For some reason, capital-E Evil and most villains just don't get humor. And we don't just mean in a "doesn't understand the joke" sense; they're usually completely humorless or they're cackling because they're complete lunatics and "Eeeeevil!" Maybe it's because of some implicit assumption that "laughter heals the soul", so someone who doesn't laugh or laughs at the wrong things can't be right in the head. Perhaps it's that humor requires perspective, which villains usually don't have in abundance.
This manifests in two different ways.
- A complete lack of humor: The villain is either incapable of understanding humor (like an evil Tin Man) or can, but they're so stone-hearted and taciturn that they find nothing funny, never even cracking witty remarks or exchanging repartee with the hero. While there are plenty of stoic Anti Heroes, heroes as a whole can generally laugh at least once in a while. Understandably, they often get placed opposite a wisecracking hero who uses them as an unwitting Straight Man.
- An especially sick and twisted sense of humor: Where a "good joke" to them is either not funny to normal people at all, goes way past Black Comedy, or a horrifying torture to the pranked... at times so horrifying that it drives them insane. These villains often have quite a bit of dark wit to them and, if they embrace a "prankster" motif, make cutting and accurate remarks and love irony, may occasionally go all the way to actually being funny, in a very dark sort of way. You can expect these deranged comedians to face especially straitlaced heroes who "never get the joke", say "You're Insane!", and get thanked for it. Often associated with Faux Affably Evil characters.
Lack of Humor:
- In Berserk, pretty much all the big villains have absolutely No Sense of Humor. Granted, Berserk is not known for rip-roaring comedy but the protagonist Guts is a Deadpan Snarker that has a habit of making fun of his enemies. Even Griffith had (has?) less of a sense of humor than him.
- Creed from Black Cat, most notably in the manga. Sure, he laughs maniacally quite a few times, but it's always because he's just crazy like that and is just showing his appreciation for watching other people die. Train, on the other hand, loves to make good-hearted sarcastic jabs at everyone — villains included. Especially noticeable during their final battle, where Train still has the energy to make fun of Creed (Train: "Eeeh? Then I guess that makes you more like a zombie!" Creed: "No, it makes me a GOD!"). Creed tends to take all of Train's comments literally, and the jokes tend to go over his head.
- Death Note, with L and Light. Light, being the Villain Protagonist, really seems to lack any sort of sense of humor. Though he does laugh a lot when murdering criminals and at one point he does make "jokes" about wanting Shinigami wings and how Ryuk probably isn't very popular with the girls. L isn't exactly the funniest person in the world, he does have more of a sense of humor. In the anime, he's actually a bit of a Deadpan Snarker.
- Father, the Big Bad of Fullmetal Alchemist. It seems when he removed all the sins from himself, he also removed any sense of humor as well.
- In Fushigi Yuugi, just try to name one of the Seiryu Seishi that had any sort of sense of humor (or even just having any sort of funny moments). All of them (definitely including Yui) are always so dead serious and never find humor in any situation. Now contrast them with the Suzaku Seishi, who all had several moments where they joked around.
- In Hikaru no Go, although they're definitely not evil, Touya Akira and Touya Koyo-meijin are Hikaru and Sai's main rivals for most of the series. And both Hikaru and Sai definitely have much more of a sense of humor than those two. Especially noticeable in the beginning. For Hikaru, however, after Sai disappears and he gets more serious, it follows this trope less.
- In the Soul Hunter manga, the Man Behind the Man Jyoka has absolutely no sense of humor. Taikoubou, at this point known as Fukki, even lampshades it at one point. A huge contrast to Taikoubou, who tends not to take many things very seriously.
- In Girls und Panzer, the more victory-obsessed and ruthless rival teams tend to lack senses of humor, largely because many of them, such as Anchovy, Katyusha and Erika take themselves too seriously. Maho, the head of Black Forest's team and Oarai's main rival, is less arrogant than most of them and also a loving older sister but is still a fairly serious individual. By contrast, the Oarai teams like goofing around on their time off, Darjeeling of St. Gloriana is said to jokes (on Assam's character sheet) and Kay finds Yukari's hasty attempt to pass herself off as "Sergeant Oddball" when she's caught infiltrating Saunders hilarious.
- While calling him outright evil is a stretch, Absalom from One Piece does not possess a good sense of humor. Oda himself once said that "even his sense of humor is invisible".
- With some exceptions, Spider-Man villains have often been typically as humorless as Spider-Man is frivolous, making remarks like, "Let's see how funny you think you are now!"
- Deadpool tends to run into this as well; some will play along at first but get sick of it when they realize he a) isn't going to shut up. Ever. and b) has no intention at all of taking anything seriously (unless he's using Obfuscating Insanity, but it's hard to tell). Taskmaster was not at all amused when Deadpool defeated him by doing the Macarena.
- In one Dylan Dog comic, Dylan's sidekick Groucho is repeatedly trying trying to tell a joke about three men about to be executed (the guillotine blade keeps stopping just above their necks, so the first two are pardoned due to an Act of God, but the third man announces that he's figured out where the fault is) to a nice old lady who is an unwitting friend and companion of the evil witch, but is constantly interrupted before he can get to the punchline. After the witch is defeated, they later sit down for some tea, and Groucho finishes the joke. She doesn't get it. And then she decides to kill them all, monstering out and revealing herself to be considerably more powerful than her late friend despite acting like a dimwitted old granny the whole time.
- Wonder Woman Vol 1: Making jokes that are or can be misconstrued to be at Priscilla Rich's expense tends to result in immediate homicide and/or torture. She is quite good at taking everything she hears personally so even people just laughing at a joke that wasn't at her expense but was said by someone else is the kind of thing she can decide is an offense worth killing over.
- A clever early scene in Titanic (1997) hints at the likability of several of the key characters. As Ismay brags about the size of the vessel, Rose (a likable character, of course) comments on how Ismay might be interested in the works of Sigmund Freud and his opinions on men and their fascination with size. Mr. Andrews and Molly Brown (both likable) are amused; Cal, Ruth, and Ismay (all varying degrees of unlikable) are either appalled or confused (keep in mind these types of jokes probably weren't nearly as stale in 1912 as they are today).
- The Name of the Rose: All of the mayhem of the story happens because one of the abbey's monks is so pious that he believes (fervently and most importantly murderously) that comedy is heresy, because mocking things supposedly will lessen the fear of God and the Devil that man is meant to have. The MacGuffin of the story, and thus the thing he hunts down to destroy (even eventually setting the abbey the story takes place on fire), is a lost chapter of Aristotle's Poetics that praises comedy.
- In The Screwtape Letters, 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 Berserk Button. "She's the sort of girl who would find ME funny!"
