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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 humour 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''
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''"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.

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.

----
!!Examples:

[[foldercontrol]]
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[[folder:Advertising]]
* 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.'''''
[[/folder]]

[[folder:Anime and Manga]]
* ''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, obviously) 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.
*** And somehow, Creator/TeamFourStar managed to [[CharacterExaggeration exaggerate]] him {{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]].
* 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]].
* [[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]] [[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 {{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''.
* ''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!
[[/folder]]

[[folder:Comedians]]
* [[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]].
-->"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
* Creator/RichardPryor, made especially funny by the fact many of the things he describes ''[[NotMakingThisUpDisclaimer actually happened to him]]''.
* I'M {{GILBERT GOTTFRIED}}, AND I'M GOING TO KILL YOU MOTHERFUCKERS FOR NOT MENTIONING ME! AND THEN I'M GOING TO RAPE A BITCH OR TWO!
** 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 Tōhoku earthquake and tsunami]] immediately after it happened, which ended up costing him his job at Geico. 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.
* 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.
[[/folder]]

[[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 who's 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!".]]
** While we're at it, anything Creator/GarthEnnis writes.
*** Special mention should go out to ComicBook/TheBoys which doesn't so much cross the line twice as dance back and forth over it laughing maniacally.
* 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.
-->'''Lawton''': 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 sunken [[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]].
* MattHowarth's ''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 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: CrowningMomentOfFunny!
* ''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.
* {{SelfDemonstrating/Lobo}}...but highly DependingOnTheWriter.
[[/folder]]

[[folder:Fanfic]]
* 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 [[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 many times, with hilariously gory violence, RuleOfCool, and [[{{Squick}} child molestation]]. And the rewrite goes all-out.
[[/folder]]

[[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.
[[/folder]]

[[folder:Films -- Live-Action]]
* ''Film/FleshForFrankenstein''. Evisceration is the order of the day - four characters are given this treatment, some of them ''multiple times''. Udo Kier finishes the movie giving a grandly defiant speech for several minutes with his gut hanging on a pole inserted through his middle.
* [[http://www.youtube.com/watch?v=O6mCUoRYN3Y This]], from ''EvilAliens''
* ''Series/{{Lexx}}''
** The movies and series are based on this trope. Everything always ends with destruction of everything that appears in path of our protagonists. Like in the following joke: joke. (Note that out of all the mischief the crew unwillingly did, this was the only one to haunt Stan, ''especially the robot on the planet''.)
--> '''Stan:''' That planet is ugly. Lexx, destroy this planet after 1 minute.\\
'''Stan:''' ''(after some bargaining with planet inhabitants)'' Ok, cancel my command.\\
''[[EarthShatteringKaboom (BOOOOM...)]]\\
'''Lexx:''' Sorry, what does word cancel means?
** But while talking about Lexx and the carnage it left behind, let's not forget [[spoiler:being responsible for the destruction of countless (they ''were counted'', but I forgot how many) planets]] AND THEN [[spoiler:'''an entire universe''']].
* The ''Franchise/EvilDead'' movies practically ARE this trope.
* As are Creator/{{Troma}} Films (''Film/TheToxicAvenger'', etc.)
* ''Franchise/RoboCop''
** In ''Film/RoboCop1987'', the prototype ED-209 enforcement drone malfunctions during a demonstration in the OCP boardroom and rips a young exec apart with an [[ThereIsNoKillLikeOverkill extended and over-the-top]] [[MoreDakka heavy machine gun burst]], while technicians desperately try to shut it down. Most of the censored versions cut this to a short burst, and make the scene look more clinical and horrifying. The original scene has the 209 continue firing for over 10 seconds, long after anyone could possibly have survived, just chewing up the body. The joke is further emphasised once the shooting is (finally) over when a single meek voice asks "should we call a medic?" Even more ironic is that this is what made it originally X rated.
** Played intentionally straight in ''Film/RoboCop2'', in a scene that is even more disturbing (and hilarious), where two [=RoboCop=] 2 prototypes are rolled out. OCP is trying to make new [=RoboCops=]. Out of the two prototypes that were taken all the way to a final showcasing, one went berserk and shot the scientists in the room before committing suicide, and one pulled off its own helmet, showing little more than a skull and some electronics before collapsing with an unearthly wail. The higher-up viewing videos of the aforementioned facepalms and mutters about the tremendous loss that the two failures represent: "Ninety million [dollars]". Video [[http://www.youtube.com/watch?v=rJDztqCG91g here]]. ''Film/IronMan2'' has an homage to this scene--complete with such humor--when Stark leaks footage of Justin Hammer's failed armor prototypes.
* The Black Knight scene in ''Film/MontyPythonAndTheHolyGrail''. One severed limb is appalling; four severed limbs is hilarious (the second line in this case probably falls at [[RuleOfThree three]]). In the Monty Python HBO interview special, they say that's exactly what they were going for. Creator/JohnCleese said the scene would be heartless and sadistic if not for the fact that the knight [[MajorInjuryUnderreaction shows no pain and doesn't really care what happens]].
** They also used humorously gratuitous violence in their sketch "Sam Peckinpah's Salad Days" (from the TV series), which brought fountains of HighPressureBlood to a picnic scene.
** And of course, a row of increasingly tasteless sketches with cannibalistic sketches which culminate in The Undertaker Sketch which is written for no other purpose than to offend.
* The 1992 comedy ''[[http://www.imdb.com/title/tt0104283/ Folks]]!'' starring Tom Selleck, may be a good example of this. The movie is not only built on a {{squick}} premise, but involves the hero enduring serious injury after serious, ''permanently disfiguring,'' injury in the course of otherwise typical slapstick violence.
* Although it doesn't involve violence on more than a slapstick level, the naked fight in ''Film/{{Borat}}'' attempts a version of this trope. Two guys fighting naked in a hotel room is already borderline after nearly a minute, taking it out into the hall is just excessive, sending them charging into a conference room... well, it depends on each viewer where you stopped laughing and whether you started again.
** Both ''Film/{{Borat}}'' and ''Film/{{Bruno}}'' are built around this trope.
*** Although Sacha does emphasize the long European tradition of mocking Americans for not being Europeans. In some parts of the world [[ValuesDissonance what he did was seen as completely normal]] (albeit the baby was to have everyone treat America as 'srs bsns', same with the nude scene just to get a reaction from the homophobes in the audience), yet all he did was suffer abuse from others, especially as Borat. No one stopped to think "wait, this guy is from a different country".
*** In {{Borat}}, the portrayal of Kazakhstan is so ignorant and over-the-top it goes beyond offensiveness. It may explain why the film got a niche popularity in Kazakhstan itself.
* The intended effect of Tom Green's film ''Film/FreddyGotFingered''. Opinions on the film lie somewhere between "a fit of twisted genius" and "why the hell did I watch this?" Beware, some of the film's more outrageous moments listed below are definitely [[NotSafeForWork NSFW]]. You have been warned:
** About 6 minutes into the film, Green leaps out of his car, runs over to a horse and masturbates its penis for no reason whilst saying "Look, Daddy, I'm a farmer!"
** Green's friend rips his knee open whilst skateboarding and Green licks the open wound.
** Later, he visits his friend in hospital and a pregnant woman in the bed next to his friend goes into labor because he's being so annoying. Green rips the baby out, cuts its umbilical cord with his teeth, and then "wakes it up" by swinging it around his head like a lasso by said umbilical cord.
** He falsely accuses his father of sexually molesting his teenage brother.
*** He also falsely accuses his brother of being a teenager. [[spoiler: Events in the film make it clear the brother is an adult and just happens to look about 13. He does work in a bank at the kind of job where you need to wear a suit, after all.]]
** Not to be forgotten: Green skinning forest animals so that he can wear their still bloody skins and prance around the wood; Green's father (played by Rip Torn) exposing his butt to Green and yelling [[spoiler: "Fuck me"]]; Green having a kinky sado-masochist relationship with a paraplegic woman; and to some the most disturbing, a neighbour kid that gets hurt progressively worse throughout the film; the disturbing part is camera sadistically lingering on the wounded kid crying.
*** Perhaps Creator/RogerEbert's infamous review puts it best:
---> This movie doesn't scrape the bottom of the barrel. This movie isn't the bottom of the barrel. This movie isn't below the bottom of the barrel. [[InsultToRocks This movie doesn't deserve to be mentioned in the same sentence with barrels]]... The day may come when ''Freddy Got Fingered'' is seen as a milestone of neo-surrealism. The day may never come when it is seen as funny.
*** Or, as [[WebVideo/BrowsHeldHigh Oancitizen]] so succinctly put it:
---> It's too normal to be {{dada}}, and too shit to be anything else!
* In fact, this is a signature of The Joker in almost any media - the one from Creator/TimBurton's ''Film/{{Batman}}'' made us laugh as he gassed a roomful of people... to music. The ''[[WesternAnimation/BatmanTheAnimatedSeries Animated Series]]'' Joker generally didn't get much of a body count, but funnily blowing up empty buildings (like the hospital from ''The Dark Knight'') was well within his reach, and in TheMovie ''WesternAnimation/BatmanBeyondReturnOfTheJoker'', he makes a few really funny one-liners while revealing that he [[ColdBloodedTorture tortured]] a child until his identity was broken and believed himself to be the Joker's son. Listing all the sociopathic hilarity that the Joker has unleashed on the world of comics would fill several pages this size.
** In ''Film/TheDarkKnight'', Joker blows the line straight to Hell before asking if you want to know how he got those bloody scars.
*** [[EyeScream "You wanna see a magic trick?" ]]
* Several gags in ''Film/{{Airplane}}'' are only funny because they manage to cross the line twice.
* ''Film/TheBigLebowski'': "What's this day of rest shit? What's this bullshit? I don't fuckin' care! It don't matter to Jesus. But you're not foolin' me, man. You might fool the fucks in the league office, but you don't fool Jesus. This bush league psyche-out stuff. Laughable, man - ha ha! I would have fucked you in the ass Saturday. I fuck you in the ass next Wednesday instead. Wooo! You got a date Wednesday, baby!"
** "Do you see what happens, Larry, when you FUCK A ''STRANGER IN THE ASS?''"
*** I think you meant [[{{Bowdlerise}} "FIND A STRANGER IN THE ALPS?!"]]
* This is why ''Film/TheProposition'''s Jellon Lamb is such a delight, especially when he gets to lines like "What is an Irishman but a nigger turned inside out?"
* An overwhelming number of scenes in Creator/PeterJackson's ''Film/BadTaste'' contain slapstick violence taken to a ludicrous extreme.
** "A headshot's the only ''true'' stopper!" Cue two point-blank cranium-destroying headshots with a large revolver.
** Or the final killing blow against the Big Bad, in which the hero [[spoiler: dives from the ceiling, chainsaw-first, towards the top of the monster's head, emerges from between its legs covered in gore, and quips that he is "born again".]]
** Same with ''[[Film/{{Braindead}} Dead Alive]]''. Lawnmower + zombies anyone?
* ''Film/RikiOhTheStoryOfRicky'' is a movie devoted to this concept, whether or not the makers intended it. Every single fight scene in the movie includes something horrifyingly violent done in such an over-the-top manner that it becomes hilarious. Picking out highlights is hard, but [[spoiler: Ricky punching a hole in a fat man's belly, a guy's skull getting smashed like an eggshell, and the one guy trying to strangle Ricky using his own intestines]] stand out as Memorable Moments.
** Not to mention the scene near the end where Riki pushes an oni into a meat grinder.
** "Alright! [[{{Pun}} You got a lot of guts, Oscar]]!"
* ''Film/TeamAmericaWorldPolice''
** The scene with the vomiting puppet. The dramatic music takes it over the top.
** Not to mention the sex scene. Just in general.
** The speech about dicks, pussies and assholes
* ''Film/TheAristocrats''. Any half-decent rendition should cross the line at least a dozen times, in every direction. Creator/BobSaget practically picks up the line and jumps rope with it in his rendition.
* ''Film/InglouriousBasterds'' does this a lot, but the most awesome one is [[spoiler: the assassination plot, where they bust in, shoot down Hitler with [=MP40's=], and empty their clips into the body of Joseph Goebbels. Then they reload, shoot the entire subsequent magazine's worth into Hitler's face and to top it off, the entire theater ''explodes''.]]
* Anything by Creator/JohnWaters. Cherish in ''Film/CecilBDemented'' takes this UpToEleven with her claim "When I was ten years old, my entire family fucked me under the Christmas tree!" Even by Waters' standards, this is a doozy.
