"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 The Three Stooges-style painful fun from outright villainous squicky sadism varies from person to person but is definitely there; crossing it makes one fan's "Nyuk nyuk!" another fan's Guilty Pleasures.
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 So Bad, It's Good, but done quite intentionally.
This isn't as easy as it sounds. Shows attempting to be Darker and Edgier 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 makes a wrong turn at Albuquerque and breaks the audience's Willing Suspension of Disbelief. 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 funny's sake; any time a little exaggeration would provoke a negative reaction, but exaggeration Up to Eleven 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 Willing Suspension of Disbelief. Still others take the over-the-top so over the top that what was before unbelievable garbage is now heart-wrenching, adrenaline rushing, undiluted 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 Black Comedy, Bloody Hilarious, Dude, Not Funny!, Refuge in Audacity, Vulgar Humor. If this happens completely by accident, that's Springtime for Hitler. Part of the Sliding Scale of Comedy and Horror.
The Hilariously Abusive Childhood depends on this trope, piling misfortune on misfortune until it becomes so ridiculous it's funny. For instance, the Boarding School of Horrors in Bleak Expectations 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 Heroic Comedic Sociopath 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 Overly Long Gag.
This Canadian PSA, which features a pop group at a school assembly singing about sex, with the audience uncharacteristically eliciting a Flat "What.". 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 Up to Eleven.
One of the Valentine brothers (the vulgar one, obviously) quotes the Konami Code 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.
Similarly to Bludgeoning Angel Dokuro-chan, Dai Mahou Touge 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...)
The same team that made Excel Saga also made Puni Puni Poemi every episode of which crosses the line just as frequently as the "Going Too Far" episode.
Baccano!'s 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 Crazy Awesome and call it a day.
Ladd Russo also loves to play hopscotch with the line, such as when he uses a dead Lemure as a puppet while taunting Chane.
In their promotional campaign months before the release, Funimation showed exactly why their dub of Axis Powers Hetalia was given a TV-MA rating. This immediately had the side effect of the fandom becoming a Broken Base over the altered dialogue.
To clarify for those not familiar with the series: the protagonists are Those Wacky Nazis, 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. And it's hilarious.
China: We're not allowed to have Christmas trees in our country because they're flammable. It kind of sucks.
The ludicrous exposition in Speed Racer does this often and unintentionally.
Gintama does this very frequently with its gags, partly due to its tendency towards Vulgar Humor.
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 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...by making a wig that they place on Kondo's groin.
Let's Bible may be the most blasphemous thing to ever come from Japan. And it's only 2 chapters long. Details here.
Ghost Stories, the Gag Dub 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 a rabbit, but because you're black..."
The main characters' personalities are also changed into a 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.
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 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 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 Sicks sends his own message by forcing a man to 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.
The second season of Boku wa Tomodachi ga Sukunai has the infamous scene where Kodaka had just discovered that Yukimura is a girl and 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!
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 love him or hate him.
"I don't know where the line is until I've crossed it!"
George Carlin, who once said "I think it's the duty of the comedian to find out where the line is drawn and cross it deliberately."
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 Too Soon for such jokes. How did he defuse the situation? By launching into a recital of The Aristocrats...it was hilarious. NASA scientists are still trying to calculate just how many times he crossed the line that night.
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 Saturday Night Live when it first started, and co-writer of 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 his outrageous attempt to create his own show that spoofed Mondo movies.
Bill Maher, of course, especially in Real Time with Bill Maher. Although applying this to political jokes is what gets him in the most trouble, he arguably goes even further outside political jokes.
Don Rickles whose act mostly consists of berating his audience, usually using every cultural, racial, and religious stereotype he can cram in.
Gabriel Iglesias doesn't usually pass too far over the line, but there's one story that's been pulled from his Comedy Central stories and even nearly got him banned from The Tonight Show. 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 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... until they offered her a hefty tip to deliver said basket.
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.
And Johnny the Homicidal Maniac! 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 Watchmen: Dan and Laurie, at dinner, are trading stories and reminisce about a 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 Rorschach and Rorschach 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 Image Comics series Bomb Queen 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 Jokers Last Laugh miniseries, The Joker uses the powers of Multi-Man to escape. 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 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 Running Gag about emo villains that crossed the line into absurdity. The line that sums up how absurdly idiotic and emo he is:
Though considering Death Is Cheap 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 (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 Daredevil fame often does this, especially in the movie. It's hard not to laugh when a Red Shirt dies from a well-aimed pencil.
