Ecchi anime Amazing Nurse Nanako has an infamous scene where Nanako must unload various things to prevent her plane from crashing, from kitchen utensils to bombs, which the latter is dropped into the temple full of Buddhist monks. One of the monks says "May the divine heaven showers their loving blessings are!" before they’re bombed. A number of watchers feel bad but can't help laughing at that scene.
Done often and well in Angel Beats!, but particularly memorable examples include Yui accidentally hanging herself and Naoi's death during the second Dwindling Party scene, when everybody's deaths have been followed by the remaining people screaming the dying one's name:
[Naoi dies] Otonashi: Anybody want to say something? Yui: ...I don't know his name.
Attack on Titan: Zackly torturing a captured noble. This wouldn't normally be funny, but the fact that the guy appears to be held in some kind of BDSM setup with a funnel up his ass can be funny to some. This example crosses the line four times when Zackly looks at his good work, literally sheds a tear and praises himself for it.
Zackly: Beautiful. This may be the greatest work of art ever conceived.
Claire Stanfield doesn't cross the line so much as he plays double-dutch with it. In any given episode he appears in, he can come off as over-the-top badass, disturbingly psychotic, or any combination thereof as many as five or six times depending on the gratuitous amount of Gorn he churns out. Most people end up filing him under Ax Crazy Awesome and call it a day.
Ladd Russo also loves to play hopscotch with the line, such as when he uses a dead Lemure as a puppet while taunting Chane. Equally good is the scene where he kills a hapless mook by punching him in the face until he dies.
CaptainKurotsuchi has skip-roped with the line since the Soul Society arc and comes of as all the more amusingfor it. Of course, the fact he's well aware of what others think manage to make some scenes even funnier.
In the Thousand-Years Blood War arc from the manga, there's the scene where Giselle Gewelle beats up her friend Bambietta. A Dark Action Girl who was turned into a zombie. By Giselle herself. It should be a terrible moment, but not only Bambietta was one of the villans and so's Giselle, but the scene is played as such a ridiculously over the topBoke and Tsukkomi Routine that it comes off as darkly funny.
The second season of Haganai has the infamous scene where Kodaka had just discovered that Yukimura is a girl and Rika decides to find out for herself by fingering Yukimura in plain sight of the entire group, followed by Rika visiblyspreading her fingers to see if Yukimura had gotten wet from it and happily announcing that Yukimura is indeed a girl.
Rika: 'Tis as clear as day now, milord! This one is most certainly a lass! Kodaka: That's what I've been saying too! Rika: Yeah, but nothing beats checking things out for yourself!
During the Future Trunks Arc of Dragon Ball Super, upon returning to the future to try and deal with Goku Black again, the security officers open fire on Goku. We then get this gem when out of context — in both the sub and the dub:
Security: Eat lead, murderer! Trunks: Don't shoot! This man isn't Black!
Dragon Ball Super: Broly has Paragus being killed by Frieza in order to turn Broly into a Super Saiyan. A dark and sad scene turned hilarious by Frieza's Bad "Bad Acting":
Four Knights of the Apocalypse dips into this with Lancelot's subplot during the Liones arc. In the space of one day, his friends are beaten half to death by law enforcement, he is sexually assaulted by a twelve-year-old, demons attack the city and beat his friends up again, and then his teacher tells him with utter seriousness that she's a pedophile who's been attracted to him since he was a preteen, and also that she's fucking an alternate magical sexdoll of him made by King Arthur. At some point, the subplot feels less like a logical series of events than the result of the author thinking "How many traumas can I put this character through in one day?"
Ghost Stories, the Gag Dub version oh so much. "I know now that it could never work between us! As much as we wanted to it could never be! Not because you're a rabbit, but because you're black..." The main characters' personalities are also changed into a born-again fundamentalist Christian, a Jewish stereotype, a little kid who may or may not be mentally disabled and often babbles incoherently, and a massive pervert who often blurts out sexist and racist things. The main character's mom also becomes a lesbian who hits on the fundamentalist Christian girl (who's a middle schooler) in a flashback.
Gintama does this very frequently with its gags, partly due to its tendency towards Vulgar Humor.
For one example, Gintoki and Kagura decide to make a replacement topknot for the Shogun using hair shaved from an unconscious Kondo's groin, which Shinpachi complains about as usual. They then note that a similarly unconscious Katsura's long, straight hair would be much better for making a replacement, and so they do...by making a wig that they place on Kondo's groin.
One of the Valentine brothers (the vulgar one, Jan) quotes the Konami Code while unloading with (two?) SMGs. At the end of a particularly gory segment early on. In fact, pretty much everything he says crosses the line twice. Like what he wants to do to Integra.
Jan Valentine: Little Hellsing chicky, we're coming to find you~! Come out, little Hellsing, I promise it will be a lot of fun! We just wanna torture you, kill you, maybe skullfuck your corpse a couple of times, burn your house to the ground, go home and masturbate, okay?
Hell Teacher Nube: The Buddhist nun who ate mermaidflesh 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.
Given that it makes fun about world history and often focuses on World War II, the entire idea of the show might fall under that. Making fun about the deadliest war in history normally would be Black Comedy at best, but having World War II presented as China beating up the entire Axis with a wok is just plain ridiculous.
In their promotional campaign months before the release, Funimation showed exactly why their dub of Hetalia was given a TV-MA rating. This immediately had the side effect of the fandom becoming a Broken Base over the altered dialogue. To clarify for those not familiar with the series: the protagonists are Those Wacky Nazis, the characters are merciless cultural stereotypes, and the whole show basically reads like World War II if World War II were a wildly inappropriate reality show. And it's hilarious.