* The maximum bloody Crazy 88 fight scene in ''Film/KillBill'' Vol 1. At first the blood is a powerful and startling effect. But after a while the ridiculously high pressure and copious volumes of blood from even minor wounds, combined with the sheer number of bodies piling up at The Bride's feet become a source of gory amusement. Note that the high pressure effect was used in O-Ren's backstory anime to good dramatic effect.
** Before that, we have O-Ren's introduction scene, where, after an [[BerserkButton insult to her heritage]], she [[spoiler: lops off a rival crimelord's head. His]] neck proceeds to shoot blood ''five feet'' into the air for a solid 10-15 seconds, which only makes it hilarious.
** After that, the fight with Gogo doesn't quite make it, but [[http://www.youtube.com/watch?v=vk2A-zOum9Y this does]].
* ''Film/KickAss'': A lot more than twice actually. Single scene example: Dave gets stabbed in the gut. The audience winces. He then staggers out into the street and gets ''flipped'' by a car. The audience starts laughing.
** ''Film/KickAss2'':
*** The attempted rape scene. [[spoiler: The Tumor holds down Night Bitch and Mother Fucker prepares to rape her...only to be embarrassed when he gets erectile dysfunction and starts playing himself to try and get "ready," all the while The Tumor and even Night Bitch are laughing at him]].
*** The Motherfucker's choice for some of the names of his team of villains. Genghis Carnage and Black Death, anyone?
-->'''Javier:''' Chris, Jesus, maybe you could pick something less ''horrifically racist?''
* Creator/LloydKaufman, director of such classics as ''Film/TheToxicAvenger'', ''Film/ClassOfNukeEmHigh'', and ''Film/TromeoAndJuliet'', pretty much makes this his code.
* Much of ''Film/{{Machete}}'''s fun comes from this. At the very least the scenes in which Machete [[spoiler: eviscerates one of the men sent to kill him and uses his intestines to swing from a window]] qualifies.
* Like ''WesternAnimation/SouthPark'', Creator/TreyParkerAndMattStone's earlier work ''Film/CannibalTheMusical'' runs on this. A musical about Alferd Packer (not a typo), a prospector in late 1800s Colorado who was tried for murder when he returned from being snowed into the Rocky Mountains [[ImAHumanitarian remarkably well fed and alone]].
* [[EverythingsDeaderWithZombies Pretty much any flick to have anything to do with zombies that isn't horror]] will use this.
* This trope is the source of the ''primary conflict'' in ''Film/TheProducers'': Due to [[YouWereTryingTooHard Trying Too Hard]] and SoBadItsGood, SpringtimeForHitler ends up being a [[CrowningMomentOfFunny Crowning Musical of Funny]], thus fouling the titular characters' tax fraud scheme.
* The ending of ''Film/PennAndTellerGetKilled'' has [[http://www.youtube.com/watch?v=mUNagJXEvG4 Teller accidentally killing Penn Jilette]], and is so (realistically) distraught at killing him shoots himself in the head in front of Penn's girlfriend. Her realistic inability to handle the tragedy causes her to spin in an anguished circle and toss herself out of the window. It crosses the line twice when this sets off an ''[[http://www.youtube.com/watch?v=OIxxVYuxl64 endless chain of suicides around the Earth]]'' as The Bee Gee's ''I Started a Joke'' plays (with the super apropos lyrics "I started a joke which started the whole world crying - but I didn't see that the joke was on me!" Penn explains in voice over that since the title of the movie was ''Penn & Teller Get Killed'', people would feel ripped off if it wasn't ExactlyWhatItSaysOnTheTin.
* ''Film/TheHouseOfYes'' has a moment in which a character relates that she once went to a costume party as Jackie Onassis in the pink dress she wore when JFK was assassinated,... complete with fake blood and brains splattered on it.
* Just like the games, ''VideoGame/{{Postal}}'' deserves to be here. The tagline for the movie: "Some movies go too far... others start there"
* While not as strong an example as some of the others, in the 2009 Film/StarTrek movie there's a scene where [[spoiler: Spock's mother falls over the edge of a cliff, making it impossible to beam her up to the Enterprise and thus killing her.]] The title for the part of the soundtrack from this scene? [[spoiler: "I've Fallen and I Can't Beam Up!"]]
* Over-the-top fighting scenes with premises that make them plausible:
** ''Franchise/TheMatrix'' trilogy
** ''Film/ShaolinSoccer''
** ''Film/GodOfCookery''
** ''Film/TheyLive''
* ''Film/FunnyGames'', both of them, are really sadistic. These movies are a satire of this trope, as well as a commentary on "torture-porn" violence.
* ''Film/TheMuppetChristmasCarol'' has JustForFun/StatlerAndWaldorf laughing about the time they shut down an orphanage on Christmas. They remember all the little tykes in the snow with their frostbitten teddy bears.
* Violence against women is really not a laughing matter, but in Denmark the [[http://www.youtube.com/watch?v=CO3LwBKxAkM egg-blowing scene]] from the 2006 comedy ''Blinkende Lygter'', about [[TrueCompanions four gangsters from Copenhagen]], who hide from their former boss in an abandoned country inn, is generally considered the funniest thing to hit the silver screen that decade.
** And yes, [[HeyItsThatGuy that is]] [[Film/CasinoRoyale Le Chiffre]] behind the long hair and the moustache.
** A lot of non-danish speakers lash out at this, calling it glorification of violence against women. However, she has spent the majority of the film constantly being a pain in the ass and emotionally dominating and abusing another of the main characters (in a sort of unaware "I'm the girlfriend so I decide everything" kind of way) up to this point - that, combined with the childishness of the situation is what makes the punch very satisfying and hilarious.
* In ''Film/TheKingsSpeech'', during the future King George VI's speech therapy sessions with Lionel Logue, it is noticed that he doesn't stutter when he's swearing. Lionel proceeds to provoke him into a ClusterFBomb that would offend a sailor, and in fact [[AvoidTheDreadedGRating was pretty much the only reason why the movie was rated R when it'd otherwise be at most PG]]. It is also ''[[Funny/TheKingsSpeech hysterical]]''.
* Lars von Trier's ''Film/TheIdiots'', like many of his films, tries to ignore the line as much as possible. On offer are (intentionally) badly shot scenes of both male and female full-frontal nudity as well [[spoiler: unsimulated sex]]. However, a greater deal of criticism instead regards the plot point of having people pretending to be mentally disabled, partially for the sake of humour. Some claim that von Trier wouldn't have gotten away with as much as he did without abusing TrueArt, while some definitely think it's more than admirable for what it eventually does with itself.
* The gentleman's club in ''Film/MysteryTeam''. Made funnier/worse by the fact that the people in question are practically seven (and they meet an ACTUAL seven year old).
* ''Tin Cup''. An interesting case, in which Roy keeps trying to get the ball in the hole on one shot over, and over, and over, and over. It goes from being painful, to pathetic, to ''hysterical'', to finally (and unlikely!) '''''triumphant'''''.
* ''Film/BlazingSaddles'' is built on this: Gratuitous use of the word 'nigger' and BlackComedyRape to name a few.
* The original CBS/Fox release of the Film/JamesBond movie ''Film/LicenceToKill'' starts with "A Very Public Service Message" from Schweppes that warns that the feature presentation contains gratuitous violence through its spokesman as said spokesman dodges numerous attempts on his life, including a razor hat boomerang, a knight's axe, an exposed electrical wire (which kills said knight, elicits a digitally altered WilhelmScream, and [[ArsonMurderAndJaywalking causes the spokesman to think it's time for dinner]]), a booby trap placed by a window, a femme fatale, a ninja, and an assassin behind a door before having four bullets emptied into him by an offscreen gun that sweeps the screen from left to right. He doesn't realize he's been shot until the cup of Schweppes he just drank starts leaking out of his bullet holes.
** Also in LTK, Franz Sanchez' response after he kills Krest [[ExplosiveDecompression by locking him inside a decompression chamber]] with ([[AppleOfDiscord supposedly]]) stolen money. It's possible the only Film/JamesBond movie where the villain gets a better BondOneLiner than Bond himself:
-->'''Perez:''' What about the money, ''Patron''?
-->'''Sanchez:''' (''{{beat}}'') Launder it.
* The [[{{Mondo}} shockumentary]] ''Traces of Death'' has footage of a bear climbing a telephone pole, getting electrocuted, falling, then wrestling with animal control.
* ''Film/TheDictator'' certainly tries this. Sacha Baron Cohen's dictator, Aladeen's every line is horrifically offensive. In one scene, he is discussing dropping nuclear weapons on Israel - but he believes the weapons will behave like the bombs in ''WesternAnimation/LooneyTunes''. In another, he plays a Wii terrorism video game and plays a level where he shoots caricatures of Jews in Munich. His advisers call for him, so he agrees to come see them right after his current level. Cue the video game narrator saying, "Bonus level, Mass Grave," then cut to Cohen miming digging one with his Wii-mote controller. Aladeen is not the only character to engage in this kind of antics.
* Dusan Makavejev said that the point of ''Sweet Movie'' was to assault the viewer with a barrage of progressively more shocking images until they were finally reborn, like the characters in it.
* Said Creator/RogerEbert, about ''Film/ShootEmUp'':
-->"I may disapprove of a movie for going too far, and yet have a sneaky regard for a movie that goes much, much farther than merely too far."
** The quote was so appropriate, it spent a long period of time as the page quote for this trope.
* The scenes in ''Film/IronMan1'' where Tony kept smacking into things while testing his suit was funny in all the wrong ways. "10% thrust." ''Splat!''
** ''Film/IronMan2'':
*** The video footage of the Hammerdroid's test malfunction [[spoiler:(twisting around so fast it snaps the pilot's spine) evokes a ThatsGottaHurt gasp of sympathy from the audience. But Hammer's mealy-mouthed attempts to gloss over the failure by insisting that the pilot survived cross it back into a joke at his expense is quite funnier, as is his later statement that people are reluctant to volunteer to test them "for some reason."]]
*** Also, Tony's birthday party. "Iron Man, how do you go to the bathroom in that suit? ...just like that." Not funny. Giving an actual technobabble answer about filtration and being able to drink that? ''Now'' it's funny.
* You could argue the entire movie is this, but when you see the scene when Film/ForrestGump explains Lt. Dan was from a long military tradition, [[http://www.youtube.com/watch?v=v9c8Rba5NVE and then you see a Death Montage of Gary Sinise (the actor playing Lt. Dan) playing a different ancestor just at the moment of his death, in a different battleground, with a war uniform more modern that the last]], you don't think that the movie is mocking those soldiers patriotism or sacrifice, but you see as questioning the intelligence and sanity of GloryHound Lt. Dan, whose desire to die in battle makes Forrest seem like a genius by comparison.
* Zazie dans la Metro somehow manages to turn a pedophile chasing a ten year old girl into something out of ''WesternAnimation/LooneyTunes''.
* The use of CountryMatters in ''Film/BeingJohnMalkovich'' is a textbook example. When the agent shakes hands with [[GrandTheftMe Craig-in-Malkovich's-body]] and says, "Sorry about the cunt at reception," it seems like an attempt to shock and feels a bit misjudged. It's with the immediate repetition, when he shakes Maxine's hand and says the same thing as if it's just part of the polite routine of introductions, that it becomes hilarious.
* ''Film/TheMummy1999''. [[BigBad Imhotep]] ''plucking out the eyes'' of [[RedShirt one of the American mercenaries the protagonists hired]]? [[NightmareFuel Horrific]]. Imhotep winding up with the guy's astigmatism? Hilarious!
* ''Film/TheJerk'': Navin Johnson, after becoming very wealthy from his Opti-Grab eyeglasses, is speaking with some developers thinking about building an apartment complex. Navin is onboard until they say they want to "keep the niggers out". Navin, who grew up in a black family, [[BerserkButton doesn't take kindly to this]], yelling [[PreAssKickingOneLiner "Sir, you are talking to a nigger!"]], and kicks everyone's ass.
* ''Film/FinalDestination'': [[GallowsHumor Death has a sense of humour like this, apparently.]] Racist dumb redneck planting a burning cross into a black guy's front lawn? That's not funny. Death disengages the handbrake to his truck, locks the front door, and sets the radio to play "Why Can't We Be Friends?", ruining his plan? That's pretty funny. Racist's leg gets caught on a hook and chain dragging behind the truck while he's trying to stop it, leaving him being dragged down the street by his truck while he's on fire, ''with the song still playing at higher volume''? That's absolutely hysterical!
%% * ''[[Film/{{Neighbors2014}} Neighbors]]'': Practically the whole movie.
* The Film/SixteenCandles scenes involing AsianAndNerdy Long Duk Dong are a mix of [[UnfortunateImplications "OMFG THAT'S SO FUCKING RACIST!"]] and [[Funny/SixteenCandles "OMFG I SHOULDN'T LAUGH BUT I CAN'T STOP!"]]. Specially one that involves a bike...
* Film/TropicThunder takes this trope and runs off with it. To put it on perspective: while there are a few instances of this, most of the time it's more [[RefugeInAudacity crossing the line and going on for about seventeen more miles, never looking back.]] And it wouldn't be half as funny and awesome as it is, if it wasn't made of this trope.
** In example? Read the blurb on Kirk Lazarus, played by Creator/RobertDowneyJr: ''"An immensely talented Australian method actor, Lazarus had a controversial "pigmentation alteration" surgery to darken his skin for his portrayal of the black character Sergeant Lincoln Osiris. Lazarus refuses to break character while filming and only speaks in his character's Black English."'' As a result Lazarus's lines would be horribly offensive, were he played by an actual black guy... but end up being hilarious '''because''' this wasn't the case.
* ''Film/{{Whiplash}}'': Many, many of Fletcher's interactions with his students can make for this. He'll often call out his students on a mistake, and then compound on this by making fun of the student for either their nervousness or for a specific aspect about them, be it weight or [[spoiler: their mother walking out on them]].