- In Max Beerbohm's Deal with the Devil 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 Satan is Good (or at least cool).
- In Star Wars Legends, when Jacen Solo loses his sense of humor and stops being a Pungeon Master, it's a sign that he's becoming evil.
- In This Rough Magic, it is revealed that beings of pure evil cannot understand humor and therefore cannot imitate it. This is the only way to be sure you aren't dealing with one, as they are otherwise perfect illusionists.
- Small Gods: Vorbis' jokes are lacking in any actual humour whatsoever. But since he's the head of the Exquisition, people laugh anyway, as if their lives depend on it. Because they do.
- Buffy the Vampire Slayer: Warren Mears acts all Laughably Evil, till Buffy turns it around on him, and Tara pays the price.
- Often appears on Doctor Who, especially with the Fourth Doctor the villains have no sense of humour; the Doctor does. The Master is an occasional exception, depending on the incarnation.
- Colonel Flagg on M*A*S*H had a sense of humor once, but got rid of it by watching The Three Stooges and jabbing himself with a cattle prod every time he felt like smiling.
- Major Neuheim of Private Schulz is a Pointy-Haired Boss, not to mention a Nazi, who is totally lacking in warmth and anything resembling a sense of humor. However, his humorlessness is itself a source of comedy.
- Pick a scene where Stargate SG-1 is captured by a System Lord, any episode. Jack will snark at the Goa'uld and they'll just glower, perhaps flaring their eyes in irritation. However, one of the funniest moments in the series is when Teal'c tells a Goa'uld joke about Setesh's emblem (and breaks down into roaring laughter). Apparently, they save their sense of humor for mocking each other.
- In Homestuck, recurring villain Jack Noir sits between no sense of humor and a subdued sick sense of humor. His most competent sidekick, the Draconian Dignitary, sits firmly in lack of humor territory, as embodied by this conversation over the status of two missing heroes (the Prince of Heart and the Rogue of Void):
- Pictured above is Mordecai Heller of Lackadaisy, a cold-blooded 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; the blood got everywhere. In general, Mordecai has trouble understanding humor. Or sexual attraction. Or loyaltynote . Or any of those things "sentimental types" keep going on about.
- Zuko of Avatar: The Last Airbender starts off as having no sense of humor, as the only time he laughed was out of spite for the pirates he was arguing with having their ship stolen. Azula has a sick sense of humor, though she has lack of humor moments as well ("It's okay, you can laugh. It's funny.")
- The Mask faces a few in his cartoon series, given a Comically Invincible Hero fits better against overtly serious villains.
- Vac Attack from The Grossery Gang webseries has no patience for crude humor, to the point of vacuuming up one of his minions for laughing at the word "duty".
Sick Sense of Humor:
- Gauron from Full Metal Panic! fits the sick sense of humor to a "T". He's basically an Ax-Crazy villain that takes jokes to the point of being Black Comedy. He's definitely made to be a stark contrast to Sousuke, who is the most Comically Serious Straight Man in the world. He really is a lot jollier than a bunch of other characters in the series...but his sense of humor is certainly disturbing, to say the least. He laughs maniacally when he kills people (or whenever Sousuke is involved), and the jokes he cracks to Muggles aren't received well. One particular example that stands out is when he "joked" with the airline stewardess (of an airplane he eventually hijacked):
Gauron: It's troublesome, isn't it? Having so many high schoolers on board?Stewardess: Ah, not really.Gauron: We should throw them all out when we get 8,000 meters above ground. Then the flight would be quiet and relaxing. Don't you think?Stewardess: Eh?!Gauron: Heh heh heh heh! Just kidding.
- And then there was the "joke" in TSR, where he confessed to Sousuke that he really wanted to "fuck his dead body up the ass" back in Khanka. Sousuke's reaction to this is, predictably, to act absolutely horrified. Gauron was laughing like a maniac while he said it, and then told Sousuke he was just kidding. Except right after he said that, he immediately negated it by confessing that what he said was true and serious. In other words, he loves having fun screwing around with poor Sousuke. However, an especially interesting thing to note about Gauron's jokes is that pretty much all of them are actually things he truly means.
- 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 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.
- Whether November 11 from Darker Than Black really counts as a true villain is up for debate, but what isn't up for debate is that a) he's technically a sociopath and b) he has the weirdest sense of humor in the series, usually consisting of delivering violent or disturbing Breathless Non Sequiturs before insisting that he was just kidding.
Mooks: ...And what do you plan to do with this 'acquisition', Mr. Smith?
November 11: Well to start I thought I'd walk through the doors of a rival company and kill 3000 of their best men.
November 11: ...Kidding.
- Genma seems to take over November 11's role in the second season in this respect, although he goes for disturbing sexual innuendo rather than gallows humor. For instance, in episode 8, he walks into a cafe where Kirihara is eating and she asks him sarcastically if he's taken up stalking as a hobby. He replies that his taste is for "budding" targets, and he looks out the window at young schoolchildren who are outside. Like November 11, he claims to be kidding, and like other examples of this trope, his "jokes" seem more like confessions than anything. He also seems very amused when doing things like running people down with a train he hijacked and armoring himself and beating up Hei.
- In Threads Of Time, Sali Tayi does laugh...when he's raping women and mass-slaughtering people. Of course, when there are situations and things that are actually...well, humorous to a normal person, he doesn't find any humor in it. Contrast him with Moon-Bin, who likes to make light-hearted, good-natured banter and teasing. And Sali Tayi wonders why Atan Hadas hates him and likes Moon-Bin...
- Black Lagoon: Apparently, blowing up someone's apartment is Balalaika's idea of an "incredibly funny joke" To be fair, that guy really had it coming.
- Naruto: Most of Nagato/Pain's jokes are very grim and sardonic in nature. Presumably, this is what happens to your sense of humor if you are so powerful; people all around you more or less consider you a Physical God, yet you are yourself nothing but a Cosmic Plaything in the face of the horrible events that broke all of your dreams, ideals, and hopes and forced you down your Start of Darkness.
- In Fullmetal Alchemist, things that Envy has found hilarious include trying to kill people while transformed into their loved ones and setting off a genocidal war by murdering a child. Envy also gets some no sense of humor moments, though, being a character who "can dish it out but not take it", leading to circumstances where Envy is the butt of a joke from the heroes and reacts with hypocritical outrage.
- In Fairy Tail both Sabertooth and Raven Tail have rather cruel senses of humor. Raven Tail gets their kicks making things hard for Fairy Tail and laugh when one of their members destroys the prized(?) possession of one of the less intelligent characters. Sabertooth (minus Rogue) tops this by laughing when one of their members physically tortures Lucy in front of a huge audience because she gave a friendship speech.
