Crosses the Line Twice



""I may disapprove of a movie for going too far, and yet have a sneaky regard for a movie that goes much, much farther than merely too far.""

- Roger Ebert on Shoot'Em Up

"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, Refuge in Audacity, Dude, Not Funny, Refuge in Vulgarity. 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 its so over the top and out of line that it becomes hilarious instead.

For the (mostly) non-vulgar variant, see Overly Long Gag.

Advertising

 * Featured at the end of an episode of The Gruen Transfer was an ad for 42Below brand Vodka. The ad mercilessly poked fun at homosexual stereotypes, then at the end said the ad was run past "two fags and a queer" to make sure it wasn't offensive.
 * And this one.
 * And this one too.
 * And here's the first one again.
 * Happy father's day?

Anime and Manga
"Mayuri: "I would never do anything unsuitable for family viewing! Get your mind out of the gutter!""
 * 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, 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.
 * He actually manages to get into the same room with her.  this is probably a blessing compared to what Alucard would have done to him had he managed to pull it off
 * 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...)
 * Sayonara Zetsubou Sensei. EVERYTHING about it.
 * While we are at it, the previous manga, Katteni Kaizo, from the same author Kōji Kumeta, is a lot about it too, especially during the later chapters.
 * Full Metal Panic!:
 * At one point, Gauron suggests that a flight attendant on a plane (that he is about to hijack) throw a group of Innocent Bystander high school students out of the plane at 8000 feet because they were too loud. Gauron crosses every line twice. When you draw a line, Gauron will cross it twice the instant you finish.
 * 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.
 * And some consider it a Crowning Moment of Funny for the whole series, as it's a spot on spoof of Refuge in Audacity shows.
 * 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 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 Crazyazy Awesome and call it a day.
 * Ladd Russo also loves to play hopscotch with the line, such as when he.
 * 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.
 * Captain Kurotsuchi of Bleach has practically skip roped with the line since the Soul Society arc and comes of as all the more amusing for it.
 * OF course, the fact he's well aware of what others think manage to make some scenes even funnier.


 * 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 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 second line was crossed when it was 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."
 * This is pretty much the entire reason for Barry the Chopper's Heel Face Turn: to provide a comic relief character.
 * 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 stomps and poops all over the line.
 * Mai Chans Daily Life is one big crossing of lines, any of the series.
 * LET'S MAKE BABY PASTE!!!
 * Hiruma's creative and liberal use of his Hyperspace Arsenal on his teammates (and everyone else) in Eyeshield 21.
 * Tako-Maria
 * 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, but because you're  ..." It can be seen (legally) on youtube by Americans here for those who need to see it to believe it.
 * 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  There's the actions of Kaitou X who decides to invite the main character to his mystery by  . Or of course, how about when the later villain   sends his own message by forcing a man to   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 and Stocking With Garterbelt go bouncing over the line, combining this with Refuge in Audacity and sometimes Refuge in Vulgarity.
 * 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.

Comedians
""I don't know where the line is until I've crossed it!""
 * Daniel Tosh lives off this trope.
 * 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.

""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.""
 * George Carlin
 * By way of Lenny Bruce.
 * 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:


 * 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!
 * 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 Crosses the Line Twice to political jokes is what gets him in the most trouble, he arguably goes even further outside political jokes.
 * Doug Stanhope.
 * Louis CK, oh so very much.
 * Bobcat Goldthwait
 * Don Rickles whose act mostly consists of berating his audience, usually using every cultural, racial, and religious stereotype he can cram in.

Comic Books
"I'll kill you! I'll kill you to death!"
 * 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 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 Joker: Last Laugh miniseries, The Joker uses the powers of Multi-Man to escape.
 * 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:

""Hail Hydra! Cut off one limb and... (waits) C'mon... Note to self: it's a metaphor.""
 * The Sensational Hydra takes a sword and slices off the arm of a random minion while reciting the Hydra oath:

"Mike Nelson, as Kingpin: I admire a man who can kill an olive at ten paces."
 * 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.

"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."
 * Preacher (Comic Book) does this everywhere. Especially notable is the recurring villain who, already introduced bald with one ruined eye, is
 * 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.
 * Can you blame them? It's like saying "If you like The Simpsons then your name begins with a D!"
 * 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.

"Harley Quinn: "Uh, fellas? Our boy is a blow-up doll. And not the fun kind."
 * Feh. Deadshot did it much earlier. In Suicide Squad, to be precise. He was ordered to throw away his guns by armed police. He complied. Bullets first.
 * And while we're at it, Harley Quinn in Suicide Squad seems to have sunken to new depths with her act.


 * Matt Howarth's Those Annoying Post Brothers is ALL about watching the Posts jump merrily over the line.
 * Evan Dorkin's Fun With Milk and 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.

Fanfic
"This is the single most disgusting nasty offensive thing I've ever read. And it's bloody amazing!"
 * Jesus and Hitler, A Romance. Pretty much Exactly What It Says on the Tin. As one review put it:


 * 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.
 * 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 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 Poke 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.
 * The entire premise of Theory of Chaos is this trope taken Up to Eleven.
 * Basically what happens is  The whole thing is just so WRONG it's hilarious, and Ruki and  comments make it that much better.
 * Virtually any story by the 6 foot dick.

