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[[quoteright:330:[[WesternAnimation/BatmanBeyondReturnOfTheJoker http://static.tvtropes.org/pmwiki/pub/images/Bang_9072.jpg]]]]
[[caption-width-right:330:[[SelfDemonstrating/TheJoker His]] act's a real ''killer''.]]

-> ''"He's an absolutely awful human being. The strange thing about comedy is that if an awful character makes people laugh, people feel affectionate towards him. It's insane because if they had to sit next to him for five minutes at a dinner, they would absolutely not be able to cope with him. They would loathe him. But because he makes them laugh, they think, deep down, he's alright."''
--> -- '''Creator/JohnCleese''', on '''[[Series/FawltyTowers Basil Fawlty]]'''

Villains can be many things... {{magnificent|Bastard}}, [[AxCrazy horrific]], [[CardCarryingVillain self-obsessed]], [[StrawNihilist philosophical]]... but special attention goes to the villain that makes you [[ActuallyPrettyFunny laugh]]. It might be because he's [[HarmlessVillain an idiot]], it might be that you empathize with him, or it might be simply that his actions are so unexpected. In any case, some villains will always be funny.

Of course, funny does not always equal weak. Praise be to the villain who can cause a chuckle from his audience, right before viciously thwarting the hero's best efforts. In fact, if done correctly, the very things that make a villain qualify can make them downright disturbing once they begin crossing the MoralEventHorizon. Villain laughing at faking someone out with [[BANGFlagGun a gun with a "BANG!" flag coming out]]? Funny. Same villain doing the exact same laugh when shooting them for real a few seconds later? ''Creepy.'' A truly well written one can manage to pull off both at once. See the trope picture for an excellent example of this subtype. Just because a character qualifies, it does not prevent them from being a CompleteMonster and there are many villains that manage to be both (again, see the page image). In these cases, what makes them funny also makes them ''very'' unsettling because of how much fun they have committing the most horrific acts possible.

Often overlaps with the HarmlessVillain (Harmless Villains are inherently funny, but funny villains are not inherently harmless), AffablyEvil, FauxAffablyEvil (who are often funny), the IneffectualSympatheticVillain and MagnificentBastard. And with LargeHam (playing a villain seems to be very fun). It's also a prerequisite for the TerribleTrio and the QuirkyMinibossSquad. Contrast with MonsterClown, because clowns make people cry. Interestingly, this either subverts or complements EvilHasABadSenseOfHumor, as does TooFunnyToBeEvil, a closely related sister trope. Tends to be the sort who CrossesTheLineTwice. See also: LaughWithMe and BewareTheSillyOnes. A villain who is laughably evil need not have an EvilLaugh, though it can help. Alternatively, they may have an UnevilLaugh.

[[noreallife]]
----
!!Examples:
[[foldercontrol]]

[[folder: Anime and Manga ]]
* Jason Beck from ''Anime/TheBigO''. When he's not being an egotistical fop, he's actually frighteningly competent. Too bad this is overshadowed by his over the top hubris, which pushes him firmly into the "Laughably" part of this trope.
* Most of the villains of early ''Manga/DragonBall'' are like this. Such villains include General Blue, who is utterly hilarious in personality (and also CampGay) but also a very deadly opponent, and Emperor Pilaf, who has no idea what he's doing. Also Majin Buu, especially in his Fat Buu form, where his antics and are so childish, goofy, and cartoonish that you almost forget that his "games" are killing millions of people, at least until the EstablishingShot of the barren wasteland where a thriving city used to be.
** Even Frieza has some hilarious lines in his dialogues.
** Beers from ''Anime/DragonBallZBattleOfGods''.
* The [[TerribleTrio Team Rocket]] trio from ''Anime/{{Pokemon}}'' are this, which is the reason why they are so popular. At least until [[TookALevelInBadass Best Wishes]], when their boss gives them an actual serious assignment.
* Tobi from ''Manga/{{Naruto}}'' was this at first. [[spoiler:Then [[BigBad he]] [[TheChessmaster decided]] [[TheManBehindTheMan to stop]] [[ObfuscatingStupidity fucking around]]]].
** Then we got [[SirSwearsALot Hidan]]. A psycho priest who laughs every time he kills his opponents. How he does it is gruesome but it's his [[PsychopathicManchild interactions with everyone tend to be hilarious]] [[BlackComedy despite the situations of some of them]].
** And to an ever so slightly less milder version of this trope, we got [[MadBomber Dei]][[MadArtist dara]]. He is also a bit crude in his methods as well, but he has his entertaining moments generously sprinkled in the series.
* Dedede in ''Anime/KirbyOfTheStars''. He's arguably more evil than his game counterpart, but also one of the most entertaining characters on the show.
* A number of villains from ''Manga/OnePiece'', such as Buggy the Clown, a VillainousHarlequin who's [[LawOfDisproportionateResponse (violently) sensitive about his nose]], and Spandam, who alternately [[KickTheDog kicks the dog in new and horrible ways]] and makes himself look like an idiot.
** On the opposite side of the power spectrum is Kaku. The second most powerful member of Cipher Pol 9, he can transform into a giraffe. No, you didn't misread that. He can transform into an actual giraffe. Even better, he can transform into a half-man/half-giraffe. One that keeps his trademark square nose. He sincerely believes giraffes to be powerful creatures and during his fight with Zoro was prone to defending them by saying such things as "Witness the power of a giraffe!". Though that ''could'' be part-denial since everyone keeps mocking him for his powers. Oh, and he uses his nose as a weapon.
*** Believe it or not, out of all the animals characters can transform into so far, the giraffe appears to be one of the very best (in this form his storm kick attack was amplified like crazy, he can shorten his neck to lengthen his arms and legs, he can shoot out his head like a cannonball ...). The only one that seems to be superior is the rare phoenix.
*** Any animal that can kick a full-grown lion ass-over-appetite ''is'' powerful, even if their goofy build and lack of vocalizations in the range of human hearing obscures that fact.
*** What makes the fight even funnier is that Kaku has just eaten his Devil Fruit, and is figuring its powers out as he goes along (bear in mind that many Devil Fruit users have to spend ''years'' learning their powers; for example, flashbacks show that when [[TheHero Luffy]] ate the [[RubberMan Gum Gum Fruit]], he had to go through quite a bit of training before he could even throw a proper punch). CrowningMomentOfFunny comes when he discovers the aforementioned "shorten neck to extend arms and legs" move, reasons that it works on the same principle as a pasta machine, then names the move "Pasta Machine." Also in his favor is that, despite being a government agent, [[AffablyEvil he's a pretty chill guy,]] even giving a good-natured laugh to a post-battle quip from one of the heroes.
* Mara from ''Manga/AhMyGoddess''. She takes time out of her busy day tormenting goddesses and attempting world conquest in order to ''knock a child's ice cream cone'' out of his hands to fulfill a snide wish by his sister. Either KickTheDog, CrowningMomentOfAwesome, or both. A truly admirable commitment to evil on any scale. For those who are wondering this happens in the first season of the TV series -- if not in Mara's first episode, then in her first or second appearance after that. The scene in question actually makes her seem oddly like a ''Franchise/{{Disgaea}}'' character, laughing maniacally at her "evil deed" and resulting in both of the kids kicking her in the shin simultaneously and high-tailing it, to her angry surprise.
* Baki and Minki from ''Manga/HellTeacherNube''. They're (nominally) evil, powerful, hugely destructive Oni, but the former ''adores'' ice cream, toys, and riding around on the little kids' train in the park, and the latter has some ''bizarre'' notions of what a good big brother/little sister relationship should be like.
* Gates of ''LightNovel/FullMetalPanic: The Second Raid'' is so over-the-top with his ChaoticEvil antics that everything he does is completely random. Despite the sadistic violence, this makes him even funnier.
* Wester from ''Anime/FreshPrettyCure''.
* Xellos from ''LightNovel/{{Slayers}}'' might fit... his antics are certainly funny enough; it's just that [[TheTrickster no one is]] [[ChronicBackstabbingDisorder sure]] [[HiddenAgendaVillain what his real goals are]], so calling him a 'villain' may or may not be accurate.
** He's TheDragon for one of the 2 remaining demon lords. He might be a DracoInLeatherPants, but his efforts always serve his Mistress.
* UsefulNotes/OdaNobunaga from the ''VideoGame/SengokuBasara'' anime. It's not because he's dumb. Or incompetent. Or even snarky, for that matter. It's just that he's so [[ObviouslyEvil mind-bogglingly, skull-stompingly, baby-eatingly evil]] that he becomes hilariously awesome just through his very existence.
* The various teens of ''Manga/RanmaOneHalf'' could conceivably come off as this, as opposed to ComedicSociopathy. Not one of them (except for Kasumi, and even she made mischief on some occasions in the early manga) has done something that doesn't make them look at least partially villainous, yet these same deeds (and the regulars who generally are villains) still manage to be funny because of their attempts at evil.
* Prince Walter from ''Anime/TheBraveOfGoldGoldran'' fits this trope.
* Almost all of the Order of the Glittering Star from ''Anime/StarDriver''. Their everyday personas are so over the top that you can't fully take their villain sides seriously - all of them being [[EvilIsHammy hammy]] certainly helps too.
* Katsuhiko Jinnai from ''Anime/ElHazardTheMagnificentWorld'' is constantly over-the-top and has a funny EvilLaugh.
* Pixy Misa from ''Anime/PrettySammy''. She is a parody of DarkMagicalGirl.
* The Golden Witch [[BigBad Beatrice]] in ''VisualNovel/UminekoNoNakuKoroNi'' [[NoFourthWall is aware that she is the villain of the series]], and is just adoring the role. She's a LargeHam and she loves to chew the scenery, just listen to it when she talks to Battler. However, this is only in the anime, since in the original sound novels she's later revealed to be a good deal more tragic, [[spoiler:not to mention that [[DiscOneFinalBoss she isn't even the main villain]] in the first place]].
* Blastmon from ''Anime/DigimonXrosWars'' is said to be immensely powerful, but has the mind of a 5-year-old and calls the other generals by nicknames. Then he's defeated by the heroes and is reduced to a hopping head for the rest of the series. Before him, there was [[Anime/DigimonAdventure Etemon]], an [[LargeHam over the top]] rockstar monkey who's both silly, and far stronger then the last BigBad.
* Prince Eccentro of ''Anime/MonColleKnights''. He's the comedian of the anime, often accompanied by a FieryRedhead and a CloudCuckooLander as two of his followers, thus why he's so popular with fans of the show.
** The aforementioned [[FieryRedhead Batch]] and [[CloudCuckooLander Gluko]] are also quite comedic. Quite often at the end of many episodes, Gluko often happily stands by and adores the scenery while Batch and Eccentro get [[HumiliationConga rather embarrassing moments]]. They even get into rather comedic situations involving Ms. Loon.
* Laharl in ''Anime/MakaiSenkiDisgaea'' has quite the reputation for having some rather funny moments. Also, in Episode 3, Vulcanus becomes this when he accidentally almost falls off a statue and causes it to fall, which leads to Flonne and Etna's clothing & personality swaps. When he finds Flonne sleeping with Laharl and Etna, he flips out and hits her with a ThisIsUnforgivable and attempts to kill all three but accidentally falls into a clam exhibit and is unable to get out for the rest of the episode. Later, while he's still trying to get out, he knocks over the same statue again, causing clothing swaps again, this time for Laharl, Etna, Flonne, and one of the Prinnies.
* Barry the Chopper of ''Manga/FullMetalAlchemist'' is an unrepentant SerialKiller whose lunacy and total inability to understand normal human morality is PlayedForLaughs. Some people view Envy as this, though that has more to do with its terrible fighting skills and [[FashionVictimVillain godawful fashion sense]] than with any real humour on its part.
** Before he went all OneWingedAngel, [[BigBad Father]] had a tendency to make small, sardonic quips while horrendous battle raged all around him - usually along the lines of "Why does everybody feel the need to demolish my home?"
* In a similar case to Barry, Ladd Russo from ''LightNovel/{{Baccano}}'' is a complete nutjob who loves killing just for the sake of killing. While it can be argued whether or not his actions are ''intentionally'' PlayedForLaughs, it's hard not to enjoy watching the guy have so much fun.
* Macine Baron from ''Manga/SteamDetectives''. A bumbling collector and inventor of steam-powered robots with a hilariously overblown Austrian accent; willing to steal the robots if he feels like it. Certain robots he's got his eye on are more-or-less SteamPunk Roombas. Upon being defeated by [[RobotBuddy Goriki]], he develops a deep affection towards "him".
* Jan Valentine of the Valentine Brothers assassination team from ''Manga/{{Hellsing}}'', he's very sadistic and cruel and he's also hilarious, he's very foulmouthed and loves to tell disgusting stories, he also treats the assignment like a game, and in the manga long after he's been killed he shows up from time to time to break the fourth wall.
* Jake Martinez from '' Anime/{{TigerandBunny}}'' is basically the T&B universe's Joker. He's a Fantastically Racist terrorist, a serial killer, a kidnapper, a mercenary and an all around egotistical asshole who's threatening despite his... questionable wardrobe. And yet he somehow manages to say and do terrible things like murder an underling who failed him (& brag about it to people who had captured said underling), threaten to destroy a city if it's heroes couldn't beat him, & force one of the heroes to help draw out his allies in ways that make them hilarious as they are horrid.
[[/folder]]