- In Code Geass, Lelouch's humour only comes up rarely, but it's all sorts of odd. The first time, in a moment of light-hearted relief, he jokes that he can make someone kill all the Japanese. She then proceeds to do so, thanks to Lelouch's Power Incontinence. It is both unfunny and horrifically poorly timed.
- The second case is telling his, due to memory loss, extremely submissive associate who thinks that she's his slave — not in a sexual way, but a "it's the 1500s, and you have no rights" way — that she should turn her top inside out. Obviously, she then proceeds to do so, only stopping because Lelouch suddenly realises that his joke has gone very wrong and stops her, rather upset that she took him seriously. Again, neither actually funny nor well-timed.
- Tron from Yu-Gi-Oh! ZEXAL. He actually thought that what he did to Droite was funny.
- Although he's not purely evil, Kaiba from Yu-Gi-Oh! counts as well. His sense of humor is warped due to his time with Gozaburo and even made a joke about the main cast nearly dying. He's mostly a Deadpan Snarker and has a few funny moments in the series, the 4Kids dub mostly.
- This is one of the biggest clues as to who the Big Bad is in Higurashi: When They Cry. It's Takano Miyo, the nurse with the tendency to make scary off-putting remarks that set everyone on edge, then laugh as if she had told a joke. Her pranks even end up sending Shion and Rena into psychotic episodes (though Tsumihoroboshi-hen implies that this is deliberate).
- Dragon Ball Z: Super Buu gives this little gem while fighting Goku and Vegeta in his own body:
- Summer Wars: Love Machine, a hacking AI gone rogue, sees literally everything it does as just being harmless pranks. At first, it sticks to stuff like fake 911 calls or locking people out of their email accounts, but soon it escalates to such wacky pranks as shutting off an old womans heart monitor so her family wont know shes having a fatal angina attack. Then it decides it would be hilarious to hack into a satellite and fling it at a nuclear power plant to see how many people the resulting explosion would kill.
- Kaido from One Piece, though his sense of humor could be more accurately described as strange than sick. This is a man who regularly attempts suicide for fun and enforces the reign of a corrupt tyrant that even he hates for no other reason than because he finds doing so amusing for reasons known only to himself.
- The Joker is either this trope or Actually Pretty Funny Depending on the Writer, such as in The Killing Joke. Or can even be both at the same time.
- Depending on the Writer, The Green Goblin falls in this trope, although like the Joker, he can be this or Actually Pretty Funny.
- Cletus Kasady, a.k.a. Carnage. Only a man like him would find literally painting the neighborhood with blood hilarious.
- In an issue of Hellboy, a woman tells a story to residents at a Japanese tavern that amounts to nothing more than a man suffering a horrible misfortune, which the other residents treat as a hysterically witty joke. This is the first tip-off that they're all evil spirits.
- Sonic the Hedgehog (Archie Comics): When Eggman reveals to the Grandmasters that he's roboticized Princess Sally, they all react with various levels of shock... except Drago Wolf, who's shown laughing his ass off.
- The Transformers: Last Stand of the Wreckers: Overlord actually laughs at Rotorstorm's "combiner" joke... then he shoots Rotorstorm's head at point blank range. Made worse by Rotorstorm's last words.
Rotorstorm: At least one of you has a sense of humour.
- Whirl from The Transformers: More Than Meets the Eye is a deranged Jerkass who delights in trolling people, so naturally his jokes and pranks tend to be as offensive and inappropriate as possible. Special mention must go to the time he regaled the crew with a silly little story about him horrifically murdering his Archenemy by breaking into the guys home, smashing his skull in, and shoving a rod up his... ahem. Rung mercifully intervenes before he can go into any more detail.
- Mad Scientist Brainstorm also gets up to this. When one of the Duobots gets fused messily and fatally into the side of the Lost Light's drive system, he snarks that at least it'll be easier to tell them apart from now on.
- Paperinik New Adventures. The Evronians' sense of humour isn't sick, it's just so weird that, to them, shouting "We'll meet again, Earthlings! And next time it'll be your end!" while retreating is an incredibly funny joke. Some of them still have standards, though (when Paperinik told them a horrible joke a low-level officer laughed himself silly, but Zondag had a Lame Pun Reaction).
- The Huns in The Wizard of Id, have a unique way of wishing their foes a happy Easter in this strip.
- In The Sandman, serial killer Nimrod opens a serial-killer convention with a disgusting joke about rape. His audience finds it hilarious.
- Ultimate X-Men: Magneto is not a man given to laughs, to put it mildly. And when he tries, it is always quite sadistic and mean-spirited.
- Dragon Ball Z Abridged:
Freeza: Oh, what's wrong, monkey? Come on now, give me something funny.
- Vegeta has a sick sense of humor in spades. When he's called on it by Goku, he acknowledges that his sense of humor is in bad taste, but he doesn't care, because he's evil.
- Freeza is much worse, the punchline to all his jokes is "someone dies".
Goku: You..you killed my best friend!
Freeza: HA! That is pretty funny. Hilarious, actually.
- My Little Portal includes the following exchange:
DISCoRD: I think you're really going to love the next test chamber. It really is quite funny.
Rarity: You call giant crushers funny?!
DISCoRD: Well, no, not really. Not unless they crush you. Then it's hilarious.
- Pinkie Pie's entire onslaught of bad pun after bad pun in Cupcakes is this, considering she's graphically disemboweling the still-living Rainbow Dash as she says them.
Pinkie Pie: I know I can be a real pancreas, but you know Im just kidney with you. You really got to learn to liver it up. Boy, these jokes are getting bladder. Guess ya gotta develop a stomach for them.
- Tom Riddle in The Very Secret Diary finds the pain and suffering of others to be quite amusing. Ginny is especially baffled when her "best friend" finds the fact that Myrtle died young and haunts the girls' bathroom to be hilarious.
- If the Emperor Had a Text-to-Speech Device has Magnus the Red 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 Slaanesh has a weird sense of humor."
- Fallout: Equestria: This is applied to, of all things, a plant. In My Little Pony: Friendship Is Magic, the magical plant poison joke cursed ponies with ironic and silly punishments. Strong Applejack becomes tiny, Motor Mouth Pinkie has her tongue swell up, so on and so on. Centuries later, poison joke has evolved into killing joke, which has much more violent curses, based on overly literal interpretations of something the victims said at any point in their lives. Xenith (a zebra) says she sometimes feels like an earth pony, and her stripes are like great wounds; they explode into literal wounds and Blood Magic is required to save her life. A Hellhound gets transformed into a powerless pony while surrounded by other Hellhounds who will kill any pony they see. And Fluttershy was transformed into a tree, cursed to watch as the plants claimed more victims but unable to do anything about it. Littlepip notes the jokes would be stupid if they weren't so horrifying.