Film
"This movie doesn't scrape the bottom of the barrel. This movie isn't the bottom of the barrel. This movie isn't below the bottom of the barrel. This movie doesn't deserve to be mentioned in the same sentence with barrels... The day may come when Freddy Got Fingered is seen as a milestone of neo-surrealism. The day may never come when it is seen as funny."
 * 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. I burst out laughing, and I'm sure I'm not the only one.
 * This, from Evil Aliens
 * Lexx Movies and series are based on this trope. Everything always ends with destruction of everything that appears in path of our protagonists. Like in this joke: Stan: That planet is ugly. Lexx, destroy this planet after 1 minute.....(after some bargaining with planet inhabitants) Stan: Ok, cancel my command. BOOOOM.. Lexx: Sorry, what does word cancel means?
 * On the other hand, out of all the mischief the crew unwillingly did, this was the only one to haunt Stan, especially the robot on the planet. But while talking about LEXX and the carnage it left behind, let's not forget AND THEN.
 * The Evil Dead movies practically ARE this trope.
 * As are Troma Films (Toxic Avenger,etc.)
 * In RoboCop, 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-top heavy machine gun burst, while technicians desperately try to shut it down. Most of the censored versions cut this to a short burst, and make the scene look more clinical and horrifying. The original scene has the 209 continue firing for over 10 seconds, long after anyone could possibly have survived, just chewing up the body.
 * The joke is further emphasised once the shooting is (finally) over when a single meek voice asks "should we call a medic?"
 * Even more ironic is that this is what made it originally X rated.
 * Averted, in that respect, in the murder of Alex Murphy (who goes on to become the titular RoboCop), who is blown to bits with shotguns and then takes a Desert Eagle .50 AE round to the temple.
 * However, 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 the above scene—complete with Crossing the Line Twice humor—when Stark leaks footage of Justin Hammer's failed armor prototypes.
 * The Black Knight scene in Monty Python and the Holy Grail. One severed limb is appalling; four severed limbs is hilarious (the second line in this case probably falls at three). In the Monty Python HBO interview special, they say that's exactly what they were going for. John Cleese said the scene would be heartless and sadistic if not for the fact that the knight shows no pain and doesn't really care what happens.
 * They also used humorously gratuitous violence in their sketch "Sam Peckinpah's Salad Days" (from the TV series), which brought fountains of 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.
 * Both Borat and Bruno are built around this trope.
 * Although Sacha does emphasize mocking American culture and their narrow-mindedness. 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".
 * 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.
 * 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 ; Green having a kinky sado-masochist relationship with a paraplegic woman; and to some the most disturbing, a neighbour kid that gets hurt progressively worse throughout the film; the disturbing part is camera sadistically lingering on the wounded kid crying.
 * Perhaps Roger Ebert's infamous review puts it best:


 * 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 Movie Batman 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 Saga, Joker blows the line straight to Hell before asking if you want to know how he got those bloody scars.
 * "You wanna see a magic trick?"
 * Several gags in Airplane! are only funny because they manage to cross the line twice.
 * "What's this day of rest shit? What's this bullshit? I don't fuckin' care! It don't matter to Jesus. But you're not foolin' me, man. You might fool the fucks in the league office, but you don't fool Jesus. This bush league psyche-out stuff. Laughable, man - ha ha! I would have fucked you in the ass Saturday. I fuck you in the ass next Wednesday instead. Wooo! You got a date Wednesday, baby!"
 * "Do you see what happens, Larry, when you FUCK A STRANGER IN THE ASS?"
 * I think you meant "FIND A STRANGER IN THE ALPS?!"
 * 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
 * Same with Dead Alive. Lawnmower + zombies anyone?
 * Riki-Oh, also known as 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  stand out as Memorable Moments.
 * Not to mention the scene near the end where Riki pushes an oni into a meat grinder.
 * "Alright! You got a lot of guts, Oscar!"
 * The scene in Team America: World Police 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.
 * In his rendition in the movie, Bob Saget practically picks up the line and jumps rope with it.
 * Inglourious Basterds does this a lot, but the most awesome one is
 * Anything by John Waters.
 * 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  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.
 * This is the entire point of Kick-Ass.
 * Lloyd Kaufman, director of such classics as The Toxic Avenger, Class of Nuke 'Em High, and Tromeo and Juliet, pretty much makes this his code.
 * Much of Machete's fun comes from this. At the very least the scenes in which Machete  qualifies.
 * Like South Park, Trey Parker and Matt Stone's earlier work Cannibal the Musical runs on this. A musical about Alferd Packer (not a typo), a prospector in late 1800s Colorado who was tried for murder when he returned from being snowed into the Rocky Mountains remarkably well fed and alone.
 * Pretty much any flick to have anything to do with zombies that isn't horror will use this.
 * This trope is the source of the primary conflict in The Producers: Due to Trying Too Hard and So Bad It's Good, Springtime for Hitler ends up being a Crowning Musical of Funny, thus fouling the titular characters' tax fraud scheme.
 * The ending of Penn and 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"
 * Madagascar 2: Alex punches an old lady in the face: Dude, Not Funny. Old lady fights back and wounds his pride: Hilarious.
 * Over-the-top fighting scenes with premises that make them plausible:
 * The Matrix trilogy
 * Shaolin Soccer
 * God of Cookery
 * They Live!
 * Funny Games, both of them, are really sadistic. These movies are a satire of this trope, as well as a commentary on "torture-porn" violence.
 * The Muppet Christmas Carol has Statler and Waldorf laughing about the time they shut down an orphanage on Christmas. They remember all the little tykes in the snow with their frostbitten teddy bears.
 * Violence against women is really not a laughing matter, but in Denmark the 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.
 * And yes, that is Le Chiffre behind the long hair and the moustache.
 * In The King's Speech, during the future King George VI's speech therapy sessions with Lionel Logue, it is noticed that he doesn't stutter when he's swearing. Lionel proceeds to provoke him into a Cluster F-Bomb that would offend a sailor, and in fact was pretty much the only reason why the movie was rated R when it'd otherwise be at most PG. It is also hysterical.
 * 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 . 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.
 * Blazing Saddles is built on this: Gratuitous use of the word 'nigger' and Black Comedy Rape to name a few.