[[folder: Comic Books ]]
* SelfDemonstrating/TheJoker is a sterling example of the trope. The trick in writing the Joker is to make his actions such that you can laugh one moment, and be horrified the next. Brilliantly brought out by many of the actors to portray him in other media, most prominently [[Film/{{Batman}} Jack Nicholson]], [[WesternAnimation/BatmanTheAnimatedSeries Mark Hamill]], [[Film/TheDarkKnight Heath Ledger]] and, most recently, [[WesternAnimation/YoungJustice Brent Spiner]]. Whether it's electrocuting a gangster while singing showtunes, casually (and cheerfully) stalking an everyday accountant in the middle of rush-hour traffic, or doing a magic trick by making a pencil [[EyeScream disappear]], you can always find it either way with the Joker. Even [[Series/{{Batman}} Cesar Romero]] qualifies, although because the show was such high {{Camp}}, he focused more on the "laughable" than the "evil".
-->'''Creator/PaulDini on the Joker:''' Joker's that perfect combination of schoolyard bully and class clown. The kind of sicko who will make you laugh just before he sticks the knife in and twists it.
** Part of what makes the Joker so terrifying is his special mixture of being funny as all get out but a CompleteMonster in many a canon (that, and his ability to switch back and forth between HarmlessVillain and CompleteMonster at random with no way to tell which he is today until the bodies start piling up). While other villains have managed to pull off this combination, the Joker is probably one of the best examples in fiction.
** The Joker even [[EvenEvilHasStandards has certain caveats on killing people]]: [[http://1.bp.blogspot.com/-N7V8dzMGtUE/TpPQ8Owu_EI/AAAAAAAAA1w/Sfg4rOBdkOw/s1600/Joker+-+Batman+686.jpg he only does it when it's funny]]. Of course, that doesn't mean [[MalevolentMutilation mutilation]] [[ColdBloodedTorture and torture]] [[DrivenToMadness to drive you batshit crazy]] are off the plate, he IS The Joker, after all.
* Speaking of the Joker, everyone's favorite VillainousHarlequin CanonImmigrant, Comicbook/HarleyQuinn.
* Creator/MarvelComics' [[http://marvel.wikia.com/Madcap_%28Earth-616%29 Madcap]], a ChaoticNeutral who acts deliberately silly, and whose power is simply to make people act uninhibited.
* Herr Starr from ''Comicbook/{{Preacher}}''. Every time he shows up he has a smartass line, but his CrowningMomentOfFunny was when he scares some poor old lady for blocking the moving walkway by shooting wildly at her.
-->"Moving [=WALKway=]! Not moving [=STANDway=], Granny Fuckwit, [=MOVING FUCKING WALKWAY=]!!!" (cue gunfire)
** By this point in the series he's had to deal with "an angel, a whore, an eunuch, several dozen idiots, an unkillable mick, a one-man holocaust in a duster coat, the occasional twenty-course banquet for the mother of all fat fuckers, inbreeding, family feuds, bulimia, a retarded child (always good for a laugh), and the utter destruction of our most sacred shrine and secret retreat in the detonation of a fifty-ton bomb." Not to mention "having my head carved into a giant gleaming dong", so it's understandable that he'd be a mite testy.
* [[Franchise/TheDCU Superboy-Prime]], with his wonderful bits of dialogue such as "[[Comicbook/CountdownToFinalCrisis I'll kill you! I'll kill you]] '''[[ShapedLikeItself to death]]'''!"
* [[Characters/GLOrangeLanternCorps Larfleeze]] of the Franchise/GreenLantern books is the WesternAnimation/DaffyDuck of the DCU.
* Jameson is a power-hungry undead MadScientist and demonologist. He's also the MetaGuy of ''Comicbook/CreatureTech'', and as such spends most of his time making [[PungeonMaster awful puns]], [[ShoutOut references to other media]], ChewingTheScenery, GettingCrapPastTheRadar, and [[LampshadeHanging hanging lampshades]] anywhere they'll fit.
* SelfDemonstrating/{{Deadpool}}, when he's the antagonist.
[[/folder]]