Preacher does this everywhere. Especially notable is the recurring villain who, already introduced bald with one ruined eye, is 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!".
Special mention should go out to The Boys which doesn't so much cross the line twice as dance back and forth over it laughing maniacally.
Managed in one Star Wars 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 Spider-ManOne More Day/Brand New Day: When 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 The Book of Bunny Suicides is all over this trope, showing increasingly bizarre and improbable ways for the cute bunnies to off themselves, and ending with a brick joke.
Transformers: More than Meets the Eye 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.
This is the single most disgusting nasty offensive thing I've ever read. And it's bloody amazing!
This piece of fanart for Team Fortress 2 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 bloody hilarious.
The same artist does it again, this time with The Spy.
Basically what happens is 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 Chaos' comments make it that much better.
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 casual instruction: "Mouths only."
Following on from that scene, the shadowdemon 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 Bella Swan Pregnant And Furious, Satan gets beaten so hard by Bella (yes, thatBella), that his internal organs start coming out of his mouth. He is left "toothless and organless", "coughing blood and trembling with pain."
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 Ice Age movies...
Some characters' antics in The Boxtrolls, such as Lord Portly-Rind using his funds to build a cheese wheel instead of a children's hospital.
Films — Live-Action
Flesh For Frankenstein. 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.
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. ''(BOOOOM...) Lexx: Sorry, what does word cancel means?
But while talking about Lexx and the carnage it left behind, let's not forget being responsible for the destruction of countless (they were counted, but I forgot how many) planets AND THEN an entire universe.
In RoboCop (1987), the prototype ED-209 enforcement drone malfunctions during a demonstration in the OCP boardroom and rips a young exec apart with an extended and over-the-topheavy 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 RoboCop 2, 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 here. Iron Man 2 has an homage to this scene—complete with such humor—when Stark leaks footage of Justin Hammer's failed armor prototypes.
They also used humorously gratuitous violence in their sketch "Sam Peckinpah's Salad Days" (from the TV series), which brought fountains of High-Pressure Blood 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 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 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.
Although Sacha does emphasize the long European tradition of mocking Americans for not being Europeans. In some parts of the world 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 Freddy Got Fingered. 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 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. 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 "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.
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 Tim Burton's Batman made us laugh as he gassed a roomful of people... to music. The 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 The MovieBatman Beyond: Return of the Joker, he makes a few really funny one-liners while revealing that he 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 The Dark Knight, Joker blows the line straight to Hell before asking if you want to know how he got those bloody scars.
Several gags in Airplane are only funny because they manage to cross the line twice.
The Big Lebowski: "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?"
This is why The Proposition'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 Peter Jackson's Bad Taste 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 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".
Riki-Oh: The Story of Ricky 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 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.
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
The Aristocrats. Any half-decent rendition should cross the line at least a dozen times, in every direction. Bob Saget practically picks up the line and jumps rope with it in his rendition.
Inglourious Basterds does this a lot, but the most awesome one is 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 John Waters. Cherish in Cecil B. Demented takes this Up to Eleven 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 Kill Bill 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 insult to her heritage, she 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 this does.
Kick-Ass: 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.
The attempted rape scene. 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?
The ending of Penn & Teller Get Killed has 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 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 Exactly What It Says on the Tin.
The House of Yes 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, 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 Star Trek movie there's a scene where 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? "I've Fallen and I Can't Beam Up!"
Over-the-top fighting scenes with premises that make them plausible:
Violence against women is really not a laughing matter, but in Denmark the egg-blowing scene from the 2006 comedy Blinkende Lygter, about 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.
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.
Lars von Trier's The Idiots, 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 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 True Art, while some definitely think it's more than admirable for what it eventually does with itself.
The gentleman's club in Mystery Team. 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.
The original CBS/Fox release of the James Bond movie Licence to Kill 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 Wilhelm Scream, and 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.
The shockumentaryTraces of Death has footage of a bear climbing a telephone pole, getting electrocuted, falling, then wrestling with animal control.
The Dictator 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 Looney Tunes. 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.
