Avataro Sentai Donbrothers: Episode 40 has Haruka/Oni Sister trying to pass driving school to get her license. The real kicker is that she's a terrible driver, and it raises a lot of red flags not just from possible collateral and property damage, but she could have faced traffic violation-related legal troubles. These implications would be ignored, purely out of comedy as with most of the heroes' antics in the show, when she rams her car at Don Murasame of all people. So much so that her "heroic" act behind the wheel is enough to convince her driving instructor to reward her a license.
Watching the treacherous Lord Refa hunted down and torn limb from limb by angry Narns? Grimly satisfying. Watching the treacherous Lord Refa hunted down and torn limb from limb by angry Narns while ''No Hiding Place'' plays in the background? Funny as ''hell'.
Centauri 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, they 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, and Stephen Furst's increasing facial contortions as Vir as the scene goes on, you can't help but laugh. And then he pours the bloody water from washing his hands on his plants, saying it helps the flowers grow.
Batman: In Gotham, a lot of the humor in Jerome Valeska's character comes from crossing the line twice, unsurprisingly, considering who he's based on. For example, it was horrifying when he tried to light a busload of cheerleaders on fire, but the way he pouted when his lighter didn't work and proceeded to ask the cheerleaders he had just doused in gasoline if any of them had a light somehow made the scene funny, as well.
Blackadder has this on a few occasions, including this gem from series 3:
Blackadder: They do say, Mrs Miggins, that verbal insults hurt more than physical pain. They are, of course, wrong, as you will soon discover when I stick this toasting fork in your head.
Aunt Whiteadder: Cold is God's way of telling you to burn more Catholics!
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. Beating up a gasman takes so long they take breathers.
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 pedophile trapped on an island covered in cameras, and a pedophile 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.
Breaking Bad: From the second episode, you wouldn't normally expect yourself to laugh at a half-dissolved corpse crashing through the ceiling and splattering all over the landing thanks to Jesse not knowing you don't put acid in your bathtub. And yet you do because the entire situation is damn hilarious, plus Walt's magnificent Oh, Crap! look helps.
The scene in "Hush" where Buffy attempts to mime staking the Gentlemen and ends up miming another action entirely shocked the network, but they kept it in because it was just so damn funny.
Season six piled on so much Deus Angst Machina that it became an in-universe example of crossing the line twice: when Giles (very dramatically) returns at the end of the season, Buffy tells 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.
The end of the "Time Haters" sketch, as the titular Haters face a 19th century slave master.
Silky Johnson:[after delivering a "The Reason You Suck" Speech to the slave master] —But the point is, is that in the future, all black people are gonna be free!! Slave: When's we gonna be free? Silky: That is a good question, my man! [Beat]How about now-ish? [Silky shoots the slave master]
It usually crosses the line just once, but one particular episode crossed it twice. In a skit, it showed The 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."
The second episode of has an In-universe example. In their protest, Annie and Shirley decide to commemorate a murdered Guatemalan journalist... with a pinata. Britta is not happy:
Britta: You guys realize he was beaten to death, right? Shirley: That's where we got the idea from.
Community has many examples of this, including a Halloween special in which the dean of the school is imagined as the devil. He describes an increasingly gruesome and painful sounding "damnation orientation" session, before being blown away. He comes back though, wielding a chainsaw and shouting, "Gay Marriage!" The show crosses the line again when Shirley gleefully narrates, "And then he chainsawed them to bits! Then he put them back together, and then he chainsawed them to bits!" Actually that whole episode qualifies as this.
The entire concept of violence is used to cross the line multiple times. Annie knocking a janitor out with chloroform? A little awkward. The plan after (and the subsequent second chloroforming of the same janitor)? Downright hilarious. This penchant for violence seems to be lampshaded later on when it's deduced, via multiple choice testing, that only one of the study group members is not mentally ill.
''Crazy Ex-Girlfriend" features this with an extended monologue about parking that has a ridiculous double entendre. It seems like an overly long gag, but then eventually becomes awesome.
Hector: I think it's a nice thing you're doing. Nicest thing I ever did for a girl was pull out. Greg: Hector... Hector: She has tandem parking, so after I'm there for a while, I have to pull out, which is such a pain 'cause it feels so great just to leave it in there. The worst is when it's all side of the street parking, 'cause then I have to park in the back. I don't get why there's a spot back there. It's so tight. It feels more like an exit. So then I'm going front, back, front, back... and it's all dirty in the back, so when I move it to the front, then that gets all dirty. I'm just happy I have a spot at all... 'cause I used to have to pay.