- The Hellboy animated film Sword of Storms recycles a moment from a graphic novel in which a Japanese woman tells a story about a man suffering a horrible misfortune, which the other tavern residents treat as a terribly witty joke. This is the first tip-off that they're all evil spirits.
- Tangled: As if we didn't have enough evidence that she was a Bitch in Sheep's Clothing, Mother Gothel proves herself to have an immensely caustic and sarcastic sense of humor... against her own adoptive daughter (that she kidnapped, admittedly; but still, you would think she would give the girl some respect).
- The following is especially cringe-worthy:
Mother Gothel: [Looking in the mirror with Rapunzel] Look in that mirror. I see a strong, confident, beautiful young lady.
Mother Gothel: [Snarky] Oh look, you're here too!
[Rapunzel's smile disappears]
Mother Gothel: [Laughing] I'm just teasing, stop taking everything so seriously!
- The following is especially cringe-worthy:
- McLeach, the Evil Poacher from The Rescuers Down Under considers trying to feed an eight-year-old kid to crocodiles to be his idea of fun.
- Oliver & Company: Hinted with Sykes and his vicious Dobermans Roscoe and De Soto.
Dodger: Roscoe, is this us losing our sense of humor?
Roscoe: Nah! I ain't lost my sense of humor!
(Roscoe kicks over the TV, breaking a few things and sending sparks flying.)
Roscoe: See? I find that funny. (chuckles maliciously)
- For being one of the most realistic Disney Villains, Sykes does show a twisted sense of humor when he kidnaps Jenny for ransom and as he's tying her up, he tells her a cruel joke of having his dogs eat her if her parents don't pay the ransom.
Sykes: Now don't cry, little girl. They only eat when I tell them to. (chuckles evilly)
- For being one of the most realistic Disney Villains, Sykes does show a twisted sense of humor when he kidnaps Jenny for ransom and as he's tying her up, he tells her a cruel joke of having his dogs eat her if her parents don't pay the ransom.
- The Hunchback of Notre Dame: For being one of Disney's darkest, evilest, and most serious villains, Judge Claude Frollo does show a sick and cruel sense of humor. Most notably when he is supervising someone being whipped, just as his new Captain of the Guard Phoebus arrives.
Frollo: You know, my last Captain of the Guard was um... a bit of a disappointment to me. [whipcrack followed by a loud scream of pain; Phoebus cringes while Frollo smirks] Well, no matter. I'm sure you'll...whip my men into shape. [grins]
Phoebus: Well... th-that's a... tre-tremendous honor, sir.
- The Cyclops from The SpongeBob SquarePants Movie is a deep sea diver who captures sea animals to sell at his gift shop. Hes weirdly sadistic and cheerful about what hes doing to his victims, apparently finding it funny for some reason. Spongebob and Patrick see him making a diorama out of some dried fish, and the whole time hes cackling like a supervillain taking over the world.
- Quest for Camelot: When evil knight Ruber finally has the sword Excalibur in his possession, he then uses his magic potion to merge the sword to his right arm. As Kayley slumps at her failure, Ruber icily rubs his fingers under her chin.
Ruber: Don't worry, little girl. I'll make sure Arthur gets it back. Or gets it in the back. (laughs) As the case may be! (to his henchmen) Throw her in the wagon.
- Buford Tannen in Back to the Future Part III, laughs his head off while trying to hang Marty, and towards the end after seemingly killing him.
- The Joker in The Dark Knight is much less clownish than most other interpretations of him, but still not immune to the occasional one-liner. A possible interpretation for his stilted manner of speech is that he's intentionally leaving space for a laugh-track that nobody else can hear. Both film versions of The Clown Prince of Crime share a common theme in their sense of humor; both are prone to telling jokes that only a murderous psychotic (i.e. The Joker) would find funny.
- Freddy Krueger in the A Nightmare on Elm Street series is constantly making bad jokes. A lot of the time, it keeps Freddy from being too scary, but other times, it just makes him even more terrifying. When Freddy Krueger turns you into a roach and makes a bad bug-related pun, what are you going to do about it? Tell him he's not funny?
- The Kurgan of Highlander is one, which isn't surprising when his native culture (as Ramirez claims) threw children to the dogs for fun.
- Calvin Candie of Django Unchained: A sadist who thinks he's a hedonistic Affably Evil Magnificent Bastard.
- Aldrich Killian in Iron Man 3: his jokes are not merely sadistic, but also incredibly laboured and dull, despite the fact that he obviously thinks he's a straight example.
- From Big Bad Wolf we have a talking Serial Killer werewolf Mitch Toblat, who in his werewolf lines just loves joking about his sadism. In one scene, he rapes a girl in front of her boyfriend, when the boyfriend mentions she's a virgin, Mitch replays "Well she ain't anymore." Then he says "Let's see if you got the balls" before castrating him.
- In Blade, Deacon Frost's idea of a joke is to make his buddy Quinn think that he's about to chop off his arm to test the sharpness of Blade's sword. Especially bad since Quinn's repeatedly had his arms cut off by Blade. Quinn's sense of humor isn't any better since he thinks Frost's prank is Actually Pretty Funny.
- Star Wars:
- In Revenge of the Sith, Palpatine tells Anakin the "Tragedy of Darth Plagueis the Wise", which is a very abbreviated version of the story told in the novel Darth Plagueis, which is released later. By reading the novel, one understands that when Palpatine called Plagueis by that title, it was more than anything else, his very twisted idea of a joke.
- Anakin himself has one of these after undergoing his FaceHeel Turn and becoming Darth Vader. While fighting for the cause of good, Anakin would hurl puns and snarky commentary at the people who were, generally, actively trying to kill him. Following his descent into evil, it's twisted inside-out and he uses it mostly on people who he has at his mercy and is currently hurting or killing as a way to exert the Empire's power, such as dropping one-liners and puns about choking while crushing the throats of his subordinates with the Force (such as telling Captain Needa in The Empire Strikes Back "Apology accepted" after Needa took responsibility for losing the Millennium Falcon to Vader and was killed by Vader as a result). Best exemplified in a scene from the novelization, when he butchers the Separatist leadership (the scene in the movie is shot silently), where he takes the opportunity to specifically mock each individual Separatist leader's last attempt to beg for their life.
Novelization!Nute Gunray: Sidious promised — he said we would be left in peace...
Novelization!Anakin: His transmission was garbled. [cuts Gunray down] He said you would be left in pieces.
- Possibly the most infamous example comes from Rogue One while performing a Psychic Strangle.
"Be careful not to choke on your aspirations, Director."