Literature
"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."
 * 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.
 * 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.
 * The Gashlycrumb Tinies, a book where twenty-six children die in alphabetized ways.
 * These lines from The Hunger Games:


 * 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.

Live Action TV
""Mercy is the mark of a great man." * stabbity* "Guess I'm just a good man." * stabbity* "Well, I'm all right...""
 * 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.
 * 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.
 * 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.
 * Supernatural runs with this trope quite a bit:
 * 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!.
 * The whole point of this episode was
 * The scene in the Buffy the Vampire Slayer 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 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".
 * From a scene in Firefly, in which Malcolm wins a duel with a truly obnoxious and stuck-up opponent that had it coming:
 * From a scene in Firefly, in which Malcolm wins a duel with a truly obnoxious and stuck-up opponent that had it coming:

"Simon: That man's psychotic. (Ironic Echo Cut to Wash, Zoe, and Mal laughing their asses off) Wash: You are psychotic!"
 * Then there's the whole "pretending Kaylee's dead" from the pilot which Simon sums up best:

"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!"
 * Several of the sketches on Mr. Show. Making fun of religious beliefs? That's just stupid and rude. Doing it with America's Funniest Home Video style sound effects and graphics? Hilarious.
 * Riffing on the East Coast/West Coast rap feud mere months, maybe even weeks after Tupac's death? WAAYY too soon. Replacing rappers with ventriloquists? Now THAT'S funny.
 * Its Always Sunny in Philadelphia. When one episode involves two characters getting addicted to crack to get better unemployment benefits...
 * Charlie answering the door, eating a banana, wearing a SS officer's uniform.
 * Nightman.
 * Charlie biting a mall Santa's ear off after realizing his mother spent his childhood Christmases sleeping with tons of men in Santa suits.
 * 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 Game Good News Week thrives on this, usually instigated by host Paul McDermott or regular Mikey Robbins. Hell, everything Mikey Robbins says tends to fall into this.
 * Podge And Rodge... Oh dear oh dear oh dear, Podge And Rodge. click here to see them try to coax a coherent sentence out of Johnny Vegas.
 * 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's still screaming.
 * Even the Doctor gets in on this in "Amy 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 Chasers 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:

"Albie: 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...."
 * 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.
 * 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.
 * Robin Williams' appearance on the penultimate The Tonight Show with Conan O'Brien, a Crowning Moment of Awesome that just happens to cross the line several times. If the crotch-grabbing and Tiger Woods marriage counselor joke weren't bad enough, irking Conan in the process, his Irish folk tune cranks it Up to Eleven with Conan and Robin eventually doing the jig.
 * 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.
 * After making a joke about Richard Hammond, Dara, the host, said "There's a line, and you can't even see the line. You're past the line and into, like, tropical tundra regions."
 * 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 2nd line when he wallops her back, then crosses the 2nd line for good at it turns into a protracted brawl that results in the 'destruction of the Internet'.
 * Chapelles 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.
 * Is Wayne Brady gonna have ta choke a bitch?
 * Parlamentet. Making fun of everything, going from skeptical junkies to hunting Moomins for being parasite carriers.
 * Arguably 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.
 * Kyle's song My Struggle as his good friend marries a Jewish man in the season 2 finale of Party Down.
 * Subverted (off-camera) and deconstructed in Studio 60 on the Sunset Strip episode "The Option Period", when Matt Albie complains about an (unseen) sketch, "Quentin Tarantino's Hallmark Movie 'Turkey Won't Die'", that a clueless special-effects guy ruins by curtailing the scripted excessive blood, thereby un-crossing the second line, so to speak.