[[folder: Fan Fics ]]
* Fanfic/DungeonKeeperAmi: The enormously popular character [[CrazyAwesome Mukrezar]] seems to engage in [[ZanyScheme zany schemes]] mostly for the [[GeniusDitz entertainment value]]. Included in his exploits is a long, long line of failed plans involving [[RingOfPower rings of power]] and bad baking. He tortures, he pillages, and he does it all as half of a [[ThoseTwoBadGuys two-man comedy act]].
* [[spoiler: Chaos]] from the ''FanFic/TamersForeverSeries''. While [[AntiHero he's not technically evil]] there's no denying that he's one of the most ruthless and hilarious characters in the series.
[[/folder]]

[[folder: Film -- Animated]]
* ''WesternAnimation/TheThiefAndTheCobbler:'' Zigzag, the EvilChancellor, is usually amusing, but is introduced by a scene where he condemns a cobbler to death for spilling tacks he happened to step on, and [[FromBadToWorse only gets worse]].
** It might also have something to do with the fact that he's voiced by ''Creator/VincentPrice''.
* The Franchise/DisneyAnimatedCanon provides us lots of Laughably Evil villains:
** ''Disney/PeterPan'': Captain Hook. Wicked! Bloodthirsty! Hilarious!
** No one makes you laugh like [[Disney/BeautyAndTheBeast Gaston]].
** Yzma and her minion Kronk from ''Disney/TheEmperorsNewGroove'' are both marvelous examples. Yzma (voiced by Eartha Kitt) is a CardCarryingVillain who's always ChewingTheScenery: Kronk combines StupidEvil and MinionWithAnFInEvil with plenty of ham.
** Willie the Giant from the "[[WesternAnimation/ClassicDisneyShorts Mickey and the Beanstalk]]" scene of ''Disney/FunAndFancyFree''. Great giant, can't pronounce the word "pistachio", also likes to be a cute, pink bunny rabbit. [[NotSoHarmlessVillain But he also is a violent kleptomaniac who wields a morning star the size of a two-story house]].
** In ''WesternAnimation/TheIncredibles'', Syndrome is another Disney villain who is both humorous and unnerving. Many of his lines will sound ''very'' familiar to anyone who is a comicbook fanboy or knows one, and his goofy, hammy demeanour can almost make you forget that the guy is guilty of mass murder, would knowingly kill children, and is essentially plotting to start killing hundreds of innocent people and get hero-worshipped for ''stopping''. Just as an example:
---> ''Elastigirl? You married Elastigirl? (notices the children) And got '''bizzaaaay!'''''
** Hades from Disney's ''Disney/{{Hercules}}''. Thanks to James Woods, he changed from being a stereotypical chilling villain to [[MotorMouth fast-talking]], tempestuous and absolutely awesome. Easily the best part of the movie.
---> '''Hades:''' ''Er, guys? [[TheExitIsThatWay Olympus would be that way...]]''
*** He manages to carry on this trait to the TV series, and to ''video games''... any ''Franchise/KingdomHearts'' cutscene featuring Hades are generally hilarious.
** Apart from the examples above, there's also Kaa from ''Disney/TheJungleBook'', WesternAnimation/{{Pete}}, any villain in ''Disney/TheRescuers'' films, Edgar from ''Disney/TheAristocats'', and Sid and Al from ''WesternAnimation/ToyStory'' and ''WesternAnimation/ToyStory2'' respectively, to name a few.
** The hyenas from ''Disney/TheLionKing''.
** The magnificent, marvelous, mad Madam Mim from ''Disney/TheSwordInTheStone''
** Prince John from ''Disney/RobinHood''
** Cruella de Vil from ''Disney/OneHundredAndOneDalmatians''
** King Candy from ''Disney/WreckItRalph''. He's a complete bastard but he's just so damn entertaining to watch. [[spoiler: Until the [[NightmareFuel/WreckItRalph climax at least]]...]]
** Disney/TheGreatMouseDetective: Ratigan, the world's greatest criminal mind. It also helps that he's voiced by a [[Creator/VincentPrice man who plays laughably evil characters]].
* Baron Ruber of ''WesternAnimation/QuestForCamelot'' twitches, talks to himself, and does silly little dances during his VillainSong.
* Megamind [[spoiler:and Titan]] from [[WesternAnimation/{{Megamind}} the appropriately named movie.]]
* Most villains from ''Animation/CatCity'', particularly the four rats.
[[/folder]]

[[folder: Film -- Live Action]]
* ''Literature/{{IT}}'', from the film of the same name.
* TheJoker from ''Film/TheDarkKnight'' and ''Film/{{Batman}}''.
* Creator/AlanRickman as the Sheriff of Nottingham in ''Film/RobinHoodPrinceOfThieves''
-->'''Guy of Gisborne:''' Why a [[CutHisHeartOutWithASpoon spoon]], cousin? Why not an axe, or...\\
'''Sherriff of Nottingham:''' Because it's ''dull,'' you twit. It'll [[PunctuatedForEmphasis HURT. MORE.]]
** Rickman's Hans Gruber from ''Franchise/DieHard'' also occasionally slips into this.
* ''Film/AustinPowers'': Dr. Evil, Number Two, Frau Farbissina and the rest of the gang.
* The Green Goblin is partially one of these in ''Film/SpiderMan1'', mostly because the character itself is supposed to be that way, but also because he is so [[LargeHam hammy]].
* In ''Extremities'', the rapist gets all the funny lines.
* Any film that's SoBadItsGood. Particular examples are [[Film/PrinceOfSpace The Phantom of Krankor]], [[Film/PumaMan Kobras]], [[Film/ManosTheHandsOfFate Torgo and The Master]], [[Film/Plan9FromOuterSpace Eros]], and [[Film/{{Troll2}} CrEEEEEdence Leeeeonorrre Gieeeellllgud.]]
* Adenoid Hynkel from Creator/CharlieChaplin's ''Film/TheGreatDictator''. He is portrayed as [[ManChild infantile]] and [[DrunkWithPower crazy from power]]. Some consider this version of reality to be too humorous.
* Ray "Bones" Barboni in ''Film/GetShorty''. He can spin on a dime between being menacingly brutal, intentionally funny, and humorously incompetent. In one scene, he beats a character half to death and almost gets his balls blown off in the process. When Dennis Farina plays villains, they are usually both funny and nasty at the same time.
* Not sure if that was intentional, but Komodo of ''Film/WarriorsOfVirtue'' IS the missing {{WesternAnimation/Looney Tune|s}}.
* Tuco in ''Film/TheGoodTheBadAndTheUgly'' - it's debatable whether he's actually evil, because some consider him the most sympathetic and relatable character in the film, but he's far from a good guy and is absolutely hilarious.
* The villain of the [=CarrotTop=] comedy ''Film/ChairmanOfTheBoard'' is the only particularly funny thing about it. It isn't worth it.
* Biff Tannen (and his relatives) from the ''Franchise/BackToTheFuture'' trilogy.
* Freddy Krueger in ''Franchise/ANightmareOnElmStreet'' sequels. Which is quite a feat from a rapist child-killer.
* LargeHam KillerDoll Chucky in the ''Franchise/ChildsPlay'' films, mostly the sequels, especially the [[Film/BrideOfChucky fourth]] and [[Film/SeedOfChucky fifth]] films.
* Not exactly evil, but the title characters in ''Film/TheUsualSuspects'' have an empathic moment where they spontaneously burst out laughing in a police line-up-- in fact, director Bryan Singer lampshades this in an interview by saying that there's a certain humanity in a bunch of guys getting along and laughing together, even if they're horrible criminals. ([[ThrowItIn The reality is that the actors themselves just couldn't get through the scene without]] [[{{Corpsing}} breaking character and cracking up.]])
* [[BigRedDevil Duamerthrax]] in the Dead Gentlemen's ''Demon Hunter'' movies. The films as a whole are [[NarmCharm pretty goofy]].
* The Octopus in FrankMiller's ''Film/TheSpirit''. Gems include the line "I'm gonna kill you all kinds of dead!" and accidentally making a clone that was only a head and a foot.
* Pam Ferris as [[DeanBitterman The]] [[SadistTeacher Trunchbull]] in ''Film/{{Matilda}}''. While ''still'' managing to keep the character ''scary'', no less.
* Brick Top from ''Film/{{Snatch}}'', a murderous gangster who feeds people to pigs and drops hilariously snarky lines.
* Loki in ''Film/{{The Avengers|2012}}''. There's something very amusing in the way he [[XanatosSpeedChess dances circles around the heroes]], while gleefully mocking them at the same time.
* Given EvilIsHammy with Film/JamesBond villains, most end up providing laughs (including ones made deliberately funny such as [[TheEvilGenius Boris Grishenko]], played by Creator/AlanCumming, in ''Film/{{Goldeneye}}'' or Professor Joe Butcher in ''Film/LicenceToKill'') - but one that's both over-the-top comedic ''and'' [[KnightOfCerebus downright threatening]] is Silva from ''Film/{{Skyfall}}''.
* Tommy Devito from ''Film/GoodFellas''.
* Zartan his moments in ''Film/GIJoeRetaliation'' while disguised as [[spoiler: the President]]. Including one scene where [[spoiler: he plays ''VideoGame/AngryBirds'' on his phone]].
* Justin Hammer's particular flavor of LargeHam in ''Film/IronMan2''.
* ''Film/{{Gamer}}'' includes the appropriately named [[NamesToRunAwayFromReallyFast Rick Rape]], who ends up being almost impossibly over-the-top until he feels like a living cartoon.
* Jack Frost from the [[Film/{{JackFrost 1997}} the horror-comedy film]] is a twisted and sadistic monster who can be funny in his lines.
* Danny [=McBride=] in ''Film/ThisIsTheEnd'' has shades of this, especially after [[spoiler:his FaceHeelTurn]]. Some of the comments from [[spoiler:Possessed!Jonah]] aren't far behind as well.
* In ''Film/ExMachina'', Nathan eventually turns out to be villainous or at least very morally dark, but he definitely has a sense of humour and continues to do some hilarious things even after he starts [[KickTheDog kicking dogs]].
[[/folder]]