The video footage of the Hammerdroid's test malfunction (twisting around so fast it snaps the pilot's spine) evokes a That's Gotta Hurt 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.
Zazie dans la Metro somehow manages to turn a pedophile chasing a ten year old girl into something out of Looney Tunes.
The use of Country Matters in Being John Malkovich is a textbook example. When the agent shakes hands with 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.
The Jerk: 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, doesn't take kindly to this, yelling "Sir, you are talking to a nigger!", and kicks everyone's ass.
Final Destination: 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!
In example? Read the blurb on Kirk Lazarus, played by Robert Downey, Jr.: "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.
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 their mother walking out on them.
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!
Nearly the entire output of author Edward Lee was written purely to evoke this trope.
Candide by 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.
In the first chapter of Starship Troopers, 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.
Edward Gorey's The Gashlycrumb Tinies, a book where twenty-six children die in alphabetized ways.
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.
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 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 Squicky. But when she smacks grandpa in the face repeatedly with the dead fetus while berating him, it becomes a stellar example of this trope.
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.
Jonathan Swift's satirical essay A Modest Proposal 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.
Live Action TV
Strangers with Candy. 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.
The "Sam Peckinpah's Salad Days" sketch, which takes Ludicrous Gibs to even more ludicrous levels. Unsurprisingly, given it contains (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 Graham Chapman 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.
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.
The Office 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.
The Office (UK) had a similar theme: David Brent's jokes failed so badly it quickly became funny for the sheer awkwardness of his self-delusion.
Similarly, Larry David's Curb Your Enthusiasm 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.
The episode "Wishful Thinking" features a wishing well that 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. 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 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 Looney Tunes 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. You Monster!.
In a fine moment of Mood Whiplash, 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 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 The Hulk, 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 CSI: Miami and Grey's Anatomy) if cruel and gruesome. It's part of what made him an Ensemble Darkhorse.
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 Deus Angst Machina that it became an in-universe example of crossing the line twice: when 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 The End of the World as We Know It plot? No - he breaks down in uncontrollable laughter. A moment later, Buffy joins him. And so does the audience.
In the first episode of Red Dwarf, Lister's shock at 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.
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:
Charlie answering the door, eating a banana, wearing a SS officer's uniform.
Charlie biting a mall Santa's ear off after realizing his mother spent his childhood Christmases sleeping with tons of men in Santa suits.
Summer Heights High.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).
Angry Boys, Lilley's newest series, contains this also, especially in the Jen Okazaki segments.
The Brass Eye 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 Panel GameGood 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.
The Master gassing the Cabinet in Doctor Who. 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 - and she'sstillscreaming.
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?
The Chaser's War on Everything 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, 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."
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 Pushing Daisies 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 another, including one with stilts. By the end it's side-splittingly hilarious.
Similarly, many of the less probable accidental deaths on Bryan Fuller's earlier show Dead Like Me, 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.
Six Feet Under 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.
Frankie Boyle on Mock the Week. There's no point in listing examples, if he's drawn breath chances are he's crossed the line a few dozen times.
While this "commercial" (from The IT Crowd) 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 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'.
Chappelle's Show. 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.
Parlamentet. Making fun of everything, going from skeptical junkies to hunting Moomins for being parasite carriers.
The characterisation in Father Ted 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.
Subverted (off-camera) and deconstructed in Studio 60 on the Sunset Strip 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?
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 geysers of blood are gushing out, then I get the Tarantino joke, and it's funny. If it's just a realistic amount of blood, then it's... extremely disturbing...
The surprising and hilarious death of Leslie Arzt in the LOST episode "Exodus, Part 2"?? Made all the more funny by Hurley's next line: "You got some... Arnst... on you."
Frankie Boyle's Tramadol Nights - 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 "tripling" himself in the 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.
Plenty of scenes in Misfits fall into this territory, such as the birth scene in the Christmas Episode, 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 buried alive or Daisy getting 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 murdering people with mozzarella and greek yoghurt).
Sue Sylvester from Glee lives and breathes this trope, especially in her "Sue's Corner" news segments. Here's her take on "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.
Two and a Half Men: 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 The League of Gentlemen. Cannibalism, serial killers, graphic toad-melting, And I Must Scream, a cursed veterinarian who despite good intentions manages to cause the agonizing deaths of all his charges, Brother-Sister Incest... sounds like a typical day in Royston Vasey, and generally played for laughs.
