%% Image and caption selected per Image Pickin' thread: http://tvtropes.org/pmwiki/posts.php?discussion=1323276817082040100
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[[quoteright:350:[[TabletopGame/{{Chess}} http://static.tvtropes.org/pmwiki/pub/images/rsz_chess_set_2855.jpg]]]]
[[caption-width-right:350:"That's... wrong. That's... brilliant."[[note]][[ComicallyMissingThePoint It's wrong because the board should be turned 90 degrees]].[[/note]]]]

->''"Half the time, the humor came from how totally out-of-control and psychotic it was. And it kicked'' ass''! I mean, sure, it was gross and vulgar, but on the other hand,'' it was gross and vulgar''!"''
-->-- '''WebVideo/TheNostalgiaCritic''' on ''WesternAnimation/TheRenAndStimpyShow''
%% One quote is sufficient. Extra quotes go on the quotes page.

''"Pain is funny. Therefore, more pain must be even funnier!"'' Thus goes the logic in a lot of comedy shows and a few adult cartoons. Sadly, that's not the case. The line separating ''Film/TheThreeStooges''-style painful fun from outright villainous {{squick}}y sadism varies from person to person but is definitely there; crossing it makes one fan's ''[[TheChewToy "Nyuk nyuk!"]]'' another fan's GuiltyPleasures.

However, if a show goes far enough with its violence, it may end up crossing the line not once but ''twice'', as it goes around the planet and crosses it again. This second crossing takes the violence from sick back to funny in its ridiculous extremes. Similar to SoBadItsGood, but done quite intentionally.

This isn't as easy as it sounds. Shows attempting to be DarkerAndEdgier with their humor this way straddle the line between sadism and comedy, and it's easy to make a mistake and fall on the wrong side of the S.S. Tightrope. Rather than cross the line a second time, the show [[MemeticMutation makes a wrong turn at Albuquerque]] and breaks the audience's WillingSuspensionOfDisbelief. Some people just don't have a second line to cross in their minds, and will dislike any turn into sadism or vulgarity.

This can also apply to things other than violence for [[RuleOfFunny funny's sake]]; any time a little exaggeration would provoke a negative reaction, but exaggeration UpToEleven is fine, that's crossing the line twice. Take action scenes, for example: some shows try to keep action scenes realistic in order to seem believable, while others go so far over the top that it breaks the audience's WillingSuspensionOfDisbelief. Still others take [[UpToEleven the over-the-top so over the top]] that what was before unbelievable garbage is now heart-wrenching, adrenaline rushing, undiluted [[CrowningMomentOfAwesome AWESOME]]. Of course, this form of the trope is just as subjective as the last, so be careful what you put down as an example.

See also BlackComedy, BloodyHilarious, DudeNotFunny, RefugeInAudacity, VulgarHumor. If this happens completely by accident, that's SpringtimeForHitler. Part of the SlidingScaleOfComedyAndHorror. When this trope ''isn't'' taken to extreme, over-the-top levels, it's mere ComedicSociopathy.

The HilariouslyAbusiveChildhood depends on this trope, piling misfortune on misfortune until it becomes so ridiculous it's funny. For instance, the BoardingSchoolOfHorrors in ''Radio/BleakExpectations'' would be abusive if the staff beat the students and deprived them of food. That they use the boys as ammo for artillery practice and make them play a game where the smallest boy is chosen as the ball, kicked and punched across the field, and finally has his head shoved in a bucket of manure to score a goal is just silly.

This is also the way the HeroicComedicSociopath holds the audience's hearts. This character does evil in such an over-the-top, outrageous fashion that the audience stops feeling any moral qualms, because it's so over-the-top and out of line that it becomes ''hilarious'' instead.

For the (mostly) non-vulgar variant, see OverlyLongGag.

* [[CrossesTheLineTwice.LiveActionFilms Live-Action Films]]
* [[CrossesTheLineTwice.LiveActionTV Live-Action TV]]
* [[CrossesTheLineTwice.{{Music}} Music]]
* [[CrossesTheLineTwice.VideoGames Video Games]]
* [[CrossesTheLineTwice.WebComics Web Comics]]
* [[CrossesTheLineTwice.WebOriginal Web Original]]
* [[CrossesTheLineTwice.WesternAnimation Western Animation]]

%% Please do not undo the folders. Thank you. %%

* Featured at the end of [[http://www.youtube.com/watch?v=NBKc3Gb37pw an episode]] of Series/TheGruenTransfer was an [[http://www.youtube.com/watch?v=hMxzKQFl7 ad for 42Below brand Vodka]]. The ad mercilessly poked fun at homosexual stereotypes, then, at the end, said the ad was run past "two fags and a queer" to make sure it wasn't offensive.
** [[http://www.youtube.com/watch?v=hNDIbBpxoBA And this one.]]
** [[http://www.youtube.com/watch?v=V2R7vfrnbp4 And this one too.]]
** [[http://www.youtube.com/watch?v=hMxzKQFl7pw And here's the first one again.]]
* Metro Trains Melbourne's rail safety ad: ''WebAnimation/DumbWaysToDie'' [[http://www.youtube.com/watch?v=IJNR2EpS0jw here]].
* [[http://www.youtube.com/watch?v=NvFNQuZgFX4 This Canadian PSA]], which features a pop group at a school assembly ''singing about sex'', with the audience uncharacteristically eliciting a FlatWhat. Just when you thought it couldn't get weirder, then came the dancers in ''penis and vagina costumes'', and the people chanting "Go Penis! Go Penis!"
* Nandos' "Last Dictator Standing" commercial amps this trope '''''UpToEleven.'''''
* A series of Pop-Tarts commercials have really pushed the boundary by portraying the Pop-tarts as sentient beings always being hunted by humans and animals out to gobble them up. Worse is that the Pop-tarts always lose; an especially weird one has a baby pop-tart eaten by a nurse as its parents ''watch''.
-->'''Mom''': Ah Jammit.
* [[https://www.youtube.com/watch?v=YbYWhdLO43Q This ad]] for the Squatty Potty, involving a unicorn pooping out ice cream... which the advertiser proceeds to eat. The entire ad is full of poop-as-ice-cream analogies, and the presentation in general is so ridiculous you have to take it seriously.

