Crosses the Line Twice

"That's... wrong. That's... brilliant."note 

"Half the time, the humor came from how totally out-of-control and psychotic it was. And it kicked ass! I mean, sure, it was gross and vulgar, but on the other hand, it was gross and vulgar!"

"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.


Examples:

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    Anime and Manga 
  • Hellsing. Mooks tend to suffer high levels of gory violence, and so does the main character, who tends to shrug it off without a thought.
    • One of the Valentine brothers (the vulgar one, Jan) 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.
      Jan Valentine: Little Hellsing chicky, we're coming to find you~! Come out, little Hellsing, I promise it will be a lot of fun! We just wanna torture you, kill you, maybe skullfuck your corpse a couple of times, burn your house to the ground, go home and masturbate, okay?
  • The anime Bludgeoning Angel Dokuro-chan bases much of its comedy on brutal and over-the-top violence.
  • 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...)
  • A number of things Gates did in Full Metal Panic!: The Second Raid can be classified as this. Some of the other things he does are outright Squick.
  • Excel Saga: Although on the whole not too bad, but the final episode was entitled "Going Too Far", it was intentionally so violent, obscene, and long (it had a running time 1 minute longer than the standard episode format) that it wasn't allowed on Japanese TV.
  • 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.
    Italy: Heh, just like the girls.
  • Captain Kurotsuchi of Bleach has skip roped with the line since the Soul Society arc and comes of as all the more amusing for it.
  • One Piece has Boa Hancock literally kick an adorable kitten that happened to be in her way to indicate that she is, in fact, a villain. Later, and after pulling a Heel-Face Turn, she kicks a puppy and a baby seal at the same time to turn it into a gag.
    • Then there's Luffy's own Hilariously Abusive Childhood. The line is crossed when it's revealed that Luffy was tied to helium balloons and released into the sky. To make him stronger.
  • One of Kimblee's lines from Fullmetal Alchemist: "That's one way of saying it. Another is that I made women and children go boom."
  • Hell Teacher Nube: The Buddhist nun who ate mermaid flesh and became immortal, thus becoming The Chew Toy for grisly punishment of all kinds and magnitudes is one thing. But then there's Minki's introduction: annoyed at boys from Doumori Elementary, and feeling particularly vindictive, she turned them all into panties. How to remove the spell? The girls had to wear them. This Is Wrong on So Many Levels that Hiroshi suffers a spectacular breakdown, looping back to heroic and trying to charge back into battle. Yes, that's right. Hot-Blooded, heroic panties.
  • 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.
  • Hiruma's creative and liberal use of his Hyperspace Arsenal on his teammates (and everyone else) in Eyeshield 21.
  • Tako-Maria As in, Maria's talking severed head, that bears an uncanny resemblance to a cute octopus based on a certain Vocaloid character.
  • Making fun of the saddest scene in an already sad anime/VN is just terrible... Unless, of course, you do it via Super Mario World autoplay.
  • 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.
  • Majin Tantei Nougami Neuro: Crosses the line so often it can only be explained as being in a quantum state
    • Lets list some examples shall we? Most of them are contained to the manga though. Lets see... there's the little girl that hires the detectives to protect her obviously pedophilic (toy-company owning) grandfather, whom she adores, and 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.
  • Detroit Metal City is about one man's descent into the mentality of a sociopath by merging with his Super-Powered Evil Side. It's Played for Laughs. And it works.
  • Panty & Stocking with Garterbelt.
  • Sengoku Basara makes only what concessions to the laws of physics that it needs to in order to prevent itself crossing the line thrice. Bonus points in this case for doing the same with history.
  • Done often and well in Angel Beats!, but particularly memorable examples include Yui accidentally hanging herself and Naoi's death during the second Dwindling Party scene, when everybody's deaths have been followed by the remaining people screaming the dying one's name:
    Naoi dies
    Otonashi: Anybody want to say something?
    Yui: ...I don't know his name.
  • The second season of 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!