- Black Mass: During dinner at the home of one of his henchmen, Whitey Bulger coldly talks about savagely killing said henchman for revealing a secret family recipe. Its not until he laughs at his own comment that anyone realizes hes joking.
- Goodfellas: Part of Tommy DeVito's (Joe Pesci's character) Establishing Character Moment, after we see that he's the Trope Codifier for "Hair-Trigger Temper" for a damn good reason, is him exploiting his reputation as a vindictive hair-trigger "kill-you-where-you-stand" psycho to scare the everliving piss out of one of his closest friends (angrily ranting against Henry Hill casually calling him 'a funny guy', which is the current page quote) for a lark. Henry himself finds it Actually Pretty Funny once he finally catches up on the prank.
- Joker (2019): Arthur Fleck is shown to have a poor grasp on comedy aside from making silly faces, but he aspires to be a stand-up comedian. His "joke diary" is shown to be full of morbid observations on living with mental illness, and when he fully embraces the Joker persona, his "jokes" take on an extremely unsettling and misanthropic bent, which Murray Franklin calls him out on (even when one of the things that made Arthur finally snap was Murray mocking his lousy comedic style on national television — guess who becomes one of the Joker's first victims).
- In Black Patch, Frenchy De Vere demonstrates that he has neutralized the shells in the gun by pointing it at his henchman Holmon and pulling the trigger twice. When nothing happens, he starts laughing his head off. Holman laughs at first, out of nerves, but then sobers up and yells at him that its not funny.
- Halloween's Michael Myers never shows emotions (except the occasional hint of rage), but at points displays a macabre sense of humor: dressing up as a ghost for no other reason than to freak out Lynda and displaying the corpses of his victims to scare their friends as they're found.
- In Edgar Rice Burroughs' A Princess of Mars, John Carter of Mars observes that Green Martians consider hitting a helpless prisoner the height of jests.
- In Robert E. Howard's Conan the Barbarian story "Shadows In The Moonlight", in Olivia's dream, when torturing a demigod to death, the torturers laugh at him. Afterwards — Daddy shows up, not pleased.
The black warriors laughed at him, jeered and taunted in a strange tongue.
- Apparently, the early interlude with Verna Zee in Tribulation Force is meant to be funny.
- The Dasati from the Riftwar Cycle find pain in and of itself to be amusing (or at least other people's pain). They are depicted as laughing hysterically while watching other Dasati torn to pieces by the local equivalent of wolves, for example.
- The Gamemakers in The Hunger Games have an incredibly dark sense of irony. Case in point: the main character has a bit of a "Fire" motif going on throughout the book, so they set a fire trap just for her.
- Dragon King of Arms from the Discworld novel Feet of Clay is a herald (and a vampire) who loves to include groanworthy wordplay in the family mottos and symbols he creates for Coats of Arms. Most of these are merely stupid, but one turns out to be an important hint to the story's mystery. Lord Vetinari is being poisoned with arsenic, and nobody can tell how it's getting into his system. One of the Coats of Arms Dragon created had the motto in Morporkian (English) rather than Laotian (Dog Latin): "Art Brought Forth the Candle". Turns out, when translated, it would be "Ars Enixa Est Candelam". There's also a fish-shaped lamp: "lampe au poisson". The arsenic was in the candles being burned in Vetinari's room. Dragon just couldn't resist the pun.
- In the Discworld book Maskerade, Director Salzella has a habit of making extremely tasteless jokes about the fates of those murdered by the Opera Ghost, and is revealed to be the one committing the murders.
- It, alias Pennywise the Dancing Clown, has a very twisted sense of humor. His jokes range from crude and sexual (and bear in mind, they're usually aimed at kids), to morbid, to mocking people's various afflictions, to describing what he did to past victims, or what he plans to do to you. This mostly carries over to the 1990 and 2017 adaptations.
- A Song of Ice and Fire
- Shagwell is an Ax-Crazy mercenary who dresses as a jester, and most of his jokes involve his love of rape and murder.
- Ramsay seems to have adopted his father's sense of humor. He doesn't laugh often, but when he does it's usually about his flayed, mind raped torture victim.
- The Ghiscari cities of Slaver's Bay also have a pretty bad sense of humor. Some of their ideas for follies (comic interludes during their Gladiator Games) include coating children in blood or honey or fish guts and then throwing them in a pit with a bear and betting on which one the bear will maul first. Or giving a pair of dwarves wooden weapons, having them fight a mock combat, and unleashing some hungry lions on them midway through. Hilarious, right?
- One scene has one of Gregor's underlings recounting a particularly nasty story about the rape of a young girl, causing everyone to laugh at the hilarious tale. This leads Arya to send an assassin after him.
- In Animorphs:
- Visser Three can get into this. In the first book, he eats Elfangor, then makes a joke about "taking a bite" out of his enemies.
- The Drode as well—he's sort of an evil Trickster Archetype who likes to joke with the Animorphs, but his jokes usually involve the genocides that he and his master Crayak are currently involved in.
- The Animorphs also has an interesting inversion of this, as one of the main protagonists, Marco, is a Sad Clown whose life philosophy seems to be based on The Killing Joke.
- Played with through Denth and Tonk Fah in Warbreaker, who make a lot of jokes about being amoral, backstabbing mercenaries Only in It for the Money, in a Lovable Rogue manner by Denth and in a somewhat more Heroic Comedic Sociopath way by Tonk Fah. What makes this example interesting is that this humor reads as typical anti-hero wit until the reader finds out the two are actually the novel's villains and they aren't joking. Particularly true with Tonk Fah, who is a murderous torture-loving sociopath.
- Roderick Whittle, aka Jack the Ripper, from Richard Laymon's Savage, has an EXTREMELY macabre sense of humor.
- In Carnage In New York and Goblin's Revenge, both Carnage and the Goblin love cracking sadistic jokes.
- The Queen from Blackadder II. She's not an outright antagonist some of the time, but she is The Caligula very much. She'll frequently joke about cutting her courtiers' heads off (and her courtiers are expected to laugh as though they find it funny.)
- BuffyVerse: Angelus, best shown in Angel Season 4 where he breaks his former friends apart with a few Hannibal Lectures.
- Doctor Who:
- "The Happiness Patrol" uses this with the agents of its "imposed happiness" dystopia: the only jokes they actually make are bad Pre-Mortem One-Liner and Bond One-Liner puns aimed at innocent people they're killing and torturing.
- The Slitheen family has a weakness for fart jokes and a generally sick sense of humour, giggling and sharing bad jokes while plotting to destroy whole planets.
- "The Runaway Bride": The Empress of the Racnoss appears to enjoy terrible jokes and puns, and insists one of her victims rephrase his pleas so she can finish him with a bad joke. She's older than many planets, and this stuff still amuses her.