Larry David's Curb Your Enthusiasm 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.
Many of the less probable accidental deaths on Bryan Fuller's 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.
Not to mention his siccing the Toclafane on Vivian Rook. The Master and Lucy run out of the room while Vivian screams, and slam the door. The Master opens it, and she's still screaming. He winces and closes it. Opens it again three seconds later — and she'sstillscreaming.
Even the Doctor gets in on this in "Amy's Choice". Upon finding out Rory's ideal world is living in the world's most quiet (and boring as hell) neighborhood with people over 90, he asks in exasperation: "How do you stave off the impulse for self harm?"
In its absurd, dysfunctional hellscape parody of a traditional talk show, The Eric Andre Show crosses the line early, often, and never looks back, both in the violence that Eric and Hannibal inflict on each other, the stagehands, the set, and themselves and in Eric's frequently horrendously inappropriate behavior towards the celebrity guests, which quickly becomes far too painful and awkward not to laugh.
Eric telling Jennette McCurdy that he's printed out one of "her nudes" and holds up a (photoshopped) sexually explicit picture of Barack Obama.
The moment she sits down, Eric immediately asks Malaysia Pargo "Are you a girl?", before promptly asking her if she was named after the Malaysian Airlines flight that went down over the Indian Ocean, which Eric describes as "the world's toilet."
The characterisation in Father Ted operates on this principle.
Take Jack. An alcoholic Irish priest? Not funny, and an offensive stereotype to boot. A priest so addicted to alcohol that he can tell a wine's vintage just from the clinking sound the bottle makes and who will drink cleaning products if alcohol is not available? Hilarious.
Then there's Dougal. A stupid priest? Not funny. A priest who is so stupid that he can't tell the difference between 'small' and 'far away'? Hilarious.
And, of course, Ted himself. A priest who steals money from orphans? Not funny. A priest who takes the (stolen) money to a casino and throws it up in the air and laughs hysterically while surrounded by scantily-clad showgirls? Hilarious.
Also, Mrs Doyle. A housekeeper who really likes making tea? Not funny. A housekeeper whose obsession with making tea leads her to persistently ask people if they want tea even when they’ve already repeatedly said no and who even has a special blend of tea for any visiting sheep who might want a cup? Hilarious.
From a scene in "Shindig" where Malcolm wins a duel with a truly obnoxious and stuck-up opponent that had it coming:
Malcolm: Sure. It would be humiliating. Having to lie there while the better man refuses to spill your blood. Mercy is the mark of a great man. [lightly stabs him with sword] Guess I'm just a good man. [stabs him again] Well, I'm all right...
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...where they are all executed.
Niles:[playing Frasier] Now, I want you to contribute, but only up to a point. Frasier:[playing Mary] So you want me to stay in my place, Massa?! Niles: She's not going to say "massa". Frasier: What, am I gettin' too uppity for you? You sherry swillin', opera lovin', Armani wearin' elitist? You have no idea how difficult it is for a black woman in a white man's world! Niles: Frasier— Frasier:[practically snapping his fingers] I DON'T THINK SO!
Sue Sylvester from Glee lives and breathes this trope, especially in her "Sue's Corner" news segments. Here's her take on "Sneaky gays". To secure a position as a rival glee coach, Sue caused the former holder of the position to tumble down a flight of stairs. This is the second time she's done this to further her nefarious plans. The first time, she subtly tripped an elderly woman. In this case, she shoved a healthy, middle-aged man down a flight of stairs. And when he survived the first tumble with nary a scratch, she wordlessly walked down to him and shoved him down another flight of stairs with an equal lack of subtlety. The man ended up in a coma.
Australian Panel GameGood News Week thrives on this, usually instigated by host Paul McDermott or regular Mikey Robbins. Hell, everything Mikey Robbins says tends to fall into this.
Go Princess Go: Zhang Peng attempts suicide repeatedly? Not funny. Zhang Peng's attempts are constantly foiled by Lu Li while a song plays in the background and the entire scene is filmed like something out of a silent movie? Funny!
