->"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."
-->-- [[SatanicArchetype Nicol Bolas]], ''[[TabletopGame/MagicTheGathering Emperor's Fist]]''

->"''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."''
-->-- '''[[TheSociopath Mr. Blonde/Vic Vega]]''', ''Film/ReservoirDogs''

->"''You just barely got that. Too bad, I was hoping I could laugh at your failure.''"
-->-- '''Solaris Paradox''', ''WebVideo/BrainScratchCommentaries''

->"''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''', ''VisualNovel/NewDanganRonpaV3''

->'''General:''' Now hold still. If I [[JackBauerInterrogationTechnique 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,''' ''VideoGame/Hitman2SilentAssassin''

->'''''"Scream''''', ''weakling! I want to'' '''''hear''''' ''your'' '''''suffering!"'''''
-->-- '''[[VillainProtagonist The Sith Inquisitor]]''', ''VideoGame/StarWarsTheOldRepublic''

->"''Everything I told you is a lie. [[ColdBloodedTorture This isn't happening to you for a reason]]...well, one reason. I enjoy it."''
-->-- '''[[AxCrazy Ramsay Snow/Bolton]]''', ''Series/GameOfThrones''

->It takes quite a bit to be considered "cruel" [[EvenEvilHasStandards 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 [[InterrogatingTheDead pursue]] [[{{Necromancer}} necromancy]] for the power to exalt the family; the Rosselini do it because they simply ''[[ForTheEvulz like it]].''
-->--''TabletopGame/VampireTheMasquerade - 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''', ''Anime/BayonettaBloodyFate''

->"You know, you're not ''nearly'' so ugly when you're screaming."
-->-- '''Bayonetta''' after defeating '''Fortituido''', ''VideoGame/{{Bayonetta}}''

->"Let me hear your sweet scream..."
-->-- '''Juri Han''', ''VideoGame/StreetFighterV''

->"''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!''"
-->-- '''[[SmugSnake Quattro]]''', ''Anime/MagicalGirlLyricalNanohaStrikers''

->"''Pain is hilarious!''"
-->-- '''Bill Cipher''', ''WesternAnimation/GravityFalls''

->'''Tyrion''': No! She is no longer yours to torment!\\
'''Joffrey''': ''Everyone'' is mine to torment!
-->--''Series/GameOfThrones''

->"''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''', ''VideoGame/BlazBlueChronoPhantasma''

->'''House:''' [[AC: 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 [[FleshGolem Uncle and Auntie]] were for, wasn't it? Someone to make suffer. [[GymClassHell I had a PE teacher just like you]]. You need to be entertained, and killing us quickly... [[ThisIsGonnaSuck wouldn't be entertainment]]...\\
'''House:''' [[AC: So entertain me.]] ''[[AC: [[DeathCourse Run]].]]''
-->--''Series/DoctorWho,'' "[[Recap/DoctorWhoS32E4TheDoctorsWife The Doctor's Wife]]"

->"''Fine, I will teach you fear, then pain. And then...well, at least the fear and pain will end.''"
-->-- '''Infinite''', ''VideoGame/SonicForces''