[[folder:Literature]]
* The title devil from ''Literature/TheScrewtapeLetters'', who [[EvilHasABadSenseOfHumor has no sense of humor himself.]] {{Lampshade|Hanging}}d at one point where he complains that the girl the Patient is falling in love with is "the sort who would find ''me'' funny."
* The ''Literature/CiaphasCain'' series tends to draw from this trope for its humor, only instead of the source being an individual villain, it is the DarkerAndEdgier nature of the ''TabletopGame/{{Warhammer40000}}'' setting itself that provides the source.
* The pigs from ''Literature/AnimalFarm'' can be this, especially [[TheDragon Squealer]]. A case in point would be the morning after the pigs get wasted on booze and it is [[LargeHam mawkishly announced]] that Napoleon (now suffering a hangover) is dying. Then: Great news! Our dear leader is going to be making a complete recovery. Anyway, I'm off to procure some books on brewing. Oink!
[[/folder]]

[[folder: Live Action TV ]]
* JohnSimm's Master in ''Series/DoctorWho'' certainly qualifies as a CrossesTheLineTwice villain.
** The Master has been like this [[OlderThanTheyThink since his introduction in 1971]]. Anthony Ainley's and Eric Roberts's portrayals stand out.
* [[Series/{{Lost}} Benjamin Linus]] is one ruthless, manipulative, and downright creepy motherfucker. [[DeadpanSnarker He also has some of the]] [[ActuallyPrettyFunny best lines in the series.]]
* All of the villains in the Creator/AdamWest ''Series/{{Batman}}'' show fit, but the best examples are all of the one-shot villains that are unique to the show. And the Riddler, whose infamous riddles would continuously be solved by a [[TheLoad Boy Wonder]] who was otherwise only good for getting kidnapped.
* All of the villains on ''Series/TheLeagueOfGentlemen''. There are very few shows that could make a pair of [[BrotherSisterIncest incestuous]] CorruptHick {{Serial Killer}}s hilarious.
* ''{{Buffyverse}}''
** Spike could be quite funny, such as when he passed out in Angel's backyard and woke up when the sun made his hand catch fire in the episode "In the Dark". Also in the episode where he watches from a roof-top while Angel saves a girl and provides sarcastic voice-over narration.
---> '''As Victim:''' Oh, how can I thank you, you mysterious black-clad hunk of a night thing?\\
'''As Angel:''' No need, little lady, your tears of gratitude are enough for me. You see I was once a badass vampire, but love, and a pesky curse defanged me, and now I'm just a biiiiiig, fluffy puppy with bad teeth.\\
'''As Victim:''' But there must be some way I can... show my appreciation.\\
'''As Angel:''' No! Helping those in need's my job, and working up a load of sexual tension and prancing away like a magnificent poof is truly thanks enough.\\
'''As Victim:''' I understand. I have a nephew who's gay, so-\\
'''As Angel:''' Say no more. Evil's still afoot. And I'm almost out of that nancy-boy hair-gel I like so much. Quickly, to the Angel-mobile! Away!
*** This little exchange was actually on the ''Buffy'' spin-off ''Angel'' and when we next see him on that show four seasons later, he's reformed his ways.
--> '''Cordelia:''' Heard you weren't evil anymore. Which kinda makes the hair silly.
** Angelus is even funny sometimes, in a sick sort of way. ("Othello and Desdemona! My favorite couple. Only Desdemona didn't love the other guy.")
** [[PhysicalGod Glory]] is the AlphaBitch with apocalyptic plans.
** The Trio start out as a mix between this and HarmlessVillain. [[spoiler: Then one of the subjects of their wacky hijinks points out that their BlackComedyRape plan wasn't quite as funny or as hot to her, retroactively pointing out the MoralEventHorizon was crossed much earlier in the ostensibly funny episode. The Trio reacts differently: Warren goes monster, Andrew becomes an IneffectualSympatheticVillain, and Jonathan tries desperately to do a HeelFaceTurn but is prevented by the other two.]]
** Before The Trio and Glory, there was the one and only chaos-worshipping Ethan Rayne. The guy is very cool and efficient in causing complete chaos, but his methods are downright ''hilarious.'' His grand entrance was in the episode "Halloween", where he opens up a costume shop. Anyone who puts on his costume ''actually becomes the thing that they were dressing up as.'' As Spike put it, was just plain neat. In "Band Candy", he spikes school band fund-raiser chocolate so that any adult that eats it turns into a stupid teenager. Best of all though, was turning [[BadassBookworm Giles]] into a [[TheBrute Fyarl]] [[DumbMuscle demon]]. Ethan Rayne at best is a DeadpanSnarker, but his methods easily place him squarely into this territory.
* Like [[VideoGame/FinalFantasyVI Kefka]] and SelfDemonstrating/TheJoker, [[MagnificentBastard Alpha]] from ''Series/{{Dollhouse}}'' can make you laugh and cross the MoralEventHorizon at the same time.
* [[Series/{{Supernatural}} The Trickster]] always manages to deliver some sick and twisted poetic justice in a way that will make you laugh--maybe because it's [[RefugeInAudacity completely ridiculous]], extremely clever, or just ActuallyPrettyFunny.
* Lord Fear in ''Series/{{Knightmare}}'' was a hilariously snarky villain.
* Yogostein, Kitaneidas, and Kegalesia in ''Series/EngineSentaiGoOnger''.
** [[Series/KaizokuSentaiGokaiger Warz Gill]] is a ManChild GeneralFailure who throws tantrum and gets into hijinx that makes him the butt of jokes and generally act like a SpoiledBrat. He still has some nasty tendencies of plots that makes even his more serious [[TheDragon Dragon]] [[EvenEvilHasStandards horrified enough.]]
* Franchise/PowerRangers has a lot of these guys, really - ranging from Squatt and Baboo the TagalongKid monster henchmen of Rita Repulsa to Flit the {{fly|Crazy}} CombatCommentator.
* ''Series/KamenRiderFourze'' has the [[GiantEnemyCrab Cancer Zodiarts]], who was the head of the high school's [[http://en.wikipedia.org/wiki/Rakugo Rakugo]] club when he was recruited by the villains, and it still shows in his tendency to make puns mid-battle.
** Sometimes Cancer gets into CrossesTheLineTwice territory, as with his "Open Mic from Hell", where he challenges people to make him laugh or lose their souls. When the LovableAlphaBitch starts a long joke, he [[KilledMidSentence zaps her mid-sentence]] and says "I never liked her anyway"; when TheStoic challenges him to a funny face contest, he [[NoJustNoReaction gives a flat "no"]] and zaps him.
* ''Series/TheSopranos'' has Paulie Gualtieri as a example.
* ''Series/TheVampireDiaries'': Even when he's balls-to-the-wall evil and murdering innocent people, Damon still makes you laugh.
[[/folder]]

[[folder:Musical]]
* Thenardier in the musical version of ''Theatre/LesMiserables'', quite an achievement considering how nasty he is in the book. [[http://www.youtube.com/watch?v=izgc7IhcGG4 "Master of the House"]] stands out as a rare moment of light relief.
* Similarly, Fagin in ''Theatre/{{Oliver}}''
[[/folder]]

