an insect's. No matter how many you kill, more will just keep being born. Playing with them and abusing them, throwing them in a cage and watching them suffer... It's so much fun!"

"Pain is hilarious!"
Bill Cipher, Gravity Falls

Tyrion: No! She is no longer yours to torment!
Joffrey: Everyone is mine to torment!

"Oh, this is amazing! The greatest banquet ever! That's right! More! Give me more! Let me hear you puny little creatures SCREAM!!!"
Yuuki Terumi, Blaz Blue Chrono Phantasma

House: Tell me why I shouldn't just kill you both now.
Amy: Well, because... Rory, why?
Rory: Because... killing us quickly wouldn't be any fun. And you need fun, don't you? That's what Uncle and Auntie were for, wasn't it? Someone to make suffer. I had a PE teacher just like you. You need to be entertained, and killing us quickly... wouldn't be entertainment...
House: So entertain me. Run.

"Fine, I will teach you fear, then pain. And then...well, at least the fear and pain will end."
Infinite, Sonic Forces

"Do you want to know why I use a knife? Guns are too quick. You can't savor all the... little emotions. In... you see, in their last moments, people show you who they really are. So in a way, I know your friends better than you ever did. Would you like to know which of them were cowards?"
The Joker. The Dark Knight

To these cursed individuals, the sweet fruit of horror is as pleasing as the caress of a razored blade across soft flesh. They relish breaking the bodies of their captives, but prize even more highly the process of crushing the spirit, for nothing is more gratifying to a Dark Eldar than securing utter dominion over one who resisted them. They drink in every nuance of woe until their captives gibber and plead for death - a mercy the Dark Eldar are famously slow to grant.
Warhammer 40,000: Codex - Dark Eldar (5th ed)

"You won't find anyone can do a job like mine well unless they get some kick out of it."
Major Hardcastle, That Hideous Strength

"This was their terror, their great accomplishment, and they were planning to enjoy it."
Verity Price on Anders Clarke and Clint Goldfein, InCryptid : Chaos Choreography

Yesterday, Dithers slipped on the chalet's icy stairs, went airborne, and managed to impale herself on the wrought-iron fence. It was spectacular! And completely and utterly random! Is there anything more sublime than that bold crimson on fresh-fallen snow?
It was almost enough to make me reconsider a change of scenery. But not quite. 23 years is a long enough vacation in the Swiss Alps.
Dr. Stanislaus Braun, Fallout 3

"I did it! Now, show me that expression! Show me despair! Show me, as clear as can be, the moment you lose all hope and die! Show me your despair as you fall to your death!"

"More pain for you means more fun for me!"

"I meant to make [Arthur] feel miserable and I made him feel great. I'm a failure as a little sister!"
D.W. Read, Arthur, "The Short, Quick Summer"
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