History Main / EvilHasABadSenseOfHumor

* Negan from ''Series/TheWalkingDead'' as in the comic book, makes incredibly dark and tacky jokes while killing people in depraved ways, such as using the term "vampire bat" to refer to his baseball bat, wrapped in barbed wire, being covered in blood from bashing someone's head in, or saying someone's "got no guts" while cutting their guts out with a knife. Part of what makes him so sick is he ''knows'' the jokes are tacky and sick and he likes that because he loves seeing the onlookers' trauma.

* Pictured above is [[FourEyesZeroSoul Mordecai Heller]] of ''Webcomic/{{Lackadaisy}}'', a [[ConsummateProfessional cold-blooded]] [[PsychoForHire psychopath]] is the truest sense of the word. Apparently, when he was told he was going to be a "hatchet man", he didn't realize it was hyperbole and dismembered his first victim in all seriousness (first for this employer, that is). He took no pleasure in the act, though; [[SuperOCD the blood got everywhere]]. In general, Mordecai has trouble understanding humor. Or sexual attraction. Or loyalty.[[note]]He ''is'' 100% loyal to his boss, but doesn't get what that implies about his boss's other employees.[[/note]] Or any of those things that "sentimental types" keep going on about.

** Slim Shady, the PsychopathicManchild VillainProtagonist of Eminem's early work, is an zigzagged example because he is genuinely LaughablyEvil most of the time, with the over-the-top slapstick, social satire, and [[InsultComic creative insults toward celebrities and political figures]] throughout these songs being genuinely hilarious… but when Slim's actually ''trying'' to be funny, this trope comes into play. In ''Music/TheMarshallMathersLP'' in particular, most of his jokes are incredibly sick comments about {{domestic abuse}}, rape, and {{homophobic hate crime}}s.

* ''LightNovel/FullMetalPanic'':

* ''LightNovel/{{Baccano}}'': Ladd Russo's sense of humor is probably right up (down?) there with Gauron's, but replace the rape jokes with extra {{Gorn}} and [[LargeHam hamminess]]. Things that Ladd finds hilarious include: killing people; killing innocent people; killing not-so-innocent people; killing people when they least expect it; killing ''ten-year-olds'' when they least expect it; freaking the shit out of his uncle by shooting an empty shotgun into his face (and then, in the manga, coming right back to his office to do it for real); punching people's skulls in while rambling on about champion boxers; dancing around like a five-year-old in a pool of a friend's blood; getting his shiny new white tuxedo stained with the blood of his victims; and using someone's corpse as a hand puppet.

* In Max Beerbohm's DealWithTheDevil story "Enoch Soames", Satan is a very well-dressed (or even over-dressed) and respectable-looking guy who is deeply offended when the narrator (Beerbohm himself, who wrote humorous fiction) laughs out loud when he announces his identity and gives him the cold shoulder in a later meeting and seems to be completely humorless. Ironically, Soames, who is tricked by the Devil, is the kind of Satanist who is a decent guy but thinks that SatanIsGood (or at least cool).

* ''WebAnimation/IfTheEmperorHadATextToSpeechDevice'' has [[spoiler:Magnus the Red]] [[NotSoDifferentRemark draw parallels]] between the Tau, the Imperium of Man, and the forces of Chaos regarding forced sterilization policies, saying with the last one that "Let's just say [[HornyDevils Slaanesh]] has a weird sense of humor."

* ''Fanfic/InfinityTrainSeekerOfCrocus'': Ai decides to note how [[LivingStatue Lampetia]] is now a sight for sore "eye" just after she lost half of her face from a sword slicing it in half.

* ''Fanfic/InfinityTrainSeekerOfCrocus'': Ai is at the cusp of being an AntiVillain who decides that if [[spoiler:Austen Plane decides to reveal that he brainwashed Yusaku and then hurled them both onto the Infinity Train]], he will hurt Specter -- who is now redeeming himself -- with him. At one point in a brawl against White Gestalt, one of his @Ignister monsters -- in the shape of a sword -- cleaves through half of the face of Lampetia -- a LivingStatue denizen and basically one of the few beings Specter actively cares for -- which leaves her with only one eye. He then notes that she's a "sight for sore eye".

** In "All In", Darcy states how Grime [[spoiler:who lost one of his arms to them]] is now ''disarmed'', complete with chopping motion.