[[/folder]]

[[folder:Jokes]]
* 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 Jerry Sandusky go to Walmart? Because children's clothes were half off!
[[/folder]]

[[folder:Literature]]
* Nearly the entire output of author Edward Lee was written purely to evoke this trope.
* ''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 Gale’s knife slit his throat before he knew what had happened. Momentarily, I’d 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/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.
[[/folder]]

[[folder:Live Action TV]]
* ''Series/StrangersWithCandy''. The episode involving syphilis crossed it '''three''' times and wrapped back around to genuinely disturbing when a teenage boy suffered brain damage from the disease and became little more than a lurching zombie.
* ''Series/MontyPythonsFlyingCircus''
** The "Sam Peckinpah's ''Salad Days''" sketch, which takes LudicrousGibs to even more ludicrous levels. Unsurprisingly, given it contains [[HighPressureBlood (literal) fountains of gore]] resulting from people getting dismembered, being impaled on tennis rackets and having their hands ripped off by a piano keyboard cover closing on them, it generated large numbers of complaints.
** "Undertakers Sketch", the final sketch of series 2, also pushes the envelope of tastelessness in classic Creator/GrahamChapman style. The sketch features a discussion between an undertaker and a customer of how to dispose of the latter's mother's corpse, to the sounds of an increasingly vocal shocked and disgusted audience, who storm the stage after the notorious final line.
--->'''Undertaker''': Look, we'll eat your mum. Then, if you feel a bit guilty about it afterwards, we can dig a grave and you can throw up into it.
*** The thing that clinched the sketch as this trope is that the invasion of the stage was itself ''arranged'' to get this sketch past the BBC censor, who felt that only the implicit apology of the apparent audience revolt would make it acceptable. It's also noticeable in the film that only about 50% of the audience had been enlisted to boo and invade the stage- the rest are clearly seen laughing.
** "Undertakers Sketch" was mentioned by John Cleese during Chapman's eulogy, which itself massively pushes the bounds of taste in homage to Chapman, who Cleese described during it as the "prince of bad taste".
--->'''Cleese''': Graham Chapman, co-author of the 'Parrot Sketch,' is no more. He has ceased to be, bereft of life, he rests in peace, he has kicked the bucket, hopped the twig, bit the dust, snuffed it, breathed his last, and gone to meet the Great Head of Light Entertainment in the sky. And I guess that we're all thinking how sad it is that a man of such talent, of such capability for kindness, for such unusual intelligence, a man who could overcome his alcoholism with such truly admirable single-mindedness, should now so suddenly be spirited away at the age of only forty-eight before he'd achieved many of the things in which he was capable, and before he'd had enough fun. Well, I feel that I should say: nonsense. Good riddance to him, the freeloading bastard, I hope he fries. And the reason I feel I should say this is he would never forgive me if I didn't. If I threw away this glorious opportunity to shock you all on his behalf.
* ''Series/{{Bottom}}'' has more than its fair share of these - sometimes feeling like a live-action Tom and Jerry. One episode has Richie chainsawing Eddie's lower legs off...twice.
** [[https://www.youtube.com/watch?v=uLvS_w9gy8g Beating up a gasman]] takes so long they take breathers.
* ''Series/{{The Office|US}}'' is a veritable master of this trope, particularly when in comes to Michael's cluelessness. He often says things that are crushingly painful and way out of line, that slowly become too awkward not to laugh... While the show may not involve actual physical violence for comedic effect, it certainly brings the pain.
** ''Series/TheOfficeUK'' had a similar theme: David Brent's jokes failed ''so badly'' it quickly became funny for the sheer awkwardness of his self-delusion.
* Similarly, Creator/LarryDavid's ''Series/CurbYourEnthusiasm'' also crosses the line and goes back again so fast it is dizzying. Whether it be a mistaken erection, or who is the ultimate Survivor he knows how to make the pain into the funny, but doesn't know when to stop.
* ''Series/{{Supernatural}}'' runs with this trope quite a bit:
** The episode "Wishful Thinking" features a wishing well that [[BeCarefulWhatYouWishFor grants warped wishes]]. Aesop aside, one little girl wishes for her teddy bear to be real. What she gets is a giant, hard-drinking, skin-mag-loving bipolar mess who eventually tries to commit suicide by blowing its brains out. Problem: the bear doesn't actually have brains. [[GoryDiscretionShot All you see is a line of stuffing fly through the air]] accompanied by a gunshot, and the bear starts crying as it realizes that it doesn't have the option of suicide.
** The episode "Mystery Spot" is a fan favorite at least partially because of this trope. The Trickster causes [[GroundhogDayLoop the same Tuesday to repeat for Sam over and over]], each repetition triggered by Dean dying. His first death or two are horribly depressing (shot with a shotgun, ''hit by a car''), but as Sam's frustration mounts, the comedy and gruesomeness of Dean's deaths rises as well (slipping in the shower, a desk dropped on him ''WesternAnimation/LooneyTunes'' style, "do these tacos taste funny to you?"). The Trickster himself says the comedy has worn thin on him, so it becomes apparent the only person laughing is the viewer. ''YouMonster''.
*** [[spoiler:In a fine moment of MoodWhiplash, after the loop is broken, Dean is shot by a mugger (on Wednesday, so it's for real), is dead before Sam even gets on the scene, and we're back to the depression.]]
*** The whole ''point'' of this episode was [[spoiler: for the Trickster to teach Sam that Dean's end of the season death was inescapable, by making it ''laughable''.]]
** The Trickster runs on this trope. His ironic punishments are usually hilarious, (killing adulterers using TheHulk, [[AnalProbe anal probing]] an abusive pledge master and forcing him to slow dance, trapping Sam and Dean in TV Land where they are forced to reenact spoofs of CSIMiami and GreysAnatomy) if cruel and gruesome. It's part of what made him an EnsembleDarkhorse.
* ''Series/BuffyTheVampireSlayer''
** The scene in the episode "Hush" where Buffy attempts to mime staking the Gentlemen and ends up miming another action entirely shocked the network, but they kept it in because it was just so damn funny.
** Season six piled on so much DeusAngstMachina that it became an in-universe example of crossing the line twice: when [[spoiler:Giles (very dramatically)]] returned at the end of the season, Buffy told him about all the horrible traumatic things that have happened ''just since he left'', never mind everything that happened before. Does he give her a hug? Tell her everything's going to be all right? Help her figure out how to stop the latest TheEndOfTheWorldAsWeKnowIt plot? No - he ''breaks down in uncontrollable laughter''. A moment later, Buffy joins him. [[CrowningMomentOfFunny And so does the audience]].
* In the first episode of ''Series/RedDwarf'', Lister's shock at [[EverybodysDeadDave being the sole survivor]] goes from tragic to funny as he persists in asking about specific people, only to be told that yes, they were counted in "everybody". When he finally clues on to the idea that everybody is actually dead, Holly laments bringing him out of stasis in the first place.
* ''Series/{{Firefly}}''
** From a scene where Malcolm wins a duel with a truly obnoxious and stuck-up opponent that had it coming:
-->'''Malcolm''': Sure. It would be humiliating. Having to lie there while the better man refuses to spill your blood. Mercy is the mark of a great man. ''(lightly stabs him with sword)'' Guess I'm just a good man. ''(stabs him again)'' Well, I'm all right...
** Then there's the whole "pretending Kaylee's dead" from the pilot which Simon sums up best:
-->'''Simon''': That man's psychotic.
-->''(IronicEchoCut to Wash, Zoe, and Mal [[Funny/{{Firefly}} laughing their asses off]])''
-->'''Wash:''' You are ''psychotic!''
* Several of the sketches on ''Series/MrShow''. Making fun of religious beliefs? That's just stupid and rude. Doing it with America's Funniest Home Video style sound effects and graphics? Hilarious.
** Riffing on the East Coast/West Coast rap feud mere months, maybe even weeks after Tupac's death? WAAYY too soon. Replacing rappers with ventriloquists? Now THAT'S funny.
* ''Series/ItsAlwaysSunnyInPhiladelphia''. When one episode involves two characters getting addicted to crack to get better unemployment benefits...
** Charlie answering the door, eating a banana, wearing a SS officer's uniform.
** Nightman.
** Charlie biting a mall Santa's ear off after realizing his mother spent his childhood Christmases sleeping with tons of men in Santa suits.
* ''SummerHeightsHigh.'' ''All of it. Repeatedly.'' In fact, one part, involving a girl who died from a drug overdose, caused an incident when the details coincided too close to a real incident that happened earlier in the year, leading to a disclaimer at the beginning of all subsequent episodes saying that the series is fictional (which is undone when the next title proclaims that it was indeed real).
** ''Series/AngryBoys'', Lilley's newest series, contains this also, especially in the Jen Okazaki segments.
* The ''Series/BrassEye Paedophilia Special'' crosses the line twice... then crosses it again back into being horrifying, then back into hilarity ''several times per minute''. Gags include a (fake) advert for a reality TV show featuring a hundred children and a single paedophile trapped on an island covered in cameras, and a paedophile being burned in a twenty-five foot long wicker phallus shortly after being released from prison. The rest of the series could qualify for this too, although not quite as much.
* Australian PanelGame ''Good News Week'' thrives on this, usually instigated by host Paul [=McDermott=] or regular Mikey Robbins. Hell, everything Mikey Robbins says tends to fall into this.
* ''PodgeAndRodge''... Oh dear oh dear oh dear, ''PodgeAndRodge''. click [[http://www.youtube.com/watch?v=r-IfoVv1r2Q here]] to see them try to coax a coherent sentence out of Johnny Vegas.
* The Master gassing the Cabinet in ''Series/DoctorWho''. A blatant act of multiple murder, yes, but it has ''freakin' hilarious'' dialogue right before the actual killing.
** Not to mention his siccing the Toclafane on Vivian Rook. The Master and Lucy run out of the room while Vivian screams, and slam the door. The Master opens it, and she's still screaming. He winces and closes it. Opens it again three seconds later - [[OverlyLongGag and she's]] ''[[OverlyLongGag still]]'' [[OverlyLongGag screaming]].
** Even the Doctor gets in on this in "Amy's Choice". Upon finding out Rory's ideal world is living in the world's most quiet (and boring as hell) neighborhood with people over 90, he asks in exasperation: ''How do you stave off the impulse for self harm?''
* ''Series/TheChasersWarOnEverything'' usually crosses the line just once, but one particular episode crossed it twice. In a skit, it showed the Ku Klux Klan wearing pink robes to support breast cancer awareness. One klansman says that ''his'' pink robes were accidental, and was due to something red getting in the wash, and adds that "it's just another reason why you should never mix coloreds with whites!"
** Another sketch, the infamous "Make a Realistic Wish Foundation" sketch, was meant to, in the words of the Chaser team, "be so over the top nobody would take it seriously". It, ah, [[DudeNotFunny didn't work]].
** And then there's the ads for their "Red Button Edition" pay TV appearances, which were funny the first couple of times...and consist of ''Osama Bin Laden'' saying "If you press the red button, you'll get special commentary. That's pretty lame. When I push a red button, I want something to blow up."
* ''Series/{{Blackadder}}'' has this on a few occasions, including this gem from series 3:
-->'''Blackadder''': They do say, Mrs Miggins, that verbal insults hurt more than physical pain. They are, of course, ''wrong'', as you will soon discover when I stick this toasting fork in your head.
-->'''Aunt Whiteadder''': Cold is God's way of telling you to burn more Catholics!
* A lot of the deaths in ''Series/PushingDaisies'' arguably fit this, but perhaps the best example is that of Harold Hundin, the dog breeder. He drank coffee that has been laced with arsenic, and when he succumbed to the poisoning, he fell onto a sharp dog brush handle in a box, stabbing him. It doesn't end there, though, because the floor was wet, so he kept slipping and falling onto the dog brush again and again, stabbing him repeatedly. Seriously, it's hilarious. There was also the episode when a car full of clowns goes into the lake, we see them pulling a clown out, then another, and [[ClownCar another]], including one with stilts. By the end it's side-splittingly hilarious.
** Similarly, many of the less probable accidental deaths on Creator/BryanFuller's earlier show ''Series/DeadLikeMe'', beginning with that of the protagonist (who was killed by a falling toilet seat from a deorbiting Russian space station). Most had their souls "reaped" first, though, leading to dumbfounded souls watching their bodies die in horrific/ridiculous ways.
* ''Series/SixFeetUnder'' was basically built on top of this trope. The department store Santa/Hell's Angel member's Big-Ass Biker Funeral (with biker flame decorations on the metal coffin) is a particularly funny/sick example.
* [[http://www.youtube.com/watch?v=O81aRaRwURM Robin Williams' appearance]] on the penultimate ''Series/TheTonightShow with Creator/ConanOBrien'', a CrowningMomentOfAwesome that just happens to cross the line several times. If the crotch-grabbing and Tiger Woods marriage counselor joke weren't bad enough, irking Conan in the process, his Irish folk tune cranks it UpToEleven with Conan and Robin eventually ''doing the jig''.
* Frankie Boyle on ''Series/MockTheWeek''. There's no point in listing examples, if he's drawn breath chances are he's crossed the line a few dozen times.
* While [[http://www.youtube.com/watch?v=P-wwqW37-gg this "commercial"]] (from ''Series/TheITCrowd'') [[DigitalPiracyIsEvil starts out serious]] and rapidly shows its comedic underpinnings, the route it takes is a little questionable... up until the line "And then steal it ''again''," at which point it has properly crossed that second line.
** Similarly the [[http://www.youtube.com/watch?v=GjaKe-bKOX8 breakup of Douglas and April]] is heartbreaking until she wallops him, arguably crosses back over the second line when he wallops her back, then crosses the second line for good as it turns into a protracted brawl that results in the 'destruction of the Internet'.
* ''Series/ChappellesShow''. Just the Clayton Bigsby sketch (blind black white supremacist) crosses the line so many times it's hard to tell which side it ends up on.
** Is [[PlayingAgainstType Wayne Brady]] gonna have ta [[Funny/ChappellesShow choke a bitch]]?
** The end of the "Time Haters" sketch, as the titular Haters face a 19th century slave master.
-->'''Silky Johnson:''' (''After delivering a TheReasonYouSuckSpeech to the slave master'') -But the point is, is that in the future, all black people are gonna be free!!
-->'''Slave:''' When's ''we'' gonna be free?
-->'''Silky:''' That is a ''good'' question, my man! (''{{beat}}'') [[BondOneLiner How about now-ish?]]
-->(''Silky shoots the slave master'')
* ''Series/{{Parlamentet}}''. Making fun of everything, going from skeptical junkies to ''hunting [[Literature/TheMoomins Moomins]] for being parasite carriers.''
* The characterisation in ''Series/FatherTed'' operates on this principle. An alcoholic Irish priest is merely an offensive stereotype. A priest so addicted to alcohol that he can tell a wine's vintage just from the clink and will drink toilet duck if alcohol is not available - hilarious. A stupid Irish priest - not funny. An Irish priest who is so stupid that he can't tell the difference between 'small' and 'far away' - hilarious.
** Similarly, stealing money from orphans - not funny. Following up the revelation with a sequence showing the title character in a casino throwing the (stolen) money up in the air and laughing hysterically while surrounded by scantily clad showgirls? Hilarious.
* Kyle's song [[BilingualBonus My Struggle]] as his good friend marries a Jewish man in the season 2 finale of ''Series/PartyDown''.
* Subverted (off-camera) and deconstructed in ''Studio60OnTheSunsetStrip'' episode "The Option Period", when Matt Albie complains about an (unseen) sketch that a clueless special-effects guy ruins by curtailing the scripted excessive blood, thereby un-crossing the second line, so to speak.
--> '''Danny''': He didn't think it was realistic.
--> '''Matt''': The prop guy?
--> '''Danny''': Yeah.
--> '''Matt''': It's called Quentin Tarantino's Hallmark Movie, "Turkey Won't Die." It's about a mortally wounded bird that will not die, ''even as it's being served.'' Did he find the premise realistic?... If [[{{Gorn}} geysers of blood are gushing out]], then I get the Tarantino joke, and [[BloodyHilarious it's funny]]. If it's just a ''realistic'' amount of blood, then it's... ''[[{{Squick}} extremely]]'' disturbing...
* The surprising and hilarious death of Leslie Arzt in the ''Series/{{Lost}}'' episode "Exodus, Part 2"?? Made all the more funny by Hurley's next line: "You got some... Arnst... on you."
* ''Series/FrankieBoylesTramadolNights'' - The title was going to be "Deal With This, Retards" and has had a sketch of an Iranian Loose Women show… where they are all executed.
* Nathan's description of [[YouDoNotWantToKnow "tripling"]] himself in the ''Series/{{Misfits}}'' season 2 finale. [[note]] For those of you who ''do'' want to know...it's when you ejaculate, vomit and shit yourself all at the same time.[[/note]]
** Plenty of scenes in ''Misfits'' fall into this territory, such as the birth scene in the ChristmasEpisode, where Nathan mistakes the afterbirth for an alien baby and starts screaming and stamping on it. Also, when genuinely terrible things happen to characters on the show they are often executed in such a way that they quickly become hilarious (such as Nathan being [[spoiler: buried alive]] or Daisy getting [[spoiler: impaled on her own "Mother Teresa Young Humanitarian of the Year" Award]]) and conversely scenes which, on paper, sound as though they ''should'' cross the line twice actually end up pretty disturbing (such as Brian [[spoiler: murdering people with mozzarella and greek yoghurt]]).
* ''Series/WhoseLineIsItAnyway'' frequently uses this trope, but the best example is perhaps [[http://www.youtube.com/watch?v=TYN964q1aw8#t=1m58s this clip]].
* Sue Sylvester from ''Series/{{Glee}}'' lives and breathes this trope, especially in her "Sue's Corner" news segments. Here's her take on [[http://www.youtube.com/watch?v=FLDrntGjvo8&feature=related "Sneaky gays".]]
** To secure a position as a rival glee coach, Sue caused the former holder of the position to tumble down a flight of stairs. This is the second time she's done this to further her nefarious plans. The first time, she subtly tripped an elderly woman. In this case, she ''shoved'' a healthy, middle-aged man down a flight of stairs. And when he survived the first tumble with nary a scratch, she wordlessly walked down to him and shoved him down another flight of stairs with an equal lack of subtly. The man ended up in a coma.
* ''Series/TwoAndAHalfMen'': Alan discovering his date has a Nazi BDSM fetishist. And him declaring it's "Not a dealbreaker." In fact, quite a lot of the jokes qualify as such.
* All over the place in ''Series/TheLeagueOfGentlemen''. Cannibalism, serial killers, graphic toad-melting, AndIMustScream, a cursed veterinarian who despite good intentions manages to cause the agonizing deaths of all his charges, BrotherSisterIncest... sounds like a typical day in Royston Vasey, and generally played for laughs.
* The [[Recap/CommunityS1E02Spanish101 second episode]] of ''Series/{{Community}}'' has an In-universe example. In their protest, Annie and Shirley decide to commemorate a murdered Guatemalan journalist... with a pinata. Britta is not happy:
-->'''Britta''': You guys realize he was ''beaten to death'', right?\\
'''Shirley''': That's where we got the idea from.
** Community has many examples of this, including a Halloween special in which the dean of the school is imagined as the devil. He describes an increasingly gruesome and painful sounding "damnation orientation" session, before being blown away. He comes back though, wielding a chainsaw and shouting, "Gay Marriage!" The show crosses the line again when Shirley gleefully narrates, "And then he chainsawed them to bits! Then he put them back together, and then he chainsawed them to bits!" Actually that whole episode qualifies as this.
** The entire concept of violence is used to cross the line multiple times. Annie knocking a janitor out with chloroform? A little awkward. The plan after (and the subsequent SECOND chloroforming of the same janitor)? Downright hilarious. This penchant for violence seems to be lampshaded later on when it's deduced, via multiple choice testing, that only one of the study group members is not mentally ill.
* In ''Series/BabylonFive'', we have Cenatauri Emperor [[TheCaligula Cartagia]] walking up to Londo & Co. in his pure white suit, except for his entirely blood-red hands, talking ''boredly'' about how his torturers--"excuse me, pain technicians, the ''used'' to be called torturers but ever since they [[WeirdTradeUnion got organized]] it's been ''pain technicians''"--just couldn't manage to make G'Kar scream, and, well, he'd just had to do it himself... On its own, the scene would be horrifying, but between the way the scene is written and Wortham Krimmer's utterly bored delivery as Cartagia you can't help but laugh.
* On ''Series/{{Leverage}}'', Parker is introduced this way with a flashback to her childhood. [[DisproportionateRetribution She blows up a presumably foster parent for taking away her bunny after she is caught stealing]]. This also leads to her career choice due to his poor choice of words:
-->'''Father:''' So be a good girl! Or, I don't know, a better thief.
** Though it is also implied that he is abusive as well.
* A lot of Barney Stinson's womanizing on ''Series/HowIMetYourMother'' relies on this: most of the "awesome" things he does are sometimes utterly despicable, usually incredibly lame, and almost always pretty pathetic, but he goes ''so'' far over the line and is [[MagnificentBastard so devoted to excellence in the field of being a terrible human being]] that he crosses back into CrazyAwesome.
--> '''Ted:''' I can't decide whether to be thoroughly disgusted or really, really impressed.
** At one point he claims he may have actually ''sold'' one of the women he's slept with. It shouldn't be as funny as it is.
*** In a perfect example of this trope, the line is funny rather than horrifying because he's so indifferent that he isn't even sure
-->'''Barney:''' I mean, at one point I'm pretty sure I sold a woman. I didn't speak the language, but I shook a guy's hand, he gave me the keys to a Mercedes, and I left her there.
* The "Canteen Boy Goes Camping" sketch from ''Series/SaturdayNightLive''. Having a sketch about a scoutmaster molesting one of his Boy Scouts? DudeNotFunny Having a sketch about a scoutmaster molesting a 27-year-old who's still in Boy Scouts? Still kinda Squicky, but kinda funny. Airing this as part of a Valentine's Day episode? Elicits that kind of laughter where it's wrong, but you can't help it.
* ''Series/BreakingBad'':
** [[spoiler: That [[HolyShitQuotient jaw-dropping moment]] where an innocent kid gets shot in Season's 5 "Dead Freight"]] would no way be funny. Someone [[http://www.youtube.com/watch?v=M_fcdP0UVqw editing a video to make it look like]] [[spoiler: Walt and Jesse were celebrating Todd shooting said kid witness (with Walt laughing, Jesse's "[[CatchPhrase Yeah]] [[ThisIsForEmphasisBitch Bitch!]]" and everything)]] makes it just hilariously fucked up in the most possible way.
** From the second episode, you wouldn't normally expect yourself to laugh at a half-dissolved corpse crashing through the ceiling and splattering all over the landing thanks to Jesse not knowing you don't put acid in your bathtub. And yet you do because the entire situation is damn hilarious, plus Walt's magnificent OhCrap look helps.
* A planet destroyed is terrible. [[Series/{{Lexx}} A planet destroyed every week...]]
* ''That's Just Me'' murders the line, brings it back to life, steals its car, sleeps with its wife, spits on it, and kills it again.
** "We're not worried about French or Canadian terrorists because people there are rich and don't suffer." "People are poor and suffer in Russia, but I'M not worried about [[TooSoon Russian terrorists!"]]
** In the second episode of the seven season, she paints herself like a Polish flag, says her name is 'Polska' and [[ItMakesSenseInContext says she's now a Polish sex slave.]]
** "What's worse than a rainy day? The Holocaust!" Said by a Jewish girl of all things.
** "You have just unleashed a nuclear war and killed us all!" "You pushed the forbidden button!" "But it was red, shiny, and looked like candy!"
* ''Series/{{Frasier}}'' can't tell his new producer-in-training Mary Thomas that he doesn't like how she works, [[WhiteMansBurden because she's black and he's afraid of looking racist.]] When he and Niles roleplay a confrontation, Frasier's portrayal of Mary as a SassyBlackWoman is so ridiculously offensive it's ''hilarious''.
-->'''Niles:''' ''(playing Frasier)'' Now, I want you to contribute, but only up to a point.
-->'''Frasier:''' ''(playing Mary)'' So you want me to stay in my place, ''Massa''?!
-->'''Niles:''' She's not going to say "massa".
-->'''Frasier:''' What, am I gettin' too uppity for you? You sherry swillin', opera lovin', Armani wearin' elitist? You have ''no idea'' how difficult it is for a ''black woman'' in a ''white man's world''!
-->'''Niles:''' Frasier--
-->'''Frasier:''' ''(practically snapping his fingers)'' I DON'T THINK SO!
* Many sketches on ''Series/TheChrisRockShow'' tended to cross the line many times, such as [[http://youtu.be/4qGYg5xOVcw this spoof commercial]] for a cereal called [[NWordPrivileges "Nigga Please"]].
[[/folder]]