[[folder:Anime and Manga]]
* Given that it makes fun about world history and often focuses on WorldWarII, the entire idea of "Axis Powers Hetalia" might fall under that. Making fun about the deadliest war in history normally would be BlackComedy at best, but having World War II presented as China beating up the entire Axis with a wok is just plain ridiculous.
** In their promotional campaign months before the release, Creator/{{Funimation}} showed exactly why their dub of ''Webcomic/AxisPowersHetalia'' was given a TV-MA rating. This immediately had the side effect of the fandom becoming a BrokenBase over the altered dialogue.
*** To clarify for those not familiar with the series: the protagonists are ThoseWackyNazis, the characters are merciless cultural stereotypes, and the whole show basically reads like World War II if World War II were a wildly inappropriate reality show. [[RefugeInAudacity And it's hilarious]].
-->'''[[NationsAsPeople China]]''': We're not allowed to have Christmas trees in our country because they're flammable. It kind of sucks.
-->'''Italy''': Heh, [[DoubleEntendre just like the girls]].
* ''Manga/{{Hellsing}}''. {{Mooks}} tend to suffer high levels of gory violence, and so does the [[FriendlyNeighborhoodVampire main]] [[{{Dracula}} character]], who [[{{Immortality}} tends to shrug it off without a thought]].
** One of the Valentine brothers (the vulgar one, Jan) quotes the KonamiCode while unloading with (two?) [=SMGs=]. At the end of a particularly gory segment early on. In fact, pretty much everything he says crosses the line twice. Like what he wants to do to Integra.
--->'''Jan Valentine:''' Little Hellsing chicky, we're coming to find you~! Come out, little Hellsing, I promise it will be a ''lot'' of fun! We just wanna torture you, kill you, maybe [[ILoveTheDead skullfuck your corpse a couple of times]], burn your house to the ground, go home and masturbate, okay?
*** And somehow, Creator/TeamFourStar managed to [[CharacterExaggeration exaggerate]] his cockiness, foul mouth, and bloodlust {{up to eleven}} in their [[WebVideo/HellsingUltimateAbridged abridged version]]. We're not joking.
* The anime ''[[LightNovel/BludgeoningAngelDokuroChan Bludgeoning Angel Dokuro-chan]]'' bases much of its comedy on brutal and over-the-top violence.
* Similarly to ''Bludgeoning Angel Dokuro-chan'', ''Anime/DaiMahouTouge'' relishes in the protagonist's sheer brutality in applying wrestling submission maneuvers for much of its comedy. This is contrasted with the fact that she usually acts like the typical sweet Magical Girl (whose spells cause just about as much havoc...)
** As well as the fact that the setting where the main character comes from is a massively CrapsaccharineWorld and she herself is a VillainProtagonist.
* A number of things Gates did in ''LightNovel/FullMetalPanic'': The Second Raid can be classified as this. Some of the other things he does are outright Squick.
** At one point, Gauron suggests that a flight attendant on a plane (that he is about to hijack) throw a group of InnocentBystander high school students out of the plane at because they were too loud. Gauron crosses ''every'' line twice. [[MemeticBadass When you draw a line, Gauron will cross it twice the instant you finish.]]
* ''Anime/ExcelSaga'': Although on the whole not too bad, but the final episode was entitled "Going Too Far", it was intentionally so violent, obscene, and long ([[ArsonMurderAndJaywalking it had a running time 1 minute longer than the standard episode format]]) that it wasn't allowed on Japanese TV.
** And some consider it a CrowningMomentOfFunny for the whole series, as it's a spot on spoof.
* The same team that made ''Anime/ExcelSaga'' also made ''Anime/PuniPuniPoemi'' every episode of which crosses the line just as frequently as the "Going Too Far" episode.
* ''LightNovel/{{Baccano}}'''s [[spoiler:[[SociopathicHero Claire Stanfield]]]] doesn't cross the line so much as he plays double-dutch with it. In any given episode he appears in, he can come off as over-the-top {{Badass}}, disturbingly psychotic, or any combination thereof as many as five or six times depending on the gratuitous amount of {{Gorn}} he churns out. Most people end up filing him under {{Ax Cr|azy}}[[CrazyAwesome azy Awesome]] and call it a day.
** [[AxCrazy Ladd Russo]] also loves to play hopscotch with the line, such as when he [[spoiler:uses a dead Lemure as a puppet while taunting Chane]].
* [[MadScientist Captain]] [[JerkAss Kurotsuchi]] of ''Manga/{{Bleach}}'' has skip roped with the line since the Soul Society arc and comes of as all the more [[ComedicSociopathy amusing]] [[SociopathicHero for it]].
** Of course, the fact [[GenreSavvy he's well aware of what others]] think manage to make some scenes even funnier.
--> '''Mayuri''': [[BlatantLies "I would never do anything unsuitable for family viewing! Get your mind out of the gutter!"]]
** In the Thousand-Years Blood War arc from the manga, there's the scene where [[spoiler: Giselle Gewelle beats up her friend Bambietta. A DarkActionGirl who was turned into a zombie. ''By Giselle herself''.]]. It should be [[KickTheDog a terrible moment]], but not only [[spoiler: Bambietta was one of the villans and so's Giselle]], but the scene is played as such a [[HamToHamCombat ridiculously over the top]] BokeAndTsukkomiRoutine that it comes off as darkly funny.
* ''Manga/OnePiece'' has Boa Hancock literally [[KickTheDog kick an adorable kitten]] that happened to be in her way to indicate that she is, in fact, a villain. Later, and after [[spoiler:pulling a HeelFaceTurn,]] she kicks a puppy and a ''[[{{Refuge in Audacity}} baby seal]]'' at the same time to turn it into a gag.
** Then there's Luffy's own HilariouslyAbusiveChildhood. The line is crossed when it's revealed that Luffy was ''tied to helium balloons'' and released into the sky. To make him stronger.
* One of Kimblee's lines from ''Manga/FullmetalAlchemist'': "That's one way of saying it. Another is that I made women and children go boom."
** This is pretty much the entire reason for [[SerialKiller Barry]] [[BloodKnight the]] [[HeroicComedicSociopath Chopper's]] HeelFaceTurn: to provide a comic relief character.
* ''Manga/HellTeacherNube'': The Buddhist nun who ate [[ShoutOut mermaid]] [[Manga/MermaidSaga flesh]] and became immortal, thus becoming TheChewToy for grisly punishment of all kinds and magnitudes is one thing. But then there's [[NobleDemon Minki's]] introduction: annoyed at boys from Doumori Elementary, and feeling particularly vindictive, [[BalefulPolymorph she turned them all into]] ''[[BalefulPolymorph panties]]''. How to remove the spell? The girls had to wear them. ThisIsWrongOnSoManyLevels that [[IdiotHero Hiroshi]] suffers a ''spectacular'' breakdown, looping back to heroic and trying to charge back into battle. Yes, that's right. HotBlooded, heroic panties.
* The ludicrous exposition in ''Anime/SpeedRacer'' does this often and unintentionally.
* ''Manga/{{Gintama}}'' does this very frequently with its gags, partly due to its tendency towards VulgarHumor.
** For one example, Gintoki and Kagura decide to make a replacement topknot for the Shogun using hair shaved from an unconscious Kondo's groin, which [[OnlySaneMan Shinpachi]] complains about as usual. They then note that a similarly unconscious Katsura's long, straight hair would be much better for making a replacement, and so they do...[[ComicallyMissingThePoint by making a wig that they place on Kondo's groin.]]
* Hiruma's creative and liberal use of his HyperspaceArsenal on his teammates (and everyone else) in ''Manga/{{Eyeshield 21}}''.
* [[VisualNovel/UminekoWhenTheyCry Tako-Maria]] [[spoiler: As in, Maria's talking severed head, that bears an uncanny resemblance to a cute octopus based on a certain Music/{{Vocaloid}} character.]]
* Making fun of the saddest scene in [[VisualNovel/{{AIR}} an already sad anime/VN]] is just terrible... Unless, of course, you do it via ''VideoGame/SuperMarioWorld'' [[http://www.youtube.com/watch?v=bfM8OuH_6vs autoplay]].
* ''Let's Bible'' may be the most blasphemous thing to ever come from Japan. And it's only 2 chapters long. [[http://thatguywiththeglasses.com/videolinks/ir/yrt/readright/21419-lets-bible Details here]].
* ''Anime/GhostStories'', the GagDub version oh so much. "I know now that it could never work between us! As much as we wanted to it could never be! Not because you're [[spoiler: a rabbit]], but because you're [[spoiler: black]]..."
** The main characters' personalities are also changed into a [[TheFundamentalist born-again fundamentalist Christian]], a Jewish stereotype, a little kid who may or may not be mentally retarded and often babbles incoherently and a massive pervert who often blurts out sexist and racist things. The main character's mom also becomes a lesbian who hits on the fundamentalist Christian girl (who's a high schooler) in a flashback.
* ''Manga/MajinTanteiNougamiNeuro'': Crosses the line so often it can only be explained as being in a quantum state
** Lets list some examples shall we? Most of them are contained to the manga though. Lets see... there's the little girl that hires the detectives to protect her obviously pedophilic (toy-company owning) grandfather, whom she adores, and [[spoiler: her attempt to kill his murderer when they fail to protect him.]] There's the actions of Kaitou X who decides to invite the main character to his mystery by [[spoiler: replacing a wall that's been painted by children for world peace with around twenty glass boxes stacked on top of one another - each containing a murdered person ground up into bloody soup - just before its unveiled on TV in front of the children]]. Or of course, how about when the later villain [[spoiler: Sicks]] sends his own message by forcing a man to [[spoiler: drive a knife into his gut and push his stomach along the ground to scrape in Sick's symbol in giant blood form]] or his family will be killed. Yeah. Every week before releasing a chapter the author had to meet with the editor because they wanted to make sure he didn't go over the top. What was considered over the top at this point is frankly impossible to know.
** When X kills a bunch of neighborhood dogs, grinds up their bodies, and places them in boxes, it's horrible and twisted. When a guy holds up a tiny box crying about his chihuahua that he had to borrow lots of money to buy, it's sad, but kind of funny at the same time. When the people he bought it from come and ask him which body he wants to give up to cover the sale, it's morbidly hilarious.
* ''Manga/DetroitMetalCity'' is about one man's descent into the mentality of a sociopath by merging with his SuperPoweredEvilSide. It's PlayedForLaughs. ''And it works''.
* ''Anime/PantyAndStockingWithGarterbelt'' is the living embodiment of this trope. All the main characters are named after lingerie. ComedicSociopathy is commonplace, and it's '''''always''''' played for laughs. The titular duo respectively have an unstoppable drive for sex and bondage. The closest thing the series has to an OnlySaneMan who can actually do something is a PedophilePriest, and his EvilCounterpart is a CombatSadomasochist ramped UpToEleven. Ghosts are made of shit, vomit, and semen. Anything it references, from Barbie to Transformers, is {{Rule 34}}ed to unbelievable extremes. '''''The soundtrack itself has a song that is literally a woman having sex, complete with {{sexophone}}'''''. ''Anime/{{FLCL}}'' is '''''CHILD'S PLAY''''' compared to this.
* ''VideoGame/SengokuBasara'' makes only what concessions to [[RuleOfCool the laws of physics]] that it needs to in order to prevent itself crossing the line ''thrice''. Bonus points in this case for doing the same with [[AnachronismStew history]].
* Done often and well in ''Anime/AngelBeats'', but particularly memorable examples include Yui accidentally hanging herself and Naoi's death during the second DwindlingParty scene, when everybody's deaths have been followed by the remaining people [[SayMyName screaming the dying one's name]]:
--> ''Naoi dies''
--> '''Otonashi''': Anybody want to say something?
--> '''Yui''': ...I don't know his name.
* The second season of ''Anime/BokuWaTomodachiGaSukunai'' has the infamous scene where Kodaka had just [[NakedFirstImpression discovered]] that [[SamusIsAGirl Yukimura is a girl]] and [[LovableSexManiac Rika]] decides to find out for herself by '''''fingering Yukimura''' in plain sight of the entire group'', followed by Rika visibly ''spreading her fingers to see if Yukimura had gotten wet from it'' and happily announcing that Yukimura is indeed a girl.
-->'''Rika:''' 'Tis as clear as day now, milord! This one is most certainly a lass!
-->'''Kodaka:''' That's what I've been saying too!
-->'''Rika:''' Yeah, but nothing beats checking things out for yourself!
* Mario Zucchero's defeat in ''Manga/JoJosBizarreAdventure Part V: Vento Aureo''. Buccellati zips off his head into the party's mercy, where Mista proceeds to hang the head with a fish hook and torture him with [[EyeScream spectacles len focus to the eye]]. While Zucchero [[AndIMustScream is unable to scream or say anything due to his mouth being zipped]], [[MemeticMutation Narancia turns on the music and the gang starts dancing.]]
* ''Anime/KillLaKill'', which was brought to you by the same people who brought to you Panty and Stocking. How powerful you are is inversely proportional to how much clothing you have on. The BigBad runs a fascist school hellbent on taking over all of Japan. The opposition is a girl repeatedly subjected to BlackComedyRape and a revolution where being scantily-clad is a requirement. One of the series' most dangerous villains is a walking source of LimitedAnimation and {{trolling}}. It really sets up how nasty [[KnightOfCerebus the real villain of the series]] is.
* ''Manga/AttackOnTitan'': Zackly [[spoiler: torturing a captured noble.]] This wouldn't normally be funny, but the fact that the guy appears to be held in some kind of BDSM setup with a funnel up his ass can be funny to some.
** This example crosses the line four times when Zackly looks at his good work, literally sheds a tear and praises himself for it.
-->'''Zackly:''' Beautiful. This may be the greatest work of art ever conceived.