The second episode of 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 Babylon 5, we have Cenatauri Emperor 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 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.
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 Saturday Night Live. Having a sketch about a scoutmaster molesting one of his Boy Scouts? Dude, Not Funny! 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.
That jaw-dropping moment where an innocent kid gets shot in Season's 5 "Dead Freight" would no way be funny. Someone editing a video to make it look like Walt and Jesse were celebrating Todd shooting said kid witness (with Walt laughing, Jesse's "YeahBitch!" 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 Oh, Crap look helps.
Supporter's chants at 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 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 War of the Pacific leaving the nation landlocked which has a lot to do with why Bolivia is so poor today.
Many of Tom Lehrer'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."
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 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!"
Bill Oddie borrowed the concept of killing birds for entertainment from Tom Lehrer and wrote Persecuting Pigeons In Trafalgar Square for Im Sorry Ill Read That Again. 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
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.
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 Played for Laughs.
If you think that's bad, listen to the parody "Grandpa Got Worked Over by a Mobster."
The directed by Shia LaBeouf and co-written by Shia LaBeouf and Marilyn Mansontrailer for the Manson album Born Villain set to the song "Overneath The Path Of Misery" already sounds insane. Then you get to the 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.
A challenger may have appeared in the form of the Stephen Lynch-inspired Bo Burnham.
The music video for "Warning" by Green Day 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"
Lady Gaga and Beyoncé do this in 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.
Arlo Guthrie'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."
"Sex Dwarf" by Soft Cell (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 enjoy it here!
The song "A Little Piece of Heaven" by Avenged Sevenfold 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.
Anal Cunt'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 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"...
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 Kĺnkel and his Kĺnkelbärs ("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 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.
One has to wonder what in the hell Mel Brooks was thinking when he recorded "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 Dos Gringos flows.
A song about pedophilia? Not funny. A song about necrophilia? Still not funny. A song about bestiality? Not even a chuckle. How about "Sado Maso Pedo Robo Necro Bestiality"? ...actually kinda funny.
Dynamite Hack's cover of Boyz in the Hood. A bunch of white guys covering a gangsta rap song with 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.
The Lonely Island, 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 here.
This sketch from Hello Cheeky, 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.
To "bring something up" was/is a term for vomiting. ("Brought up my lunch", etc.) Im Sorry Ill Read That Again was a sketch comedy which was 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 Parody CommercialKruger's Supermarket, which emphasizes how cruelly they kill the animals to get the best taste out of the meat.
Pogo et ses amis (warning: subtitles), so very much. A Quebecois stop-motion animated short chronicling a day in the suburban life of Pogo the clown and his friends Ed, Albert and 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 The Simpsons) and a cameo from a local right-wing politician. It's hilarious, especially if you understand French.
Da Orks of Warhammer 40,000 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 Aksents 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!
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 Cards Against Humanity, which is Apples to Apples for people with a twisted sense of humor.
In the "Attitude" sourcebook for 4th edition 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."
A Very Potter Musical 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.
Reefer Madness. The Musical has Jesus show up to tell the main character to stop smoking pot...and that's at the halfway point.
The Book of Mormon. 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? Fuck you, God. How does it crosses the line a second time? With the following sentence sung out loud by women and men alike: 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 fuck a baby Played for Laughs. And then someone else tries to do it, being none other than the most important prophet for a whole religion!. Trey Parker and Matt Stone indeed.
Titus Andronicus 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 From Bad to Worse. There is even a very blatant "Your Mom" 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 The Revengers Tragedy 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.
Bulletstorm crosses the line twice in not only violence but also in swearing; the game loves its obscenities beyond the point of all reason.
Dwarf Fortress 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 a "special excretion" for the newly modded "appendage" Only in Dwarf Fortress.
Bad endings in the Fate/stay night 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 lampshaded 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 Tsukihime where you get eaten by a shark. On the top floor of a hotel.
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!
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...
The Black Baron. 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 Mudflap, whose offensiveness is on par with (if not higher than) the Baron's. He did not get away with it, which tells something about Madworld.