[[folder: Professional Wrestling ]]
* Wrestling/ChrisJericho was one of these in Wrestling/{{WCW}} and in his early days in Wrestling/{{WWE}} as a dumb blonde muscle headed diva who thought he was a lot better than he really was. He beat Wrestling/{{Goldberg}}...or rather, a pale imitation in "Gilberg", and he ''almost'' lost to that! He knew 1004 holds and they were almost all ARMBAR!
* Wrestling/{{Rikishi}} during his "bad man" phase. Yes, he tried to run over Wrestling/StoneColdSteveAustin with a motor vehicle but he was still the man whose most prominent feature was his ass. In fact, this little stretch of his WWF career is considered one of the worst {{heel}} runs ever because people weren't laughing in any way intended.
* When the Knights of the UK were put on edge, bad things happened. In [[Wrestling/{{Paige}} Britani]]'s case though, it was almost adorable. She's tried to use unwilling wrestlers such as Wrestling/CheerleaderMelissa as ventriloquist dummies, for example.
* After Wrestling/SantinoMarella failed to get over as the "Milan Miracle", he got over this way, typically throwing silly insults at his opponents. Usually he's a weak character who gets whipped on, to get the audience cheering for a big, strong hero.
* Since no one has kicked out of Wrestling/BryanDanielson's inside cradle all year, you may now refer to him as "'''Mr.''' Small Package!" Why are you laughing? What's so funny? You're all just [[YouKeepUsingThatWord jealous]] because you'll never rate on his manliness meter!
[[/folder]]

[[folder: Tabletop Games ]]
* Da Orkz of ''TabletopGame/{{Warhammer 40000}}'' are a race of {{Psychopathic Manchild}}ren who fill in as the ''comic relief'' of the setting, in no small part due to [[CrossesTheLineTwice crossing the line twice]]. Most factions in Warhammer 40k will wage genocidal war on you because they hate you with the burning fire of a thousand suns. The Orks will wage genocidal war on you because they want a ''larf!''
** Since 40K is in many ways ''TabletopGame/{{Warhammer}}'' [[RecycledInSPACE IN SPACE]]!, the Orcs and Ogres in ''Warhammer Fantasy'' have similar traits.
* ''TabletopGame/InNomine'' features Kobal, the Demon Prince of Dark Humor. There is also his "blood brother" Haagenti, the Demon Prince of Gluttony, who also holds purview over torture and sight gags (which many consider to be a form of torture).
* ''TabletopGame/{{Pathfinder}}'' goblins, bless their psychopathic little hearts. Their culture honors pyromania, kleptomania, illiteracy, random slaughter and suicidal courage.
* Goblins in any given ''TabletopGame/MagicTheGathering'' setting tend to be psychopathic, destructive, homicidal, genocidal, suicidal and absolutely hilarious.
[[/folder]]