* [[Creator/LewisBlack Lewis Black's]] immortal lines on his [[Series/TheDailyShow Daily Show]] [[http://www.thedailyshow.com/watch/tue-october-16-2012/back-in-black---lance-armstrong--butt-chugging---farm-animal-sex segment.]]
* Creator/DanielTosh lives off this trope.
** One of the better known examples was when Tosh was doing stand-up and crossed the line when he made a rape joke. A female member of the audience heckled him for being offensive. Tosh then crossed the line a second time by asking how funny it would be if that girl got raped right now.
** That and slowly whittling his jokes down to where only three or four people get it.
** While he certainly qualifies, Tosh claims that within his circle of friends, his sense of humor is actually the more mild/mainstream. Take from that what you will.
* Lisa Lampanelli's racist humor crosses every possible line in every possible way.
* Jimmy Carr has based his entire stand-up career on crossing the line twice, thrice, quarce, whilst using as many rude words as possible. Needless to say, you either love [[LoveItOrHateIt love him or hate him]]. A radio host once asked him if there are any lines he's unwilling to cross. Jimmy said he leaves that up to the audience: if he tries out a new joke and [[DudeNotFunny nobody laughs]], then evidently that one is going too far. If the audience does laugh, however, then obviously the joke must be funny, so he'll keep using it.
-->"I don't know where the line is until I've crossed it!"
* Creator/GeorgeCarlin, who once said "I think it's the duty of the comedian to find out where the line is drawn and cross it deliberately."
** By way of Creator/LennyBruce.
* Ralphie May
* Creator/BillHicks
* His specialty is vulgarity rather than violence, but Creator/SachaBaronCohen certainly counts.
* For similar reasons, Frankie Boyle. Dara O' Briain to Frankie on ''Series/MockTheWeek'':
-->"There's a line in the sand, right, and you can't even see the line in the sand. You are actually out of sand, into, like, into tropical tundra regions."
* Creator/DavidCross
* [[Creator/AndyKaufman Andy-freaking-Kaufman.]] He was insane, though, so it's to be expected.
* This is the entire point of the infamous joke "Film/TheAristocrats".
* Creator/DenisLeary
* Music/BoBurnham
* Creator/PattonOswalt
* Creator/NormMacDonald
** All of "Best Disease Ever" from the title onward, concluding with hypothetical Alcoholics Anonymous member Richie K in Norm's cheerful deadpan.
--> One time I was under the influence of the demon rum, and I started punching my newborn in the face. I kinda looked down on my fist and it was all bloody with, uh, I don't know what it was. It was either from my knuckles or my son's ''skull''.
* Creator/RichardPryor, made especially funny by the fact many of the things he describes ''[[NotMakingThisUpDisclaimer actually happened to him]]''.
** This is pretty much Gottfried's whole act. He once famously joked about 9/11 only three weeks after the event at the Friar's Club roast of Hugh Hefner. The audience booed Gottfried, feeling it was much TooSoon for such jokes. How did he defuse the situation? By launching into a recital of TheAristocrats...it was hilarious. NASA scientists are still trying to calculate just how many times he crossed the line that night.
** He also [[http://www.buzzfeed.com/mjs538/the-10-worst-gilbert-gottfried-tsunami-jokes tweeted about the 2011 Tokyo earthquake and tsunami]] immediately after it happened, which ended up costing him his job at Aflac. TooSoon indeed.
* From about the same time as Andy Kaufman, we have Michael O'Donoghue, who was an editor for the National Lampoon and it's radio show, head writer for ''Series/SaturdayNightLive'' when it first started, and co-writer of ''Film/{{Scrooged}}.'' This is the man who had an office full of nude amputee pin ups, spray painted the word "DANGER" on the NBC studio wall after asking what the show lacked, and almost got a skit to air portraying the head of NBC as Hitler in the bunker. Needless to say, they fired him over [[ExecutiveMeddling his outrageous attempt to create his own show]] that spoofed {{Mondo}} movies.
* Bill Maher, of course, especially in ''Series/RealTimeWithBillMaher''. Although applying this to political jokes is what gets him in the most trouble, he arguably goes even further outside political jokes.
* DougStanhope, arguably more than anyone else on this list.
* LouisCK, oh so very much.
* '''Creator/FrankieBoyle'''
* Creator/BobcatGoldthwait
* Creator/DonRickles whose act mostly consists of berating his audience, usually using every cultural, racial, and religious stereotype he can cram in.
* Creator/GabrielIglesias doesn't usually pass too far over the line, but there's one story that's been pulled from his Creator/ComedyCentral stories and even nearly got him banned from ''Series/TheTonightShow.'' The story begins with Gabriel and a friend passing through a town and learning an old comedy buddy of theirs is performing. Gabriel wants to prank call the buddy, tell them they [[http://www.youtube.com/watch?v=RbppTv4pCGQ have a gift basket]] for him, and describe it as being filled with all sorts of items that black people are stereotypically known to like. Then Gabriel & his friend realize they have a couple of hours to kill and proceed to actually ''make'' the basket...
** And then ''asking for help assembling said racist gift basket from staff at the store, as well as the black woman at the reception desk at the hotel.'' The staff were, according to the story, delighted about the idea, and very helpful; while the receptionist was decidedly less so... [[EveryManHasHisPrice until they offered her a hefty tip to deliver said basket]].
* Creator/SarahSilverman. Dear lord.
* Jerry Sadowitz.
* Anthony Jeselnik
* The late Robert Schimmel's act basically opened up the door to his (and everyone else's) bedroom. And it was hilarious.
* He never knew when to stop: Arabic poet Abu Nuwas. Folk tales made him jester of Harun al-Rashid and gave us the following jewel. He once hid behind a curtain and pinched Harun in the backside. Harun was royally miffed and sentenced him to death. But he was a good ruler and gave Nuwas the opportunity to defend his action. "I'm so sorry, Lord! I thought it was your wife!" Harun had to laugh so hard that he pardoned him.
* Creator/JeffDunham. This is pretty much the point of Achmed the Dead Terrorist.