"Britta: You guys realize he was beaten to death, right? Shirley: That's where we got the idea from."
 * And who can the forget 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.
 * 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  or Daisy getting  ) and conversely scenes which, on paper, sound as though they should cross the line twice actually end up pretty disturbing (such as Brian  ).
 * Whose Line Is It Anyway frequently uses this trope, but the best example is perhaps this clip.
 * 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 subtle 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 will 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 in Two and A Half Men 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:

"Father So be a good girl! Or, I don't know, a better thief."
 * 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.
 * 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 Wortham Krimmer's utterly bored delivery as Cartagia you can't help but laugh.
 * On Leverage, Parker is introduced this way with a flashback to her childhood. She blows up a presumably foster parent for taking away her bunny after she is caught stealing. This also leads to her career choice due to his poor choice of words:

"Ted: I can't decide whether to be thoroughly disgusted or really, really impressed."
 * Though it is also implied that he is abusive as well.
 * This is being blamed for Work It not even finishing its first season. Apparently, most everyone listened to GLAAD's complaints about the show's portrayal of crossdressers.
 * A lot of Barney Stinson's womanizing on How I Met Your Mother relies on this: most of the "awesome" things he does are sometimes utterly despicable, usually incredibly lame, and almost always pretty pathetic, but he goes so far over the line and is so devoted to excellence in the field of being a terrible human being that he crosses back into Crazy Awesome.


 * 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.

Music
"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!"
 * 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."
 * There also is "The Masochism Tango".
 * 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":

"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"
 * "I wanna Go Back to Dixie" even features, in the live introduction, "The following song, on the other hand, goes too far."
 * "I Got It from Agnes" is a song about the spread of an STD among a rather... close circle of friends. That itself is pretty outrageous. But then it has lines like "She got it from her daddy, who just gives her everything" and "She then gave it to Daniel, whose spaniel has it now"...
 * Bill Oddie borrowed the concept of killing birds for entertainment from Tom Lehrer and wrote Persecuting Pigeons In Trafalgar Square for I'm Sorry Ill Read That Again. Animal abuse? Not funny. Animal abuse lovingly detailed and sung to a cheery melody? Wonderful.

"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.""
 * Seeing as it's a Christmas song, "Grandma Got Run Over by a Reindeer" probably qualifies.
 * In a similar vein, Weird Al's song "The Night Santa Went Crazy", where Santa holds his elves hostage, kills (and eats) his reindeer, and (in one version) is shot in the head by the SWAT team. Giving Santa a gun is doing one thing.
 * Jingle BOMBS
 * Speaking of Santa going off the deep end, The Killers' song "Don't Shoot Me Santa" talks about Santa coming to shoot a boy who "couldn't let [the people who bullied him] off that easy" and has been "killin' just for fun" Of course, it is Played for Laughs.
 * The musical piece Ya(c)kety Sax, better known as the theme for The Benny Hill Show, has been said to "make anything funny".
 * It does.
 * Damn right!
 * Seriously.
 * Always.
 * Makes you run faster, too.
 * New challengers? Warning: Tengen Toppa Gurren Lagann spoilers! Certainly some YouTubers think these two may have broken the streak.
 * Can't forget Tribute.avi
 * Here's proof that even 9/11 can be funny.
 * I should email this to the people in it, as they would be insulted.
 * Yes, even Hiroshima. And on that note, Hitler.
 * Hell, if you don't believe us try it yourself.
 * Pretty much anything by Stephen Lynch. Grandfather gets a special mention.
 * I see your "Grandfather" and raise you a "For the Ladies".
 * 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"
 * The video for Amanda Palmer's "Oasis". Seriously, just watch it.
 * 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.

"Caught you / Sniffing my boxers Who the fuck does that /"
 * Weird Al Yankovic has at least a couple of these on every album, i.e. "Mr. Frump In The Iron Lung", "Christmas At Ground Zero", "Good Old Days", "Trigger Happy", "The Night Santa Went Crazy"...
 * Add "Weasel Stomping Day" to that list.
 * "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. Most unsexy use of sex in a music video I've ever seen. The video was CONFISCATED BY THE POLICE enjoy it here!
 * The Doug Anthony All Stars. 'Nuff said.
 * "Banging in the Nails" by the Tiger Lillies.
 * 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.
 * Kevin Murphy has the song "Larry's Fine", about Larry Fine. It starts off as a typical ode to his physical endurance, but quickly becomes a homosexual escapade...before the trademark physical abuse begins again.
 * 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.
 * Slim Shady. That is all. Well, maybe I'll just give you a quick example. "I tied A ROPE AROUND A PENIS AND JUMPED FROM A TREE! I know, you wanna grow up to be just like me."- Role Model
 * "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"...
 * "Shave 'em Dry" by Lucille Bogan. From 1935, and unspeakably NSFW. "More innocent time", my ass.
 * The Bloodhound Gang is a master of this—when they're not pulling off either Refuge in Audacity or Refuge in Vulgarity. See the first couple of lyrics from "Altogether Ooky":


 * In Sweden there is an entire genre of music called "Könsrock" (Genitalia rock) that is pretty much the embodiment of this trope. By far the most infamous of those bands is Onkel Kånkel and his Kånkelbärs ("Uncle Dingleberry and his Dingleberries"). They were brought to the attention of the authorities when a schoolteacher had read the lyrics to one of their song which describe, in detail  Fortunately, for all of us who appreciate freedom of speech, any attempt to ban them, failed.
 * Voltaire's "Cantina" is all about a poor guy who visits Mos Eisley's infamous cantina and ends up receiving all kinds of unwanted sexual attention from everyone there (up to and including Han, Chewie, Greedo, and even Obi-Wan). It's quite hilariously disturbing.
 * GWAR

Radio
"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."
 * This sketch from Hello Cheeky, which is so short it can be transcribed.