[[folder: Video Games ]]
* Edwin from ''VideoGame/BaldursGate'' and its sequel is sociopathic, irritable and has a massive ego but is genuinely cranky to the point of amusement and bumbling enough to be this trope. Half the laughter comes from him being sulky.
* Many, if not all, of the main enemies in the ''Franchise/SuperMarioBros'' series. From [[SelfDemonstrating/{{Bowser}} Bowser's]] kidnapping of the princess turning out to be lovesickness, [[VideoGame/SuperMarioBros2 Wart]] being the tyrant of a dream world while [[WeaksauceWeakness critically weak to vegetables]] (he hates the taste), to even the names of many of the stage bosses (King Caliente's Spicy Return!). Not to mention anyone who's an antagonist in an RPG or spinoff (*[[VideoGame/SuperPaperMario Chunks Awaaaay!]]* ) ([[VideoGame/MarioAndLuigi I HAVE FURY]]!).
** Special mention also goes to [[MonsterClown Dimentio]], who often has rather quirky behaviors that count as somewhat comical, and yet commits genuinely horrific actions while cracking jokes.
** However, Bowser is portrayed in a more serious manner in the main series platform games. Especially ''VideoGame/SuperMario64'' and ''VideoGame/SuperMarioGalaxy''.
*** He's a more serious threat in terms of malice in said games, but is still a comical [[LargeHam ham]] of the highest order personality wise, so fits this trope to a tee.
---->'''Bowser:''' I'm HUUUUUUUUGE!!!!
** Let's not get started on Bowser in ''VideoGame/MarioParty''. Especially in 7, where he'll take a picture of the characters and make you pay for it.
* Jester from ''VideoGame/DevilMayCry 3'' is funny as [[{{Pun}} Hell]].
* [[VideoGame/FinalFantasyVI Kefka]], a rare example of a villain who can make you laugh, even when he's gleefully crossing the MoralEventHorizon. It also doesn't help that he's the ''Franchise/FinalFantasy'' equivalent of SelfDemonstrating/TheJoker.
** Another example from that game might be the octopus Ultros. Ultros isn't really that threatening, truth be told, but he's a [[FountainOfMemes goldmine of hilarious one-liners]].
** Recurring villain Gilgamesh, a LargeHam prone to hilariously bizarre proclamations mid-battle.
* Caulder of ''[[VideoGame/NintendoWars Days of Ruin]]'' fame is a [[CatchPhrase fascinating]] example. Among other things, he [[spoiler:releases a biological weapon and attacks civilians]] [[ForScience for the lulz.]] And he makes it funny.
** There's also Waylon, a greedy coward whose [[AtLeastIAdmitIt honesty about his selfishness]] gives him all of the game's [[ActuallyPrettyFunny best lines]].
* Many of the demons in the ''Franchise/{{Disgaea}}'' series (except the psychopaths like [[VideoGame/Disgaea2CursedMemories fake/real Zenon, evil Adell]], super evil [[VideoGame/Disgaea3AbsenceOfJustice Mao]], etc) qualify for this trope.
* ''VideoGame/{{Rayman}}'': The VideoGame/RavingRabbids. DAAAAAAAAAAAAAAAAAHHHHHHHH!
* ''VideoGame/CityOfHeroes'''s Dr. Aeon. While he's one of the non-harmless examples of the trope, it's more because he's [[GeniusDitz such a scatter-brained moron]] that he ends up posing as much of a danger to the world [[TheChewToy as to himself]].
* Foxbat from ''VideoGame/ChampionsOnline''. He's been described as an evil version of Adam West-era Batman.
* Zorbak in ''VideoGame/AdventureQuest'' has transcended evil. He's Ebil! Mwahahah!
** Escherion, the very first Lord of Chaos in ''VideoGame/AdventureQuestWorlds'', becomes this trope at the end of the Chiral Valley saga when the hero reflects his inversion spell right back at him, inverting him and causing him to suffer the HumiliationConga of ending up casting every spell he tries to cast on him/her on himself, and eventually turn himself into a harmless frog, which is a rather funny scene, to say the least.
---> '''Hero:''' (after Escherion turns into a frog) Huh... I guess you inverted your powers. Every spell you try to cast on me, you actually cast on yourself.\\
'''Escherion:''' *ribbit ribbit*\\
'''Hero:''' I'm sure you just said something very rude in froggy.
* The Lich Palawa Joko in ''VideoGame/GuildWars: Nightfall'' once terrorised the ''entirety'' of the continent of Elona, whose forces were the greatest threat said continent faced until the Charr invasion many centuries later. Being unable to die or be killed, he had to be [[SealedEvilInACan sealed away]] at the location of his defeat, and there he would have remained... if the plot hadn't required that you release him from his imprisonment for several ''very good'' reasons. But that's okay, all Joko wants is to reform his undead Army Of Darkness, which you've got to help him with as well. Astoundingly, he fails to be a threat for the remainder of the game, and while you're dealing with the BigBad he's spending the rest of the time [[HilarityEnsues hilariously failing to get any sort of organisation from his mindless minions]]. What a guy. [[spoiler:By the second game, he has gotten his act together, and how]].
** Mad King Thorn is generally loved by players and seen as wacky and amusing. The fact that he and his minions will happily recall the horrors they inflicted on their subjects, such as once having ''an entire village flayed alive'', makes this somewhat inexcusable.
* Many of the player character's evil options in the ''VideoGame/KnightsOfTheOldRepublic'' games are hilarious. And then there's [[RoboticPsychopath a certain over-eager assassin droid.]]
-->"Definition: Love is making a shot to the knees of a target 120 kilometres away using an Aratech sniper rifle with a tri-light scope."
* The dark sided Sith Inquisitor from ''VideoGame/StarWarsTheOldRepublic'' is quite a comedian. They seem to get the most opportunities to either crack jokes or outright mock their enemies (especially the Jedi) in the funniest way possible. This extends to photo-bombing victory speeches on the Holonet, wagging fingers at Jedi Knights for losing their cool during a battle, and even impersonating Republic officers.
--> Inquisitor: "Master Ramos needs to brush up on his Jedi teachings. <3"
* [=GLaDOS=] from ''VideoGame/{{Portal}}'', [[spoiler: Wheatley]] and Cave Johnson in the sequel. Completely lacking in any sort of ethics, whether business or moral, but certainly quick with a quip.
* The player in ''VideoGame/EvilGenius''. Think [[Film/AustinPowers Dr. Evil]].
* ''VideoGame/RatchetAndClankUpYourArsenal'', Dr. Nefarious.
-->"QWAAAAAAARRRRR-" *KRZT* [[SoapWithinAShow "I don't have the capacity for love, Janice. I was cursed by a tribe of gypsy ninjas when I was a kid!" "I know, Lance... I was in that tribe of gypsy ninjas!"]] [[PercussiveMaintenance *THWACK*]] "-RRRRK!"
* King Dedede from the ''VideoGame/{{Kirby}}'' series.
* Dr. Wily, from the ''VideoGame/{{Mega Man|Classic}}'' series. He pulls off evil plots like holding a Russian scientist's daughter hostage and [[TheVirus spreading a robot virus]], yet tends to use silly-looking robots, frequently [[FascinatingEyebrow wiggle his eyebrows]], and [[PoseOfSupplication beg for mercy]] upon his defeat. [[OverusedRunningGag Every single time]]. The guy is a living paradox. The best example of this, is the time he stole the world's strongest robots, while wearing a rather [[PaperThinDisguise flimsy disguise]]. This is quite subject to a FunnyAneurysmMoment when you find out that [[spoiler: the horrible, horrible robot war that took up most of ''VideoGame/MegaManX''[='=]s story was his fault.]]
* Hazama of ''VideoGame/BlazBlue'' fame is a walking CrowningMomentOfFunny. He's also [[FauxAffablyEvil the kind of guy who crosses the]] MoralEventHorizon ''nine times'' before he's even woken up. This perception has changed over time, however. As Hazama/Terumi becomes more and more saturated and pretty much everywhere and his motives comes off extremely shallow, BrokenBase was formed, some just think he stops being laughable altogether.
* Naturally Dr "Eggman" Robotnik of the ''Franchise/SonicTheHedgehog'' series, and only seems to be leaning further this way as of recently. Many alternate media representations are similar (see below). What do you expect from an egg shaped scientist who makes toy-like robots?
* [[VideoGame/{{Bulletstorm}} General Sarrano]] is an evil, manipulative, foul-mouthed bastard who delights in the suffering of others, gleefully betrays everyone around him, and is generally an all-around un-fun guy to be around. At the same time, he's a hilariously over-the-top jackass with a never-ending stream of creative invective to toss at anyone and everyone around him.
* Every villain in the ''Franchise/CrashBandicoot'' series.
* Ditto for the entire RoguesGallery of ''VideoGame/EarthwormJim'' (even more so in the [[WesternAnimation/EarthwormJim cartoon]]).
* Most of the minor villains from the ''VideoGame/PokemonMysteryDungeon'' series. However, they are often [[ShooOutTheClowns phased out]] when the not-so-hilarious BigBad shows up.
* King Bohan and Flying Fox from ''VideoGame/HeavenlySword''. King Bohan is voiced by Creator/AndySerkis and is funny even when being a total bastard. Flying Fox has a very shrill voice and is even hammier than Bohan.
* Kaos, the BigBad of ''VideoGame/{{Skylanders}}''. He's got the personality [[Creator/RichardStevenHorvitz and voice]] of WesternAnimation/InvaderZim, LargeHam and all. Though it should be noted he's actually [[BewareTheSillyOnes far more competent than his personality would imply.]] Doesn't make him any less fun to watch, however.
--> '''Kaos:''' My [[HugeHolographicHead head]] is awesome, I tell you! Fear it! Fear my ''GIANT FLOATING HEAD!''
* In the first ''VideoGame/{{Mother}}'' game, Hippies will try to attack Ninten with rulers. They'll also try to shout into a bullhorn that Ninten's mother was looking for him.
* [[spoiler:Cicero]], from ''[[VideoGame/TheElderScrollsVSkyrim Skyrim]]''. He's a jester who is a touch unstable, and also happens to be [[spoiler:the Night Mother's keeper, an important position in the Dark Brotherhood]].
* [[spoiler:Hades]] from ''VideoGame/KidIcarusUprising''. [[OoCIsSeriousBusiness The few times]] when they gets dead serious, however, it's actually pretty terrifying.
* [[CrazyAwesome Sho Minamimoto]] from ''VideoGame/TheWorldEndsWithYou'', if only for how bizarre he is. Even when he's planning genocide and [[spoiler:planning to KillTheGod]], he's somehow hilarious. A language or math certainly helps in that.
* Handsome Jack in ''VideoGame/{{Borderlands 2}}''. He is ''evil''. Absolutely, totally evil. And he is such an epic asshole that every conversation with him is side-splittingly hilarious.
** Many, many other antagonists and enemy mooks also fit the bill.
* "Evil" maybe pushing it, but playing [[Franchise/MassEffect Commander Shepard]] as a Renegade can result in some truly hilarious moments and bouts of InsaneTrollLogic.
* It seems ''GrandTheftAuto'' has a thing for this, so of course ''VideoGame/GrandTheftAutoV'' upped the ante with player character Trevor. Abusive, psychopathic, and hilarious.
** In ''VideoGame/GrandTheftAutoSanAndreas'', you have Mike Toreno, the paranoid government agent. Disrespecting dead women to a monologue on how all modern conspiracy theories are nowhere near the truth.
** Jerry Martinez and Lance Vance from ''VideoGame/GrandTheftAutoViceCityStories''.
* Dokurubo from ''VideoGame/SakuraWarsSoLongMyLove'' is a perfect example of this. When the New York Combat Revue challenge him the second time after comforting Rikaritta Aries, He responds to their appearance with "You guys!". But then, he ask who they are, much to the frustration of the team. Sagitta calls him out for stupidity as Rikaritta just announced who they are. In the boss battle, Dokurobu will also try to trick the team into doing a Victory Pose. Despite being dumbfounded at first, Shinjiro see though it and insults him for it. When Shinjiro also insulted Dokurobu's armour, he get angry and gives it a different name: "The Star Division is Stupid!" armour.
* Veigar, the Tiny Master of Evil, from ''VideoGame/LeagueOfLegends'' literally embodies this trope. This hilarious little yordle is a self-proclaimed EvilOverlord and from time to time delivers gems like "I am evil! Stop laughing!"
* [[PsychoForHire Hasta]] in ''VideoGame/TalesOfInnocence'', though more so in the Vita remake. His strange speech pattern and laid-back manner make it hard to take him seriously, even after he murders some innocents for the sake of getting the party's attention and stabs Luca [[ISurrenderSuckers after getting him to let his guard down.]]
* The Bonne family in MegamanLegends, while they're tearing apart buildings, looting, and generally making nuisances of themselves they do it in an utterly hilarious way. Besides the accidents the servebots get into, Tiesel Bonne screaming at the servebots to close the hatch on his dangerous HumongousMecha or even just the way Tronne Bonne gets chased up a lamppost by a small dog. It's perfectly summed up by one of the citizens on Saul Kada island which the Bonnes have taken over.
-->'''Citizen''': I don't know whether to laugh at the bonnes or run away from them!
* Several members of Organization XIII from KingdomHearts are this, especially Xigbar. Xigbar is there, casually tossing out surfer slang, wearing an eye patch, explaining (badly) what love is to Roxas, and is a lot of fun to watch. Until you play Birth By Sleep and Kingdom Hearts 3D. [[spoiler: Where it's revealed that he caused a lot of the problems in Birth By Sleep and KH3D because he willingly let himself become "Half Xehanort" and it's implied that -unlike several other members of the New Organization who were either forced, brainwashed, or a part of the original Xehanort (ItMakesSenseInContext)- knew what would happen if Master Xehanort succeeds and went along with it anyway.]] Demyx is funnier, but he isn't evil enough to completely pull this off.
* In ''VisualNovel/DanganRonpa'' we have Monokuma, the self-proclaimed headmaster of the Despair Academy. His funny antics and quirks never quite manage to make up for the way he gleefully sets up the murders, watches everyone with cameras and his abilty to violently self-destruct. Played with, since he is a robot that is controlled by the real mastermind the same presumably goes for them. And [[spoiler: oh boy it does. Junko Enoshima is an AxeCrazy psychopath who experiences mood swings so violently that they might as well be different personalities. Her shifting her behaviour from a high and mighty EvilOverlord, to a {{Kawaiiko}} complete with ArtShift might seem amusing, if she didn't talk about how she randomly killed her sister [[ForTheEvulz out of boredom]] and her part in causing the collapse of human society ''at the same time''.]]
* The Roborobo/Rubberrobo Gang from {{Medabots}} are an organization of total goofballs who dress in full-body rubber costumes with antennae sticking out of the head portion and shades covering their eyes. While their leaders tend to be competent (sometimes), their rank and file are such [[MinionWithAnFInEvil complete and total nitwits]] that it can be hard to take them seriously ''at all''. In fact, the first time we see one of their members in the first game in the series, he's just stolen a rare medal (the heart and soul of the series' robotic {{Mons}})... Only to lose it after being clocked in the head with a stray frisbee thrown by the protagonist and subsequently sent fleeing in panic when said protagonist's dog came to fetch it.
* Uncle Jack of ''VideoGame/WeHappyFew'' is just meant to be a NonIronicClown, but his tendency towards BlackComedy (especially jokes involving murdering [[DefectorFromDecadence Downers) means that he comes across more as this.
[[/folder]]