    Comedians 
  • Lewis Black's immortal lines on his Daily Show segment.
  • Daniel Tosh lives off this trope.
    • One of the better known examples was when Tosh was doing stand-up and crossed the line when he made a rape joke. A female member of the audience heckled him for being offensive. Tosh then crossed the line a second time by asking how funny it would be if that girl got raped right now.
    • That and slowly whittling his jokes down to where only three or four people get it.
    • While he certainly qualifies, Tosh claims that within his circle of friends, his sense of humor is actually the more mild/mainstream. Take from that what you will.
  • Lisa Lampanelli's racist humor crosses every possible line in every possible way.
  • Jimmy Carr has based his entire stand-up career on crossing the line twice, thrice, quarce, whilst using as many rude words as possible. Needless to say, you either love 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."
  • Ralphie May
  • Bill Hicks
  • His specialty is vulgarity rather than violence, but Sacha Baron Cohen certainly counts.
  • For similar reasons, Frankie Boyle. Dara O' Briain to Frankie on Mock the Week:
    "There's a line in the sand, right, and you can't even see the line in the sand. You are actually out of sand, into, like, into tropical tundra regions."
  • David Cross
  • Andy-freaking-Kaufman. He was insane, though, so it's to be expected.
  • This is the entire point of the infamous joke "The Aristocrats".
  • Denis Leary
  • Bo Burnham
  • Patton Oswalt
  • Norm MacDonald
  • Richard Pryor, made especially funny by the fact many of the things he describes actually happened to him.
  • I'M GILBERT GOTTFRIED, AND I'M GOING TO KILL YOU MOTHERFUCKERS FOR NOT MENTIONING ME! AND THEN I'M GOING TO RAPE A BITCH OR TWO!
    • This is pretty much Gottfried's whole act. He once famously joked about 9/11 only three weeks after the event at the Friar's Club roast of Hugh Hefner. The audience booed Gottfried, feeling it was much 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.
    • He also tweeted about the 2011 Tōhoku earthquake and tsunami immediately after it happened, which ended up costing him his job at Geico. Too Soon indeed.
  • From about the same time as Andy Kaufman, we have Michael O'Donoghue, who was an editor for the National Lampoon and it's radio show, head writer for 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.
  • Doug Stanhope.
  • Louis C.K., oh so very much.
  • Frankie Boyle
  • Bobcat Goldthwait
  • 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.
  • Sarah Silverman. Dear lord.
  • Jerry Sadowitz.
  • Anthony Jeselnik
  • The late Robert Schimmel's act basically opened up the door to his (and everyone else's) bedroom. And it was hilarious.
  • He never knew when to stop: Arabic poet Abu Nuwas. Folk tales made him jester of Harun al-Rashid and gave us the following jewel. He once hid behind a curtain and pinched Harun in the backside. Harun was royally miffed and sentenced him to death. But he was a good ruler and gave Nuwas the opportunity to defend his action. "I'm so sorry, Lord! I thought it was your wife!" Harun had to laugh so hard that he pardoned him.

    Comic Books 
  • Fillerbunny.
    • 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:
      I'll kill you! I'll kill you to death!
    • 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.
    Mike Nelson, as Kingpin: I admire a man who can kill an olive at ten paces.
  • 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!".
    • While we're at it, anything Garth Ennis writes.
      • 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-Man One 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.
  • Some of the best humor in Secret Six comes from how blasély sociopathic Deadshot is.
    Lawton: What, guy clearly had a gun. It was self defense.
    Spy Smasher: He didn't have a gun, Lawton!
    Deadshot: All right, so it was murder. Who cares.
    Harley Quinn: "Uh, fellas? Our boy is a blow-up doll. And not the fun kind.
  • Matt Howarth's Those Annoying Post Bros is ALL about watching the Posts jump merrily over the line.
  • Evan Dorkin's Fun with Milk & Cheese crosses the line twice on a slow day.
  • What do you expect of a comic called "The Little Asshole" written by a beloved author of children books and satirical novels.
  • Ultimate X-Men: Mr. Sinister pushing a man in a wheel chair down the stairs: That's Terrible. Doing so while declaring Stairs to be the greatest enemy of Professor Xavier: Crowning Moment of Funny!
  • 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.
  • Lobo...but highly Depending on the Writer.