%% * ''ComicBook/{{Batman}}'': [[Characters/BatmanTheJoker The Joker]].

-->'''Jerome:''' Don't bother calling security, they're rather... ''[secretary screams off-screen]'' ...headless.

-->'''Jeremiah:''' ''[[[DissonantSerenity cheerfully]]]'' She has your eyes! For now.

* Anton Chigurh from ''Literature/NoCountryForOldMen'' is utterly serious in everything that he does, to the extent that he's [[EvilIsPetty perfectly willing to kill a man just because he]] [[HatesSmallTalk tried to make polite small talk]] with Chigurh. Tellingly, when Carson Wells is asked to describe Chigurh, his immediate response is that he "doesn't have a sense of humor".

* ''WesternAnimation/TheOwlHouse'' has [[spoiler: The Collector]], a [[KidsAreCruel childlike]] HumanoidAbomination who is amused by and jokes about Emperor Belos’ [[spoiler: consistent destruction and recreation of his “nephew” made in his [[CainAndAbel dead brother’s]] image, the draining spell’s [[FinalSolution end result]], and Belos’ gradual transformation into a monstrous sludge creature.]] They generally treat everyone and everything around them as simple playthings to be used for their own entertainment and fun.

'''Vegeta:''' Creator/ChristopherReeve! ''[crushes Goku's legs]''\\

** Alan Jonah too. He introduces the Titan-admiring Dr. Mariko to the newborn Titan he's holding captive ''without'' sharing some critical details with her in advance -- namely that it's a nightmarish BodyHorror TwoBeingsOneBody, ''or'' that it can speak, ''or'' that fact number two is because half of the Titan is an InhumanHuman Dr. Vivienne Graham.

* ''Film/TheLordOfTheRingsTheTwoTowers'': Amongst the Uruk-hai, [[Characters/MiddleEarthFilmSauronsEvilForces Uglúk]] boisterously cracks a couple dark jokes during his screentime, when getting his men to give a prisoner some "medicine" in the form of the orcs' suspiciously red pouch water, and when fresh orc kill is back on the menu.

[[caption-width-right:258:Don't [[IncrediblyLamePun axe]] questions you don't want to know the answer to.]]

* Pinkie Pie's entire [[HurricaneOfPuns onslaught of bad pun after bad pun]] in ''Fanfic/{{Cupcakes}}'' is this, considering that she's [[spoiler:graphically [[GuttedLikeAFish disemboweling]] the still-living Rainbow Dash as she says them]].

* In ''Literature/TheScrewtapeLetters'', none of the devils have any sense of humor at all, but they are played for laughs. In fact, being laughed at seems to be Screwtape's BerserkButton. "She's the sort of girl who would find ME funny!"

** In "Bullies", Valmont uses the dragon talisman to injure Captain Black. Later, as the Dark Hand attacks Fort Knox, Jackie is sneaking when he hears Valmont joking about Black's injuries, saying "I understand he had a doctor's appointment." As the Dark Hand laughs, [[BerserkButton Jackie gets so mad that he slams his hand on a rail]], [[SoMuchForStealth giving himself away]].

* ''WesternAnimation/{{Amphibia}}'': In "Olivia & Yunan", Andrias tells the titular duo that if '''anyone''' resists his plans... they're to give said parties a stern talking-to.
-->'''Lady Olivia:''' Oh.\\

'''King Andrias:''' Just kidding. '''Terminate''' them!

* Emperor Belos from ''WesternAnimation/TheOwlHouse'' is secretly [[spoiler: a 17th century WitchHunter, who seeks to [[FinalSolution kill every witch on the Boiling Isles]]. He's also made a long line of {{Expendable Clone}}s to serve as his right hand man, the Golden Guard, all of whom believe they're his nephew and that they're helping the people of the Boiling Isles... And because he thought it would be funny, Belos named all of them ''Hunter''.]]

'''Goku:''' What?\\
'''Vegeta:''' Creator/ChristopherReeve! ''[Vegeta crushes Goku's legs]''\\
'''Goku:''' AHHHH! [[DudeNotFunny That was in terrible taste]]!

* In ''ComicBook/TheSandman'', SerialKiller Nimrod opens a [[CriminalConvention serial-killer convention]] with a disgusting joke about rape. His audience finds it hilarious.