- The version of The Master who interacted with the Tenth Doctor is an example of this, a result of him being specifically an Evil Counterpart to Ten's manic personality.
- Game of Thrones:
- Joffrey Lannister is a Creepy Child through and through, and as such has an immature and deeply sadistic sense of humour. As far as he's concerned, the more someone suffers, the funnier it is. In one instance, at Tyrion's wedding, he takes away his uncle's stool so that Tyrion has to ask Sansa to kneel for the fastening of the bridal cloak, causing the guests to laugh at Tyrion. For his own wedding, Joffrey commissions a very tasteless performance where a bunch of dwarves, representing the other challengers to the throne, ride around on pigs. This culminates with the dwarf representing Renly having simulated sex with a pig. While completely tasteless on its own it is also political idiocy as Joffrey's new bride was once married to Renly and her brother was Renly's gay lover. The support of his Tyrell in-laws is what is keeping Joffrey and the other Lannisters in power and this 'joke' pretty much spits in their faces. Appropriately, almost no one at the wedding laughs at the performance, showing that they themselves are sympathetic characters and only fear of Joffrey's retribution keeps the others from booing.
- Along with getting plenty of sadistic laughs out of physically torturing his victims, Ramsay Bolton's idea of a joke is to eat a pork sausage in front of a prisoner whom he recently castrated.
- Gotham: Both characters that end up being different takes on the Joker are prone to this, unsurprisingly. Jerome Valeska is heavily inspired by the Heath Ledger version of the character, and as such, a large percentage of his jokes are of the Crosses the Line Twice variety. Both Jerome and his brother Jeremiah alternate between this trope and actually pretty funny, though.
Jerome: Don't bother calling security, they're rather..." *Secretary screams off-screen* "...headless."
- When a secretary runs off at the sight of him:
Jeremiah (cheerfully): She has your eyes! For now.
- Then there's Jeremiah's quip to Barbara Kean in the finale, when he's about to kidnap her daughter, the future Comic Book/Batgirl.
- An episode of Law & Order: Special Victims Unit starts with a rapist calling the mother of his latest victim to taunt her, saying things like "Your daughter can't come to the phone. She's all tied up." Said daughter is Bound and Gagged and trying to scream for help.
- Luke Cage (2016): Shades is in custody after Willis Stryker's hostage situation. Inspector Ridley tries to get him to talk, but he'll only say "Lawyer". Eventually, with her patience wearing thin, she tries to ask him about Cottonmouth. Shades admits he was at the club when Cottonmouth was killed. He even saw who did it. Ridley asks him for the killer's name.
Inspector Ridley: Was it Stryker?
Shades: He goes by... "Lawyer".[beat] Do you need me to spell it? [Ridley gets up and marches out of the interrogation room while Shades breaks out laughing]
- Moriarty from the BBC series Sherlock finds it hilarious to make the hostage he's forcing to parrot his demands say "gottle o' geer".
- From Stargate Atlantis, Todd as a people-eating space vampire has a quite morbid sense of humor. He arranges an alliance with the humans by offering to shake hands (from which Wraith feed on people) before noting that he was joking and comments on some fruit he prepared for a later meeting with "I hope they prove as delicious as the farmers who grew them".
- Negan from 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.
Negan: What? Was the joke really that bad?
- Jade from Victorious really gets a kick out of watching people in pain and getting hurt. In an episode where the main characters must stop using their cellphones, she's disappointed when she misses a video where an old lady is dangling from a rollercoaster. Another time, she encourages a friend to give away ice cream to kids at the park, knowing their mothers will take it the wrong way.
- The Comedian in The Amazing Extraordinary Friends could be considered a sane version of The Joker. While he is Actually Pretty Funny some of the time, his favourite jokes always result in people being injured or killed.
- The Dark Eldar/Elves in Warhammer 40,000.
- According to Memetic Mutation, so does Kharn.
- Nurgle's followers are commonly seen joking around and having one hell of a time. Seeing as Nurgle is the god of disease and decay, however, it should come as no surprise that the jokes they tell go to extreme degrees of Toilet Humour and Black Comedy.
- Orks, on the other hand, favor a more lowbrow form of humor. For example, watching gretchin get killed by the dozen or setting one of their own people on fire to see them "do da burny dance" (to be fair, they'll also do that to non-orks as well).
- In Dungeons & Dragons, Asmodeus and Demogorgon are noted as both having senses of humor; though they find humor in the fact that their underlings (or, in Demogorgon's case, chief rivals) are constantly plotting/fighting amongst themselves instead of uniting against them.
- In the Planescape campaign, the worst part of the Hive in Sigil is home to a mysterious predator called Kadix, who is at least part-demon. He is intelligent and has a sick sense of humor, which leads him to display the remains of his victims in humorous ways. For example, he has been known to arrange the heads of a group of bird-like humanoids so as to resemble eggs in a nest, or the skeletons of a man and a woman in an embrace.
- Myrkul in the Forgotten Realms was well-known for his dark sense of humour and his love of irony, mind-games, and paradoxes. Myrkul was the Neutral Evil God of the Dead; needless to say, what amused him usually involved a body count.
- This is the entire raison d'être of Kobal, the Demon Prince of Dark Humor in In Nomine. He himself has the sickest sense of humor in the setting (with only Haagenti, his protege, coming close), but it's more than that. Kobal's goal is to increase human suffering by replacing empathy with mockery, and making evil's sense of humor the norm. He also does a sideline in opposing the Archangel of Destiny; the funniest joke is ruining the life of a person with a bright future.
- In Sweeney Todd, Todd himself somewhat lacks a sense of humor, given his grim and saturnine personality, but he also has elements of this, such as promising enemies "the closest shave you'll ever know". His partner-in-crime, Mrs. Lovett, consistently has a sick sense of humor, and their duet "Little Priest" embodies this trope, as they gleefully sing about all of the people they plan to make into pies.
- The Riddler in Batman: Arkham Asylum, who asks the Riddle of the Sphinx and claims the answer involves cutting off a baby's legs. And, of course, The Joker.
- Caesar in Fallout: New Vegas gives this gem if you accept his invitation to his camp while in bad standing with the Legion and he asks why you would come despite all you've done to make his life a living hell.
Courier: "You guaranteed my safety."Caesar: "And you fell for that? Really? Because I'm going to have you killed now."[Beat]Caesar "...relax, I'm fucking with you."
- Also, if you tell him you're taking in the glory of seeing him, he'll remark that he should put out your eyes so that he's the last thing you ever see. Then again, he's the only guy in the faction with a sense of humor.