Rintaro Aida in Homeroom is a Hot Teacher with a laser-focused crush on one of his students, Sachiko Sakurai. He secretly engineers bully attempts by doing things like gluing her seat all so he can swoop in and be her "hero", and after school he stalks her to her house and mixes sleep-inducing drugs in her tea so he can sleep next to her naked while she's out cold (though he draws the line at outright raping her). All of this would make him seem like a completely gross and despicable character, but he's so Ax-Crazy and over-the-top it's hard not to be entertained by him, with his obsessive rants about Sakurai often being accompanied by overly dramatic music.
Ted: I can't decide whether to be thoroughly disgusted or really, really impressed.
At one point he claims he may have actually sold one of the women he's slept with. It shouldn't be as funny as it is. In a perfect example of this trope, the line is funny rather than horrifying because he's so indifferent that he isn't even sure.
Barney: I mean, at one point I'm pretty sure I sold a woman. I didn't speak the language, but I shook a guy's hand, he gave me the keys to a Mercedes, and I left her there.
While this "commercial"starts out serious and rapidly shows its comedic underpinnings, the route it takes is a little questionable... up until the line "And then steal it again," at which point it has properly crossed that second line.
Similarly the breakup of Douglas and April is heartbreaking until she wallops him, arguably crosses back over the second line when he wallops her back, then crosses the second line for good as it turns into a protracted brawl that results in the 'destruction of the Internet'.
When Denholm is told that the police have arrived to investigate his pension fund, he jumps out the window to his death in an absurdly calm and casual manner. Shortly after is a flashback where he can be seen falling behind the window of a lower floor behind Moss. Someone on the floor screams "JESUS!" upon seeing Denholm, but Moss thinks he was overreacting to his speech about computer viruses instead.
When one episode involves two characters getting addicted to crack to get better unemployment benefits... while the other two characters treat a "work for welfare" program like a slave auction.
Charlie answering the door, eating a banana, wearing a SS officer's uniform.
Charlie biting a mall Santa's ear off after realizing his mother spent his childhood Christmases sleeping with tons of men in Santa suits.
Frank setting Dee on fire as she attempts to rescue a box of kittens, causing her to throw the box away as she tries to put herself out. This ends up happening twice.
The gang invites all their enemies to Dennis and Mac's apartment to squash their beefs, but the ensuing arguing ends up with the apartment catching on fire. The gang gets out... but not before blockading the front door from the outside. With everyone else still inside.
Kamen Rider Ex-Aid, a video game medical drama, is no stranger to humor that is just morbid, so it's only natural that some of the jokes cross into this territory.
Getting a Game Over in battle leads to affected person dissolving into pixels. Second time uses this as a spoof — way to punctuate one of the characters being probably the pinkiest force of nature possible this side of Power Rangers.
Working oneself to death by exhaustion is usually disturbing, especially since in Japan note There is even a word for it, karoshi., this happens quite a bit. However, it quickly stops being disturbing because said person dying just revives by being shot out of a warp pipe Mario style and treats dying like all he needed was a cup of coffee. And this happens no less than 12 times.
Kamen Rider Build: Being accused of murder is not funny. Being accused of murder 330 times in row is petty. Keeping count and acting annoyed over the number is this trope.
John: Of course we did! They're good workers, and their corpses make a solid foundation material. That's an architectural fact.
John's take on the segment regarding the aftermath of the Charleston, South Carolina, church shooting, where one of the news reporters points out the procedure of moving the Confederate flag flown in front of the state's capitol.
John: Yeah, it needs a two-thirds vote. They were originally going to make it three-fifths, but even they thought it might be a bit on the nose.
In the Season 4 premiere, John reveals that he's become so traumatized by all the things Trump did in his first few weeks as president that after one particular news alert, he actually said out loud, "Oh, thank God, it's just that Mary Tyler Moore is dead."
Since the UK prohibits the use of parliamentary footage in comedy, the Brexit update segment, which uses such footage, had to be replaced for the show's UK broadcast. As an alternative, Gilbert Gottfried reads from portions of the provisional Brexit agreement in his trademark shrill voice, followed by an excerpt of Bigfoot erotica. John threatens the UK with more Bigfoot erotica if Brexit isn't stopped (or at least the law about parliamentary footage).
Gilbert: [A]nd between his legs swung what I can only describe as a glistening, furry forest log. Picture a mink biting an apple. My mouth instinctively dropped open in surprise, and if I'm honest, anticipation. This is going to be the Loch Ness Monster all over again!