"David Hatch went to the countryside to bring up his babies, which serves him right for eating them."
 * To "bring something up" was/is a term for vomiting. ("Brought up my lunch", etc.) I'm 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.

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

 * 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!
 * This chess set.
 * That destroyed the line. There was no crossing, it just blew it up.
 * I find that incredibly offensive! The black king and queen are reversed (the king is always the higher of the two pieces) and the board is orientated the wrong way. The bottom right corner should always be white. HOW DARE THEY!
 * Er...no pun intended, right? Also, there exists a chess set, probably still in Corning, New York, of Jews versus Christians.
 * 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

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? . How does it crosses the line a second time? With the following sentence sung out loud by women and men alike:  . And that is just the fourth song in the story. Later you will find someone intending to  . 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 dialouge, and It Got 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.

Video Games
"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!"
 * Dwarf Fortress tends to have some grisly moments, but when you combine loads of free time with modding abilities, you get this. 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  Only in Dwarf Fortress.
 * The Dwarf Fortress community as a whole does this. Take, for instance, the program that farmed mermaids, drained the tank they were in, causing them to suffocate, and butchered them for their valuable bones. as one player put it, "bay12 doesn't have moral event horizons, it has goals"
 * 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").
 * Don't forget the infamous ending in Tsukihime where you get eaten by a shark. On the top floor of a hotel.
 * I Wanna Be the Guy is something like this, except the line is between "frustrating" and "funny", rather than "vulgar" and "funny".
 * For many fans of Nintendo Hard games, this is the reasoning. Dying repeatedly in the same spot, or to a death trap that was absolutely impossible to see coming, is simply hilarious.
 * Also, check out many Let's Play segments, like the Sonic the Hedgehog 2006 finale.
 * Ellis invokes this in Left 4 Dead 2 with one of his stories about Keith.

"loroldonfarm: Did he drop any good loot?"
 * 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.
 * 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 Play Station 3 version Ninja Gaiden Sigma 2 had to be cleaned up anyway, turning all the blood into "purple mist".
 * 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".

"Maurice Chavez: Dios mío, you shot him! There's blood!... and pubic hair!... all over the studio!!"
 * 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!
 * The GTA Radio is this in spades. One great example from Vice City Public Radio:

"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"!"
 * EVERYTHING ABOUT the GTA series crosses the line twice!
 * The ability to have the likenesses of the late Kurt Cobain and Johnny Cash sing any song in Guitar Hero 5 is one gigantic, disrespectful disgrace to those two people's legacies. Still, put either of them as the singer and then just try keeping a straight face as they rap, do big gay dances, and cover Bon Jovi and Rammstein songs, among other things.
 * Conker's 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 intro cutscene is unforgettable: I~ am, the Great Mighty Poo, and I'm going throw my shit. At. You. (Obviously NSFW)
 * Quite fittingly, Nintendo Capri Sun had a field day with that particular boss. You know, IN THE BATHROOM!
 * This is the rejected icon for the Child Killer perk from Fallout. So so wrong, and yet so, so right...
 * Pretty much ANY game made by Nippon Ichi. In pretty much every way.
 * 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 Yuuki is a prime example of this trope, and it is one of the reasons as to how he can be so audacidly monsterous, while still remainning so Laughably Evil likable. In the 2nd game's True Ending he has Mind Raped Noel into embracing her Super-Powered Evil Side; Mu-12, Sword of the Godslayer: Kusanagi, by revealing everything about her Cloning Blues past to her, and when Ragna arrives for his Big Damn Heroes moment to save his sister's clone, only to realize that he's too late, Hazama gives us this gem of a Villainous Gloat:


 * 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.
 * That's the main selling point of Blood.
 * The final battle in God of War III allows you to cross the line as many times as you want.

Web Comics
"Pantsman: Well that was good, but where's the fifth member? (Next panel shows a cat with a bloodstained mouth.) Pantsman: Bugsy!..."
 * VG Cats ran a strip in which Aeris goes back in time to abort Leo. He 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.

"Redcloak: And again when I found out about the Basilisk Staring Contest. Xykon: Technically, the paladin won that one. Jirix: He never blinked."
 * An average strip of Saturday Morning Breakfast Cereal crosses the line twice, and then once more in a hidden comic. Like this, or this. Some cross the line about fifteen times.
 * This one may have set the record for most line-crossing in a comic ever. And it did it in ONE PANEL.
 * Xykon of The Order of the Stick is a Complete Monster, and yet... 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.