[[folder:Music]]
* Supporter's chants at [[UsefulNotes/TheBeautifulGame association football matches]] are sometimes jaw-droppingly offensive. The whole point, of course, is to rile up the opposing fans and irritate the opposing players, especially if one sings about them personally. Chants about traumatic real events in the opposing club's history (the death of players or fans, for instance) are particularly frowned-upon, although most football fans will have joined in with one such chant in their time, whatever they may tell you. Heard at Anfield to the tune of "English Country Garden":
-->''How many people lived and died,\\
In the [[http://en.wikipedia.org/wiki/Munich_air_disaster Munich Air Dis-aaaster?]]\\
Too many lived and not enough died,\\
In the Munich Air Dis-aaaster!''
** Fans of the Chilean national team apparently chant "Vamos a la playa" ("let's go to the beach") when playing Bolivia. Chile conquered Bolivia's coastline in the UsefulNotes/WarOfThePacific leaving the nation landlocked which has a lot to do with why Bolivia is so poor today.
* Many of Music/TomLehrer's songs, with particular mention of "I Hold Your Hand In Mine" and "Poisoning Pigeons in the Park".
** Tom Lehrer said of "I Hold Your Hand in Mine" that "of all the songs I've ever sung, that's the one I've got the most requests ''not'' to."
** There also is "TheMasochismTango".
** And "We Will All Go Together When We Go", in which the description of the effects becomes steadily more gruesome (sung most cheerfully).
** Also, "The Irish Ballad":
-->She set her sister's hair on fire! (Rickety-tickety-tin)
-->And as the smoke and flame grew higher, she danced around the funeral pyre,
-->Playing a violin!
** "I wanna Go Back to Dixie" even features, in the live introduction, "The following song, on the other hand, goes too far." The song skewers [[SweetHomeAlabama culture that romanticizes the Deep South]] with lines such as "Poll tax, how I love ya, how I love ya, poll tax!" and "Put my white sheet on again, I ain't seen one good lynching in years!"
** "I Got It from Agnes" is a song about the spread of an STD among a rather... ''close'' circle of friends. That itself is pretty outrageous. But then it has lines like [[ParentalIncest "She got it from her daddy, who just gives her everything"]] and [[BestialityIsDepraved "She then gave it to Daniel, whose spaniel has it now"]]...
** Bill Oddie borrowed the concept of killing birds for entertainment from Tom Lehrer and wrote ''Persecuting Pigeons In Trafalgar Square'' for ''Radio/ImSorryIllReadThatAgain''. Animal abuse? Not funny. Animal abuse lovingly detailed and sung to a cheery melody? Wonderful.
-->Promenading in St: James\\
I play lots of little games\\
Coating Nelson's column with great care\\
With some stuff that looks like paint\\
But I promise you -- it ain't\\
A-persecuting pigeons in Trafalgar Square
* Doesn't even begin to describe [[Music/PassengerOfShit MC Bushpig]] and his over-the-top {{Horrorcore}}.
* Seeing as it's a ''Christmas song'', "Grandma Got Run Over by a Reindeer" probably qualifies.
** In a similar vein, Weird Al's song "The Night Santa Went Crazy", where Santa holds his elves hostage, kills (and eats) his reindeer, and (in one version) is shot in the head by the [=SWAT=] team. Giving Santa a gun is doing one thing.
** Jingle BOMBS
*** Speaking of Santa going off the deep end, The Killers' song "Don't Shoot Me Santa" talks about Santa coming to shoot a boy who "couldn't let [the people who bullied him] off that easy" and has been "killin' just for fun" Of course, it is PlayedForLaughs.
** If you think that's bad, listen to the parody "Grandpa Got Worked Over by a Mobster."
* The directed by ShiaLaBeouf and co-written by ShiaLaBeouf and Music/MarilynManson [[InsistentTerminology trailer for the Manson album Born Villain]] set to the song "Overneath The Path Of Misery" already sounds insane. Then you get to the [[http://www.youtube.com/watch?v=hB0Dp9TrR1c actual video]] (criminally NSFW). Shaving women's heads, child molestation, Shakespere quotes, sex and cheek piercing with a giant needle, with Manson sliding it back and forth as if he's using it to have sexual intercourse with her cheek all sounds like it should be offensive. But then they top everything else and have Marilyn Manson graphically insert an eyeball into a woman's vagina. The line has not been seen since.
* The musical piece Ya(c)kety Sax, better known as the theme for ''Series/TheBennyHillShow'', [[SoundtrackDissonance/YaketySax has been said to]] "[[http://www.google.com/search?hl=en&q=yakety+sax+world+trade+center make anything funny]]". Hell, if you don't believe us [[http://bennyhillifier.com/ try it yourself.]]
* Pretty much anything by Stephen Lynch. [[http://www.youtube.com/watch?v=lpp937YfO2Y&feature=related Grandfather]] gets a special mention.
** I see your "Grandfather" and raise you a [[http://www.youtube.com/watch?v=_DItLB_aUbA "For the Ladies"]].
** A challenger may have appeared in the form of the Stephen Lynch-inspired [[http://www.youtube.com/watch?v=9Fg-dQxQOEs Bo Burnham]].
* The music video for "Warning" by Music/GreenDay does something like this. It follows a young man doing every single thing you have ever been warned not to do. After some point you stop yelling at the man to "Don't eat that raw meat!" and things like that, and just start laughing at how amazing it is he's managed to survive this long.
* A lot of stuff by ''The Vandals''. Example? The song "Fourteen"; lyrics include "I can't make love to you because you're fourteen", and "there will come a day when love like ours is not a crime, just give it time". Sick. Also funny. Also the Christmas album "Oi to the World" which includes the songs "My First X-Mas (As A Woman)", "Christmas Time For My Penis" and "Hang Myself From The Tree"
* The video for Amanda Palmer's "Oasis". [[http://www.youtube.com/watch?v=8C17yfGyJjM Seriously, just watch it.]]
* Music/LadyGaga and Music/{{Beyonce}} do this in [[http://www.youtube.com/watch?v=GQ95z6ywcBY Telephone]]: after killing every single person - and a dog - in the restaurant, they decide on doing a dance dressed in outfits bearing the American flag, with all the dead corpses lying around them.
* ArloGuthrie's 18 minute 60's protest song against the draft does this when he's describing what he did when asked to talk to the shrink at the recruiting office.
--> And I went up there, I said, "Shrink, I want to kill. I mean, I wanna, I wanna kill. Kill. I wanna, I wanna see, I wanna see blood and gore and guts and veins in my teeth. Eat dead burnt bodies. I mean kill, Kill, KILL, KILL." And I started jumpin' up and down yelling, "KILL, KILL," and he started jumpin' up and down with me and we was both jumpin' up and down yelling, "KILL, KILL." And the sergeant came over, pinned a medal on me, sent me down the hall, said, "You're our boy."
* Music/WeirdAlYankovic has at least a couple of these on every album, i.e. "[[http://www.youtube.com/watch?v=4AKRqDtzOlQ Mr. Frump In The Iron Lung]]", "[[http://www.youtube.com/watch?v=iwgFRy3XK8o Christmas At Ground Zero]]", "[[http://www.youtube.com/watch?v=ceVXIs7Ihyw Good Old Days]]", "[[http://www.youtube.com/watch?v=rN6avab0fIY Trigger Happy]]", "[[http://www.youtube.com/watch?v=Tb-Mce9VpmY The Night Santa Went Crazy]]"… Add "Weasel Stomping Day" to that list.
* "Sex Dwarf" by Music/SoftCell (yes, the duo that covered "Tainted Love"). One of the most shockingly perverted, sleazy, aggressively homoerotic songs in existence... and utterly hilarious for it. The video was CONFISCATED BY THE POLICE [[http://vimeo.com/10458506 enjoy it here!]]
* The Music/DougAnthonyAllStars. 'Nuff said.
* "Banging in the Nails" by the Tiger Lillies.
* The song [[http://www.youtube.com/watch?v=VurhzANQ_B0 "A Little Piece of Heaven"]] by Music/AvengedSevenfold is about a guy who kills his girlfriend, eats her heart, has sex with her dead body, and then she comes back from the dead, kills him, and they get married and go on a mass killing spree. And it's freaking awesome.
* [[Series/MysteryScienceTheater3000 Kevin]] [[Podcast/RiffTrax Murphy]] has the song [[http://www.youtube.com/watch?v=GkGO3tGnZME "Larry's Fine"]], about [[Film/TheThreeStooges Larry Fine]]. It starts off as a typical ode to his physical endurance, but quickly becomes a [[EvenTheGuysWantHim homosexual escapade]]...before the trademark [[RunningGag physical abuse]] begins again.
* Music/AnalCunt's lyrics tend to follow a simple pattern, usually consisting of "I saw that you were adjective/I thought it would be funny if something bad happened/so I did something sociopathically awful." As a result, reading said [[http://www.darklyrics.com/a/analcunt.html lyrics]] tends to be like reading the Twitter feed of the most psychopathic person in the history of the world.
* "Tell Your Sister I'm Single" by Tyler Dickerson is already audacious enough from just its title. But then you get to the bridge "Let's keep it in the family / Yeah, you can call me daddy"...
* "[[http://www.youtube.com/watch?v=2ko2VXpW7_g Shave 'em Dry]]" by Lucille Bogan. [[OlderThanTheyThink From]] '''[[OlderThanTheyThink 1935]]''', and ''unspeakably'' [[NotSafeForWork NSFW]]. "More innocent time", my ass.
* The Music/BloodhoundGang is a master of this. See the first couple of lyrics from "Altogether Ooky":
-->Caught you / Sniffing my boxers
-->Who the [[PrecisionFStrike fuck]] does that / [[spoiler: at Red Lobster?]]
* In Sweden there is an entire genre of music called "Könsrock" (Genitalia rock) that is pretty much the embodiment of this trope. By far the most infamous of those bands is Onkel Kånkel and his Kånkelbärs ("Uncle Dingleberry and his Dingleberries"). They were brought to the attention of the authorities when a schoolteacher had read the lyrics to one of their song which describe, in detail [[spoiler: how an 85-year old man gets a 9-year old girl drunk and rapes her in the forest, all portrayed in a whimsical humoristic fashion.]] Fortunately, for all of us who appreciate freedom of speech, any attempt to ban them, failed.
* Music/{{Voltaire}}'s "Cantina" is all about a poor guy who visits [[Franchise/StarWars Mos Eisley's infamous cantina]] and ends up receiving all kinds of [[BlackComedyRape unwanted sexual attention]] from everyone there (up to and including Han, Chewie, Greedo, and even Obi-Wan). It's quite hilariously disturbing.
* One has to wonder what in the hell Mel Brooks was thinking when he recorded "[[http://www.youtube.com/watch?v=yu2NqfISm9k To Be Or Not To Be]]", considering Brooks is Jewish. Spoiler- it has nothing to do with Shakespeare.
* This trope is the source from which the comedy of the ''Music/DosGringos'' flows.
* A song about pedophilia? Not funny. A song about necrophilia? Still not funny. A song about bestiality? Not even a chuckle. How about "SadoMasoPedoRoboNecroBestiality"? ...actually kinda funny.
* Dynamite Hack's cover of Boyz in the Hood. A bunch of white guys covering a gangsta rap song with [[NWordPrivileges usage of the N-word]] should be horribly offensive, but the fact that, at the same time, they took a violent gangsta rap song and made a laid-back acoustic cover of it makes it funny again.
* Music/TheLonelyIsland, ''big time''. Nearly every single song of theirs uses this in their lyrical content, with "Like A Boss", "Spell it Out", "We're Back!", and "Natalie's Rap" being among the prime examples. In fact, just look at the ''names'' of some of their songs to get an idea of how much they love this trope: "Jizz In My Pants", "Dick In A Box", "I Just Had Sex", "Motherlover", "I Fucked My Aunt", "Trouble on Dookie Island", "3-Way (The Golden Rule)"...
* Any song by the AIDS. Their music is absurdly vulgar, yet so strange and goofy that it is difficult to take their offensive content seriously. You can listen to them [[https://myspace.com/theaidsareback/music/songs here]].
[[/folder]]

[[folder:Radio]]
* 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.
[[/folder]]

[[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]]

[[folder:Tabletop Games]]
* Da Orks of ''TabletopGame/{{Warhammer 40000}}'' 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!
* TabletopGame/{{Paranoia}}: each player is given several clones of his character on the (justified) assumption that the Friend Computer and/or fellow players will find horrible and creative ways of destroy them
* Crossing the line is the whole point of ''TabletopGame/CardsAgainstHumanity'', which is ''Apples to Apples'' for people with a twisted sense of humor.
* 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."
[[/folder]]

[[folder:Theatre]]
* ''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.
[[/folder]]