[[folder:Web Comics]]
* Most villains in ''Webcomic/SluggyFreelance'' are funny at some point, since the comic is so frequently toeing the line between serious stories and crazy comedy.
** [[DemonLordsAndArchdevils Lord Horribus]]: One moment he's begging for his teddy bear (making him vice president to his empire, no less) and getting hit in the head with anvils in the middle of his Dramatic Entrance, the next he's killing off significant characters.
** Darksoul in the Oceans Unmoving" storyline is a borderline example, whose humor mostly comes after you find out the plot twist; [[spoiler: He is actually the present day Bun-bun, while the Bun-bun shown is from the past; present day Bun-bun (Darksoul) has Laser Guided Amnesia, and his pseudo-deadpan snarking is actually him ticked off on the fact that he has no idea what's going on; everything his past self is involved in is ridiculously random ("Leaf people?"), and he knows he should know what's going on]].
* Lord Attez seems this way in ''Webcomic/CwensQuest''. Although we only see [[http://www.drunkduck.com/Cwens_Quest/index.php?p=314161 very little of him]], it seems pretty clear he is a hysterical & horrible person from his [[http://www.drunkduck.com/Cwens_Quest/index.php?p=432637 various traumatized children]].
* Black Mage in ''Webcomic/EightBitTheater'' could be downright hilarious, whether plotting against his teammates or [[ButtMonkey while suffering]].
* Richard from ''Webcomic/LookingForGroup''.
* [[BigBad Xykon]] from the ''Webcomic/TheOrderOfTheStick''. He may be a horrible threat, but he gets some of the best lines and comedic moments.
** And now we have [[MagnificentBastard Tarquin]], a man of [[DeadpanSnarker remarkably dry wit]] and a [[DangerouslyGenreSavvy love of heroic tropes]] who celebrated his reunion with his son with a festival of lights... made out of immolated prisoners.
** Tarquin himself actually [[http://www.giantitp.com/comics/oots0788.html invokes this trope]] while talking about [[TheBrute Thog]]
---> '''Tarquin:''' But once he won the first two or three bouts I threw his way, I couldn't just slit his throat in the night, you know? [[LeaningOnTheFourthWall He's a crowd favourite. It's weird, no matter how many no matter how many people he kills, the audience still think he's lovable.]]
* [[BigBad Zenith]] from Webcomic/CommanderKitty. She constantly forgets why her MixAndMatchCritter boyfriend has [[http://www.commanderkitty.com/2010/04/25/plot/ elephant feet]], mistakes [[TheUnintelligible unintelligible ferret speak]] [[http://www.commanderkitty.com/2010/09/12/table-for-blue/ for a language her target uses only to think with]], and gets [[http://www.commanderkitty.com/2010/12/12/nothing-to-see-here/ chased out of a restaurant by its overly eager staff]].
[[/folder]]

[[folder:Web Original]]
* Tez On Toast in later episodes of ''WebVideo/KateModern'', in a decidedly un-harmless way.
* Music/DoctorSteel.
* There will be blood / It might be yours / So go kill someone / Signed [[WebVideo/DoctorHorriblesSingAlongBlog Bad Horse]]
* ''WebVideo/DiamandaHagan'' runs on this.
* Psycho Gecko, the main character of ''Literature/WorldDominationInRetrospect'' is dangerous and hilarious. He even weaponized the "Why did the chicken cross the road?" joke.
* Tom Foolery from the ''Roleplay/GlobalGuardiansPBEMUniverse''. Given that he's an {{Expy}} of both the Joker and the Toyman, his falling into this trope is expected.
* This is basically a recruitment must have for LetsPlay/{{Sips}} and LetsPlay/{{Sjin}}'s company, Sipsco. Typically most recruits are amoral, show little concern for the well-being of others, and have brilliantly dark senses of humour. A textbook example would be [[spoiler:Zips]] in ''[[Machinima/YogscastMinecraftSeries Sipsco Space Programme]]'', who is dangerously unstable as far as his mind is concerned, as well as a MadBomber and traitor. On top of all this, he's such a {{Cloudcuckoolander}} that his mental antics just become fantastically funny.
* LetsPlay/HatFilms are presenting themselves as this in "Hat Corp", where they are essentially the main antagonists. They are capable of being pointlessly cruel to others, such as Sjin and LetsPlay/LewisBrindley, submitting entire groups of mobs to [[ForTheEvulz unnecessarily painful deaths]] and basically being [[BigBadDuumvirate the biggest threat on the server]]. They are also funny in their cruelty, with acts so over-the-top that it's hard not to laugh.
[[/folder]]