"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"?"
 * That's tame compared to what Xykon does in "Start Of Darkness". Rich Burlew has stated that he wanted to make a villain that has no sympathy from his audience.
 * Comic 755. Where to start?
 * This Rooster Teeth comic features this - draw your own conclusions on whether it crosses the line, or is telling people to start stepping back.
 * This Shortpacked strip. Anything with the words "rape therapy" in it, in fact.
 * For that matter, pretty much everything Mike does in Shortpacked!, and most of what he does in Roomies! and It's Walky! too. This is a sterling example.
 * And speaking of Mike and this trope, this strip inspired Kumata's first post (look for, ironically, the drunk!Mike avatar) in this thread, which eventually leads to Kumata's third post on the second page.
 * Pretty much anything involving Black Mage of Eight Bit Theater, like how his Hadoken spell works.
 * Not to mention his repeated orphaning and traumatizing of Onion Kid, and his repeat murders of his companions. Hell, he more or less defines it.
 * Some of the things other characters do qualify as well, like how Red Mage plans to get a ride off an island.
 * Most things Sarda does, especially what he does after Ranger tries to kill him.
 * Hellbound regularly Crosses The Line Twice, like in this strip for example.
 * Randy Milholland of Something*Positive often goes here. When you start out like this, you're only going to go further and soon you're writing strange super-powers. And that's without looking for the storyline where Kim rapes Davan (Found here).
 * 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:

"Sweral: You did kill and eat Reakk's cat. Tryka: It looked like my mom!"
 * Not to mention Jason's musical about the crucifixion, "Nailed!"
 * In this and the following Loserz strips, the line is crossed twice. At least.
 * In Sluggy Freelance, much of the demonic rampage shown during "That Which Redeems" is played this way.

"Axel: But really, is drowning a kid in tequila such a reprehensible crime? Aerith: Yes."
 * 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.
 * Ansem Retort.
 * 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.)
 * The very first strip has Axel laughingly reminiscing on blowing up an orphanage. It turns out this is a regularly scheduled hobby of his.


 * 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.
 * Cyanide & Happiness has this in spades, but nowhere is it more apparent than in The Depressing Comic Weeks.
 * Sexy Losers pretty much runs on a combination of this, Squick, Refuge in Audacity, NSFW, and Fan Disservice.
 * The undead, firewielding warlock Richard from Looking for Group, unlives this trope; See his big musical number "Slaughter Your World".
 * In his first encounter with the allegiance conflicted elf Cale, he tries to make Cale realize and give into the Exclusively 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.
 * Truly the act of a benevolent and enlightened being.
 * 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.
 * Van Von Hunter has this example.
 * 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.
 * Penny Arcade does this at least every other week.
 * Used in this strip of LICD.
 * In Homestuck, the Trolls have a curious Pokémon meets Alien game called Fiduspawn. The details are yours to peruse, fair reader, but can be succinctly summarized as "Face Full of Alien Wingwong on stuffed dolls." And judging by its facial expressions the doll is quite alive during the process.
 * Honestly, Homestuck does this all the time. There are very few horrible things that happen in there that Hussie doesn't also try (and, most of the time, succeed) getting you to laugh at as well.
 * And we can't forget what Vriska decides to do to help the guy she crippled intentionally for a laugh. Why, give him a house entirely composed of stairs, of course!
 * There's also.
 * Exploitation Now, sweet gobs Exploitation Now! Prior to the last storyline, at least.
 * Channel Ate. About 90% of the comics are this.
 * Ctrl Alt Del, here.
 * Fireman Comics from Something Awful were the epitome of this. (Archived here)
 * In one comic, a man approaches a fireman to lead his son's cub troop camping trip. The fireman agrees, then buries all the children alive and starts a forest fire. When the man comes back to the fire station concerned about his missing child, another fireman refuses to help unless the worried father helps him cheat on his taxes. He then goes back on his word and instead of helping, uses the fire truck to deliver his tax forms. The fireman also steals the poor man's wallet, then seduces his wife using flowers bought with the victim's own money.
 * A Softer World, all the time. For example.
 * The entire point of Electric Retard. Killing small children and a giant angry naked Hitler are just the tip of the iceberg.
 * The entire point of Electric Retard. Killing small children and a giant angry naked Hitler are just the tip of the iceberg.