[[folder:Comic Books]]
* ''Fillerbunny''.
** And ''Comicbook/JohnnyTheHomicidalManiac''! Particularly early on, a good deal of the humor comes from the over-the-top violence and murders committed by the title character.
* An in-comics example from ''Comicbook/{{Watchmen}}'': Dan and Laurie, at dinner, are trading stories and reminisce about a [[TooKinkyToTorture sadomasochist]] who used to dress up as a supervillain in an attempt to get beaten up. Laurie asks what happened to him; Dan says he tried it on [[SociopathicHero Rorschach]] and Rorschach [[DroppedABridgeOnHim dropped him down an elevator shaft]]. Cue a moment of stunned silence... and then hysterical laughter.
** "Oh '''god''', I'm sorry, that isn't funny. '''Ha ha ha ha ha'''!"
* The Creator/ImageComics series ''Comicbook/BombQueen'' is pretty much this trope, using a villain ruling a 'free' city that encourages rape, incest, drug use, murder, and occasionally cutting up children for meat. All played for laughs.
* In the ''ComicBook/JokersLastLaugh'' miniseries, SelfDemonstrating/TheJoker uses the powers of Multi-Man to escape. [[spoiler: Multi-Man's ability is to resurrect with a new super power any time he is killed. Since he has no control over ''what'' power he comes back to life with, The Joker [[ButtMonkey kills him over and over and over]] until Multi-Man has a power The Joker finds useful. MM is clearly horrified and suffering, but each successive panel depicts the means of death in more and more bizarre/humorous (at least to The Joker) fashion. e.g. Joker with a drum labeled "Hot Oil", holding a hand mixer caked in gore. Adding insult to injury (heh), when The Heroes later need to escape from the same prison under different circumstances, they run across Multi-Man, who has this power...]]
** To be completely honest, most of the more over-the-top things the Joker does fall under this trope, along with some not so over-the-top things as well. The man simply crosses the line so many times he's not even aware there ''is'' a line.
*** He's the Joker. He plays Jump-rope with the line.
* Superboy Prime ripping Risk's arm off: gruesome. Superboy Prime ripping Risk's ''other'' arm off with exactly the same sound effect: running gag.
** Superboy Prime is a RunningGag about emo villains that crossed the line into absurdity. The line that sums up how absurdly idiotic and emo he is:
---> I'll kill you! [[ShapedLikeItself I'll kill you to death!]]
** Though considering DeathIsCheap and Superboy Prime comes from beyond the fourth wall, the above line makes some sense. This also helps justify some of his over the top sociopathy making this trope work for him. From his perspective, these guys are all comic book characters whose lives exist to entertain him.
* The Sensational Hydra ([[spoiler:a Skrull who takes over Hydra briefly]]) takes a sword and slices off the arm of a random minion while reciting the Hydra oath:
-->"Hail Hydra! Cut off one limb and... (waits) C'mon... Note to self: it's a metaphor."
* Bullseye of Comicbook/{{Daredevil}} fame often does this, especially in [[Film/{{Daredevil}} the movie]]. It's hard not to laugh when a RedShirt dies from a well-aimed pencil.
-->'''[[Podcast/RiffTrax Mike Nelson, as Kingpin]]:''' I admire a man who can kill an olive at ten paces.
* Comicbook/{{Preacher}} does this everywhere. Especially notable is the recurring villain who, already introduced bald with one ruined eye, is [[spoiler: mistakenly matched up with a prostitute of the wrong gender and gets raped. Then he gets a scar across his head that make him look like a, in his own words; giant penis. Then he gets his foot eaten by cannibals. Then his entire genitals are destroyed by an attack dog and he has to pee through a tube. Near the end of it all his favourite pastimes are plotting revenge against the main character, and standing in front of a mirror repeatedly drawing his gun while screaming "DOOM COCK! DOOM COCK!".]]
** This is what Creator/GarthEnnis attempts to achieve in anything he writes.
* Managed in one ''Franchise/StarWars'' comic, in which Vader uses the Force to interrupt Jedi Master Tsui Choi's leap at a squad of clone troopers. While it should be a horrible moment, as a sympathetic Jedi is about to be slaughtered, the image of his leap just...''stopping'' in midair is rather entertaining.
* A more meta-example surrounds Franchise/SpiderMan ''Comicbook/OneMoreDay[=/=]ComicBook/BrandNewDay'': When [[Creator/JoeQuesada Quesada's]] friend Marc Guggenheim tried to defend Spider-Man selling his marriage to the devil he said that if you don't like it "...then you're pro-gay marriage." This statement was just crazy enough for most people to assume that he wasn't homophobic but just mentally unstable.
* The comic book ''Literature/TheBookOfBunnySuicides'' is all over this trope, showing increasingly bizarre and improbable ways for the cute bunnies to off themselves, and ending with a brick joke.
* Some of the best humor in ''Comicbook/SecretSix'' comes from how blasély sociopathic ComicBook/{{Deadshot}} is. At one point he shoots a man for essentially no reason at all.
-->'''Deadshot''': What, guy clearly had a gun. It was self defense.
-->'''Spy Smasher''': He didn't have a gun, Lawton!
-->'''Deadshot''': All right, so it was murder. Who cares.
** This is a general trait for the character. In Comicbook/SuicideSquad, he was ordered to throw away his guns by armed police. He complied. ''[[AxCrazy Bullets]] [[ExactWords first]]''.
** And while we're at it, Comicbook/HarleyQuinn in Suicide Squad seems to have sunk [[UpToEleven to new depths]] with her act.
--> '''Harley Quinn''': "Uh, fellas? [[SomebodySetUpUsTheBomb Our boy is a blow-up doll]]. [[Funny/SuicideSquad And]] ''[[Funny/SuicideSquad not]]'' [[Funny/SuicideSquad the fun kind]]."
* Creator/MattHowarth's ''ComicBook/ThoseAnnoyingPostBros'' is ALL about watching the Posts jump merrily over the line.
* Evan Dorkin's ''ComicBook/FunWithMilkAndCheese'' crosses the line twice on a ''slow'' day.
* What do you expect of a comic called ''[[Creator/WalterMoers "The Little Asshole"]]'' written by a beloved author of children's books and satirical novels?
* ''ComicBook/UltimateXMen'': Mr. Sinister pushing a man in a wheel chair down the stairs: [[AndThatsTerrible That's Terrible]]. Doing so while declaring Stairs to be the greatest enemy of Professor Xavier: Funny!
* ''ComicBook/TransformersMoreThanMeetsTheEye'' brings you the My First Blaster (TM Brainstorm labs), complete with big grip for little hands, with real lights and sounds, for those who just can't use a real gun. Don't let the bright colors and the orange safety cap fool you though, this thing is still very much an actual weapon. It just happens to be one that congratulates you for managing to hit your target.
* Lobo, but that is definitely DependingOnTheWriter.
* In ''ComicBook/{{Runaways}}'', Klara haltingly describes to Karolina and Molly how her parents forced her to marry an old drunk who forces her to go out and take dangerous jobs to earn money that he wastes on booze, and then trails off as she mentions how he also forces her into "[[MaritalRapeLicense marital duties]]". Molly... doesn't quite grasp the euphemism.
-->"Oh my god... he makes you do '''chores?!?'''"