Ninja Gaiden II, the 360 one, has bloodshed to such ridiculously over-the-top extents that it avoids being offensive or disturbing.
And yet, the PS3 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 World of Warcraft 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. You can guess what happens next
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!
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!
Conkers Bad Fur Day 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 The Great Mighty Poo in a showdown of musical proportions. This game does everything offensive and rolls with it to absurdity.
The 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.
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 Mortal Kombat's selling points. The fatalities tend to fall under this, since you're adding insult to injury, or further injury to injury, whatever.
The final battle in God of War III allows you to cross the line as many times as you want by punching Zeus in the face until the screen is completely covered in blood... and then punching him some more.
Surgeon Simulator 2013 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? Bloody hilarious.
The Shin Megami Tensei 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 Team Fortress 2 makes the Soldier so 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 Hot-BloodedCloud Cuckoo Lander and thus tends to loudly proclaim nonsense or act like the Large Ham 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 Those Wacky Nazis 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.
VG Cats 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.
This one may have set the record for most line-crossing in a comic ever. And it did it in ONE PANEL. 
The double punchline in this strip is a particularly good example.
Xykon of The Order of the Stick. 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 tortures he's inflicted on O-Chul.
An in-universe example also appears when Davan and Jason create the '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!"
In this and the following Loserz strips, the line is crossed twice.
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; Seinfeld Is Unfunny hit hard in the new millennium.
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 blocked out by the author giving an address to complain to.)
Axel: But really, is drowning a kid in tequila such a reprehensible crime?
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.
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.
In his first encounter with the allegiance conflicted elf Cale, he tries to make Cale realize and give in to the Always Chaotic Evil 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 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 Lawful Good (sometimes Chaotic Good) Cale's best friend. Richard even killed a smurf and made Cale a wallet from its hide.
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 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.
Blur the Lines 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. And it works.
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.
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 "Carpel Tunnel Of Love" is one Happy Tree Friends 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.
This video combines a disturbing scene from Higurashi: When They Cry 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.
Bastard Operator from Hell basically has a Magnificent Bastard 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).
The Nostalgia Chick'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 stops being disturbing by this point.
Related is a collaboration video that The Nostalgia Chick did with 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. And then Benzaie shows up in nothing but a bowtie.
And now there's 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...
And there's every episode of Ask That Guy, 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.
Yeah, OK, so we have Wissenschafts prisons. So what? It's all 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 Camp Gay Link who keeps hitting on women despite his best efforts, and a sadistic Groin Attack-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 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 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, 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 Alcoholism
Ma-Ti attempting to give a review. No fucking clue as to what:
(Puppet voice) And thats why Mary Poppins got an abortion, and became a revolutionary.
Also from Bargo. Three words: Hand Puppet Sex Trade.
A handful of YouTube Poops tend to do this, AwfulFawful's in particular.
ThisAce Combat video. PJ getting killed? Not funny. PJ getting killed followed by Mor- sorry, AWACS Thunderhead being revealed as the perpetrator, who was just trying to get them to "cut the chatter"? Hilarious overkill.
Dragon Ball Z Abridged is a case study in this trope. It's The Abridged Series of an anime featuring numerous evil villains, the abridged version leaves in all of their Moral Event Horizon 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 Stock Phrases as he mows down civilians, or Dodoria saying he (or rather, she) likes kids because "they don't leave much of a mess."
This video of a recreation of a Spongebob scene does things... Differently. NSFW.
The Ultimate Orgy flash cartoon by NSFW studios IS this trope.
Black People Are Annoying zig-zags the heck out of the line when it comes to racism. Crosses the first time when one guy says black people are annoying. Crossed a second time when the rest of the interviewees start to agree with him. Crossed a third time when 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 the black people agree with them. Crossed a fifth time when the black people suggest that it be changed to Mexicans. Crossed a sixth time when the white people get offended by that. Crossed a seventh time when the white people say they were joking and are totally cool with changing it to Mexicans.
The second episode No DecencyGag Sub of Okane Ga Nai. In the original, during the Russian Roulette scene the characters use a red paint bullet. In the sub, it's an aborted fetus.
Yu-Gi-Oh! The Abridged Series has "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!"
Hellsing Ultimate Abridged. 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. 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.
Nullmetal Alchemist devotes the entire character 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, Equivalent Exchange 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.