Web Original
""Oh, seig heil! Didn't hear you come in.""
 * Remixes or gag dubs of the scene in Death Note where ) are disturbingly popular. Here, have a Death Note/My Neighbor Totoro remix, a Death Note/Kirby remix, and a Death Note/The Producers gag dub. Immoral hilarity indeed.
 * The Torture Game 2. Great for stress relief.
 * A Teen Titans Hentai parody (obviously Not Safe for Work) on newgrounds. BOOYAH!
 * Pretty much anything on Newgrounds. Before "Everything, by Everyone.", their slogan was "The Problems of the Future, Today!"
 * Papa Smurf, can I lick your ass?
 * Happy Tree Friends in all its gory glory. But don't take our word for it. Be warned, not for the initially faint of heart. Also, beware over-saturation; violence does desensitize.
 * Don't forget 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 no Naku Koro ni 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.
 * Survival of the Fittest has a rampage by Wade Wilson, along with Carson Baye's death.
 * And now we can add... pretty much everything Jimmy Brennan does. His first thread (possibly NSFW due to Cluster F-Bomb) is a prime example of it; he starts out by peeing himself and running around screaming and crying. And then... well, let's just say according to him Craig Hoyle will rape everyone and wear their skins as a coat (which reached Memetic Mutation territory). One could also make a case for Richard Han's death as well, in which he falls off a cliff, and apparently has enough time to think out what his last words were going to be ("YOU WIN THIS TIME, GRAAAVIIIIITYYYYYYYYY-"). And then if that weren't enough, he falls into another thread, still screaming.
 * The somewhat popular G-Mod Christian Brutal Sniper series (viewable here), crosses the line so many times with it's joyously-nonchalant killer of a protagonist, it's freaking hilarious.
 * This video of Euphemia from Code Geass  to Caramelldansen.
 * 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).
 * This mash-up of the Omaha Beach scene from Saving Private Ryan using sound effects from Team Fortress 2. This version using Finding Nemo qualifies.
 * Similarly, at the end of James Rolfe's Maximum Overdrive review, where he puts ACDC songs in famous movies. While Harry Potter doesn't qualify for this trope, SPR gets "For Those About to Rock" (a song with cannon fire!), Return of the Jedi gets "Thunderstruck" (at the Electric Torture scene!), and Cinderella "has got 'The Jack'..."
 * Derrick Comedy videos use this a lot. It mixes this and Overly Long Gag in kp
 * Mario! Wario! Lucario!
 * Sweethearts. Aww...
 * 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 now there's Spooning With Spoony 2!
 * And there's every episode of Ask That Guy With The Glasses, where his horrifically nonsensical answers benefit greatly from deadpan delivery and the way everything piles up on itself until you can't possibly take it seriously.
 * Sometimes he doesn't even wait until the Q&A:

"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 10 gallons 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."
 * Then Bennett The Sage cranks that up a notch.
 * On the same site, this Facts About Germany video.

""Especially the middle one.""
 * 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

"( Puppet voice) And thats why Mary Poppins got an abortion, and became a revolutionary."
 * 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:


 * Also from Bargo. Three words: Hand Puppet Sex Trade.
 * On a related note... Keyboard Kid.
 * This Ace Combat video.  Not funny.   followed by Mor- sorry,   being revealed as the perpetrator, who was just trying to get them to "cut the chatter"? Hilarious overkill.
 * "2 Girls 1 Cup" crosses the line twice.
 * If the video itself doesn't, the reaction videos certainly do. Kermit's reaction (which even got a reaction reaction) is by far one of the most hilarious.
 * Dr. Tran, anyone?
 * The infamous "No Russian" mission from Modern Warfare 2 crossed the line even for many gamers. For others? MO-MO-MO-MO-MONSTER KILL!!!
 * Slug Bait! I'd ruin it if I were to tell you what happened. Watch it for yourself. And read the lyrics, most importantly.
 * The Ganonator: Morshu getting shot once for a Ballistic Discount? Disturbing, maybe. Morshu getting shot many times... and then his guts fall out... followed by ? Hilarious.
 * Even TV Tropes has examples!
 * This fan video about Kamina doing his first combine goes wrong, it becomes depressing... But then straddles on to funny.
 * Go watch the Mass Effect 2 Death Compilation. Naturally, getting any of these in the actual game can be heartbreaking, or even blue-screen inducing. However, after a while,  becomes less horrifying and more... morbidly funny. Or am I the only one?
 * This Fail Blog entry.
 * Dragonball Z Abridged is a case study in this trope. It's an Abridged Series of an anime featuring numerous Complete Monster 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 likes kids because "they don't leave much of a mess."
 * Alex DeLarge: International Man of Mystery. "Oh, behave!"
 * This video of a recreation of a Spongebob scene does things... Differently. NSFW.
 * Introducing: MLP fleshlights! And no, that "e" is not supposed to be an "a"...
 * 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  Crossed a second time when   Crossed a third time when   Crossed a fourth time when   Crossed a fifth time when   Crossed a sixth time when   Crossed a seventh time when
 * The Onion: "Congress Takes Group of School Children Hostage."
 * This Onion video.
 * Another Onion video about gymnast Shawn Johnson.
 * 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.
 * 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.
 * Pokemon: The 'Bridged Series features Brock as a Memetic Molester with an obsession with breeeeeeding among other things, and has stuffed Misty inside a sack on at least two separate occasions. At one point while inside the sack, Misty finds what she believes to be a dead squirrel.

Western Animation
"Zapp: (proudly, in a body cast) I had snu-snu!"
 * Metalocalypse. The whole show.
 * Superjail is about the same.
 * Futurama is good at this.
 * 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 "Beast With A Billion Backs", Bender wants to make a Deal With The Robot Devil. The Robot Devil will give Bender what he wants (an army), but only if Bender is willing to give up his firstborn son. Bender fulfills his end of the bargain by reuniting with his long-lost robot son—then punting the robot child into a vat of molten metal. The Robot Devil expresses amazement at Bender's brutal act (commenting that it's brutal even by his standards), and Bender simply replies, "No backsies." Admit it, you laughed.
 * In "Bender's Game", miners of dark matter in Alaska are effecting the environment. A white rabbit is barely visible in the snow and then a truck passes covering it with grime and it has the saddest little face. Then when you're starting to feel bad, it gets eaten by a polar bear.
 * Nothing compared to the third-season episode, "Amazon Women In the Mood", where the plot focuses on several main characters being 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.