* In ''FanFic/QueenOfAllOni'', when Jade goes trick or treating, if she didn't like what she got, she goes back and throws LIVE RATS in the poor people's faces!
* ''[[http://www.fanfiction.net/s/6130321/1/bJesus_b_and_bHitler_b_A_Romance Jesus and Hitler, A Romance]]''. Pretty much ExactlyWhatItSaysOnTheTin. As one review put it:
-->This is the single most disgusting nasty offensive thing I've ever read. And it's bloody amazing!
* [[http://humon.deviantart.com/art/Kangaroo-Wife-148578041?offset=0 This piece]] of fanart for ''VideoGame/TeamFortress2'' references a throwaway line in the game about Sniper's "Kangaroo Wife", but rather than go the obvious route it subverts it... then crosses it... then crosses it again, all while being [[CrowningMomentOfFunny bloody hilarious]].
** The same artist does it again, this time with [[http://humon.deviantart.com/art/Sleeping-with-your-parents-149534607 The Spy]].
* ''FanFic/MyImmortal'' pretty much runs on this, either [[TrollFic intentionally]] or not.
** As does ''Fanfic/ThirtyHs'', which crosses the line so many times it may win the all-time achievement award for line-crossing.
* [[spoiler: The death of Mami]] in ''Anime/PuellaMagiMadokaMagica'' was disturbing. Some of the fanart reacting to that, like [[http://danbooru.donmai.us/post/show/853948/-_-beret-blonde_hair-blush-boots-breasts-charlotte this one]] (NSFW ads)... Not so much.
** It's more like it's ''more common'' to see [[spoiler:Mami and Charlotte]] to be together in a completely happy situation. To the point that it's one of the more common [[CrackPairing pairings]] in the show's {{Shipping}} fandom.
* ''FanFic/LatiasJourney'' crosses the line a ''billion'' times. It is ''unimaginably'' {{gor|n}}y but it is so over the top that it starts getting funny.
* Arguably, the later installment of the ''Fanfic/PokeWars'' series are getting to be like this.
* ''Fanfic/TheLastWar'' goes so over the top in its [[RonTheDeathEater portrayal of Ron]] as the Potterverse's answer to [[Series/EastEnders Trevor Morgan]] that it becomes a total farce very quickly. Even before the [[Series/TheATeam A-Team]] show up.
* The entire premise of ''[[FanFic/TamersForeverSeries Theory of Chaos]]'' is this trope taken UpToEleven.
** Basically what happens is [[spoiler: a Doumon¬ bewitches all the tamers except for Takato into becoming the embodiment of each of the seven deadly sins so we now have Rika Nonaka as a ''frieking avatar of lust!''.]] The whole thing is just so WRONG it's hilarious, and Ruki and [[spoiler:Chaos']] comments make it that much better.
* Virtually any story by [[http://www.fanfiction.net/u/975122/the_6ft_dick the 6 foot dick]] ([[NamesToRunAwayFromReallyFast With such a name, what did you expect?!]]).
* [[http://www.mediaminer.org/fanfic/view_ch.php?id=19769&cid=49552&submit=View The Legend of Link: Lucky Number 13]] does this on occasion by treating extreme violence and shady morality casually.
** When Link goes to save Takara and Varia, he is confronted by camouflaged soldiers. He drives them into a fear-driven frenzy and uses magic to jam their guns so they are forced to bash and pummel each other to death. The bastards deserve it, but the drama ends the moment Link reasons there's "something missing" and, for ''no reason other than his amusement'', follows up with a [[CompellingVoice casual instruction]]: [[ImAHumanitarian "Mouths only."]]
** Following on from that scene, the [[SymbioticPossession shadow]] [[HeroicComedicSociopath demon]] goes on to ''graphically'' mutilate and kill 12 women and 28 children (the families of the scientists responsible for Takara and Varia's torment) on Link's orders. Deadly serious? Yes. Morally questionable? Absolutely. The shadow demon musing on a name for itself, then treating the survivors' shocked silence the way an inexperienced comedian would regard an audience that wasn't laughing? ''Hilarious.''
-->Still, no one spoke, which seemed to make the creature genuinely uncomfortable.
-->"No? Shade? Shady?"
-->The men stood silent, tears and mucus streaming down their faces, but the creature continued. Its flippancy and their inability to make it respect their loved ones' lost lives made them cry harder.
-->"The Hand, then? Handy? No? None of those?"
* In Fanfic/BellaSwanPregnantAndFurious, [[spoiler: Satan]] gets beaten so hard by Bella (yes, ''that'' [[Literature/{{Twilight}} Bella]]), that ''his internal organs start coming out of his mouth''. He is left "toothless and organless", "coughing blood and trembling with pain."
* [[http://www.fanfiction.net/s/8388109/1/Cartman-s-Revenge Cartman's Revenge]], also on Website/DeviantArt as [[http://soyouwillhateme.deviantart.com/art/South-Park-Tasteless-Theatre-317613973 South Park: Tasteless Theatre]] is a disgusting satirical lampooning of the Aurora Theatre Shooting that was released [[TooSoon a week after the fact]]. Not mention the author has gone on record stating that he thought up the idea ''moments after it happened'' and planned to release the story the ''[[TooSoon day after the fact]]'', but thought it would be too tasteless.
* A fan fic that I'll just say this [[http://stories.wwoec.com/Peach.doc "it goes into a detailed account of Bowser Jr's spiky shell, unknowingly, used for the sexual pleasure of Peach, as she births him."]] (NSFW DL only)
* [[FandomSpecificPlot A very common plot]] in fanfiction of the ''Anime/{{Pokemon}}'' anime is to rewrite the story from the beginning, with Ash supposedly being smarter and more awesome. [[SturgeonsLaw As one might expect]], most do nothing but turn him into a GodModeStu. However, ''Fanfic/TheGreatestThereWasOrEverWillBe'' manages to avoid this trap simply by making Ash so far ahead of his canon self that it becomes comical -- imagine Ash channeling the heroine of ''Manga/MedakaBox'', and one wouldn't be too far off.
* ''FanFic/SonicXDarkChaos'' crosses the line tons of times, with hilariously gory violence, RuleOfCool, UnfortunateImplications galore, and [[BlackComedyRape black comedy]] [[{{Squick}} child molestation]]. [[CrapsackWorld The setting in general]] crosses tons of lines too - one of the Jewish Republic's most powerful units are HumongousMecha powered by ''the souls of Holocaust victims'', and the Muslims of the Emirate of Mecca pacify captured populations with ''female genital mutilation on a planetary scale'' (to be honest, the Muslims themselves except for Abduhl and [[AFatherToHisMen al-Walim]] are so near-cartoonishly evil that they alone could be considered this trope).
** Most of the BlackComedy in the story falls headfirst into this trope;
-->'''D'Arnazhee''': Looks like these Jews couldn't find any foreskins. [[CrowningMomentOfFunny Not really 'chosen people' material]].
--> '''Beelzebub [[spoiler: after raping Chris and nearly raping Cosmo]]''': [[{{Squick}} They were a bit tight]], but don't worry, [[BrainBleach I think they've loosened up now]].
** Episode 68 gives us [[ComicallyMissingThePoint this gem]] when Jesus starts angsting about all the people killed in the Angel invasion of the galaxy;
--> '''al-Walim''': Look on the bright side, [[TakeThat at least they weren't aborted]].
--> '''Tobit''': And you got rid of the gays. I mean, you know how much Allysion hates fags.
* As with most interpretations of the character, The Joker absolutely skips rope with the line in one of his two brief appearances in ''FanFic/AngelOfTheBat''. Most of the presentations of death in the story are very dark handled seriously. But then The Joker kills some workers and employees of Arkham Asylum, his reasons for doing so including "Making bad meatloaf", "Stealing an extra package of cream cheese" and "I just never liked you." When confronting TheFundamentalist (and later BigBad) Daniel Lebowitz, Joker says he doesn't like religion because it promotes bigotry, and he prefers to kill everyone instead of specific people.
* FanFic/SupperSmashBrosMishonhFromGod makes all gays and 'lesbans' into licentious [[HollywoodSatanism Hollywood Satanists]], who want nothing more than to turn others gay by 'rapping' them, so that they change to being homosexual. Anytime this happens, it is done completely inaccurately, and is extremely over-the-top that it becomes a complete laugh.