[[folder:Video Games]]
* ''VideoGame/{{Bulletstorm}}'' crosses the line twice in not only violence but also in swearing; the game loves its obscenities beyond the point of all reason.
* ''VideoGame/DwarfFortress'' tends to have some grisly moments, but when you combine loads of free time with modding abilities, you get the tale of Obok Meatgod. This is so terrible it crosses past the point where death comedy is funny and becomes just PURE EVIL.
** The thread is then shifted to the militant uses for the new mod, including [[spoiler: a "special excretion" for the newly modded "appendage"]] Only in ''Dwarf Fortress''.
** The ''Dwarf Fortress'' community as a whole does this. Take, for instance, the program that [[VideoGameCrueltyPotential farmed mermaids, drained the tank they were in, causing them to suffocate, and butchered them for their valuable bones.]] as one player put it, "bay12 doesn't have [[MoralEventHorizon moral event horizons]], it has goals". Ironically, the above mermaid-farming system actually ''was'' a MoralEventHorizon, as when Toady One found out about it he immediately wrote a patch to devalue mermaid bone. [[EvenEvilHasStandards Even Dwarf Fortress has standards]].
* Bad endings in the ''VisualNovel/FateStayNight'' game. Getting your stomach obliterated by a crazed giant? That's one of the better choices.
** The ridiculousness of some of the deaths (you have to actively try for a few) is {{lampshade|Hanging}}d in the post-death 'Tiger Dojo,' which coaches you on what to do differently next time. When Saber kills you, she appears super-deformed, angsting in the background - unless you got that death from pure stupidity, in which case she's nowhere to be seen, no matter ''what'' she did to you ("she doesn't get depressed if the fault isn't all hers").
* The infamous ending in ''VisualNovel/{{Tsukihime}}'' where you get eaten by a shark. ''On the top floor of a hotel.''
* ''VideoGame/IWannaBeTheGuy'' is something like this, except the line is between "[[NintendoHard frustrating]]" and "funny", rather than "vulgar" and "funny".
** For many fans of NintendoHard games, this is the reasoning. Dying repeatedly in the same spot, or to a death trap that was absolutely impossible to see coming, is simply hilarious.
* Also, check out many LetsPlay segments, like the ''LetsPlay/SonicTheHedgehog2006'' finale.
* Ellis [[InvokedTrope invokes this]] in ''VideoGame/Left4Dead2'' with one of his stories about Keith.
--> '''Ellis''': My buddy Keith tried camping out on top of a building once. He was shooting crows, but the police were too busy tear gassin' him to ask what he was doin' up there. He screamed for an entire year every single time he opened his eyes! Oh man! At first it was funny, then it just got sad, but then it got funny again! Oh man!
* ''VideoGame/MadWorld'' not only crosses the line twice, it stomps all over the line, rubs the line into the dirt, and smears a bloody gangster corpse across the line just to obliterate it even further. When one mini-game involves ''using a spiked baseball bat to chuck {{mooks}} at a giant dart board for points...''
** [[UncleTomfoolery The Black Baron]]. [[spoiler:Does the fact that he isn't actually black, just in blackface, make it more, or less, offensive?]]
*** On a somewhat related note concerning the Baron, his voice actor would later go on to voice [[Film/{{Transformers}} Mudflap]], whose offensiveness is on par with (if not higher than) the Baron's. [[http://blackpoliticalthought.blogspot.com/2009/06/jive-talking-twin-transformers-spark.html He did not get away with it]], which tells something about ''Madworld''.
* ''VideoGame/NinjaGaiden II'', the 360 one, has bloodshed to such ridiculously over-the-top extents that it avoids being offensive or disturbing.
** And yet, the {{P|layStation3}}S3 version ''Ninja Gaiden Sigma 2'' had to be cleaned up anyway, turning all the blood into "purple mist".
*** Although that's more of a technical thing as the blood splatters and limbs flying around caused the framerate to nosedive.
* Not from the game itself, but from one of the ''VideoGame/WorldOfWarcraft'' forums: the brother of a player called Nano logs into Nano's account to tell everyone that Nano has passed away, they've had the funeral, "he was a good person and I'm sure many of you would agree".
-->'''loroldonfarm''': Did he drop any good loot?
** Another from ''World of Warcraft'' where a character died in real life and they planned an elaborate in-game funeral announcing it on the forums and asking people to be respectful and not disturb it. [[TemptingFate You can guess what happens next]] [[http://www.youtube.com/watch?v=IHJVolaC8pw]]
*** Also, players of high level characters will sometimes escort lower level characters through instances, deliberately drawing as many enemies as they can before setting off a high-power area effect attack. One enemy dying? Not funny. Two enemies dying? Still not funny. Several dozen enemies dying at the exact same moment, with identical, perfectly synchronized actions, expressions, and vocalizations? Utterly hilarious!
* The Radio/GTARadio is this ''in spades''. One great example from [[VideoGame/GrandTheftAutoViceCity Vice City]] Public Radio:
-->'''Maurice Chavez''': ''Dios mío'', you shot him! There's blood!... and ''pubic hair!''... all over the studio!!
** On a show in Liberty City Stories, gourmet chef Richard Goblin happily allows a pregnant cow to give birth into a frying pan, then proceeds to stab the cow to death. Just to top it off, Goblin eagerly slurps up some of the cow blood before exclaiming "It's fresh!".
** In an episode of 'Just or Unjust' in GTA IV, a man rapes a thirteen year old girl, impregnates her, stalks her and then laughs when she is torn apart by lions in front of him. He has his throat ripped out moments later by the same lion, so it kinda evens out...
** EVERYTHING ABOUT the GTA series crosses the line twice!
* ''VideoGame/ConkersBadFurDay'' was one of the earliest games to do this. You think climbing up the side of a giant mountain of literal shit was bad enough? Wait until you go inside and fight [[ExactlyWhatItSaysOnTheTin The Great Mighty Poo]] in a showdown of musical proportions. This game does everything offensive and rolls with it to absurdity.
** The intro cutscene is unforgettable: [[http://www.youtube.com/watch?v=0w5neFPat1w I~ am, the Great Mighty Poo, and I'm going throw my shit. At. You.]] (Obviously NSFW)
*** Quite fittingly, LetsPlay/NintendoCapriSun had a field day with that particular boss. [[CatchPhrase You know, IN THE BATHROOM!]]
* [[http://kotaku.com/5481821/fallout-2s-rejected-childkiller-icon-is-uh-whoa- This]] is the rejected icon for the Child Killer perk from ''VideoGame/{{Fallout}}''. So ''so'' wrong, and yet so, ''so'' right...
* ANY game made by Creator/NipponIchi. In every way.
* The ''VideoGame/{{Postal}}'' series is full of this: pissing on a pizza and eating it; using a cat as a silencer; setting a gay club on fire; playing catch with a dog using a head or a grenade; pissing on people, making them throw up; tasering someone until they collapse, crying and pissing themselves in pain as you kick them in the face then douse them in gasoline and flick matches at them, setting them on fire, followed by kicking them a few more times, pissing on them again to put the fires out, and finally finishing them off by knocking their head off with a shovel or dropping a molotov cocktail on the ground just out of reach (but close enough that they're well within the blast radius) and watching them crawl toward it on charred limbs and belly, ostensibly in an effort to snuff it out, and see it explode in their face, sometimes splattering their head into little, bloody, bony chunks; the whole slaughterhouse sequence in the second game...
** Did we mention that both blood AND vomit have liquid physics applied to them? You can induce vomiting on someone at the top of a hill, then decapitate them (the vomit will keep spraying forth from the neck) and watch a mixed stream of blood and bile run down the hill and pool at the bottom. Get your angles right and the head will bounce down the hill right alongside the fluids.
* ''VideoGame/BlazBlue'''s Hazama / [[CardCarryingVillain Terumi]] [[{{Troll}} Yuuki]] is a prime example of this trope, and it is one of the reasons as to how he can be so [[AxCrazy audacidly monstrous]], while still remaining so {{laughably|Evil}} [[LoveToHate likable]]. In the 2nd game's True Ending he has {{Mind Rape}}d [[TheWoobie Noel]] into embracing her SuperPoweredEvilSide; [[YouAreNumberSix Mu-12]], [[RageAgainstTheHeavens Sword of the Godslayer:]] [[JapaneseMythology Kusanagi]], by revealing everything about her CloningBlues past to her, and when [[AntiHero Ragna]] arrives for his BigDamnHeroes moment to save his sister's clone, only to realize that [[YouAreTooLate he's too late]], Hazama gives us this gem of a [[EvilGloating Villainous Gloat]]:
-->'''Hazama'''/'''Terumi''': Awwww, that's so cute... Who's my good little sword? It's you! Yes you are! Yes you are! Oh now don't get jealous Rags, but this sword is all mine from now on, OK? Isn't she nice, though? It wasn't cheap, but I thought "Hell Hazama, you deserve it... Spoil yourself! Spring for the 'Ragna's Little Sister' model"!
* This is one of ''Franchise/MortalKombat'''s selling points. The fatalities tend to fall under this, since you're adding insult to injury, or further injury to injury, whatever.
* That's the main selling point of ''VideoGame/DukeNukem''. Same with Duke's Build Engine brothers ''VideoGame/{{Blood}}'' and ''VideoGame/ShadowWarrior1997''.
* The final battle in ''VideoGame/GodOfWar III'' allows you to cross the line as many times as you want by [[spoiler: punching Zeus in the face until the screen is ''completely'' covered in blood... and then punching him some more.]]
* ''VideoGame/SurgeonSimulator2013'' gleefully does it with style. Drill bit stuck in the patient and bleeding out? Gruesome. Trying in vain to get the drill bit out as it ''spins in the patient''? [[{{Pun}} Bloody]] hilarious.
* The ''Franchise/ShinMegamiTensei'' franchise gives us Mara, who is literally a giant green penis with tentacles in a golden chariot. Mara became one of the most popular demons in the franchise, and said popularity grew when Mara started spewing puns based on how he's a giant penis, with the words "thrust" and "penetrate" being common. Said puns get to the point where his own stats contain jokes on his appearance, with the most recurring being a weakness to ice.
* Blatant jingoism, nationalistic insults, and casual stereotyping really shouldn't be amusing, but ''VideoGame/TeamFortress2'' makes the Soldier so [[PatrioticFervor proudly patriotic]] to the point of blind idiocy and patent absurdity that he becomes damn-near the funniest thing in the game and its supplemental materials. It helps that he's a HotBlooded CloudCuckooLander and thus tends to loudly proclaim nonsense or act like the LargeHam he naturally is, taking any offensive edge off his words by virtue of being so deranged and moronic as to be hilarious.
* ''Super Mario World Dark Horizon''. Mario going against ThoseWackyNazis in an alternate universe version of World War 2 where the Mushroom Kingdom and Earth merged via Nazi super science is potentially crossing it far enough, but to the have Mario fight through the war on terror and take down Osama Bin Laden and the Taliban, who have now allied themselves with the Nazis? Super Saiyan Hitler with final boss level powers from a magical meteor? Mario actually taking down an Iraqi nuclear missile? The game's so ridiculously over the top it's almost hilarious. And then every level just finds another way to offend just about everyone for the sake of it.
[[/folder]]

[[folder:Web Comics]]
* ''WebComic/VGCats'' ran a strip in which Aeris is being annoyed by Leo's tasteless jokes, so she goes back in time to abort him on the day he was conceived. The artist got a bit of backlash for this, so his next strip had Pantsman introduce a toe-tapping dance routine... ''the Fetal Five''. Consisting of ''four'' bloodied fetuses.
--> '''Pantsman''': Well that was good, but where's the fifth member?
--> * Next panel shows a cat with a bloodstained mouth.
--> '''Pantsman''': Bugsy!...
* Any given strip of ''Webcomic/SaturdayMorningBreakfastCereal'' crosses the line ''at least'' twice. [[http://www.smbc-comics.com/index.php?db=comics&id=33#comic This one]] probably crosses the line about fifteen times.
** This one may have set the record for most line-crossing in a comic ever. And it did it in ONE PANEL. [[http://www.smbc-comics.com/index.php?db=comics&id=1685#comic]]
** The double punchline in [[http://www.smbc-comics.com/?id=3231#comic this strip]] is a particularly good example.
* Xykon of ''Webcomic/TheOrderOfTheStick''. What he did to the Sapphire Guard (drove them insane with a magical symbol inscribed on a superball, leading them to slaughter one another) crosses the line so many times that the end result is hilarious. The same goes for the various [[ColdBloodedTorture tortures]] he's inflicted on O-Chul.
-->'''Redcloak:''' And again when I found out about the Basilisk StaringContest.\\
'''Xykon:''' Technically, the paladin won that one.\\
'''Jirix:''' [[TakenForGranite He never blinked.]]
** That's tame compared to what Xykon does in "Start Of Darkness". Rich Burlew has stated that he wanted to make a villain that has no sympathy from his audience.
** [[http://www.giantitp.com/comics/oots0755.html Comic 755.]] Where to start?
* This ''Creator/RoosterTeeth'' [[http://www.roosterteeth.com/media/viewItem.php?id=472 comic]] features this - draw your own conclusions on whether it crosses the line, or is telling people to start stepping back.
* [[http://shortpacked.com/comic/book-3-is-totally-gay/02-wikimania/rape/ This]] ''Webcomic/{{Shortpacked}}'' strip. Anything with the words "rape therapy" in it, in fact.
** For that matter, pretty much everything [[http://www.walkypedia.com/index.php/Mike_Warner Mike]] does in ''Shortpacked!'', and most of what he does in ''Roomies!'' and ''It's Walky!'' too. [[http://www.itswalky.com/d/20010828.html This]] is a sterling example.
*** And speaking of Mike and this trope, [[http://shortpacked.com/comic/book-9/10-faz-gets-his-comeuppance/hatefuck/ this strip]] inspired Kumata's first post (look for, ironically, the [[InVinoVeritas drunk!Mike]] avatar) in [[http://www.blanklabelcomics.com/community/viewtopic.php?t=10808&start=0 this thread]], which eventually leads to Kumata's third post [[http://www.blanklabelcomics.com/community/viewtopic.php?t=10808&postdays=0&postorder=asc&start=25 on the second page]].
* Pretty much anything involving Black Mage of ''Webcomic/EightBitTheater'', like [[http://www.nuklearpower.com/2004/11/27/8-bit-chronicles-3-of-3/ how his Hadoken spell works]].
** Not to mention his repeated orphaning and traumatizing of Onion Kid, and his repeat murders of his companions. Hell, he more or less defines it.
** Some of the things other characters do qualify as well, like [[http://www.nuklearpower.com/2006/03/23/episode-676-supernatural-selection/ how Red Mage plans to get a ride off an island]].
** Most things Sarda does, especially [[http://www.nuklearpower.com/2009/01/31/episode-1089-special-delivery/ what he does after Ranger tries to kill him]].
* ''Webcomic/{{Hellbound}}'' regularly Crosses The Line Twice, like in [[http://loneverse.com/hellbound/hellbound.php?date=2007-01-25 this strip]] for example.
* Randy Milholland of ''WebComic/SomethingPositive'' often goes here. When you start out like [[http://www.somethingpositive.net/sp12192001.shtml this]], you're only going to go [[http://www.somethingpositive.net/sp08312003.shtml further]] and soon you're writing [[http://www.superstupor.com/sust11262007.shtml strange super-powers]]. And that's without looking for the storyline where Kim [[BlackComedyRape rapes]] Davan ([[http://www.somethingpositive.net/sp01282003.shtml Found here]]).
** An in-universe example also appears when Davan and Jason create the '[[http://www.somethingpositive.net/sp03142003.shtml anti-play]]': A play that is ''intentionally'' written to be as offensive as humanly possible. Davan even lampshades the trope:
--->'''Davan:''' Y'know, Jason, there's a fine line between parody and basically wearing a sign that says, "please lynch me".\\
'''Jason:''' And it's our job to spread our posterior cheeks and empty our bowels upon that line - in a literary sense, of course. Now, we need a dance number. How's this for a song - "God Wants More Animal Testing"?
** Not to mention Jason's musical about the crucifixion, ''"Nailed[[ExcitedShowTitle !]]"''
* [[http://bukucomics.com/loserz/go/219 In this]] and the following ''Webcomic/{{Loserz}}'' strips, the line is crossed twice.
* In ''WebComic/SluggyFreelance'', much of the [[DemonicInvaders demonic rampage]] shown during "That Which Redeems" is played this way.
-->'''Sweral:''' You ''did'' kill and eat Reakk's cat.
-->'''Tryka:''' ''It looked like my mom!''
** [[http://www.sluggy.com/daily.php?date=041006 This]] strip is probably the best example, though. Demons invading Canada and eating a young boy alive? Horrific. The American news media digitally inserting "eh?" at the end of boy's screams so he sounds more Canadian? Hilarious.
** Really, a ''lot'' of the strip came off this way in the early years; SeinfeldIsUnfunny hit ''hard'' in the new millennium.
* ''Webcomic/AnsemRetort''.
** To give a slightly more specific example: the main characters ("heroes" is stretching the definition somewhat) have travelled in time, and need to recruit allies. ''They win the support of Jesus Christ by telling him how much porn is available in the future''. (A panel in which Jesus reveals his favourite kind of porn is [[LampshadeHanging blocked out by the author giving an address to complain to]].)
** The very first strip has Axel laughingly reminiscing on blowing up an orphanage. It turns out [[ButForMeItWasTuesday this is a regularly scheduled hobby of his]].
--->'''Axel:''' But really, is drowning a kid in tequila such a reprehensible crime?
--->'''Aerith:''' Yes.
** In fact, it's pretty safe to say that whatever line was supposed to be there was completely annihilated by the time we got to the first strip.
* ''[[Webcomic/TheNonAdventuresOfWonderella Wonderella]]'''s home planet having blown up? Quasi-tragic. Finding out that it is actually still around? Heartwarming. Finding out that it's actually a hallucination caused by your mum so she can arrange a surprise party. Priceless.
* ''Webcomic/CyanideAndHappiness'' has this in spades, but nowhere is it more apparent than in [[http://www.explosm.net/comics/727/ The]] [[http://www.explosm.net/comics/1239/ Depressing]] [[http://www.explosm.net/comics/1775/ Comic]] [[http://www.explosm.net/comics/2011/ Weeks]].
* ''Webcomic/SexyLosers'' pretty much runs on a combination of this, {{Squick}}, {{N|otSafeForWork}}SFW, and FanDisservice.
* The undead, firewielding warlock Richard from ''Webcomic/LookingForGroup'', ''unlives'' this trope; See his [[IAmSong big musical number]] [[http://www.youtube.com/watch?v=fcbazH6aE2g "Slaughter Your World"]].
** In his first encounter with the allegiance conflicted elf Cale, he tries to make Cale realize and give in to the AlwaysChaoticEvil nature that his race are notorious for by defining evil as not "helping an aged dwarf woman across the road" but instead "shooting her in the face with arrows until it stops being funny".
** Shortly after Cale and Richard's initial meeting, they walk into a village that Richard apparently has visited once before. According to the guards, he burned down an orphanage during his last visit. According to Richard, that was an act of self-defence, the [[TheDogShotFirst orphanage attacked him first]].
** Burning the head off a gnome guard because he just denied you the authority to pass any further: Not very funny. Painting eyes and lips on your hand, placing it slightly above what remains of said Gnome's charred neck and making good use of your ventriloquism skills to have the gnome give you authority to pass, and apologize for his earlier rudeness, on the other hand...
** Or having his minions do a musical dance number when the group finds the bodies of allies. Then using the bones to make a throne.
*** And yet, despite all of this, he's become LawfulGood (sometimes ChaoticGood) Cale's best friend. Richard even killed a smurf and made Cale a wallet from its hide.
* ''Webcomic/{{Concession}}'': The casual, petty murders barely even blip anymore as far as webcomics are concerned... but then comes the sex with crossdressing ten-year-olds. And a girl is eventually introduced with a ''harem'' of them.
* ''Tomoyo42'sRoom'': A story about [[Manga/CardcaptorSakura Sakura]] and Tomoyo. This has everything, from baseball practice with aborted fetuses to a girl taking her recently decapitated dog and squeezing it to squirt her friend with blood. It's heartwarming.
* ''Webcomic/VanVonHunter'' has [[http://www.vanvonhunter.com/vvh232.html this example.]]
* ''Webcomic/BlurTheLines'' features a comic where the protagonist Rick encounters a bitter ex-boyfriend who wants to get back at his girlfriend (who broke up with him because he "gave lousy oral") by getting multiple guys to masturbate into condoms and then dumping the sperm on her car. The line was crossed again by Rick when he suggests that the bitter ex give oral sex to the guys in the process to prove he can give good oral. [[http://www.blur-the-lines.com/?p=140 And it works.]]
* ''Webcomic/PennyArcade'' does this at least every other week.
* Used in [[http://www.leasticoulddo.com/comic/20090129 this strip]] of [[Webcomic/LeastICouldDo LICD.]]
* In ''Webcomic/{{Homestuck}}'', the Trolls have a curious ''Franchise/{{Pokemon}} [[JustForFun/XMeetsY meets]] Franchise/{{Alien}}'' game called [[http://mspaintadventures.com/?s=6&p=004002 Fiduspawn.]] The details are yours to peruse, fair reader, but can be succinctly summarized as "FaceFullOfAlienWingWong on ''stuffed dolls''." And judging by its facial expressions the doll is ''quite'' alive during the process.
** Honestly, Homestuck does this ''all the time.'' There are very few horrible things that happen in there that Hussie doesn't also try (and, most of the time, succeed) getting you to laugh at as well. [[spoiler: Dream Jade dies? A few panels later we see her body, [[http://www.mspaintadventures.com/?s=6&p=003872 already stuffed into a silly pose.]] Tavros dies? [[http://www.mspaintadventures.com/?s=6&p=005200 Lands in funny position]], and later Terezi does an investigation on him, including [[http://www.mspaintadventures.com/?s=6&p=005272 whacking him in the face repeatedly with the arse of a stuffed dragon.]] Feferi dies? [[http://www.mspaintadventures.com/?s=6&p=005233 Lands on a pile of horns which HoNk.]] Kanaya dies? We get [[http://www.mspaintadventures.com/?s=6&p=005249 Karkat's reaction.]]]]
** What Vriska decides to do to help the guy she crippled intentionally for a laugh. Why, [[http://www.mspaintadventures.com/?s=6&p=004249 give him a house]] [[http://www.mspaintadventures.com/?s=6&p=004250 entirely composed of stairs]], of course!
** [[spoiler: You are now [[BigBad Jack Noir.]] [[KickTheDog You have just murdered an innocent family]]. What will you do?]]
** There's also [[spoiler: Equius' death, which is [[http://www.mspaintadventures.com/?s=6&p=005345 presented]] in a way that's both horrifying and [[CrowningMomentOfFunny silly]] ]].
** There's also the culmination of uu having Dirk draw "porn" that is so tame it could be shown in TV for preschoolers and then we get this
--> ''uu'': IT IS NOT AS TITILLATING AS I DESIRE
--> ''uu'': HAVE THE MALE EAT THE CHILD
** And later... [[spoiler:You love having a dead sister. Having a dead sister is an experience you would highly recommend to everybody.]]
*** And yet another one shortly afterwards when he spends four panels giving [[spoiler:Gamzee]] the bad news with a machine gun...while calming elevator music plays. And then makes sure to DoubleTap.
** In the spinoff ''Webcomic/ParadoxSpace'', all of Headed for Stardom is this. [[spoiler:Gamzee]] hosts a talent show with [[spoiler:the heads of the dead trolls]].
* ''Webcomic/ExploitationNow'', sweet gobs '''Exploitation Now'''! Prior to the [[CerebusSyndrome last storyline]], at least.
* ''Webcomic/ChannelAte''. About 90% of the comics are this.
* ''WebComic/CtrlAltDel'', [[http://www.cad-comic.com/cad/20030505 here.]]
* Fireman Comics from ''Website/SomethingAwful'' were the epitome of this. ([[http://web.archive.org/web/20080215014056/www.somethingawful.com/hosted/fireman-comics/archive.htm Archived here]])
** In one comic, a man approaches a fireman to lead his son's cub troop camping trip. The fireman agrees, then buries all the children alive and starts a forest fire. When the man comes back to the fire station concerned about his missing child, another fireman refuses to help unless the worried father helps him cheat on his taxes. He then goes back on his word and instead of helping, uses the fire truck to deliver his tax forms. The fireman also steals the poor man's wallet, then seduces his wife using flowers bought with the victim's own money.
* A Softer World, all the time. For [[http://asofterworld.com/index.php?id=247 example]].
* The entire point of Webcomic/ElectricRetard. Killing small children and a giant angry naked Hitler are just the tip of the iceberg.
* It's subtle, but in one comic of ''Webcomic/GrrlPower,'' [[http://www.grrlpowercomic.com/archives/192 Sydney goes into a Thai diner, and orders something really spicy.]] Declaring it to be not spicy enough (to general astonishment) she goes and get some spicy sauce off the shelf. One of the sauces she grabs is called "Ring of Fire," with the caption "Guaranteed to make you feel like the prettiest boy in prison."
* In ''Webcomic/TheAdventuresOfDrMcNinja'', Dan [=McNinja=] manages to make ''terrorists hijacking a plane'' funny.
-->'''Dan:''' [[http://drmcninja.com/archives/comic/23p42/ Oh, don't give me that look!]] We wouldn't have had to do this if you hadn't made such a big deal about the gorilla! Honestly, so rude.
* Most strips of ''Webcomic/ThePerryBibleFellowship''
* ''WebComic/{{Precocious}}'': [[http://www.precociouscomic.com/archive/comic/2009/06/03 "Neglectful parent joke! Ha Ha! * writes angry letter* "]]
* WebComic/DirtPony: [[http://dirtpony.com/archives/77/ MACHOKE used POUND!]] (warning, very much NotSafeForWork or brain.)
[[/folder]]