This video. The first few seconds makes it look very offensive, while the rest of it makes it one of the most offensively funny things ever.
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.
The jokes in the Netflix original series Orange Is The New Black 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.
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.
Ebola-Chan, the anthropromorphic verision of the Ebola Virus.
In-universe in the Homestar Runner 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 Coach Z puts it on.
In "Bender's Big Score", their Take That 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 "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 raped to death as a punishment. The humor comes from the fact that most of the (all male) characters condemned to death are 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.
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)
Avatar: The Last Airbender has a non-violent example in the episode "The Ember Island Players", when they were re-enacting Jet's death. Making fun of what is probably the most tragic event in the series where a Government Conspiracy kidnapped, brainwashed, and killed a teenager? Dude, Not Funny! 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.
"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, 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 Batman Gambit 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! 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 Cartman's biological father, and covered up the truth to protect his football career. Cartman's reaction? He's devastated — because 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, South Parkruns on this trope.
Relatedly, every time the MPAA told the creators they objected to something in 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.
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 Made of Iron (borderline Implacable Man) 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 shoots himself when he finds out he is on Dateline with Chris Hansen. At first it's in really bad taste, and then it becomes hilarious when 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.
"It's a Jersey Thing", just that whole episode. Taken as an attack on Jersey Shore instead of the actual state of New Jersey, it's just an irreverent Take That. It doesn't cross the line at all. Well, maybe at the point where they call Bin Laden for help... but not before that. The episode's climax, when 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 Scooby-Dooby Doors 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.
Russell Crowe decides to fight cancer. He can't find cancer, so he beats up a man with cancer.
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 Hilarious in Hindsight 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 "take that"sSeth Mac Farlane 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.
In "Brian Griffin's House of Payne" — when Stewie 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 molested Lois, and has sex with a girl who is implied to be a sex slave, in the same episode.
In one episode, Lois is seduced and cheats on Peter (with Bill Clinton) 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 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 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 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.
Aqua Teen Hunger Force 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, 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 ( 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.
[adult swim]'s bumper preceding this episode on its original air date lampshades this by stating "...Shake does a horrible thing."
The 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 Non Sequitur Thud.
A similar situation happens in a Baseball Episode of Tiny Toon Adventures. 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.
Drawn Together 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.
Korgoth of Barbaria 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 Elfen Lied 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.
Invader Zim 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.
The Simpsons 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 "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 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 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 "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.
The Hansel and Gretel parody in "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.
Wonder Showzen tried to do this with almost every sketch, sometimes even crossing the line a third time.
In an episode of My Life as a Teenage Robot, 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). The Powerpuff Girls had an even more violent dodgeball incident on the Gangreen Gang.
Monkey Dust 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.
The Boondocks has managed to milk comedy and pathos out of exorcisms, Prison Rape, 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 Spongebob Squarepants 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 The Venture Bros., 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".
Goes right back to horrific 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 Wonder Boy outfit and tells Captain Sunshine he can fuck Wonder Boy and his greatest enemy at the same time.
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.
In one episode of 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 her real job is to kill the over-emotional robots by launching them all into the sun.
Frisky Dingo: 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.
If The Ren & Stimpy Show 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 Almost Naked Animals centers around making Lovable Coward Octo 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 Disney Channel, this happens with startling regularity on Phineas and Ferb— mostly in Harmless Villain Doofenshmirtz's Imagine Spots. 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 infant. Another can be found in the episode where he planned to use a space laser (inator) 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.
Total Drama: Chris Mc Lean. Almost everything he makes the contestants do fits this trope, but 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 interns.
Dannyhimself does this an awful lot. Most notable: Him sneaking out of the girl's locker room while being intangible twice.
In-Universe example. A conversation between Jerk Ass secret agent Archer and his hilariously abusive mother Malory about his...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.
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 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 tobreakhim. 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!
Code Monkeys utilizes this with its pixel animation surprisingly well. To give just one character example, Mr. Larrity associates "orphanage" with "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.
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 Sickipedia. There's a reason why Frankie Boyle and Sickipedia appear to have reached something of a "steal and steal alike" agreement.
Mel Brooks 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 Too Soon doesn't qualify, this trope usually kicks in.
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 Idaho has no authority to issue hunting tags in Washington, D.C.