[[folder:Films -- Animated]]
* ''WesternAnimation/{{Robots}}'': Has a classic single example of the trope. After Aunt Fanny's {{Fartillery}} causes a nearby street lamp bot to literally keel over, the next morning, his body was replaced by a ''tape outline''. Then again, it's Blue Sky, makers of the ''WesternAnimation/IceAge'' movies...
* ''WesternAnimation/{{Madagascar}} 2'': Alex punches an old lady in the face: DudeNotFunny. [[WhenEldersAttack Old lady]] [[CurbStompBattle fights back]] and [[GroinAttack wounds his pride]]: Hilarious.
* Some characters' antics in ''WesternAnimation/TheBoxtrolls'', such as Lord Portly-Rind using his funds to build a cheese wheel instead of a children's hospital.
* ''WesternAnimation/TheAngryBirdsMovie'': Red kicking a blue bird into the ocean.

* Three men and a woman were marooned on a desert island. After one week, the woman felt so guilty about what she had been doing that she committed suicide. After another week, the three men felt so terrible about what they had been doing they buried her. After another week the three men felt so terrible about what they had been doing they dug her back up.
* Why did (insert name of child molester here) go to Walmart? Because children's clothes were half off!
* The [[http://www.reddit.com/r/Jokes/comments/28g0ap/little_timmy_went_to_a_brothel/ "Dead Frog"]] joke crosses it numerous times.
* Why did little Suzy fall off the swing? She had no arms. Knock knock. Who's there? Not little Suzy. What did Little Suzy get for Christmas? A scooter! Just kidding, she couldn't open the box.
* The entire point of TheAristocrats, a joke that's meant to be a ''challenge'' to come up with [[UpToEleven the most vulgar, offensive and outright]] ''[[UpToEleven wrong]]'' story one can think of all for the purposes of making [[DudeNotFunny things that should never be considered funny]] funny.
** The joke is that a group of performers, usually described as a family, are auditioning for an agent or for a gig, sometimes at a circus. The person evaluating them asks to see their act, so they proceed to perform a long series of absolutely terrible things, from killing and torturing animals, to perverse sexual acts, to defecating or urinating. Eventually the act stops and the bewildered audience of one asks what the hell they call their act. ''"The aristocrats!"'' [[DontExplainTheJoke (Because this is the sort of thing aristocrats supposedly get up to.)]]
* A man sees a crying woman by a pond. She is in a wheelchair and has no arms or legs. He asks her why she is crying and she answers that she has never been hugged. Feeling pity, he hugs her then jogs away. The next day he finds her crying again and she says she has never been kissed. The man kisses her and jogs away again. On the third day the man sees her crying and asks her thrice. She tells him she has never been fucked. The man picks her up...and throws her in the pond telling her, "You're fucked now!"

%%* Nearly the entire output of author Edward Lee was written purely to evoke this trope.
* In ''Literature/ABrothersPrice'', one of the Whistler sisters tells the other that the neighbour's boy, Balin Brindle, is rumoured to have [[ParentalIncest fathered his younger sisters.]] The reply? "And? At least we know he's fertile".
* ''Literature/{{Candide}}'' by Creator/{{Voltaire}} has horrible things happening to almost all of the characters. Several times one character is forced to flee abandoning others to gruesome deaths. But as they often manage some to survive in some incredibly improbable way as it progresses the horrible events become funny.
** Made even worse by the recurring quote "All is for the best in the best of all possible worlds" with all the atroities around, often repeated just after something especially terrible happened. Well justified as the book was intended to be a sarcastic approach to the government, society and philosophy, particularly Gottfried Leibniz's optimism.
* The entire plot of Shakespeare's ''Theatre/TitusAndronicus'' could be this. According to [[http://alivion.livejournal.com/88232.html this guy]], it is.
* In the first chapter of ''Literature/StarshipTroopers'', Rico drops a bomb into a room full of people. It's a ''talking'' bomb, programmed to announce, in the enemy's language, that it is a bomb, and count down until it explodes. Rico winces as he throws it, but the image of the whole thing is just hilarious. It's helped by the long-ish countdown, and that it's intended more to freak the enemy out than to actually kill anybody.
* Creator/EdwardGorey's ''The Gashlycrumb Tinies'', a book where twenty-six children die in alphabetized ways.
* These lines from ''Literature/TheHungerGames'':
-->We were resting a moment by a stream when we saw him. A young buck, probably a yearling by his size. His antlers were just growing in, still small and coated in velvet. Poised to run but unsure of us, unfamiliar with humans. Beautiful.\\
Less beautiful perhaps when the two arrows caught him, one in the neck, the other in the chest. Gale and I had shot at the same time. The buck tried to run but stumbled, and Gales knife slit his throat before he knew what had happened. Momentarily, Id felt a pang at killing something so fresh and innocent. And then my stomach rumbled at the thought of all that fresh and innocent meat.
** A pretty hefty portion of the humor in the series is this. For instance, "The Head Shackle" from Mockingjay.
* ''Literature/PaperTowns'':
** At the prom afterparty, Ben sets a county record for longest keg-stand. Radar describes him as some kind of "autistic savant".
** During the road trip, [[spoiler:Radar is bought a T-shirt with a Confederate flag on it that reads "Heritage not Hate". Radar is black]].
* ''[[Literature/TheWayfarerRedemption Pilgrim]]'' has a bit that has achieved a fair bit of infamy in fantasy circles. In brief: a woman is used by her grandfather to channel the soul of his long-dead wife (her grandmother), so that she basically possesses their granddaughter and they have hot, passionate sex while the granddaughter [[AndIMustScream is still conscious and powerless to do anything about it.]] She gets pregnant, and over the course of the pregnancy manages to regain control of her body, forcing grandma's soul into the unborn fetus instead. She then ''beats herself into miscarrying in front of her grandfather's eyes'', expels the aborted fetus, and crushes it's already-dead skull with her foot. All very macabre, twisted and {{Squick}}y. But when she smacks grandpa in the face repeatedly with the dead fetus while berating him, it becomes a stellar example of this trope.
* [[http://www.amazon.com/Supervillainous-Confessions-Costumed-Evil-doer-ebook/dp/B0050BQSZA Supervillainous!: Confessions of a Costumed Evil-doer]] has the dubious honor of being home to a supervillain named White Power, who is decked out in Ku Klux Klan robes and has the power to make white people violently racist. In one scene he and the rest of his team parachute into a prison yard and start to kill a bunch of inmates. When the guards come out he points to a group of black inmates and says "They did it!", prompting the guards to immediately attack said inmates.
* Creator/JonathanSwift's satirical essay ''Literature/AModestProposal'' definitely qualifies. Eating babies to prevent overpopulation is rather dark and gruesome. However, saying that they make for a delicacy, great gloves, and should have women act like cows to raise them up for being eaten is just plain hilarious.
* The vampire feast in ''Literature/AlmostNight'' features various animals being drained of blood and killed. Then their corpses are used as playthings such as impromptu pillow fights, and sword fights for birds. Carlisangel even tortures one for kicks during the first one.
* The French novel/prose poem ''Literature/LesChantsDeMaldoror'' crosses the line so many times that it becomes impossible to tell if it's meant to be funny or not. In one episode, the main character, sitting on a clifftop armed with a rifle, calmly watches a ship leave harbour during a storm, hit some rocks, and sink. Amid the mass of survivors, one sixteen-year-old boy swims bravely towards the shore, and the main character takes some time to admire the boy's beauty and bravery [[spoiler: and then shoots the kid in the head.]] Then, a group of sharks attacks the remaining survivors. The main character watches all the survivors getting eaten, then identifies an especially large female shark as the most savage one. He waits until all the surviving humans are dead, picks off all the other sharks with his rifle, then dives into the sea, swims up to the female shark [[spoiler: and fucks her.]]

* Too Many Examples to list in [[{{Podcast/TheScathingAtheist}} The Scathing Atheist]]. One notable example was when the brought on the hosts of the CognitiveDissonance Podcast in episode 128, where they listed jokes about the controversy regarding fetuses and Planned Parenthood.
** One week Noah made a passing joke of making a top ten list of analogies involving puppy rape. Guess what was in the show the following week?