[[folder:Web Original]]
* Remixes or gag dubs of the scene in Death Note where [[spoiler: Light dies]] are disturbingly popular. Here, have a [[http://www.youtube.com/watch?v=hEJVIJA-cjI Death Note/My Neighbor Totoro remix]], a [[http://www.youtube.com/watch?v=rCwbyXxSZl4& Death Note/Kirby remix]], and a [[http://www.youtube.com/watch?v=HuJGjXxGb3Y Death Note/The Producers gag dub]]. Immoral hilarity indeed.
* [[http://www.newgrounds.com/portal/view/439144 The Torture Game 2.]] Great for stress relief.
** A ''WesternAnimation/TeenTitans'' {{hentai}} parody (obviously NotSafeForWork) on newgrounds. '''BOOYAH!'''
** Pretty much anything on [[http://www.newgrounds.com Newgrounds]]. Before "Everything, by Everyone.", their slogan was "The Problems of the Future, Today!"
* [[Franchise/TheSmurfs Papa Smurf,]] [[http://www.albinoblacksheep.com/flash/papasmurf can I lick your ass?]]
* ''WebAnimation/HappyTreeFriends'' in all its gory glory. [[http://happytreefriends.atomfilms.com/ But don't take our word for it]]. Be warned, not for the initially faint of heart. Also, beware over-saturation; violence ''does'' desensitize.
** Babies falling onto rotating helicopter blades, characters having their skin pulled off, pulled backwards through the kitchen sink with the garbage disposal running, beaten by a shovel or this crowning moment of sadistic majesty: a squirrel scout dying spasmodically as the two beaters on an electric egg beater enter her eye sockets and turn her brains to jelly (which then leaks out of their head).
** The video for Fall Out Boy's [[http://youtube.com/watch?v=k3O5uy-MBBk "Carpel Tunnel Of Love"]] is one WebAnimation/HappyTreeFriends gag after another. So-gory-it's-funny moments include: bee-sting in the eye (done twice), screams of pain synced to "Whoo-hoo"s in the music, impalement, decapitation (of the band's cartoon dopplegangers, no less), and two characters having flying pipes shoot through their heads. All this in a music video of a band whose average fan is about 13 years old.
*** Possibly BECAUSE the band's average fan is 13 years old.
* [[http://www.youtube.com/watch?v=HpM2Y5Wq8C8 This video]] combines a disturbing scene from ''VisualNovel/HigurashiWhenTheyCry'' with the song "What Is Love" by Haddaway. The scene was utterly fucked up in the original; it's gut-bustingly hilarious with the musical accompaniment.
* ''Roleplay/SurvivalOfTheFittest'' has a rampage by [[AxCrazy Wade Wilson]], along with [[TheScrappy Carson Baye's]] [[AndThereWasMuchRejoicing death]].
** And now we can add... pretty much everything [[SmallNameBigEgo Jimmy Brennan]] does. [[http://s10.zetaboards.com/SOTF_V2/topic/7283191/1/ His first thread]] (possibly NSFW due to ClusterFBomb) is a prime example of it; he starts out by [[BringMeMyBrownPants peeing himself]] and running around screaming and crying. And then... well, let's just say according to him ''[[GentleGiant Craig Hoyle]]'' will rape everyone and wear their skins as a coat (which reached MemeticMutation territory). One could also make a case for [[http://s10.zetaboards.com/SOTF_V2/topic/7317305/1/#new Richard Han's death]] as well, in which he falls off a cliff, and [[NotTheFallThatKillsYou apparently has enough time to think out what his last words were going to be]] ("YOU WIN THIS TIME, GRAAAVIIIIITYYYYYYYYY-"). And then if that weren't enough, he falls ''[[http://s10.zetaboards.com/SOTF_V2/topic/7315953/1/#new into another thread]]'', still screaming.
* The somewhat popular G-Mod Machinima/ChristianBrutalSniper series (viewable [[http://www.youtube.com/watch?v=iczmIosE4z4 here]]), crosses the line so many times with it's joyously-nonchalant killer of a protagonist, it's freaking hilarious.
* [[http://www.youtube.com/watch?v=CsTVkiXxDUo This video]] of Euphemia from ''Anime/CodeGeass'' [[spoiler: killing "Elevens"]] to [[MemeticMutation Caramelldansen]].
* ''Literature/BastardOperatorFromHell'' basically has a MagnificentBastard that utterly devastates the lives of all around him for his own amusement and self-profit. Sometimes, it delves into pretty dark territory (at least relative to the fact that it's an ostensibly realistic series based around a business workplace).
* [[http://youtube.com/watch?v=CTGrjcgSeAA This mash-up]] of the Omaha Beach scene from ''Film/SavingPrivateRyan'' using sound effects from ''VideoGame/TeamFortress2''. [[http://www.youtube.com/watch?v=Y2El7BFm04Y This version]] using ''WesternAnimation/FindingNemo'' qualifies.
* Similarly, at the end of Creator/JamesRolfe's ''Film/MaximumOverdrive'' [[http://www.spike.com/video/maximum-overdrive/3061650 review]], where he puts [[Music/{{ACDC}} AC/DC]] songs in famous movies. While ''Film/HarryPotter'' doesn't qualify for this trope, ''SPR'' gets "For Those About to Rock" (a song with cannon fire!), ''Film/ReturnOfTheJedi'' gets "Thunderstruck" (at the ElectricTorture scene!), and ''Disney/{{Cinderella}}'' "has got 'The Jack'..."
* Derrick Comedy videos use this a lot. It mixes this and OverlyLongGag in [[http://www.derrickcomedy.com/2007/05/21/kp/ kp]]
* [[http://www.youtube.com/watch?v=-KOlVl77SkQ Mario! Wario! Lucario!]]
* [[http://www.youtube.com/watch?v=3_KyJRiOVVE&feature=channel_page Sweethearts. Aww...]]
* WebVideo/TheNostalgiaChick's video "Top 10 Disturbing and Inescapable Christmas Songs" featured Alan Jackson's "Please Daddy (Don't Get Drunk This Christmas)", accompanied by clips of a man assaulting his wife in case you didn't get why the song is so disturbing. After repeatedly smacking her to the ground and curb-stomping her, he starts hitting her with her own arm and saying "Why're ya hittin' yerself? Why're ya hittin' yerself?" and ''giving her noogies''. It [[{{Narm}} stops being disturbing]] by this point.
** Related is a collaboration video that WebVideo/TheNostalgiaChick did with [[WebVideo/TheSpoonyExperiment the Spoony One]], appropriately titled ''"Spooning with Spoony."'' It pretty much involves the Chick waking up next to Spoony and That Chick With The Goggles in bed with no idea what just happened, though she pretty quickly figures it out. It rapidly goes from disturbing to hilarious as the video progresses. [[spoiler: And then Benzaie shows up in nothing but a bowtie.]]
*** And now there's [[http://thatguywiththeglasses.com/videolinks/thatguywiththeglasses/specials/14606-spsp02 Spooning With Spoony 2]]! [[note]] Amusingly enough, this was Doug's idea. So the two main victims were the ones who came up with the episodes in the first place...[[/note]]
** And there's every episode of ''WebVideo/{{Ask That Guy|WithTheGlasses}}'', where his horrifically nonsensical answers benefit greatly from deadpan delivery and the way everything piles up on itself until you can't possibly take it seriously.
*** Sometimes he doesn't even wait until the Q&A:
----> ''"Oh, seig heil! Didn't hear you come in."''
*** Then Bennett The Sage cranks that up a notch.
** On the same site, [[http://www.thatguywiththeglasses.com/blog/7594 this]] Facts About Germany video.
-->Yeah, OK, so we have Wissenschafts prisons. So what? It's all [[ForScience for the sake of science]]. They do very useful tests and experiments with the prisoners there. For example, they once tested how many wigs a man must eat before a wig comes out of his ears. They also tested what happens to a man if you knot his penis and let him drink of water. And last year, they tested how long you have to leave two men in a room until one man eats the other one. Could you live without the answers to these questions? I don't think so. Yes, I know it sucks to do science experiments with prisoners, but the good news is, um, we are also making the best porn movies in the whole world.
** Also pretty much the regular schtick of Video Game Confessions. So far we have a masochistic, Stockholm Syndrome-afflicted Princess Peach, a raving drug addict Sonic, a CampGay Link who keeps hitting on women [[UnsettlingGenderReveal despite his best efforts]], and a sadistic GroinAttack-happy Samus Aran.
** Tickle Me Amy. A deadpan childlike voice demanding increasingly vulgar sex acts including "shit on Amy's face" and "give Amy golden shower" is made hysterical due to ostensibly coming out of a cute monkey doll. The [[WebVideo/TheNostalgiaCritic Critic's]] expression of frozen horror helps a lot too.
** On his Siskel and Ebert tribute, he shows a rapidly scrolling list of the "religions he's prejudiced against". This is pausable and most of them ''can'' be made out. Some of those include [[spoiler: m Baha'i Faith, Confucionism, Catholic, Muslim, Shinto, Zoroastrianism, The Force, Druze Jainism, Methodism, Taoism, Wicca, The Movement, Mandaeans and Sabians, Unitarian, Universalism, Hellenistic, Left-handed path science, [[RuleOfFunny Whatever religion the Oompa Loompas practice.]]]]
---> "''Especially'' the middle one."
** In his Stephan King mini-series reviews, he gets increasingly hammered through the drinking game in play. Hilarious enough, but then you realize that it's Stephen King, the author famous for recovering from ''[[ComicallyMissingThePoint Alcoholism]]''
** Ma-Ti attempting to give a review. No fucking clue as to what:
---> (Puppet voice) And thats why Film/MaryPoppins got an abortion, and became a revolutionary.
** Also from Bargo. Three words: Hand Puppet Sex Trade.
* On a related note... [[http://www.youtube.com/watch?v=oQp7Id8iRA4 Keyboard Kid.]]
* A handful of WebVideo/YouTubePoop[=s=] tend to do this, [=AwfulFawful=]'s in particular.
* [[http://www.youtube.com/watch?v=UR-SIn8oCZQ This]] ''VideoGame/AceCombat'' video. [[spoiler: PJ getting killed?]] Not funny. [[spoiler: PJ getting killed]] followed by Mor- sorry, [[spoiler: AWACS Thunderhead]] being revealed as the perpetrator, who was just trying to get them to "cut the chatter"? Hilarious overkill.
* ''"[[ShockSite 2 Girls 1 Cup]]"'' crosses the line twice. If the video itself doesn't, the reaction videos certainly do. [[http://www.youtube.com/watch?v=hIsSC8ftezY&feature=related Kermit's]] [[http://www.youtube.com/watch?v=4oSdPHUGU3A reaction]] (which even got a [[http://www.youtube.com/watch?v=PVrAY0tR9HA reaction reaction]]) is by far one of the most hilarious.
* ''WebAnimation/DrTran'', anyone?
* The infamous "[[MurderSimulators No Russian]]" mission from ''VideoGame/ModernWarfare 2'' crossed the line even for many gamers. For others? '''MO-MO-MO-MO-''[[http://www.youtube.com/watch?v=701ViESIejQ MONSTER KILL!!!]]'''''
* [[http://www.youtube.com/watch?v=ojO3XvBIT0Y Slug Bait!]] Telling you what happens would ruin it. Watch it for yourself. And read the lyrics, most importantly.
* ''[[http://www.youtube.com/watch?v=0SlWeXaThtE&feature=response_watch The Ganonator]]'': Morshu getting shot once for a BallisticDiscount? Disturbing, maybe. Morshu getting shot many times... and then his guts fall out... followed by [[spoiler: a hamburger]]? Hilarious.
* Even Wiki/TVTropes has examples!
* [[http://www.youtube.com/watch?v=cnDa7bLg8QY This]] fan video about Kamina doing his first combine goes wrong, it becomes depressing... But then straddles on to funny.
* Go watch the ''VideoGame/MassEffect2'' [[http://www.youtube.com/watch?v=ZkRxe_R6SqI Death]] [[http://www.youtube.com/watch?v=OVifl3BBZ0I Compilation]]. Naturally, getting any of these in the actual game can be [[TearJerker heartbreaking]], or even [[HeroicBSOD blue-screen inducing]]. However, after a while, [[spoiler: seeing someone get taken away by seeker swarms only to have them pop up fine and dandy five minutes later... and then another one... and another...]] becomes less horrifying and more... morbidly funny. Or [[DudeNotFunny am I the only one?]]
* [[http://failblog.org/2010/03/27/sympathy-fail/ This]] Fail Blog entry.
* ''WebVideo/DragonBallZAbridged'' is a case study in this trope. It's TheAbridgedSeries of an anime featuring numerous evil villains, the abridged version leaves in all of their MoralEventHorizon moments of gratuitous violence. Yet there's always some detail that goes far enough to make the violence funny, whether it's Vegeta turning Goku into a squeaky toy by cracking his ribs, Freeza counting StockPhrases as he mows down civilians, or Dodoria saying he [[spoiler: (or rather, she)]] likes kids because "they don't leave much of a mess."
** Four episodes in and Season 3 [[UpToEleven has already done this multiple times for every episode.]]
* [[http://www.youtube.com/watch?v=mxENtpLRXcQ Alex DeLarge: International Man of Mystery]]. "Oh, ''behave!''"
* [[http://www.youtube.com/watch?v=3LPzT4opyww This video]] of a recreation of a Spongebob scene does things... Differently. NSFW.
* The Ultimate Orgy flash cartoon by NSFW studios IS this trope.
* [[http://www.youtube.com/watch?v=SeaweVywMfM Black People Are Annoying]] zig-zags the heck out of the line when it comes to racism. Crosses the first time when [[spoiler: one guy says [[ExactlyWhatItSaysOnTheTin black people are annoying]].]] Crossed a second time when [[spoiler: the rest of the interviewees start to agree with him.]] Crossed a ''third'' time when [[spoiler: the camera turns around and shows all the interviewers are black, something the interviewees would have seen right from the start.]] Crossed a ''fourth'' time when [[spoiler: the black people agree with them.]] Crossed a '''''fifth''''' time when [[spoiler: the black people suggest that it be changed to Mexicans.]] Crossed a '''''sixth''''' time when [[spoiler: the white people get offended by that.]] Crossed a '''''seventh''''' time when [[spoiler: the white people say they were joking and are totally cool with changing it to Mexicans.]]
* ''Website/TheOnion'':
** [[http://www.theonion.com/articles/congress-takes-group-of-schoolchildren-hostage,26207/ "Congress Takes Group of School Children Hostage."]]
** [[http://www.theonion.com/video/overcome-stress-by-visualizing-it-as-a-greedy-hook,17828/ This Onion video.]]
** [[http://www.youtube.com/watch?v=-nuUwN4MAcA Another Onion video]] about gymnast Shawn Johnson.
* The second episode ''[[http://www.youtube.com/user/RucknTrigger No Decency]]'' GagSub of ''Manga/OkaneGaNai''. In the original, during the Russian Roulette scene the characters use a red paint bullet. In the sub, it's an aborted fetus.
* ''WebVideo/YuGiOhTheAbridgedSeries'' has "[[http://www.youtube.com/watch?v=WziyFLzOS_4 The Vagina Monologues]]", a re-dub of the first episode with most of the words replaced with vagina. Not only are the voice actors constantly cracking up, but some of the lines now have hilarious implications: "For some reason, playing a children's card game has caused my vagina to become severely injured!" Spoken by an old man.
--> "No, it's because this vagina doesn't make any ''sense''. Nobody can figure out how to do it!"
* ''WebVideo/HellsingUltimateAbridged''. Hellsing Ultimate is a gruesome and violent anime. The abridged series doesn't change the characters very much...except for Alucard. He goes from being a very serious character to an immature asshole who seems to go out of his way to piss people off. Much of the humor is derived from making fun of how violent the show is. [[http://www.youtube.com/watch?v=TgnIjJexut4 Here's episode 1]]. Warning: Lots of language, violence, and very mean words.
** Episode 5 gives one of the greatests line-crossing lines ever: the Major declaring that they'll completely destroy London, including its many landmarks... but not the Holocaust Museum. Because he hates when people deny Nazis' achievements.
* ''WebVideo/PokemonTheBridgedSeries'' features Brock as a MemeticMolester with an obsession with '''''breeeeeeding''''' [[ILoveTheDead among other things]], and has stuffed Misty inside a sack on at least two separate occasions. At one point while inside the sack, Misty finds what she believes to be a dead squirrel. [[spoiler:It's actually Brock's dead mother. [[FridgeHorror How Misty could possibly mistake human remains for a dead squirrel in the pitch-black interior of a sack makes her mini-freakout all the more appropriate]].]]
* ''WebVideo/NullmetalAlchemist'' devotes the entire character [[TheCaligula King Bradley]] to this. He dedicated an entire holiday to making fun of Mexicans, publicly executed anyone who wore green clothing on what is remembered as the worst St. Patrick's Day ever, and generally gets off to committing genocide and other atrocious acts.
-->'''Bradley''': (about the Philosopher's Stone) Why with that puppy, EquivalentExchange goes right out the window! You can create things out of thin air! Wish I had the bleedin' stone; I could create a good excuse for executing all those rotten foreigners! Ah, just joshing, I don't need an excuse.
* [[http://www.youtube.com/watch?v=B0Rau01wbeo This video.]] The first few seconds makes it look very offensive, while the rest of it makes it one of the most offensively [[CrowningMomentOfFunny funny]] things ever.
* WebAnimation/LlamasWithHats: Carl's antics cross the line so many times the line pretty much self-destructs. Then [[SerialEscalation he crosses it again.]]
* [[https://www.youtube.com/watch?v=-evIyrrjTTY This Land is Mine]]. Special mention goes to the children being used as bloody dominoes by the archer at 1:05.
* In an episode of WebVideo/GameGrumps, Creator/{{Egoraptor}} discusses a possible epitaph for a pedophile's gravestone: [[http://www.youtube.com/watch?feature=player_detailpage&v=9pvBS_YV9Us#t=287s "At least I did it."]]
* ''WebVideo/TheAngryVideoGameNerd'' can get like this when he begins a scatological tirade. It's funny because [[VulgarHumor someone strung together that many vulgar and disgusting words into a single thought]].
* The [[WebVideo/HitlerRants Downfall parodies]], full stop. It's UsefulNotes/AdolfHitler and his wacky adventures with his RagtagBunchOfMisfits!
* [[http://www.youtube.com/watch?v=2bwcrAe8Rqo Legos 9-11]] is a flash animation by Tmst, that basically has George W. Bush simulating 9-11 as if it was done with LEGO. Naturally, since it's a satire against the then-president's intelligence and the last part of it has him invade Legoland because he choked on a LEGO man through his stupidity, it very easily falls into this trope.
* Have you ever wanted to know more about ducks when watching your favorite [[WesternAnimation/{{Ducktales}} childhood cartoons]]? The answer is no. '''[[http://www.youtube.com/watch?v=_1v_EcjeIkg No, you have not.]]'''
* During LetsPlay/TheRunawayGuys' Super Msash Bros tournament, LetsPlay/AttackingTucans disses [[LetsPlay/ProtonJon Proton Jon's]] upload schedule saying that the reason he doesn't upload very often is because Jon has AIDS. [[http://www.youtube.com/watch?v=0Zjl6U69_4A&list=PLQ-nEMx5LgUkA3bnr5Uot8q-BEEACBqCi#t=12m14s Jon didn't like that.]]
* The jokes in the Netflix original series ''Series/OrangeIsTheNewBlack'' sometimes do this, such as the ones based on the insane racism of the prisoners, or when Vause threatens to rape Doggett, or when Chapman threatens to rape Dina.
* [[http://www.catsthatlooklikehitler.com/cgi-bin/seigmiaow.pl Cats that look like Hitler.]] Enough said.
* An ImageMacro of [[http://i.imgur.com/yQ8lPdr.jpg Malaysia Airlines Flight 370]] that called them 2014's hide-and-seek champions. So badly TooSoon it becomes funny again.
* '''''[[Webesite/TimeCube TIMECUBE]]'''''. Good god, Gene Ray insults Christians and scientists alike and calls everybody idiots and at one point calls free speech in America "Bullshit". But they way he insults everybody so much, the weird fonts, and the ''huge length of the page'' among others make this one of the most hilarious sites on the internet.
* [[http://knowyourmeme.com/memes/ebola-chan Ebola-Chan]], the anthropromorphic verision of the Ebola Virus.
* In-universe in the ''WebAnimation/HomestarRunner'' episode "Costume Commercial". The "Marzipan" "costume" is just a g-string, succubus tail, and cat ears. To quote Marzipan herself, "This is so offensive... that it's not really offensive anymore!"
** Crosses the line a third time when [[spoiler:[[DiscoDan Coach Z]] puts it on]].
[[/folder]]