- A non-evil example: In Poker Night at the Inventory, the Heavy tells the story of how an Engineer massacred his team, so he took vengeance on the Engineer. Painfully. And with lots of blood. Crying out for his mother. While laughing uproariously and acting out his shrieking in pain. Tycho is visibly disturbed. Max looks slightly ill. Strong Bad sums it up:
Strong Bad: That is some BLEEPED-up BLEEP, man.
- For those curious he shoved guy's wrench down his throat. Head-first. All the way down. eehhhhhgh!
- Or then there's the time when Strong Bad asks for a funny story, and instead Heavy tells the story of the day he watched an injured sparrow die in the cold when he was a boy. Strong Bad insists that that wasn't a funny story at all. Heavy agrees that "No. It's not." All are baffled at how that question led to that answer.
- In an Establishing Character Moment from Suikoden II, Luca Blight and the Highland Army set fire to a town, killing all the townsfolk they can find. One woman even begs for him to spare her, saying she'll do anything. His demand is that she crawls around and act like a pig, which she complies. His response? Gleefully laugh in her face, yell "Die pig!" and kill her anyway.
- Twisted Metal is rife with this, some of the characters have it as their background, and then, of course, there's Calypso and, in Twisted Metal 4, Needles Kane. A minor subversion, however, due to Needles simply being in it For the Evulz, occurs when General Warthog wins. Warthog wishes for a world of eternal warfare so he can play wargames all the time. With both possible wish granters being vicious, bloodthirsty curs, it seems like such a dream wouldn't end well for the rest of us, as they tend to reward selfish or savage wishes by playing them straight, but in his Twisted Metal 4 incarnation, Needles is more like The Joker. And so, his wish is granted...Warthog is turned into a talking toy a la Tommy Lee Jones in Small Soldiers and dropped into a sandbox full of toy vehicles.
- AM from I Have No Mouth and I Must Scream is this in spades. Though he is WAY too horrifically evil as a character to be even classified as Laughably Evil.
- Handsome Jack from Borderlands 2 has an incredibly immature and crude sense of humor that seems to wholly revolve around the extreme suffering of others. This is made clear bright and early with a sidequest on the Southern Shelf, where you round up audio recordings of him meeting Helena Pierce, a heavily scarred but friendly NPC from the previous game. First, he mocks her for the scarring while laughing heavily, then he puts on a temporary pose of contrition...then he shoots her in the head and starts laughing his ass off about the sounds her head made when exploding.
- Clarence in Penumbra: Black Plague, being Philip LaFresque's personal manifestation of the Tuurngait virus, is this, particularly when he makes Philip hallucinate and kill a monster that was actually a friendly character Philip had tried to reach for most of the game. And then Clarence tries to pass the event off as a joke. Needless to say, Philip spends most of the endgame working to get Clarence out of his head once and for all.
- Nate from The Walking Dead: 400 Days. His little joke about rating the attractiveness of a female zombie gets a bit out of hand, to say the least.
- Gangrel in Fire Emblem Awakening. Making jokes about Emmeryn's Heroic Suicide, right after it happens, to her brother really cements this.
- The Umgah in Star Control have this as their collective hat. Dropping a planetoid on an inhabited world? Hilarious. Enlisting the Spathi as the Ur-Quan's newest battle thralls? All in good fun. Impersonating the gods of the psychopathic Ilwrath and telling them to attack a peaceful race? They had a good laugh about that one.
- Hoyt Volker in Far Cry 3, a South African slaver who runs a company of Ruthless Modern Pirates operating from the Rook Islands. After unmasking protagonist Jason Brody at a high-stakes poker game, he cuts off one of Jason's fingers, and right before he and Jason have a knife fight, he holds up the finger and says, "Aw, Jason, now we'll never be married." Hoyt is a Complete Monster.
- A Sith officer commanding a guard camp outside Freedon Nadd's tomb in Knights of the Old Republic II: The Sith Lords complains in his log about being kept completely in the dark as to what's going on. He relates asking a Sith Master for details on the worsening situation, only to be told that it was a "surprise". The officer laments that he hates Sith with a sense of humour — "Sith jokes are rarely pleasant".
- Final Fantasy VI: Things that Kefka find a real knee-slapper: mind-controlling Terra via Slave Crown and making her burn more than 100 of his own soldiers; setting Edgar's castle on fire after he refused to cooperate with the Empire; poisoning the water supply of Doma, killing everyone inside, including the captured imperial soldiers; the prospect of executing Celes and the rest of the rebels at the siege in Narshe, murdering the espers at Thamasa to turn them into Magicite to harness their powers and killing General Leo after he tried to stop him; disrupting the Warring Triad, throwing the wold balance off, murdering Emperor Gestahl when he was having nothing of that and then nonchalantly kicking the Emperor's body off the Floating Continent; becoming the god of magic in a ruined world and then doing nothing but smiting anyone that does as much as looking at him funny from atop his debris tower.
- Xom, God of Chaos, from Dungeon Crawl. Though canonically just "chaotic" and not "evil" for mechanical purposes, as far as gods go, he's far more of a Bad Boss than the actually evil gods. Xom's idea of a great gift is to take the calculation other gods use to determine appropriate gifts and reverse it, e.g. giving a wizard who can't use armor a set of powerfully enchanted plate mail. And even when he's pleased with the player, he'll sometimes randomy curse or harm them for some excitement.
- The animated web series Caillou the Grown Up, which shows the title character of Caillou as still behaving like a small child at 22 and not above using threats to force his parents to let him have his way, has an example in the episode "Caillou the Grownup Goes on Vacation", where Caillou has the gall to crack an "Eye/I" pun after throwing a knife into a man's eye when the man tried to beat him up in retaliation to ruining his kids' sand castles at the beach.
- Nurse Worse, the co-host of Dr. Crafty finds herself on the receiving end of this after her and Dr. Crafty resurrect The Sanderson Sisters from Hocus Pocus. Mary and Sarah quickly surround Nurse with the unmistakable intention to eat her. Sarah says that the sisters would love to have her for dinner and Winifred reminds Winifred and Sarah "Now, now sisters. Don't play with your food." Sarah, the Psychopathic Woman Child she is, complains "Oh phooey" like a little kid denied a new toy. It's left up to the imagination what kind of play Sarah intended with poor Nurse.
- In Goblins, Dellyn Goblinslayer thought fellow adventurer and XP whore Minmax would appreciate the humour found in owning an unwilling slave Yuan-Ti and raping her to and from the brink of death nightly. He judged...poorly.
- Xykon of The Order of the Stick, an affably evil sort, is this in his universe. Considering how many lines he crosses to make his snarks, the trope doesn't quite hold true for those of us reading his exploits, however.
Thog: "thog just thinking of funny joke thog learned from guards. what's black and white and red all over?"