    Fanfic 
  • In Queen Of All Oni, when Jade goes trick or treating, if she didn't like what she got, she goes back and throws LIVE RATS in the poor people's faces!
  • Jesus and Hitler, A Romance. Pretty much Exactly What It Says on the Tin. As one review put it:
    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.
  • My Immortal pretty much runs on this, either intentionally or not.
    • As does Thirty Hs, which crosses the line so many times it may win the all-time achievement award for line-crossing.
  • The death of Mami in Puella Magi Madoka Magica was disturbing. Some of the fanart reacting to that, like this one (NSFW ads)... Not so much.
    • It's more like it's more common to see Mami and Charlotte to be together in a completely happy situation. To the point that it's one of the more common pairings in the show's Shipping fandom.
  • Latias Journey crosses the line a billion times. It is unimaginably gory but it is so over the top that it starts getting funny.
  • Arguably, the later installment of the Poké Wars series are getting to be like this.
  • The Last War goes so over the top in its portrayal of Ron as the Potterverse's answer to Trevor Morgan that it becomes a total farce very quickly. Even before the A-Team show up.
  • The entire premise of Theory of Chaos is this trope taken Up to Eleven.
    • 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.
  • Virtually any story by the 6 foot dick (With such a name, what did you expect?!).
  • The Legend of Link: Lucky Number 13 does this on occasion by treating extreme violence and shady morality casually.
    • When Link goes to save Takara and Varia, he is confronted by camouflaged soldiers. He drives them into a fear-driven frenzy and uses magic to jam their guns so they are forced to bash and pummel each other to death. The bastards deserve it, but the drama ends the moment Link reasons there's "something missing" and, for no reason other than his amusement, follows up with a casual instruction: "Mouths only."
    • Following on from that scene, the shadow demon goes on to graphically mutilate and kill 12 women and 28 children (the families of the scientists responsible for Takara and Varia's torment) on Link's orders. Deadly serious? Yes. Morally questionable? Absolutely. The shadow demon musing on a name for itself, then treating the survivors' shocked silence the way an inexperienced comedian would regard an audience that wasn't laughing? Hilarious.
    Still, no one spoke, which seemed to make the creature genuinely uncomfortable.
    "No? Shade? Shady?"
    The men stood silent, tears and mucus streaming down their faces, but the creature continued. Its flippancy and their inability to make it respect their loved ones' lost lives made them cry harder.
    "The Hand, then? Handy? No? None of those?"
  • In Bella Swan Pregnant And Furious, Satan gets beaten so hard by Bella (yes, that Bella), that his internal organs start coming out of his mouth. He is left "toothless and organless", "coughing blood and trembling with pain."
  • Cartman's Revenge, also on DeviantArt as South Park: Tasteless Theatre is a disgusting satirical lampooning of the Aurora Theatre Shooting that was released a week after the fact. Not mention the author has gone on record stating that he thought up the idea moments after it happened and planned to release the story the day after the fact, but thought it would be too tasteless.
  • A fan fic that I'll just say this "it goes into a detailed account of Bowser Jr's spiky shell, unknowingly, used for the sexual pleasure of Peach, as she births him." (NSFW DL only)
  • A very common plot in fanfiction of the Pokémon anime is to rewrite the story from the beginning, with Ash supposedly being smarter and more awesome. As one might expect, most do nothing but turn him into a God Mode Stu. However, The Greatest There Was Or Ever Will Be manages to avoid this trap simply by making Ash so far ahead of his canon self that it becomes comical — imagine Ash channeling the heroine of Medaka Box, and one wouldn't be too far off.
  • Sonic X: Dark Chaos crosses the line tons of times, with hilariously gory violence, Rule of Cool, Unfortunate Implications galore, and black comedy child molestation. The setting in general crosses tons of lines too - one of the Jewish Republic's most powerful units are Humongous Mecha powered by the souls of Holocaust victims, and the Muslims of the Emirate of Mecca pacify captured populations with female genital mutilation on a planetary scale.
    • Most of the Black Comedy in the story falls headfirst into this trope;
    D'Arnazhee: Looks like these Jews couldn't find any foreskins. Not really 'chosen people' material.
    Beelzebub after raping Chris and nearly raping Cosmo: They were a bit tight, but don't worry, I think they've loosened up now.
    • Episode 68 gives us this gem when Jesus starts angsting about all the people killed in the Angel invasion of the galaxy;
    al-Walim: Look on the bright side, at least they weren't aborted.
    Tobit: And you got rid of the gays. I mean, you know how much Allysion hates fags.