John's incredibly dark comment on Senator John Kennedy's (self-admittedly poorly sung) COVID-19 vaccine endorsement:
John: Okay, I don't love that, and not just because it's the worst thing to come out of a Kennedy's mouth since the back of a Kennedy's head.
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 movies and series are based on this trope. Everything always ends with destruction of everything that appears in path of our protagonists. Like in the following joke. (Note that out of all the mischief the crew unwillingly did, this was the only one to haunt Stan, especially the robot on the planet.)
Stan: That planet is ugly. Lexx, destroy this planet after 1 minute. Stan:[after some bargaining with planet inhabitants] OK, cancel my command. [BOOOOM...] Lexx: Sorry, what does word cancel means?
But while talking about Lexx and the carnage it left behind, let's not forget being responsible for the destruction of countless planets AND THEN an entire universe.
The surprising and hilarious death of Leslie Arzt in the Lost episode "Exodus, Part 2" from mishandling nitro-leaking dynamite. Made all the more funny by Hurley's next line: "You got some... Arnst... on you."
The casual sexism displayed in some of the ad breaks and occasionally from characters like Mr. Hart and Dr. Nielsen is a pinpoint skewering of what a lot of entertainment in the time periods being referenced was actually like, yet also provides some of the show's biggest laughs.
The Lagos ad in Episode 5 turns the horrific inciting incident from Captain America: Civil War into a cheesy paper towel commercial, complete with Symbolic Blood. "Lagos. For when you make a mess you didn't mean to!"
The end of Episode 6 with Wanda expanding the barrier and taking the majority of S.W.O.R.D. agents and Darcy prisoner in Westview... Not funny. Her turning them into literal clowns and their weapons into circus equipment... Yeah, that's funny.
Sparky dying? Very sad. Agnes potentially killing him? Even worse. Agatha bringing the Big Cruella Energy with a The Munsters-style theme song while cackling about how she murdered Sparky? Hilarious!
Hawkeye: Murder? Not funny. People being eaten by animals? Horrifically not funny. The protagonists wondering what to do with a tiny shrunken van full of Mooks being carried away by a cute owl, while said mooks scream hysterically, and the protagonists just shrug and go with it? Hilarious.
Nathan's description of "tripling" himself in the season 2 finale. note For those of you who do want to know... it's when you ejaculate, vomit and shit yourself all at the same time.
Plenty of scenes in Misfits fall into this territory, such as the birth scene in the Christmas Episode, where Nathan mistakes the afterbirth for an alien baby and starts screaming and stamping on it. Also, when genuinely terrible things happen to characters on the show they are often executed in such a way that they quickly become hilarious (such as Nathan being buried alive or Daisy getting impaled on her own "Mother Teresa Young Humanitarian of the Year" Award) and conversely scenes which, on paper, sound as though they should cross the line twice actually end up pretty disturbing (such as Brian murdering people with mozzarella and greek yoghurt).
The "Sam Peckinpah's Salad Days" sketch, which takes Ludicrous Gibs to even more ludicrous levels. Unsurprisingly, given it contains (literal) fountains of gore resulting from people getting dismembered, being impaled on tennis rackets and having their hands ripped off by a piano keyboard cover closing on them, it generated large numbers of complaints. note Though Peckinpah himself loved it and would show a copy of the sketch to friends.
"Undertakers Sketch", the final sketch of series 2, also pushes the envelope of tastelessness in classic Graham Chapman style. The sketch features a discussion between an undertaker and a customer of how to dispose of the latter's mother's corpse, to the sounds of an increasingly vocal shocked and disgusted audience, who storm the stage after the notorious final line.
Undertaker: Look, we'll eat your mum. Then, if you feel a bit guilty about it afterwards, we can dig a grave and you can throw up into it.
The thing that clinched the sketch as this trope is that the invasion of the stage was itself arranged to get this sketch past the BBC censor, who felt that only the implicit apology of the apparent audience revolt would make it acceptable. It's also noticeable in the film that only about 50% of the audience had been enlisted to boo and invade the stage- the rest are clearly seen laughing.
"Undertakers Sketch" was mentioned by John Cleese during Chapman's eulogy, which itself massively pushes the bounds of taste in homage to Chapman, who Cleese described during it as the "prince of bad taste".