China: We're not allowed to have Christmas trees in our country because they're flammable. It kind of sucks. Italy: Heh, just like the girls.
The premise revolves around a group of guys questing to find out which type of monster girl is the best by having sex with them and then posting the reviews at the local tavern. In just the first episode of the anime, there's Naughty Tentacles, a Hermaphrodite angel boy and full frontal nudity including visible genitalia on the girls in the uncensored version. Furthermore, the series is actually a Shōnen, not a seinen or hentai.
Episode 3 of the anime adaptation takes this to a new level with The Genderswap Inn, with "Chalmy" getting dommed by Piltia with toys, "Zelzel" being restrained and done by a slime girl, "Fem-Stunk" getting shown how women enjoy it by a 659-year-old elf woman,note who everyone else acts like she's some old hag and "Clitorim" getting a full scene with the hyena girl, complete with her humping him onscreen. It's sufficiently ero enough that the censored version straight-up blacks out several entire scenes.
The manga-only chapter 24 beats all of the above by a long shot. The scene opens with the gang visiting the Aquari-Harem, which specializes in soul transfer and has all of the Reviewers placed inside the bodies of various sea creatures to have sex for the next few hours. Stunk ends up in the body of a snail and immediately goes for a female snail nearby that turns out to be the biological daughter of the snail he's possessing. What follows is essentially a snail on snail rape scene followed by Stunk musing about how he'll be spending the next few hours:
Volume 4, chapter 31 has the succubus film auction, and the last video viewed, the one of the golems at The Sex Marionette being prepped for the installation of their soft parts, gets rather graphic in terms of ribaldness. For one, the golem being modified is conscious, with her personality core installed and active. For a second point, she feels everything as they take a drill, and then a file, to her crotch (to hollow and smooth it out for the installation of the soft part), and her erotic reactions are very spectacular, especially when they start inserting and fitting the soft part in and she starts feeling sensations from that part as well; in-universe, the entire spectacle is so spicy that the auction price for this specific succubus film skyrockets after the viewing.
Kill la Kill, which was brought to you by the same people who brought to you Panty and Stocking. How powerful you are is inversely proportional to how much clothing you have on. The Big Bad runs a fascist school hellbent on taking over all of Japan. The opposition is a girl repeatedly subjected to Black Comedy Rape and a revolution where being scantily clad is a requirement. One of the series' most dangerous villains is a walking source of Limited Animation and trolling. It really sets up how nasty the real villain of the series is.
Similarly to Bludgeoning Angel Dokuro-chan above, Magical Witch Punie-chan relishes in the protagonist's sheer brutality in applying wrestling submission maneuvers for much of its comedy. This is contrasted with the fact that she usually acts like the typical sweet Magical Girl (whose spells cause just about as much havoc...) As well as the fact that the setting where the main character comes from is a massively Crapsaccharine World and she herself is a Villain Protagonist.
Majin Tantei Nougami Neuro: Crosses the line so often it can only be explained as being in a quantum state
Lets list some examples shall we? Most of them are contained to the manga though. Lets see... there's the little girl that hires the detectives to protect her obviously pedophilic (toy-company owning) grandfather, whom she adores, and her attempt to kill his murderer when they fail to protect him. There's the actions of Kaitou X who decides to invite the main character to his mystery by replacing a wall that's been painted by children for world peace with around twenty glass boxes stacked on top of one another - each containing a murdered person ground up into bloody soup - just before it's unveiled on TV in front of the children. Or of course, how about when the later villain Sicks sends his own message by forcing a man to drive a knife into his gut and push his stomach along the ground to scrape in Sick's symbol in giant blood form or his family will be killed. Yeah. Every week before releasing a chapter the author had to meet with the editor because they wanted to make sure he didn't go over the top. What was considered over the top at this point is frankly impossible to know.
When X kills a bunch of neighborhood dogs, grinds up their bodies, and places them in boxes, it's horrible and twisted. When a guy holds up a tiny box crying about his chihuahua that he had to borrow lots of money to buy, it's sad, but kind of funny at the same time. When the people he bought it from come and ask him which body he wants to give up to cover the sale, it's morbidly hilarious.
Boa Hancock literally kicks an adorable kitten that happens to be in her way to indicate that she is, in fact, a villain. Later, and after pulling a Heel–Face Turn, she kicks a puppy and a baby seal at the same time to turn it into a gag.
Then there's Luffy's own Hilariously Abusive Childhood. The line is crossed when it's revealed that Luffy was tied to helium balloons and released into the sky. To make him stronger.
Panty & Stocking with Garterbelt is the living embodiment of this trope in Anime. All the main characters are named after lingerie. Comedic Sociopathy is commonplace, and it's always played for laughs. The titular duo respectively have an unstoppable drive for sex and bondage. The closest thing the series has to an Only Sane Man who can actually do something is a Pedophile Priest, and his Evil Counterpart is a Combat Sadomasochist ramped up. Ghosts are made of shit, vomit, and semen. Anything it references, from Barbie to Transformers, is Rule 34ed tounbelievable extremes.The soundtrack itself has a song that is literally a woman having sex, complete with sexophone. FLCL is CHILD'S PLAY compared to this.
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.
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.
The ludicrous exposition in Speed Racer does this often and unintentionally.
Umineko: When They Cry: Tako-Maria. As in, Maria's talking severed head, that bears an uncanny resemblance to a cute octopus based on a certain Vocaloid character.