* This sketch from ''Radio/HelloCheeky'', which is so short it can be transcribed.
-->'''Boy:''' Mummy? When's Daddy coming home?
-->'''Mother:''' Daddy won't be coming home any more, Julian. Daddy is...up high, in the sky.
-->'''Boy:''' Has he gone to heaven?
-->'''Mother:''' No, he's flying to the south of France with his secretary.
-->'''Boy:''' Is that why [[CheatingWithTheMilkman Uncle Milkman's]] upstairs with his boots off?
-->'''Mother:''' Yes. Go and play in the motorway.
* To "bring something up" was/is a term for vomiting. ("Brought up my lunch", etc.) ''Radio/ImSorryIllReadThatAgain'' was a sketch comedy which was [[BlackComedyBurst usually]] plenty bawdy and occasionally touched on dark ideas, but often kept a light heart or a non-serious tone about it. This is all the context you need to get the next absolutely terrible yet horribly fantastic pun.
-->''David Hatch went to the countryside to bring up his babies, which serves him right for eating them.''
* One of the most popular and most requested sketches from ''The Mark & Brian Radio Program'' is the ParodyCommercial [[http://www.youtube.com/watch?v=88QdZrM9xrc Kruger's Supermarket]], which emphasizes how cruelly they kill the animals to get the best taste out of the meat.
* ''TheBrewingNetwork'': Pretty much all of the humor of Lunch Meet.
* As mentioned at the top of this very page, ''Radio/BleakExpectations'' does this with [[BoardingSchoolOfHorrors St. Bastards]], the most sadistically cruel school in all Georgian Britain.
** And there's also the Chinese... ''[[OpiumDen restaurant]]'' in Series 2, followed shortly thereafter by Abraham Bagel, a parody of the GreedyJew who is in fact [[spoiler:a Catholic]].
** The subversion of a "release the dogs" moment. Setting dogs on abused factory workers? Not funny. Dropping dead dogs on said factory workers, on the other hand...
* ''Radio/OldHarrysGame'' uses this a lot.
** Everything [[LaughablyEvil Thomas]] says or does.
** This exchange, in the episode where the Professor starts interviewing the damned to find the true account of history.
-->'''The Professor''': [A]nd a Nazi who claimed he was just following orders.\\
'''Satan''': They all said that.\\
'''The Professor''': Yes, but [[NeverMyFault this one was Hitler.]]
** One episode had a Muslim suicide bomber confused as to why he ended up in Hell when he gave his life for Allah and blew up an American top-secret military base, which skirts if not crosses the line into DudeNotFunny territory. Then it becomes funny again after Satan reveals the "top-secret military base" was actually just a barber shop.

[[folder:Short Films]]
* Creator/DonHertzfeldt's animations have all sorts of violence inflicted on stick figures that go between horrible and hilarious routinely.
* Jim Reardon, before he went on to do animation for ''WesternAnimation/TheSimpsons'', created [[http://www.youtube.com/watch?v=A15v4tTab0Y this student short]] about [[ComicStrip/{{Peanuts}} Charlie Brown]] gunning his classmates down in a ''Film/{{Scarface|1983}}''-style rampage. A perfect example of a film which straddles the line between "appalling" and "the most hilarious thing ever made." (Warning: video NotSafeForWork Or Sanity.)
* ''Film/ForkliftDriverKlaus - [[http://www.youtube.com/watch?v=Nr3QwofYfHs The First Day On the Job]]''.
* ''[[http://www.youtube.com/watch?v=MELPIUpjqmw Pogo et ses amis]]'' (warning: subtitles), so very much. A Quebecois stop-motion animated short chronicling a day in the suburban life of [[http://en.wikipedia.org/wiki/Pogo_the_Clown Pogo the clown]] and his friends [[http://en.wikipedia.org/wiki/Ed_Gein Ed]], [[http://en.wikipedia.org/wiki/Albert_Fish Albert]] and [[http://en.wikipedia.org/wiki/Zodiac_Killer Mister Z]]. The whole thing is presented like an episode from a children's show, with voices provided by locally known actors (including the voice actors for Ned Flanders and Mr. Burns in the Quebec translation of ''WesternAnimation/TheSimpsons'') and a cameo from a local right-wing politician. It's hilarious, especially if you understand French.

[[folder:Tabletop Games]]
* ''TabletopGame/{{Warhammer 40000}}'':
** Da Orks do not live this trope; they ''are'' this trope. Psychotic, belligerent monsters (in a galaxy already filled to the brim with the psychotic, the belligerent and the monstrous) taken so far past the utter screaming extreme that they become endearing instead, not at all hurt by their ridiculous {{Funetik Aksent}}s or their treatment of warfare as a cross between a mass migration, holy war, looting party and ''pub crawl'', with a bit of genocide thrown in for good measure. Deyz show all deze udder gretchin gitz 'ere 'ow itz don'. Follow me, ladz! WAAAGH!
** The setting in general is this on several levels, considering the absolute grimdarkness it revels in. One of the common jokes is that the Eldar literally Squicked a god (the god of sex no less) into existence and that the Catholic-Space-Nazi Imperium are the ''good guys''.
** Most things related to Slaanesh tends to pole dance on the line. Slaaneshi Chaos Space Marines tend to be genetically engineered drug addicts, possible sex maniacs, and often sport literal breast plates (with one boob no less). In previous editions they even went into battle wielding guitars.
* TabletopGame/{{Paranoia}}: each player is given several clones of his character on the assumption that The Computer and/or fellow players will find horrible and creative ways of destroy them. It usually happens.
* Crossing the line is the whole point of ''TabletopGame/CardsAgainstHumanity'', which is ''Apples to Apples'' for people with a twisted sense of humor. Crossing the line ''twice'' is how you win.
* In the "Attitude" sourcebook for 4th edition ''TabletopGame/{{Shadowrun}}'' the electronically recorded memories of a dead Street Samurai are reviewed and commented upon by fellow Shadowrunners. One fellow he'd worked with was known for keeping a cloth bag filled with stray cats; in a fight he would grab one by the tail, whirl it around, then hurl it at someone's face. One of the Runners comments on how this bit of animal cruelty is the most disgusting thing he'd ever heard of and he wanted nothing to do with a psycho like that. Then the memory log notes the crazy cat guy's specialty: the Cat-astrophe, where he attaches a bomb to the cat first. The same Runner responds, "okay, I take it back. That's just awesome."
* The game ''Public Assistance: Why Bother Working for a Living?'' is a parody of the American welfare/government assistance program where the object of the game is to stay on welfare as long as possible to make easy money (and even do illegal things on the side like prostitution, having illegitimate children, and selling drugs) whereas doing things people do a daily basis like working a 9-5 job and paying bills is considered a detriment to the player's success and such areas on the board are actually called "Worker's Burden" to simulate the burden of making income.