    Films — Animated 
  • 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...
  • Madagascar 2: Alex punches an old lady in the face: Dude, Not Funny!. Old lady fights back and wounds his pride: Hilarious.
  • 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.

    Jokes 
  • Three men and a woman were marooned on a desert island. After one week, the woman felt so guilty about what she had been doing that she committed suicide. After another week, the three men felt so terrible about what they had been doing they buried her. After another week the three men felt so terrible about what they had been doing they dug her back up.
  • Why did Jerry Sandusky go to Walmart? Because children's clothes were half off!
  • The "Dead Frog" joke crosses it numerous times.
  • Why did little Suzy fall off the swing? She had no arms. Knock knock. Who's there? Not little Suzy. What did Little Suzy get for Christmas? A scooter! Just kidding, she couldn't open the box.
  • The entire point of The Aristocrats, a joke that's meant to be a challenge to come up with the most vulgar, offensive and outright wrong story one can think of all for the purposes of making things that should never be considered funny funny.

    Literature 
  • In A Brother's Price, one of the Whistler sisters tells the other that the neighbour's boy, Balin Brindle, is rumoured to have fathered his younger sisters. The reply? "And? At least we know he's fertile".
  • 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.
  • The entire plot of Shakespeare's Titus Andronicus could be this. According to this guy, it is.
  • 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.
  • These lines from The Hunger Games:
    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.
  • The vampire feast in Almost Night features various animals being drained of blood and killed. Then their corpses are used as playthings such as impromptu pillow fights, and sword fights for birds. Carlisangel even tortures one for kicks during the first one.

    Radio 
  • 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.
    Boy: Is that why Uncle Milkman's upstairs with his boots off?
    Mother: Yes. Go and play in the motorway.
  • To "bring something up" was/is a term for vomiting. ("Brought up my lunch", etc.) 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 Commercial Kruger's Supermarket, which emphasizes how cruelly they kill the animals to get the best taste out of the meat.
  • The Brewing Network: Pretty much all of the humor of Lunch Meet.
  • As mentioned at the top of this very page, Bleak Expectations does this with St. Bastards, the most sadistically cruel school in all Georgian Britain.
    • And there's also the Chinese... restaurant in Series 2, followed shortly thereafter by Abraham Bagel, a parody of the Greedy Jew who is in fact a Catholic.
    • The subversion of a "release the dogs" moment. Setting dogs on abused factory workers? Not funny. Dropping dead dogs on said factory workers, on the other hand...

    Short Films 
  • Don Hertzfeldt's animations have all sorts of violence inflicted on stick figures that go between horrible and hilarious routinely.
  • Jim Reardon, before he went on to do animation for The Simpsons, created this student short about Charlie Brown gunning his classmates down in a Scarface-style rampage. A perfect example of a film which straddles the line between "appalling" and "the most hilarious thing ever made." (Warning: video Not Safe for Work Or Sanity.)
  • Forklift Driver Klaus - The First Day On the Job.
  • 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.

    Tabletop Games 
  • Warhammer 40,000:
    • Da Orks do not live this trope; they are this trope. Psychotic, belligerent monsters (in a galaxy already filled to the brim with the psychotic, the belligerent and the monstrous) taken so far past the utter screaming extreme that they become endearing instead, not at all hurt by their ridiculous Funetik 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!
    • The setting in general is this on several levels, considering the absolute grimdarkness it revels in. One of the common jokes is that the Eldar literally Squicked a god (the god of sex no less) into existence and that the Catholic-Space-Nazi Imperium are the good guys.
  • 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."

    Theatre 
  • Me and My Dick. The whole freaking thing.
  • 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.