Cleese:Graham Chapman, co-author of the 'Parrot Sketch', is no more. He has ceased to be, bereft of life, he rests in peace, he has kicked the bucket, hopped the twig, bit the dust, snuffed it, breathed his last, and gone to meet the Great Head of Light Entertainment in the sky. And I guess that we're all thinking how sad it is that a man of such talent, of such capability for kindness, for such unusual intelligence, a man who could overcome his alcoholism with such truly admirable single-mindedness, should now so suddenly be spirited away at the age of only forty-eight before he'd achieved many of the things in which he was capable, and before he'd had enough fun. Well, I feel that I should say: nonsense. Good riddance to him, the freeloading bastard, I hope he fries. And the reason I feel I should say this is he would never forgive me if I didn't. If I threw away this glorious opportunity to shock you all on his behalf. Anything, for him, except mindless good taste.
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. To quote the show's host, Dara O'Briain: He hasn't merely crossed the line in the sand, but moved into arctic tundra regions so he can't even see the line in the sand.
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.
NTSF:SD:SUV::: After having his death faked, the President of the Navy is forced to lay undercover in a four-star hotel room. He's so horrified by this situation that he compares himself to Anne Frank.
The Office (US) is a veritable master of this trope, particularly when in comes to Michael's cluelessness. He often says things that are crushingly painful and way out of line, that slowly become too awkward not to laugh... While the show may not involve actual physical violence for comedic effect, it certainly brings the pain.
The Office (UK) had a similar theme: David Brent's jokes failed so badly it quickly became funny for the sheer awkwardness of his self-delusion.
The murals in Pawnee City Hall in Parks and Recreation. One shows a train running over buck-toothed, coolie-hatted Chinese while whiskey-swilling Irishmen point and laugh, another a Native Chief in full headdress, tied to a tree, as two soldiers prepare to shoot him point-blank with a cannon, one showing a wedding between a white woman and a Native man being attacked by both groups, one showing a man punching a woman in the stomach as people watch and wave money around...
Parlamentet. Making fun of everything, going from skeptical junkies to hunting Moomins for being parasite carriers.
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.
Psychopath Diary: Dong-sik tries to murder Mu-seok? Not funny. Dong-sik fails terribly at murdering Mu-seok while an exasperated In-woo watches? Funny.
A lot of the deaths in Pushing Daisies arguably fit this, but perhaps the best example is that of Harold Hundin, the dog breeder. He drank coffee that has been laced with arsenic, and when he succumbed to the poisoning, he fell onto a sharp dog brush handle in a box, stabbing him. It doesn't end there, though, because the floor was wet, so he kept slipping and falling onto the dog brush again and again, stabbing him repeatedly. Seriously, it's hilarious. There was also the episode when a car full of clowns goes into the lake, we see them pulling a clown out, then another, and another, including one with stilts. By the end it's side-splittingly hilarious.
In the Red Dwarf episode "The End", Lister's shock at being the sole survivor goes from tragic to funny as he persists in asking about specific people, only to be told that yes, they were counted in "everybody". When he finally clues on to the idea that everybody is actually dead, Holly laments bringing him out of stasis in the first place.
Due to its high levels of Black Comedy, The Revolution Will Be Televised tends to run on this when its more offensive characters appear. Examples include the Camp Gay host of Double Fist TV turning up outside the real MI6 offices to ask if they can use their infamous torture chambers as a kinky nightclub, encouraging the people of Britain to help Tony Blair get a sainthood for dropping "bombs of democracy" on Iraq and their response to a magazine naming Tony Blair "most influential person of the year" (sending alternate covers with Adolf Hitler and other various tyrants winning the award instead).
In "A Guest In The Yard", the white homeless bum and freeloader Gus, when ordered by Sanford and Lamont (both of whom are black) to leave their property, threatens that he'll never contribute to the NAACP, which makes for a pretty egregiousreaction. Fred fires back with the priceless response that he, in return, will never contribute to the KKK.
In "Legal Eagle", when Fred is put on trial for speeding.
Fred: Listen, why don't you arrest some white drivers? Cop: I do. Fred: You do? Well, where are they? Look at all these niggas in here! Look around here! There's enough niggas in here to make a Tarzan movie!
Esther: Who you callin' ugly, sucker? Fred: I'm callin' you ugly. I could stick your face in some dough and make some gorilla cookies.