* ''Theatre/MeAndMyDick''. The whole freaking thing.
* ''Theatre/AVeryPotterMusical'' has a couple examples, but the Ron/Hermione kiss must be seen to be believed. It's funny, but mostly just... ''wrong''. ''A Very Potter Sequel'' does this with Umbridge and all her plot.
* ''Film/ReeferMadness''. The Musical has Jesus show up to tell the main character to stop smoking pot...and that's at the halfway point.
* ''Theatre/TheBookOfMormon''. Just... well, it does starts as a black comedy ''mocking'' religious organizations in general, and then we have ''Hasa Diga Eebowai''. It's a song about how the Africans resolve to endure with famine, poverty, and AIDS; they just throw their hands to the sky and say a seemingly innocent phrase: ''Hasa Diga Eebowai''. What does it mean? [[spoiler: Fuck you, God]]. How does it crosses the line a second time? With the following sentence sung out loud by women and men alike: [[spoiler: Fuck you God in the ass, mouth and cunt!]]. And that is just the fourth song in the story. Later you will find someone intending to [[spoiler: fuck a baby PlayedForLaughs. And then someone else tries to do it, being none other than the most important prophet for a whole religion!]]. Creator/TreyParkerAndMattStone indeed.
* ''Theatre/TitusAndronicus'' is Shakespeare's bloodiest play. The Rape of Philomela is used as the basis for a secondary plot line, lampshaded in the dialogue, and it goes FromBadToWorse. There is even a very blatant "YourMom" joke.
** Two of Titus's sons are framed for the murder of their sister's fiancé, and Titus cuts off his own hand to secure their release... except he's been lied to, and he only gets their heads back, along with his hand. So, he grabs one head, has his brother take the other, and orders his handless, tongueless daughter to carry his hand by picking it up in her teeth.
** After Aaron is arrested, he tells his captors about his hobbies, including this gem: "Oft have I digg'd up dead men from their graves,And set them upright at their dear friends' doors, Even when their sorrows almost were forgot; And on their skins, as on the bark of trees, Have with my knife carved in Roman letters,'Let not your sorrow die, though I am dead.'"
** It has been described as the Kill Bill of the Elizabethan era.
* This is the basic MO of many Jacobean and Elizabethan revenge tragedies. Shakespeare was unusual in how soberly (apart from in Titus, which crosses the line twice for the whole genre, that some critics see it as an intentional parody) he dealt with his tragedies.
** Thomas Middleton's ''Theatre/TheRevengersTragedy'' jumps back and forth over the line constantly. The title character Vindice exhumes his beloved's skeleton, dresses her, fills her mouth with poison, and then tricks her murderer into making out with it. Hilarious. Not quite dead, Vindice and his Brother then proceed to kick the dying man to death. Not so funny.
* ''{{Theatre/Hamlet}}'' can be played as a BlackComedy, and it works incredibly well if the actors involved are good. It mostly comes off as this. Notably, Hamlet casually dragging a dead body offstage while saying, "Goodnight, Mother!" can get a big laugh out of the audience.
* Norwegian playwright ''Johan Herman Wessel'' managed this in his parodic play ''Love without stockings'', taking the DrivenToSuicide trope up to hilarious levels, because ''every single member'' of the cast commits suicide one after another, passing the same knife around. Made doubly hilarious because of a bowl of pea stew, also passed around at the same time.

* Many Internet Radio shows do this in terms of sheer vulgarity since there is virtually no censorship; wonder how far it can go; this line says it all: "Oh god they said that Jesus gave it to his mother!"
** After The Forking Show (ATFS), a podcast spinoff of a now defunct Australian radio show called The Spoonman, crosses the line in every podcast. One notable, repeated example: Bringing slavery to Australia (both played for laughs and discussed seriously).
* The cartoons in ''The Rejection Collection'' crossed the line once when they were rejected by ''The New Yorker,'' but crossed it a second time when they were funny enough to be published in this book.
* Bringing guns into an NBA locker room and threatening a teammate with them? Crossing the line. At a game, pantomiming shooting his teammates as a joke? This trope. Nice job, Gilbert Arenas.
* The funnier jokes on [[http://www.sickipedia.org Sickipedia]]. There's a reason why Frankie Boyle and Sickipedia appear to have reached something of a "steal and steal alike" agreement.
* Creator/MelBrooks on what he does for a living: "If I cut my finger, that's tragedy. If a man walks into an open sewer and dies, that's comedy!"
* Any tragic event will lead to jokes. ''Immediately''. When TooSoon doesn't qualify, this trope usually kicks in.
* Attempted rape? Not funny. [[AutoTuneTheNews Antoine Dodson?]] [[http://www.youtube.com/watch?v=hMtZfW2z9dw Funny]].
** AutoTune can make almost any video funny. Crazy fan nails Justin Bieber in the head with a water bottle? Tasteless. Auto-Tune the resulting clip into a song? Hilarious!
* Meta-Example: DarthWiki/TropesThatWillNeverHappen is full of this, especially the "Too Dangerous" section.
* [[http://i.imgur.com/DmwF26o.jpg Knitler.]]
** And while we're on the topic of dictators, have a look at [[http://ostoon.blogspot.fi/2012/12/nyotaika-sekai-no-dokusaisha-retsuden.html The World's Dictators-Anime Girl Edition!]]
* The entire point of the Apples to Apples-like card game called [[JustForPun Cards Against Humanity]].
* During the Jimmy Saville pedophile scandal, one audience member texted this message to a BBC Morning Radio program which got read out live on air:
--> [[http://www.youtube.com/watch?v=A9yJUOdVyUc "I wish everyone would stop criticising Jimmy Savile. He was a nice man. When I was eight he fixed it for me to milk a cow blind-folded."]]
* At the memorial service for Creator/GrahamChapman, Creator/JohnCleese delivered a scathing set of insults, followed by pointing out that if the deceased had been alive, he'd have done it himself.
-->'''Cleese:''' Anything for him but mindless good taste.
* A baby once flipped the bird at its parents. And not just any baby, but a ''[[http://www.thesun.co.uk/sol/homepage/features/4686203/baby-flips-out-during-routine-scan.html fetus]]''. Apparently, the ultrasound disturbances were pissing the young thing off.
* [[http://www.ftlcomm.com/ensign/cropson/2002/canola/canola.html Tisdale, Saskatchewan]] is famous for its [[http://en.wikipedia.org/wiki/Rapeseed rapeseed]] and honey so naturally they picked [[Literature/TheBible "the land of rape and honey"]] as their slogan. Music/{{Ministry}} saw the slogan on a ''souvenir mug'' and just had they make an album title out of it.
* Art in the SocialistRealism style is generally derided for being bombastic, over-the-top and self-aggrandizing. [[http://www.mockduck.net/2009/09/06/oafish-state-sponsored-art/ The statue at the bottom of this page]] (erected after the liberation of Berlin) is all of those things and so much more: a Soviet soldier in BadassLongcoat rescuing a baby with one hand and wielding a {{BFS}} in the other, while pulling a CaptainMorganPose on a [[SmashTheSymbol smashed swastika]]. Subtle. ''Awesome''.
* This version of [[http://knowyourmeme.com/memes/jews-vs-nazis-beer-pong Beer Pong]].
* Recounting [[https://en.wikipedia.org/wiki/Eric_Gill#Personal_life the dark and secret life of type designer Eric Gill]] (whose eponymous sans-serif font is all over Britain, even today) often fits this trope. His diaries, not made public until the 1980s, describe in great detail how he had [[BrotherSisterIncest a sexual relationship with his sister]]. And [[FromBadToWorse how he molested all his children]]. But that still wasn't enough. [[RuleOfThree For the trifecta]], [[spoiler:he molested his dog]].
* You can buy [[http://www.bitterwallet.com/wp-content/uploads/2010/09/Screen-shot-2010-09-10-at-08.09.50-499x151.png plush versions of deadly illnesses]]
* Some humourous Amazon reviews of the anti-vaccination book ''[[Literature/MelaniesMarvelousMeasles Melanie's Marvelous Measles]]'':
** [[http://www.amazon.com/review/R2ALP6J4FPWE2W/ This one]] lists a ton of fictional children's books whose {{Alliterative Title}}s use the format "[name]'s [adjective] [disease]". This leads to fun titles like "Bertha's Blossoming Bulimia", "Carol's Colorful Chlamydia", "Dominic's Domineering Dementia", "Hillary's Hilarious HIV", "Lisa's Lovely Lassa Fever", "Prunella's Practically Preventable Prion" and "Sam's Saintly Schizophrenia".
** "I'm so happy I bought a hard copy version of this book. If I bought an audiobook, I never would have gotten my money's worth as both of my daughters went deaf from Measles Encephalitis. They now have a great book and a lifelong disability to remind them how much I truly love them!"
** [[http://www.amazon.com/gp/review/R3Q3E92SBF8MF1 This one]] calls "Benevolent Bubonic Plague" a "gentle, all-natural diet aide", says that the USA only won UsefulNotes/WorldWarII because FDR got polio instead of the vaccine, and uses some InsaneTrollLogic to justify the 1-star rating.
** [[http://www.amazon.com/gp/review/RB8XCLHNG0E9M This one]] is about someone suffering from 30+ "benign" diseases like tuberculosis and malaria. He says that he would've been able to fight them off and become stronger from them if his parents hadn't decided to "weaken" him with vaccines.
** [[http://www.amazon.com/gp/review/R2JE6MZF457YA1 This one]] is written in YeOldeButcheredeEnglishe and says that modern medicine is some sort of witchcraft.

[[folder:Real Life]]
* Fringe Republican candidate Rex Rammell of Idaho replied to a question during a debate about wolf tags by saying that many Idahoans would gladly buy "Obama tags", referring to then-president Barack Obama. He later refused to apologize for the remarks on the grounds that everyone knows that [[RefugeInAudacity Idaho has no authority to issue hunting tags in Washington, D.C.]]