"Cartman: Oh let me taste your tears, Scott! Oh, the tears of unfathomable sadness! Mmm-yummy!"
 * 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.
 * And let's not forget Hedonism-bot...
 * Avatar: The Last Airbender has a non-violent example in the episode "The Ember Island Players", when they were re-enacting '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.
 * Don't forget 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.
 * Not to mention that they made Actor!'s Famous Last Words
 * The fans' Ho Yay jokes about Aang and Gyatso. Usually squick, but when Chris Hansen gets involved...
 * South Park, "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,
 * Not only that, Cartman even got Scott's favourite band, Radiohead, to see Scott cry, and insult him for it! What a jerk.

"Dib: ...spleen? Zim: Three different colors."
 * It's even more twisted. In "201" we learn that Scott's father was also . Cartman's reaction? He's devastated—because   It's not Crosses 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 Park runs 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.
 * They actively rip the movie industry wherein it's ok to show people dying in bloody fashion, but if the F word is uttered suddenly the movie MUST BE RATED R BECAUSE IT WILL CORRUPT THE CHILDREN OF OUR GREAT NATION.
 * 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.
 * Of course, 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  At first it's in really bad taste, and then it becomes hilarious when
 * 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
 * "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.
 * Family Guy has 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...)
 * It makes the after-effects even better. Brian is allowed a single "revenge strike" on Stewie, but Brian opts not to do it right away. Naturally, as Brian waits longer and longer, Stewie gets more and more scared, and it seems like the rising terror Stewie inflicts on himself is a far greater torture than Brian's eventual retaliation will be. Then,
 * 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"s Seth MacFarlane 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 table lamp. Yes, the implication is that Peter was about to commit murder over a TV show. Or at least assault.
 * The whole show has become this ever since around the season 4-6 era.
 * Terri Schiavo: The Musical. Yes, it's Exactly What It Says on the Tin...with preschoolers. And it's hilarious.
 * In "Brian Griffin's House of Payne"—when Stewie
 * Carter is implied to have, and has sex with a girl who is , 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.
 * 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, . 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 . 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).
 * Adult Swim's bumper preceding this episode on its original air date lampshades this by stating "...Shake does a horrible thing."
 * 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.
 * Crossing the Line Twice is 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.
 * And then he gets interrogated on his anatomy...

"Taqu'il's Lawyer: I see a celebration of life, like Hoop Dreams or Finding Forrester. Maybe they're going to find Forrester!...In Poland."
 * "I love you, cold unfeeling robot arm!" ^_^
 * The Itchy and Scratchy Show.
 * 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 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."
 * In the opener of the 2011 Treehouse of Horror special, Homer steals candy for charity and drives off to the desert to eat them, only to be trapped under rocks in a ditch. Terrible, but then he chews his arm off with Vampire Teeth. And chews off the wrong arm. Then when he has no arms, he sees the candy is actually all vegetables planted by Bart and Lisa. Hilarious, but then you think of how he may die from blood loss...
 * 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 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.
 * Robot Chicken. Just a few examples.
 * The Boondocks has managed to milk comedy out of Exorcisms, Prison Rape, beating up blind people and important historical figures using derogatory words, just to name a few.
 * 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 toliet plunger.
 * In a scene in The Venture Brothers, 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".
 * "They hit me with a truck..."
 * The fact that Dr. Venture powered his pleasure chamber with the trapped soul of an orphan? Horrific. The fact that his only defense is that he didn't use all of it? Hilarious.
 * Goes right back to horrific 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.
 * In American Dad! 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.
 * The montage of Joker killing Batman a good dozen times in the "Emperor Joker" episode of Batman the Brave And The Bold. Death by crushing, acid, fire, sawblades, guillotine, sharks, spikes, train, electric chair... What Do You Mean It's for Kids??
 * 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.
 * 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 death camp uniforms. Taqu'il's (Jewish) lawyer doesn't help fix the problem.


 * If The Ren and Stimpy Show managed to cross the line once, the Adult Party Cartoon was an exercise in crossing the line twice, particularly "Onward and Upward" where grossout jokes were repeated ad nauseam, and "Naked Beach Frenzy'' where the nudity card was stretched to the breaking point.
 * 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.
 * Chris McLean. Almost everything he makes the contestants do fits this trope, but
 * Not to mention the interns.

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).
 * Witness Divine Interventions, a website that deals in religious-themed sex toys, including a Baby Jesus butt plug. You heard me.
 * 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. 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.
 * Radio personality Alex Jones seemed to have based his entire career on this; unfortunately for him, his most outrageous and controversial claims (like claiming the tragic Sandy Hook shooting was a False-Flag Operation) crossed a line that he proved unable to cross the second time.