In one episode of Santa Clarita Diet, Sheila and Joel decide to lure a Nazi to their plastic-covered storage unit, so that Shiela can murder and eat him. However, upon his arrival he mentions he brought a friend with him, and the couple realize the friend is wheelchair-bound. The couple briefly ponder if it is still ethical to eat a handicapped Nazi, wondering if it a hate crime to murder someone in a wheelchair. Sheila arguing that he wouldn't want to be treated any differently because of it, and Joel arguing that he would if it meant he survived. Sheila promptly kills both Nazis when they angrily reveal themselves to be virulently racist/misogynistic homophobes, and the one in the wheelchair gets offended when he thinks they are discriminating against him for his disability.
The "Canteen Boy Goes Camping" sketch. Having a sketch about a scoutmaster molesting one of his Boy Scouts? Dude, Not Funny! Having a sketch about a scoutmaster molesting a 27-year-old who's still in Boy Scouts? Still kinda Squicky, but kinda funny. Airing this as part of a Valentine's Day episode? Elicits that kind of laughter where it's wrong, but you can't help it.
In a more recent episode hosted by Dwayne Johnson, there's a sketch where an Indiana Jones parody (Johnson) and his two sidekicks are about to enter a temple in a jungle when the natives appear and fire a poisoned dart at him. The Short Round parody sucks the poison out, then later gets shot himself. Dr. Bones sucks out the poison saying that he was repaying the Short Round's kindness earlier. Then the doctor gets shot in the nipple, the Short Round sucking. The sketch ends with both of them getting shot in the crotch, and the two of them aligning themselves to suck the poison out of each other, with the female sidekick (who spent the entire sketch complaining that she couldn't suck out the poison/get it sucked out of her) carried off by the natives.
Later in the same episode, during the Weekend Update segment, Colin Jost brings up a story about how the opening of a show based on a real-life serial killer had gotten complaints about how it seemed to glorify serial killing, with the clip they played featuring a cheery upbeat song timed in such a way that the singer goes "WOO!" when the picture of one of the killer's actual victims appears on-screen. Jost then begins suggesting other songs for the theme music, beginning with "This is How We Do It" and ending with "Oops, I Did It Again."
Roy: I want to remind you guys that Webster's Dictionary defines "evil" as "profoundly immoral". Baroness Antarctica: We know what "evil" means! Roy: Well, seems like you don't, because you built a freeze ray. I mean, Benito Mussolini used to feed people castor oil until they literally died of diarrhea. I mean, that's got to be where the goalposts are, right?
That same sketch also includes this gem:
Member: How...? How do you even build a child molesting robot? Roy: Well, that's a great question. What you do is you start by building a regular robot, then you molest it and hope it continues the cycle.
A Weekend Update Segment featured then-writer Al Franken giving a report on how nasty California's Senate Race had become to Weekend Update Host Norm Macdonald. Cue a fake political ad which consisted of a picture of Senator Diane Feinstein and a voice over that ominously intoned "Diane FEINSTEIN is against prayer in public school... And why not? SHE'S A JEW!" cut back to a vaguely disappointed looking Al Franken sitting next to a shocked Norm Macdonald who can only manage a weak "Wow..." after a moment or too.
"A Bear Ate My Parents" with Horatio Sanz. The sketch ends with him committing suicide after being confronted by an (unwitting) singing-telegram performer in a bear costume.
A notorious sketch from one of the John Goodman episodes was probably aiming for this trope but instead crash-landed (quite literally) in Nightmare Fuel territory. Happy tourists on a plane to Hawaii are (cheerfully) informed by the pilot that there is a vicious king cobra loose on the plane. Then, a few seconds later, he announces that the cobra is only on one side of the aisle, so the passengers on the other side don't have to worry. Then he announces that there are now twelve cobras on the plane, but that one side has seven cobras while the other side only has five. This is followed by the most ghoulish and terrifying hissing imaginable, which then yields to people screaming in pain and terror as the still-invisible cobras begin to strike. Only then do the cobras make their appearance, and they are freakishly albino and have glowing red eyes; the fact that they are obviously puppets is apparently supposed to make them comical, but instead it creates a plunge straight into the Unintentional Uncanny Valley. To make matters worse, the main characters have to remain absolutely still so that the cobras looming over them aren't provoked to bite them...for several hours. By the time their flight is even remotely close to Hawaii, their bodies are literally gushing sweat. Finally, one of the cobras make its way into the cockpit and bites the pilot...and the venom for some reason warps his mind, making him psychotic and causing him to imagine that an "old Indian" is appearing before him in the ocean, beckoning him on. He steers the plane straight down toward the water and creates a fiery collision, killing himself and everyone else on board who was still alive (including the cobras, of course, not that that did any good). As the flames surge toward the TV screen, a gigantic albino cobra puppet with a woman's voice appears right in the face of the viewers and gloats, laughs and tells jokes about what just occurred in her hissy voice. And as if all this weren't grisly enough, this was the very last sketch of the evening's program, which goes off the air at one o'clock in the morning. No doubt countless herpetophobes checked very carefully under their beds before retiring that night.