[[folder:Western Animation]]
* ''WesternAnimation/{{Metalocalypse}}''. The whole show.
* ''WesternAnimation/{{Superjail}}'' is about the same.
* ''WesternAnimation/{{Futurama}}'' is good at this.
** In "Bender's Big Score", their TakeThat against Fox Network starts out funny, but then just gets petty. But when the Professor claims that the executives were ground into a powder, which the Professor then pours down his pants to stop the burning? Back to funny again.
** In "Beast With A Billion Backs", Bender wants to make a [[DealWithTheDevil Deal With The Robot Devil]]. The Robot Devil will give Bender what he wants (an army), but only if Bender is willing to give up his firstborn son. Bender fulfills his end of the bargain by [[CrowningMomentOfHeartwarming reuniting with his long-lost robot son who was waiting for him for years to come back]] -- then ''punting the robot child into a vat of molten metal''. The Robot Devil expresses amazement at Bender's brutal act (commenting that it's brutal even by ''[[EvenEvilHasStandards his]]'' standards), and Bender simply replies, "No backsies." Admit it, you laughed.
** In "Bender's Game", miners of dark matter in Alaska are effecting the environment. A white rabbit is barely visible in the snow and then a truck passes covering it with grime and it has the saddest little face. Then when you're starting to feel bad, it gets eaten by a polar bear.
** Nothing compared to the third-season episode, "Amazon Women In the Mood", where the plot focuses on several main characters being [[BlackComedyRape raped to death as a punishment]]. The humor comes from the fact that most of the (all male) characters condemned to death are [[FetishFuel actually looking forward to being raped by bone-crushingly giant women]]. As exemplified in the scene where the verdict is passed, and the reactions switch instantly back and forth from bottomless horror to utter joy... except for Kif, who remained horrified through the whole ordeal.
--->'''Zapp:''' What are you, gay?
*** It breaks down exactly how you figure. At the sentencing, Zapp is excited. Kiff is horrified. Fry... cannot decide, so his expression ALTERNATES between joy and fear.
** Hedonism-bot...
-->'''Hedonsim-bot:''' I apologize for nothing!
* In one episode, Dr. Zoidberg goes berserk while at a gym, frothing at the mouth and acting like a maniac. He interrupts an exercise class for pregnant women, and startles one so much she gives birth.
--> '''Trainer:''' Is there a doctor in the house?
--> '''Zoidberg:''' '''I'm''' a doctor.
--> ''(several more babies are born)''
* ''WesternAnimation/AvatarTheLastAirbender'' has a non-violent example in the episode "[[WhoWouldWantToWatchUs The Ember Island Players]]", when they were re-enacting [[spoiler:Jet]]'s death. Making fun of what is probably the most tragic event in the series where a GovernmentConspiracy kidnapped, brainwashed, and killed a ''teenager''? DudeNotFunny Representing his Brainwashed nature with wacky hair, hooks for hands, ''googly eyes'', and droning "Must... serve... Earth King" while his death is depicted with a hollow rock prop falling on top of him that the actor ''fails to get into properly''? Hilarious.
** The flower in his mouth, or the actor's beer-belly. Zuko and Sokka's responses to the reenactment didn't detract from the funny either.
** They made [[spoiler:Zuko]]'s FamousLastWords [[spoiler: Honor!]]
** The fans' HoYay jokes about Aang and Gyatso. Usually squick, but when [[http://www.deviantart.com/download/147835901/Avatar_Discovers_Shipping_3_by_Booter_Freak.png Chris Hansen]] gets involved...
* ''WesternAnimation/SouthPark'',
** "[[Recap/SouthParkS5E4ScottTenormanMustDie Scott Tenorman Must Die]]": After a series of petty torments, Cartman takes a revenge that crosses the line so many times it's difficult to know whether to be horrified or not. For anyone that is unfamiliar, Cartman, [[spoiler: after being tricked into buying Scott (a random teenage boy)'s pubic hair for ten dollars, and then getting scammed again when he attempted to recoup his losses (including being forced to sing "I'm a Little Piggy" in an attempt to get his money back), then being publicly mocked by having the "Piggy" video shown after his own video trick is dismissed, he engages in a BatmanGambit that results in Scott eating a bowl of chili ''made from the remains of his recently killed parents''.]] Cartman even got Scott's favourite band, Radiohead, to see Scott cry, and insult him for it! [[ArsonMurderAndJaywalking What a jerk.]]
--->'''Cartman:''' ''Oh let me taste your tears, Scott! Oh, the tears of unfathomable sadness! Mmm-yummy!''
** It's even more twisted. In "201" we learn that Scott's father was also [[spoiler: Cartman's biological father, and covered up the truth to protect his football career]]. Cartman's reaction? He's devastated -- because [[spoiler: his dad was a ginger!]] It's not crossing the line twice so much as obliterating it.
** In the DVD commentary to "It Hits the Fan", Parker and Stone say that the network wouldn't let them say "shit" a few times but were fine with them saying it '''162''' times (and keeping count on-screen). Actually, ''WesternAnimation/SouthPark'' [[BlackComedy runs on this trope.]]
** Relatedly, every time the MPAA told the creators they objected to something in ''[[WesternAnimation/SouthParkBiggerLongerAndUncut Bigger, Longer, and Uncut]]'' Parker and Stone just made it ''worse'', and were then told it was okay. Possibly, the MPAA was afraid of seeing what the pair would do if they objected to the second version.
** It's said that they made ''Team America'''s sex scene [[CensorDecoy much dirtier than they intended to be]] knowing the MPAA would want to cut stuff from it.
** Another especially extreme example is in "Night of the Living Homeless" from season 11, where someone decides to "take the easy way out" and shoot himself in the head... Before turning out to be MadeOfIron (borderline ImplacableMan) and surviving multiple gunshots, ending with him spending his last moments slipping on his own blood. This manages to cross the line about fifty times in thirty seconds. It is entirely possible to survive a single bullet wound to the head, depending on where you're hit and how big the bullet is. So long as you get medical attention quickly to keep you from bleeding out. But the point is, if it's survivable with treatment... it's not a very quick death. Certainly not an INSTANT death.
** In 'Le Petit Tourette', a pedophile [[spoiler: shoots himself when he finds out he is on ''{{Series/Dateline}}'' with Chris Hansen.]] At first it's in really bad taste, and then it becomes hilarious when [[spoiler: he's followed by many other pedophiles who proceed to shoot themselves as well.]] Then there was the guy who did it because there were no brownies.
** "[[Recap/SouthParkS14E9ItsAJerseyThing It's a Jersey Thing]]", just that whole episode. Taken as an attack on ''Series/JerseyShore'' instead of the actual state of New Jersey, it's just an irreverent TakeThat. It doesn't cross the line at all. Well, maybe at the point where they [[spoiler: call Bin Laden for help... but not before that.]] The episode's climax, when [[spoiler:Al Qaeda saves South Park by flying hijacked planes into the Jersey Shore people]], crosses the line infinity times.
** "[=HUMANCENTiPAD=]" crosses the line Graham's number times.
** "Cartman Joins NAMBLA" doesn't merely destroy the line. It takes it out back, shoots it in the head, runs it over with a tank, and dumps its remains in a river. To recap, Cartman decides he needs new, more mature friends, so he decides to join the North American Man-Boy Love Association after misunderstanding Dr. Mephisto, who wanted Cartman to join the North American Marlon Brando Look Alikes. The pedophile NAMBLA group decides to use Cartman as a poster child and urges Cartman to invite his friends to a banquet to honor Cartman where the pedophiles also attempt to have sex with the boys. Meanwhile, in the B plot, Kenny is threatened when his parents decide to have another baby, so he spends most of the episode trying to either injure his fathers' testicles or abort the fetus, which eventually devolves into his father simultaneously vomiting, defecating, and bleeding into a trash can after Kenny crushes his testicles, gives him a chocolate milk and vodka drink laced with extra-strength abortion pills, and breaks his nose on an amusement park ride. This culminates with a ScoobyDoobyDoors segment with the children, both NAMBLA groups, the FBI, and Kenny chasing his mother with a plunger. The episode ends with Kenny's father being mistakenly raped by all the members of the pedophile NAMBLA. After watching this episode, you may not even be sure the line exists anymore.
** Creator/RussellCrowe decides to fight cancer. He can't find cancer, so he beats up a man ''with'' cancer.
* ''WesternAnimation/FamilyGuy''
** Stewie beating the crap out of Brian when he owed him money becomes funny again about when Stewie pulls out a gun and shoots him in the knees. (The line, of course, varies. Other didn't find it funny in the slightest until the flamethrower...)
*** What makes this particular event HilariousInHindsight is that during the initial run of the show, Stewie's predilection for ray guns stemmed from the censors. According to them, Stewie was not allowed to use real weapons because "authentic" violence from a baby was just too much, but laser guns were OK. This scene is a one of the major [[TakeThat "take that"s]] Creator/SethMacFarlane et al. threw at the censors during their post-cancellation "invincible" period.
** There's also the episode when Peter claims Chris is dying so his favorite show can come back on the air. When the charity points out they've bought the rights to Chris' death, Peter says he healed him. Fast-forward to people dancing on the Griffin's lawn asking for Peter to heal them. Lois, who still doesn't know about Peter's flimflam, wonders if that's chanting she's hearing. Peter assures her that's ridiculous, while edging towards her holding a fire poker. Yes, the implication is that Peter was about to commit murder (or at least assault) over a TV show.
** The whole show has become this ever since around the season 4-6 era.
** Terri Schiavo: The Musical. Yes, it's ExactlyWhatItSaysOnTheTin...with preschoolers. And it's ''hilarious.''
** In "Brian Griffin's House of Payne" -- when Stewie [[spoiler: falls down the stairs and cracks open his skull, only to wake up, vomit, and pass out again, it's pretty funny. Then it gets pretty squick. Until a raccoon is seen snacking on the exposed brain tissue, and Chris' only reaction is that raccoons look like little robbers. And then Peter and Lois' reaction to the whole ordeal...yeah.]]
** Carter is implied to have [[spoiler:molested Lois]], and has sex with a girl who is [[spoiler:implied to be a sex slave]], in the same episode.
** In one episode, Lois is seduced and cheats on Peter (with UsefulNotes/BillClinton) and the fallout is treated as troubling and difficult for the couple to reconcile over. Then he seduces Peter too, and it's just hilarious.
** One cutaway joke has two Jewish slaves working on the pyramids with one of them saying to the other that all peoples have to go through hard times but they are getting theirs early and after this it will be all smooth sailing for them. {{Hulu}} uploaded the clip on Website/YouTube where one of the long time most liked comments is "It's funny because of the Holocaust."
** In the episode where Brian goes back to college, the seminar on rape.
-->'''Teacher''': Look to your left. Now, look to your right. Statistics indicate that [[RapeAsComedy both of those men will rape you.]]\\
'''Girl in class''': *looks to her left*\\
'''Guy on left''': I'm not gonna rape you.\\
'''Girl''': *looks to her right*\\
'''Guy on right''': I might.
** A pre-cancellation example: In the episode where Chris moves away to become an artist, Peter reveals that he has a button on hand that he can press to blow up Chris, and it seems like a little too much {{Flanderization}}. Then it turns out that it doesn't work because Peter put the chip in the wrong baby, followed by some random girl exploding, and it's hilarious.
** In the episode Herpe The Love Sore after Stewie [[spoiler: gets herpes from Brian]] no one wants to be around him. He mentions that he's lonelier than a Kennedy family reunion. A cutaway shows said reunion with all the tables empty except for one guy. The guy asks "Where is everybody? Oh Yeah they're dead." He then immediately gets shot in the head by an unknown assailant. That crosses the line so much there's no name for the number of times it does. Brafillion? No that's not it but it's close.
* ''WesternAnimation/AquaTeenHungerForce'' occasionally waddled into the deep end of the pool, killing Carl in horrible ways, turning him into an eyeball monster, or with horrific clones and grisly murders.
** Then there's the episode in which Meatwad plays a video game that lets him contact the dead. Shake essentially gets mad that Meatwad is better at the game than him, [[spoiler: So he kills himself in order to get into the game and beat him]]. The act of him doing is an odd cross of funny and morbidness, and it crosses the line by explaining, in detail, all the horrible things he does to do it ([[spoiler: He drowns himself in a pool of piranhas by drugging himself with sleeping pills and sticking a hose in his mouth connected to Carl's car's tailpipe,]]). It then goes back to being funny after Carl completely disregards it (More concerned that Shake did it in HIS pool with HIS car's gasoline).
--> '''Carl''': Fryman, I am so sorry... that I won't be able to press charges.
*** Creator/AdultSwim's bumper preceding this episode on its original air date lampshades this by stating "...Shake does a horrible thing."
* The [[WesternAnimation/{{Animaniacs}} Slappy the Squirrel]] skit "Soccer Coach Slappy" has the running gag of Skippy, a young boy squirrel who happens to be Slappy's nephew, getting hit with the soccer ball, resulting with him crying upon impact. At first, it's rather disturbing, but it gets funnier with each subsequent ball to the face, complete with NonSequiturThud.