[[folder:Western Animation]]
* Cartman from ''WesternAnimation/SouthPark''. An individual whose antics can sometimes backfire and lead to his humiliation, but he shows that he's capable of this, for example being able to team up with Cthulhu.
** Saddam Hussein as well, particularly in [[WesternAnimation/SouthParkBiggerLongerAndUncut the movie]].
* Roger Smith from ''WesternAnimation/AmericanDad''.
* Stewie Griffin from ''WesternAnimation/FamilyGuy''.
* Don Karnage in ''WesternAnimation/TaleSpin''. Let's see: [[JustAStupidAccent Funny accent]]? Check. [[AmbiguouslyGay Eccentric and flamboyant]]? Check. [[SurroundedByIdiots Incompetent Minions]]? Check. Ruthless pirate who thinks nothing of dropping a child twenty thousand feet to his death or setting a town on fire with a LightningGun? Erm... check.
* All the villains in ''WesternAnimation/DarkwingDuck'', with the possible exception of KnightOfCerebus Taurus Bulba. Negaduck is a good example of a villain who pulls of both [[LargeHam hilarious]] and [[AxCrazy dangerous]] at the same time.
-->'''Negaduck:''' "When I throw...'' '''THE SWITCH!!!!!'''"''
** Even Bulba has his moments:
--->'''Darkwing (taken by surprise after already doing his dramatic intro):''' Er... I am the terror that flaps in the night. I am... the sur-surprise in your... cereal box...\\
'''[[DeadpanSnarker Bulba]]:''' Yes, yes, I know. I heard.
* Prime Evil, from ''WesternAnimation/FilmationsGhostbusters'', was absolutely hilarious, thanks to a) the writing and b) Alan Oppenheimer's LargeHam acting.
* Like everything else in ''WesternAnimation/{{Freakazoid}}'', the villains were hilarious.
* SelfDemonstrating/LexLuthor in the ''Film/{{Superman}}'' movies is funny for many reasons, but it meshes well with the character. Luthor in ''SupermanBrainiacAttacks'' is ridiculously campy, and it doesn't... work... well...
** Bizarro is a creature with all the powers of the Man of Steel, and [[DumbMuscle an intellect that insults egg plants by association]]. To be fair, he may actually be quite competent, especially in the Franchise/{{DCAU}} where [[TooDumbToFool he is the only one to notice]] that something is wrong with Lex Luthor (namely that Lex and Flash are body swapped), but because he expresses himself in opposite action every time he speaks, no one gives him the time of day.
--->'''Bizarro:''' "Ever since [[ItMakesSenseInContext you plug into monkey's head,]] you acting [[MetaphoricallyTrue perfectly sane and rational.]]" ''[[{{Beat}} (pauses thoughtfully)]]'' "[[Funny/JusticeLeague Am you Bizarro's mommy?]]"
* Most of the villains in ''WesternAnimation/KimPossible'' are laughable, especially [[HarmlessVillain Dr. Drakken]] (with [[DeadpanSnarker Shego's running commentary]] serving to [[LampshadeHanging highlight]] his laughability). Even the ScaryDogmaticAliens, who can't grasp English idioms and have [[InventionalWisdom a goddam Off-button in their ship]] (except when [[MoralEventHorizon they threaten to kill Kim]] and [[DeadGuyOnDisplay mount her]] [[BerserkButton in front of Ron]]).
* In ''WesternAnimation/TransformersAnimated'', Blitzwing by himself is funny, particularly when his "random" personality is in control ("Ooh, I wanna see him turn into a fire truck, can I, can I, can I?"), but him and Lugnut sniping at each other is hilarious.
** Extra points for being a pretty competent and evil villain - one notable appearance includes tearing off [[CombatMedic Ratchet's]] ''hand'' (and making a reference to ''[[ImAHumanitarian eating]]'' it some episodes later. [[ComedicSociopathy Hilariously]].).
** Other villains have their moments, too, some more than others. Swindle, for example, is an ArmsDealer who acts like nothing so much as an overly-excited infomercial host. (In fact, his mannerisms were based partly on Ron Popeil.) And, because this show is so MerchandiseDriven, you can have your own little plastic Swindle for just $10.99! ButWaitTheresMore!
* ''WesternAnimation/DaveTheBarbarian'''s Dark Lord Chuckles, The Silly Piggy. It's in the name. For bonus points, this is how he actually announces himself.
* Bebop and Rocksteady from the 1980s ''[[WesternAnimation/TeenageMutantNinjaTurtles1987 Teenage Mutant Ninja Turtles]]'' cartoon. Sometimes Shredder and Krang get in on it, too.
* Essentially '''all''' the villains from ''WesternAnimation/TheVentureBrothers'', but the Monarch stands out.
* SelfDemonstrating/TheJoker from ''WesternAnimation/TheBatman''. From his bizarrely eclectic outfit to his equally bizarre way of fighting, the man simply cannot pass on the opportunity to do ''anything'' with a comedic twist. Naturally, [[TheyChangedItNowItSucks some fans were not pleased]].
** Others found him the funniest Joker yet and quite terrifying.
** SelfDemonstrating/TheJoker from the DCAU universe definitively qualifies as well. In fact, he even supplies the Trope Picture (more specifically, it was taken in his first scene in ''WesternAnimation/BatmanBeyondReturnOfTheJoker'' [[HaHaHaNo where he briefly fakes out Bonk with execution, shortly before doing so for real]]).
* Aku from ''WesternAnimation/SamuraiJack'' is so much fun to watch that you often forget he's MadeOfEvil, as he takes a break from hunting Jack to villainously order a pizza, subjects frightened children to his terrible storytelling, and swears revenge in a helium voice while in the form of a kangaroo rat.
** The "storytelling" thing may have been an attempt to raise the next generation to [[VillainWithGoodPublicity revere him]]. It fails, obviously.
* Any villain on ''WesternAnimation/ThePowerpuffGirls'' other than [[VileVillainSaccharineShow Dick Hardly]]. Mostly [[CampGay Him]] and to a slight lesser extent Mojo.
* The titular [[VillainProtagonist protagonist]] of ''WesternAnimation/InvaderZim''. Or just the Irkens in general, really. Who knew planet-scale genocide could be such a riot?
* Dr. Robotnik/Eggman of the ''Franchise/SonicTheHedgehog'' games is humorous but legitimately threatening most of the time. However, in ''WesternAnimation/AdventuresOfSonicTheHedgehog'', he is depicted as bumbling and hilarious, aided by the stellar {{Large Ham}}ming of the late Long John Baldry.
** Almost all renditions of the doctor are this in heavy doses (save maybe [[KnightOfCerebus the]] ''WesternAnimation/SonicSatAm'' version, though even he [[TheComicallySerious isn't void of comical moments]]).
* Heloise from ''WesternAnimation/JimmyTwoShoes'' is an AxCrazy EnfantTerrible known for her {{yandere}} attraction to Jimmy. As you might guess, she's quite hilarious. [[TheCaligula Lucius]] can be this as well.
* [[TheDevilIsALoser The Red Guy]] from ''WesternAnimation/CowAndChicken''.
* Jetstorm from ''WesternAnimation/BeastMachines'' is AxCrazy even by ''Franchise/{{Transformers}}'' but his LargeHam personality and horrible sense of humour make him one of the most enjoyable villains in the entire franchise.
-->"This is Captain Jetstorm speaking. Please feel free to run about the tarmac and flee for you miserable little lives."
** Ditto for [[WesternAnimation/BeastWars Inferno]]! (though mainly for his LargeHam, UndyingLoyalty, InsistentTerminology, AxCrazy, etc.) At least before his VillainDecay...
--->"FFFOOOORRR TTTHHHEEE RRROOOYYYAAALLLTTTYYYYY!!!"
* Skybite of ''Anime/TransformersRobotsInDisguise'' is the IneffectualSympatheticVillain version.
** Any Predacon who isn't Megatron/Galvatron.
* ''WesternAnimation/PhineasAndFerb'' has Dr. Heinz Doofenshmirtz. Yes, he wants to take over the entire Tri-State area, and has created everything from Killer Robots and mind-control helmets... [[IneffectualSympatheticVillain but he's so bad at it, it's hilarious]]! Compared to his alternate universe self, Doof-2 from ''WesternAnimation/PhineasAndFerbTheMovieAcrossThe2ndDimension'', [[EvenEvilHasStandards he's a pretty decent guy]]. Doof-2 was willing to kill complete innocents and his alternate-self, just for the sake of it. Though he still fills this trope by, among other things, announcing their doom with a sock-puppet.
* Every villain from ''WesternAnimation/TheLittleFlyingBears'', most notably Skulk and Sammy.
* Discord from ''WesternAnimation/MyLittlePonyFriendshipIsMagic'' is much like SelfDemonstrating/TheJoker in terms of this trope. One moment you'll be laughing at him, the next you'll be completely horrified as he {{break|TheCutie}}s and {{brainwash|ed}}es the Mane Cast.
* A few villains in ''WesternAnimation/TheSpectacularSpiderMan'' fit into this, namely the Green Goblin, who effortlessly makes jokes and quips back at Spidey while at the same time being a relatively AxCrazy MagnificentBastard. Rhino also counts too, as he is a typical DumbMuscle with several funny lines and scenes, but gleefully attempts to "[[WhatDoYouMeanItsForKids impale Spider-Man's heart on his horn]]".
* Skeletor from ''Franchise/MastersOfTheUniverse'' became this in ''WesternAnimation/HeManAndTheMastersOfTheUniverse1983'' --in the original minicomics he was a fairly serious villain, but since censors were constantly breathing down Creator/{{Filmation}}'s neck about what they perceived to be a horribly violent cartoon about a sword-swinging barbarian, they decided to make the scary man with a SkullForAHead less scary by playing him for laughs. Though still an evil schemer, the cartoon Skeletor was turned into a LaughingMad DeadpanSnarker who kept cracking one-liners in which he insulted the world in general and lamented how he was SurroundedByIdiots. [[WesternAnimation/HeManAndTheMastersOfTheUniverse2002 The 2002 remake]] of the show turned him a little more menacing and threatening, but kept his sarcasms and general tendency to get all the best lines in the show.
* ''WesternAnimation/TransformersPrime'' Knock Out who has the most hilarious lines in the show, and is quite vain of his appearance that he can be considered as metrosexual.
* Varrick from ''WesternAnimation/TheLegendOfKorra'' counts as one.
* ''WesternAnimation/GravityFalls'' has Bill Cipher, a powerful "dream demon" who combines bone-chilling sociopathy with a jovial, irreverent demeanor and a twisted sense of humor.
-->'''Bill:''' Here, kid! Deer teeth, for you!
-->'''Gideon:''' AAAH! You're ''insane''!
-->'''Bill:''' Sure I am, what's your point?
* Lord Hater from ''WesternAnimation/WanderOverYonder'', despite his serious personality, is pretty comical at times.
* ''BobsBurgers'' has Louise, who takes ComedicSociopathy to its logical extreme by ''actually'' being a sociopath. She's described on TheOtherWiki as being "manipulative and agressive...more than willing to exploit people", not exactly terms usually used to describe a protagonist. Her actions aren't always even harmless to the other protagonists of the show, and she very seldom expresses anything approaching remorse. However, that doesn't keep her from being absolutely hilarious.
* As a {{black comedy}} show, ''WesternAnimation/TheBoondocks'' has more than its fair share of funny villains:
** Uncle Ruckus is a hardcore [[PoliticallyIncorrectVillain white supremacist]]... [[BoomerangBigot who happens to be black]]. He usually appears {{once an episode}} to make [[RefugeInAudacity outrageous comments]].
** Colonel H. Stinkmeaner, an evil old man who likes to mess with other people [[ForTheEvulz for his own amusement]]. His personality and actions are so [[EvilIsHammy over-the-top]] that it's hard not to laugh along with him.
** Ed Wuncler III and Gin Rummy are a duo of {{stupid crooks}} who go around town robbing people, but most of the time they're [[StupidEvil too dim-witted]] to succeed with any of their crimes.
** Deborah Leevil is a [[EvilIsHammy hammy]] and {{card carrying|villain}} supervillainess who who wants to [[BoomerangBigot destroy black people]]... through the mind-rotting power of [[Creator/{{BET}} a certain TV channel]].
* Peridot in ''WesternAnimation/StevenUniverse'' is callous in the extreme, even towards members of her own species, and talks about nightmarishly cruel experiments in [[spoiler:Gem fusion]] like she's recording the heights of soybeans, but at the same time her dorkiness, constant frustration, ridiculous facial expressions, and one particular scene where she [[https://www.youtube.com/watch?v=CuDqJ6QvT5M soars away on a helicopter made from her own techno-fingers while giggling like a loon]] (clip contains spoilers) make her a source of constant amusement in her few appearances so far.
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