- While he's more restrained about it than Xykon, the Evil Overlord Tarquin has shades of this. For example, when shrugging off the dangers involved in forcing a woman to marry him, he comments that previous brides have also had cold feet — cut to a flashback image of Tarquin torturing a woman into marrying him with cold spells. You also have to give credit to his ability to simultaneously do something nice for his son and brutally crush a slave revolt, which he accomplishes by tying the captured slaves to posts arranged to spell out his son's name, then setting them alight.
- Qarr finds the horrifying effects of Vaarsuvius casting Familicide to be uproariously hilarious.
- Thog's take on an old pun:
Roy: "A newspaper."
Thog: "a zebrafolk who talks back! haw haw haw haw!"
[Cut to a panel of two guards whipping an anthropomorphic zebra bloody.]
- Nale finds Malack turning Durkon into a vampire hilarious. Malack himself sees nothing humorous about it.
- Belkar has a pretty sick sense of humor too. Case in point: he once turned a kobold's head into a salsa bowl as a joke. But he didn't think Durkon being vamped because he tried to save Belkar was funny at all.
- The strip reveals that its version of vampires are actually demonic creatures made of negative energy which possess the bodies of vampirized individuals, sometimes pretending to be them. The High Priest of Hel, who is used in the reveal, controls the body of an innocent person and finds it hilarious to mislead his victim's friends about the nature of vampirism as well as to commit horrific actions while "in-character". He also has some touches of the humorless version of the trope in that rather than simply having a sick sense of humor, being literally Made of Evil, he does not understand and is repulsed by positive emotions.
- Girl Genius: Castle Heterodyne is "dangerous, twisted and worst of all...it likes to think it has a sense of humor".
- Black Mage from 8-Bit Theater soon after Black Belt's death, he starts telling a bunch of jokes whose "punchline" is simply that Black Belt is dead.
- Discord from My Little Pony: Friendship Is Magic. There's a line between Surreal Humor and Surreal Horror, but Discord doesn't seem to care where that line is. Even after being, heh, "reformed" he still has a particularly nasty sense of humor.
- The Joker, in Batman: The Animated Series.
- The Joker, in The Batman.
- The Joker, in Batman: The Brave and the Bold. (Observant readers will have noticed a pattern forming.)
- Codename: Kids Next Door: The Delightful Children usually gloat and make jokes about how their enemies are going to meet their demise or be humiliated by them.
Delightful Children: "So Kids Next Door, what do you say about a trip to Pluto? Have a 'delightful' flight! *Cue Evil Laugh*"
- Subverted with Negative!Numuh Two in Operation POOL. Since the good Numbuh Two has an awful sense of humor, his evil counterpart has a great sense of humor.
- The Monkey King in Jackie Chan Adventures, whose sense of humor ranges from absurd concepts like West Side Story-esque greaser frozen chickens to Joker-esque delight at running someone through a sawmill. He lets loose the nasty part of his personality very quick.
Jade: (trying to stop him from mutilating Jackie): You can't! It's... not funny!Monkey King: Haven't you noticed? I have a weird sense of humor!
- Although at one point when Jackie complains that him attacking him dressed as a reaper wasn't funny, the Monkey King conceded the point...and then switched to a luau.
- 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, Jackie gets so mad that he slams his hand on a rail, giving himself away.
- On The Spectacular Spider Man, the Green Goblin tends to do this, giggling insanely and occasionally cracking rhymes about his various schemes.
- Gravity Falls has plenty of Black Comedy, but the self-proclaimed Above Good and Evil demon Bill Cipher seems to get a kick out of doing things like ripping the teeth out of a deer's mouth and summoning a head that's always screaming.
Bill: (slapping a body he's currently possessing in the face) Pain is hilarious!
- Mr. Cat. He takes delight in tormenting other people, even his own best friends, in various ways, ranging from burning Stumpy's comic book collectionnote to trying to kill people with chainsaws.
- Olaf. In Episode 121, he tricks Kaeloo, Stumpy, Quack Quack, and Mr. Cat into thinking that they've all been fired from the show just so he can get a laugh out of it.
- She-Ra and the Princesses of Power: At one point, under the effects of a truth spell, Double Trouble confesses that since they can't cry on cue, when they need to tear up for a role, they think about children falling - they're tears of laughter, not sorrow, but no-one can tell the difference.
- Total Drama's one and only Chris McLean has a notoriously sadistic sense of humor, finding the pain, suffering, and misery of the contestants (and others) hilarious, as well as actively trying to anger or annoy them for his own cheap laughs. This became especially pronounced in later seasons as his jerkass and Psychopathic Manchild qualities were massively flanderized.
- Lucius Heinous VII from Jimmy Two-Shoes is frequently shown to have a mean sense of humor, laughing gleefully at his subjects' misery, playing mean-spirited pranks for fun, and find amusement in hurting or humiliating others (particularly Samy). However, he's also a gargantuan Butt-Monkey, so it all works out.
- Young Justice: Black Beetle from season two finds things like potential nuclear meltdowns, brutally beating people who aren't anywhere near his power level (which is all the heroes), and executing helpless prisoners to be utterly hilarious.
- The Simpsons: Mr. Burns, being an obscenely wealthy, evil old man, gets a kick out of watching people suffer.
- In "Last Exit to Springfield," a window cleaner is dangling outside of his office after the scaffolding broke and fell from under him, and Mr. Burns, rather than call for help, laughs loudly. He soon gets bored and closes the blinds, while the man screams as he falls.
- In "$pringfield," while touring the delapidated boardwalk where he plans to build his casino, Burns remembers when he was young child he would go and play in the bumper cars. His happiest memory was of him bumping into and crippling an Irish maintance worker, a memory that causes him to laugh uncontrolably for several days.
- In "Homer vs. Dignity," needing money, Homer is hired as Burn's "prank monkey," a position in which Homer does something for Burn's amusement, and Mr. Burns would give him a few bucks. First, he throws puding at Lenny, then he eats a rare first edition Spider-Man comic in front of a distraught Comic Book Guy, which Burns finds humorous. Homer then begins to question his new position when getting run over by a ciclist causes Mr. Burns to start laughing, and when he puts on a diaper and acts like a baby in a stadium bathroom. When Mr. Burns pays Homer to dress up as a panda, under the guise that someone donated a female to the zoo, Homer gets shocked with cattle prods, to the joy of Mr. Burns. When the male panda assaults Homer, Mr. Burns just stands by and laughs like a madman while Homer is ultimately raped by the male panda and it's only after talking to Lisa that Homer decides to quit his new position. When Homer gets hired to play Santa Claus in the Thanks Giving Parade, Mr. Burns offers him a million dollars to throw fish guts at the audience, but when Homer refuses, Mr. Burns merrily does the deed himself.