* A similar situation happens in a BaseballEpisode of ''WesternAnimation/TinyToonAdventures''. Hampton - who obviously doesn't want to play - gets beaned with the ball, and it's not funny the first time; but when it happens again and again, even ''after the coach takes him out and has him warm the bench'', it starts to get funny. Finally, at the end, when Hampton claims that he "learned my head was a magnet for baseballs" you can't help but laugh.
* ''WesternAnimation/DrawnTogether'' has a number of these. An example is in Captain Hero's childhood montage where he falls off of his training bicycle and scrapes his leg in a stereotypically childish manner. When he reveals his "scrape", it turns out that a chunk of his leg is missing. Basically the whole point of ''Drawn Together''.
* ''WesternAnimation/KorgothOfBarbaria'' frequently demonstrates that it is one of the most violent and gory cartoons ever made (some of the violence puts even shows like ''Happy Tree Friends'' and ''Manga/ElfenLied'' to shame). Over the course of the pilot episode, at least 20 characters are brutally killed in comically over the top, graphic, and creative ways.
* ''WesternAnimation/InvaderZim'' employs this trope for almost everything the titular character does. For example, stealing a major organ from each of his classmates in order to perpetuate his {{Masquerade}} is horrifying, but stealing too many organs and becoming a ridiculously bloated blob of stolen organs to the point where an intestine rolls out of his mouth like a tongue is hilarious.
** And then he gets interrogated on his anatomy...
--> '''Dib:''' ...spleen?
--> '''Zim:''' Three different colors.
** "I love you, cold unfeeling robot arm!"
** And [[WhatTheHellHero Zim's abandonment]] of the blob-creature from "Abducted"...
* ''WesternAnimation/TheItchyAndScratchyShow''.
* ''WesternAnimation/TheSimpsons'' itself has long thrived on this, especially in the earlier seasons.
** "Duffless" (1992) has a sequence that goes from offensive to hysterical fairly quickly when Homer and a roomful of other Springfield citizens who've been arrested for DUI are shown a short film that Chief Wiggum promises will [[ScareEmStraight "scare the pants off of you."]] The film begins (after Chief Wiggum accidentally shows home movie footage of a barbecue he had where he ate a hot dog in a kiddie pool wearing nothing but a Speedo and spraying his wife with a hose as part of a prank) with a blood-splattered accident scene on the highway, which smarmy actor Troy [=McClure=] laments before [[MoodWhiplash abruptly switching to his obnoxiously cheery greeting]] of "Hi, I'm Troy [=McClure=]! You might remember me from..." The film continues with a montage of gory car crashes and vehicular manslaughters (which we never actually see) set to "wacky" chase music and with Troy providing a cheesy 1950s-style narration full of [[{{Pun}} Incredibly Lame Puns]] like "Here's an appealing fellow. In fact, they're a-''peeling'' him off of the sidewalk!" The other DUI offenders are visibly shocked or horrified by this spectacle, with one of them struggling not to vomit - but Homer laughs uproariously, commenting that [[ComedicSociopathy "It's funny 'cause I don't know him."]] The films that we might remember him from? Alice's Adventures Through the Windshield Glass and The Decapitation of Larry Leadfoot.
** In the opener of "[[Recap/TheSimpsonsS23E3TreehouseOfHorrorXXII Treehouse of Horror XXII]]", Homer steals candy for charity and drives off to the desert to eat them, [[Film/OneHundredAndTwentySevenHours only to be trapped under rocks in a ditch.]] Terrible, but then he chews his arm off with Vampire Teeth. [[EpicFail And chews off the wrong arm]]. Then when he has no arms, he sees the candy is actually all vegetables planted by Bart and Lisa.
** The Hansel and Gretel parody in "[[Recap/TheSimpsonsS12E1TreehouseOfHorrorXI Treehouse of Horror XI]]". Homer drops the children off in the woods and says "maybe you'll run into your other brother and sister". Cue them finding skeletons of two children identical to them.
--> '''Lisa:''' Let's face it, they're not good parents.
* ''Series/WonderShowzen'' tried to do this with almost every sketch, sometimes even crossing the line a ''third'' time.
* In an episode of ''WesternAnimation/MyLifeAsATeenageRobot'', XJ-9 (aka Jenny) is accidentally sent to kindergarten. Because of her... lack of want to be there, and the teacher's complete and total obliviousness to what she really is, Jenny becomes the black sheep of the class. It all comes to a head when she is repeatedly hit with a ball at recess while trying her hardest to be nice. The result? Jenny takes the ball, and plays hardcore- dodgeball/pinball on all the 5 year olds present, demolishing the class, possibly causing many concussions. The teacher is horrified, but all the kids are ''impressed'' (once they regain consciousness, at least). ''WesternAnimation/ThePowerpuffGirls'' had an even more violent dodgeball incident on the Gangreen Gang.
* ''WesternAnimation/MonkeyDust'' lives (or rather lived) off this trope what with the suicides, pedophile jokes, drugs abuse and random sex scenes in it. Most people never managed to cross the line a second time.
* ''WesternAnimation/RobotChicken''. [[http://robotchicken.wikia.com/wiki/The_World%27s_Most_One-Sided_Fistfights Just]] [[http://robotchicken.wikia.com/wiki/Care_Bear_Genocide a]] [[http://robotchicken.wikia.com/wiki/Rainbow_Brite_Breaking_%26_Entering few]] [[http://robotchicken.wikia.com/wiki/Give_a_Mouse_a_Cookie of]] [[http://robotchicken.wikia.com/wiki/Screw_Youssical_the_Musical the]] [[http://robotchicken.wikia.com/wiki/She-Ra%27s_Aunt_Flo relevant]] [[http://robotchicken.wikia.com/wiki/Misery,_My_Sweet_Babboo examples.]]
* ''ComicStrip/TheBoondocks'' has managed to milk comedy and pathos out of exorcisms, PrisonRape, blind people getting beaten up, and historical figures (namely Dr. Martin Luther King, Jr.) using racist language and yelling at a crowd of black people over losing their way.
* Some ''WesternAnimation/SpongebobSquarepants'' episodes. Especially "Krusty Krushers". Like spinning around [=SpongeBob=] and Patrick to pieces, cementing the two in the ring. (Either the first or second cross). Autographing the wet cemented remains with," Jim was here", on [=SpongeBob=] and "My foot was here", on Patrick. (Hillarious either way). Or earlier, them getting gargled only to be returned to normal with a toilet plunger.
** Bear in mind that [=SpongeBob=] and Patrick don't mind the pain at all and actually giggle while the wrestlers write on them while they are encased in cement.
** In "Dying for Pie":
-->'''Mr. Krabs''': The boy ''cries you a sweater of tears'', and you ''kill him''.
** And Squidward getting maimed in "The Camping Episode" is freaking hilarious.
* In a scene in ''WesternAnimation/TheVentureBrothers'', Brock is torturing an enemy henchman for information by squeezing his testicles, then abruptly stops when he feels a lump. The henchman is distressed at the news. This somehow turns the scene from "nasty" to "hilarious".
** "[[http://video.adultswim.com/the-venture-bros/car-rage.html They hit me with a truck...]]"
** The fact that Dr. Venture [[PoweredByAForsakenChild powered his pleasure chamber with the trapped soul of an orphan]]? Horrific. The fact that his only defense is that he didn't use ''all'' of it? Hilarious.
*** Goes right back to horrific [[FridgeLogic if you consider]] what was the sequence of events that led to the conclusion that an ''orphan'' was the solution?
** ''Handsome Ransom.'' The ''entire'' episode is nothing but crossing the line twice. Perhaps the most notable example would be when the Monarch puts on the [[KidSidekick Wonder Boy]] outfit and tells Captain Sunshine he can [[PrecisionFStrike fuck]] Wonder Boy and his greatest enemy at the same time.
* ''WesternAnimation/AmericanDad''
** A counter was made saying 100 characters would die for their 100th episode. It actually goes a while without anyone dying until Stan blows the legs off a dog just to see which one has a tracking chip that's also an explosive, which at first is in bad taste until he comes out saying he helped the dog and it will be okay, only to have the counter show its first death. Another example came later in the episode, when an entire bus full of minor characters falls off a cliff. Announcing that a hundred recurring characters are going to die over the course of one episode seems like a cheap ratings ploy, but to actually kill dozens of them in a single fiery explosion is just too over-the-top to be tragic.
** Principal Lewis knocking out Steve with a coffee pot? Oh my God! Leering over and evilly laughing at him? Laugh-out-loud funny.
** Roger testing out his eggnog in "Season's Beatings" on the rats.
** Everything about Roger's Ricky Spanish persona.
* The montage of Joker killing Batman a good dozen times in the "Comicbook/EmperorJoker" episode of ''WesternAnimation/BatmanTheBraveAndTheBold''. Death by crushing, acid, fire, sawblades, guillotine, sharks, spikes, train, electric chair... WhatDoYouMeanItsForKids
* In one episode of ''WesternAnimation/{{Robotomy}}'', the main characters join the "Sunshine Class", a group over-emotional robots who are treated like mentally-challenged children, in order to skip out on a test. The second line crossing is when the teacher of the class reveals that [[spoiler:her real job is to kill the over-emotional robots by launching them all into the sun]].
* ''WesternAnimation/FriskyDingo'': In the premiere of the second season, Taqu'il has gotten in hot water for releasing an album entitled "Ballocaust." The cover has him wearing an SS-themed basketball jersey and cap while holding a basketball emblazoned with a swastika as well as a chain around the neck of a bald woman wearing a ''bikini modeled after Nazi death camp uniforms.'' Taqu'il's (Jewish) lawyer doesn't help fix the problem.
-->'''Taqu'il's Lawyer:''' I see a celebration of life, like ''HoopDreams'' or ''Film/FindingForrester''. Maybe they're going to find Forrester!...In Poland.
* If ''WesternAnimation/TheRenAndStimpyShow'' managed to cross the line once, the ''Adult Party Cartoon'' was an exercise in crossing the line twice (and then some), particularly "Onward and Upward" where grossout jokes abounded past what was acceptable (and tolerable), and "Naked Beach Frenzy'' where the nudity card broke the scale.
* An episode of ''WesternAnimation/AlmostNakedAnimals'' centers around making LovableCoward Octo [[BringMyBrownPants ink the bed]] repeatedly. Audacious in its own right. The second line-cross comes when his friends realize that his ink stains are in their likeness, and Howie is just trying to get one in his likeness.
* For an animated program on Creator/DisneyChannel, this happens with startling regularity on ''WesternAnimation/PhineasAndFerb''-- mostly in HarmlessVillain Doofenshmirtz's {{Imagine Spot}}s. An obvious example is the time he planned to found a college of Evilology and, among the projects, the audience was shown the (smoking) skeletal remains of an [[BlackComedy infant]]. Another can be found in the episode where he planned to use a space laser ({{in|sistentTerminology}}ator) to destroy stuff. Including morning talk show hosts. After (theoretically) using it, the host's arms are still intact, clutching at his mug of coffee. The rest of him is nowhere to be seen.
* ''WesternAnimation/TotalDrama'': Chris McLean. Almost everything he makes the contestants do fits this trope, but [[spoiler: placing a C-4 charge on Owen's face takes the cake. And that was just the first episode of the 4th season.]] Not to mention the [[TheyKilledKennyAgain interns.]]
* WesternAnimation/{{Danny|Phantom}} ''himself'' does this an awful lot. Most notable: Him sneaking out of the girl's locker room while being intangible ''[[RunningGag tw]][[PowerPerversionPotential ic]][[Radar/DannyPhantom e.]]''
* In-Universe example. A conversation between JerkAss secret agent WesternAnimation/{{Archer}} and his hilariously abusive mother Malory about his...[[AnythingThatMoves habits]]:
-->'''Archer''': Don't you want a grandkid?
-->'''Malory''': Well if I did, I'd just scrape all of your previous mishaps into a big pile and knit a onesie for it.
-->'''Archer''': ...Jesus ''[[BlackComedy Christ!]]''
** And pops up again in Season 4, when Archer states that hearing that Lana went without sex for 2 years was the third-saddest thing he'd heard that day.
-->'''Archer:''' Pam told me about a little girl who drowned [[HeroicSacrifice trying to save a puppy]].
-->'''Lana:''' Jesus, what was the ''second'' saddest?
-->'''Archer:''' [[ShootTheShaggyDog The puppy drowned too.]]
** And, hilariously enough, his reaction to the idea of his mother being dead. Or at least, Lana's reaction:
-->'''Lana''': "Jesus Christ, he's '''got an erection!'''
** ''Archer'' could best be described as "Crosses The Line Twice: The Animated Series." Probably in excess of 75% of the show's humor depends on this.
* The ''WesternAnimation/{{Recess}}'' episode, "The Box". The episode is about Miss Finster coming up with a new form of playground punishment- the box - which is just a square drawn on the blacktop. T.J. laughs at it at first, but after he's put in the box, it slowly begins [[GoMadFromTheIsolation to]] [[SanitySlippage break]] [[TroubledFetalPosition him]]. It gets to the point where Miss Finster decides to keep him in there for two more minutes than the ten he was supposed to stay in. By the time his punishment is up, poor T.J. is in the fetal position, singing "This Old Man", and speaking in the third person. Yep. A teacher psychologically tormenting a nine-year-old boy...you know, for kids!
* ''WesternAnimation/CodeMonkeys'' utilizes this with its pixel animation surprisingly well. To give just one character example, [[PointyHairedBoss Mr. Larrity]] associates "orphanage" with "''[[KillItWithFire arson]]''" and his reply to potentially life-threatening choices is often a simple "Don't care!". To say nothing of the eight wives he's had killed and/or stuffed, most certainly for inheritance reasons.
* A lot of ''WesternAnimation/MoralOrel'', especially its first season.
* ''WesternAnimation/TripTank'' is pretty much a SketchComedy version of this.
[[/folder]]

[[folder:Other]]
* 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]].
[[/folder]]

[[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.]]
[[/folder]]

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