    Other 
  • Many Internet Radio shows do this in terms of sheer vulgarity since there is virtually no censorship; wonder how far it can go; this line says it all: "Oh god they said that Jesus gave it to his mother!"
    • After The Forking Show (ATFS), a podcast spinoff of a now defunct Australian radio show called The Spoonman, crosses the line in every podcast. One notable, repeated example: Bringing slavery to Australia (both played for laughs and discussed seriously).
  • The cartoons in The Rejection Collection crossed the line once when they were rejected by The New Yorker, but crossed it a second time when they were funny enough to be published in this book.
  • Bringing guns into an NBA locker room and threatening a teammate with them? Crossing the line. At a game, pantomiming shooting his teammates as a joke? This trope. Nice job, Gilbert Arenas.
  • The funnier jokes on 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.
  • Attempted rape? Not funny. Antoine Dodson? Funny.
    • Auto-Tune can make almost any video funny. Crazy fan nails Justin Bieber in the head with a water bottle? Tasteless. Auto-Tune the resulting clip into a song? Hilarious!
  • Meta-Example: Tropes That Will Never Happen is full of this, especially the "Too Dangerous" section.
  • Knitler.
  • The entire point of the Apples to Apples-like card game called Cards Against Humanity.
  • During the Jimmy Saville pedophile scandal, one audience member texted this message to a BBC Morning Radio program which got read out live on air:
  • At the memorial service for Graham Chapman, John Cleese delivered a scathing set of insults, followed by pointing out that if the deceased had been alive, he'd have done it himself.
    Cleese: Anything for him but mindless good taste.
  • A baby once flipped the bird at its parents. And not just any baby, but a fetus. Apparently, the ultrasound disturbances were pissing the young thing off.
  • Tisdale, Saskatchewan is famous for its rapeseed and honey so naturally they picked "the land of rape and honey" as their slogan. Ministry saw the slogan on a souvenir mug and just had they make an album title out of it.
  • Art in the Socialist Realism style is generally derided for being bombastic, over-the-top and self-aggrandizing. The statue at the bottom of this page (erected after the liberation of Berlin) is all of those things and so much more: a Soviet soldier in Badass Longcoat rescuing a baby with one hand and wielding a BFS in the other, while pulling a Captain Morgan Pose on a smashed swastika. Subtle. Awesome.
  • This version of Beer Pong.
  • Recounting the dark and secret life of type designer Eric Gill (whose eponymous sans-serif font is all over Britain, even today) often fits this trope. His diaries, not made public until the 1980s, describe in great detail how he had a sexual relationship with his sister. And how he molested all his children. But that still wasn't enough. For the trifecta, he molested his dog.
  • You can buy plush versions of deadly illnesses
  • Some humourous Amazon reviews of the anti-vaccination book Melanie's Marvelous Measles:
    • This one lists a ton of fictional children's books whose Alliterative Titles use the format "[name]'s [adjective] [disease]". This leads to fun titles like "Bertha's Blossoming Bulimia", "Carol's Colorful Chlamydia", "Dominic's Domineering Dementia", "Hillary's Hilarious HIV", "Lisa's Lovely Lassa Fever", "Prunella's Practically Preventable Prion" and "Sam's Saintly Schizophrenia".
    • "I'm so happy I bought a hard copy version of this book. If I bought an audiobook, I never would have gotten my money's worth as both of my daughters went deaf from Measles Encephalitis. They now have a great book and a lifelong disability to remind them how much I truly love them!"
    • This one calls "Benevolent Bubonic Plague" a "gentle, all-natural diet aide", says that the USA only won World War II because FDR got polio instead of the vaccine, and uses some Insane Troll Logic to justify the 1-star rating.
    • This one is about someone suffering from 30+ "benign" diseases like tuberculosis and malaria. He says that he would've been able to fight them off and become stronger from them if his parents hadn't decided to "weaken" him with vaccines.
    • This one is written in Ye Olde Butcherede Englishe and says that modern medicine is some sort of witchcraft.

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

Alternative Title(s):

Crossing The Line Twice, Cross The Line Twice