Norm: This week, in the O.J. Simpson trial, the infamous "bloody glove" was finally introduced into evidence. And O.J. didn't help his case any by blurting out, "There it is! I've been looking all over for that thing!"
Six Feet Under was basically built on top of this trope. The department store Santa/Hell's Angel member's Big-Ass Biker Funeral (with biker flame decorations on the metal coffin) is a particularly funny/sick example.
The scene in The Mandalorian with the two Scout Troopers (who are played by comedians Jason Sudeikis and Adam Pally) at the beginning of Chapter 8 is both appalling and hilarious. It's appalling because they physically abuse the Child (a.k.a. Grogu or Baby Yoda), but it loops into being hilarious when one of them worries that they might have accidentally killed him by bopping him on the head, finds out he's still alive, gets his finger bitten, and then punches the child in the face (it also helps that the scouts get brutally killed by the Child's nanny IG-11 shortly after). The complete bored indifference with which they react to Moff Gideon killing his own men just makes it all the more hilarious. To make it even more funny, many Twitter users jokingly treated hitting the Child like both actors'Moral Event Horizon (despite the fact that the Child is portrayed by a puppet).
The Mandalorian Chapter 10's running gag where the Child, repeatedly, breaks into the incubator of the episode’s client to swallow her eggs whole. It's dark, but he does it so often when her entire lineage is on the line that it's hilarious.
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.
Subverted (off-camera) and deconstructed in Studio 60 on the Sunset Strip episode "The Option Period", when Matt Albie complains about an (unseen) sketch that a clueless special-effects guy ruins by curtailing the scripted excessive blood, thereby un-crossing the second line, so to speak.
Danny: He didn't think it was realistic. Matt: The prop guy? Danny: Yeah. Matt: It's called Quentin Tarantino's Hallmark Movie, "Turkey Won't Die." It's about a mortally wounded bird that will not die, even as it's being served. Did he find the premise realistic?... If 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...
Studio C is so squeaky clean that you wouldn't think that this trope would come into play, yet it does. In the "Lost Plane Crash" sketch, all the survivors (except the Only Sane Man Jeremy) think they're stranded far away from civilization, when in reality it's a stone's throw away. Believing the pilot to be dead, Matt says, "Well, at least now we have food. These peanuts... will make a great garnish."
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).
The episode "Wishful Thinking" features a wishing well that grants warped wishes. Aesop aside, one little girl wishes for her teddy bear to be real. What she gets is a giant, hard-drinking, skin-mag-loving bipolar mess who eventually tries to commit suicide by blowing its brains out. Problem: the bear doesn't actually have brains. All you see is a line of stuffing fly through the air accompanied by a gunshot, and the bear starts crying as it realizes that it doesn't have the option of suicide.
The episode "Mystery Spot" is a fan favorite at least partially because of this trope. The Trickster causes the same Tuesday to repeat for Sam over and over, each repetition triggered by Dean dying. His first death or two are horribly depressing (shot with a shotgun, hit by a car), but as Sam's frustration mounts, the comedy and gruesomeness of Dean's deaths rises as well (slipping in the shower, a desk dropped on him Looney Tunes style, "do these tacos taste funny to you?"). The Trickster himself says the comedy has worn thin on him, so it becomes apparent the only person laughing is the viewer. You Monster!. In a fine moment of Mood Whiplash, after the loop is broken, Dean is shot by a mugger (on Wednesday, so it's for real), is dead before Sam even gets on the scene, and we're back to the depression. The whole point of this episode was for the Trickster to teach Sam that Dean's end of the season death was inescapable, by making it laughable.
The Trickster runs on this trope. His ironic punishments are usually hilarious, (killing adulterers using the Hulk, anal probing an abusive pledge master and forcing him to slow dance, trapping Sam and Dean in TV Land where they are forced to reenact spoofs of CSI: Miami and Grey's Anatomy) if cruel and gruesome. It's part of what made him an Ensemble Dark Horse.