In Erfworld, Parson Gotti is Trapped in Another World in forced servitude as Chief Warlord to Lord Stanley the PlaidTool, who summoned him as a last resort to repel an invading coalition composed of pretty much every other nation in existence. They're outnumbered more than 10 to 1, and Parson attempts a desperate plan to use their dwagons (yes, dwagons, with a "w") to target the enemy's siege engines, hoping to buy a little time. He manages to take out about half of the enemy siege units... but then about half of his dwagons and warlords are lost in the counterattack. Their best spellcaster is rendered catatonic, another is driven mad, and another is killed outright; only two remain unscathed. Stanley, suspecting betrayal, takes their remaining dwagons and one of the casters and goes off to create a new kingdom elsewhere, leaving Parson behind to face the assault.
He wins the unwinnable war, only to set things in motion that shake the very foundation of Erfworld. His side now having literally gamebreaking units, wiping out sides left and right.
The Order of the Stick seem to spend their time watching things get worse. Blame Cerebus. Holes torn in reality. Roy dying. Shojo dying. The team is split up. Roy's body is used as a bone golem. Haley is even DEEPER in debt to the Thieves' Guild. Vaarsuvius makes a Deal with the Devil, then crosses the Moral Event Horizon within five strips... but comes back enough to feel guilt for killing 60 people accidentally. Rich Burlew is an awesome writer, but seriously — is the moon going to slam into the planet next?
Mike's mother Hazel gets engaged to a Tuxedo and Martini supervillain who, not realizing the connection, kidnaps the male Roomies; this leads to Roger going berserk and tearing a room of his Mooks to pieces, in the first (and angstiest) of many "full-court" fights against them.
TsundereCrazy Survivalist Margaret realizes she's killed someone for the first time (something even the cast page had explicitly pointed out she hadn't done "yet") when the shotgunned body of Roger's mother, who had tried to eat her, turns human in front of her.
When Marsha finds out that April is carrying Mike's child, her chronic jealousy leads to a knife fight, that ends with April accidentally killing Mike, on the same day Dave gives Mike's biological father a fatal heart attack in front of Mike's sister — and Dave's beta love interest — Blue.
Finally, Marsha tries to kill April only to be interrupted by Hazel...who kills Marsha, turns her into a cyborg, and puts April into a coma — making sure she can still feel pain — until Mike's son is born.
8-Bit Theater mostly consists of things going From Bad To Worse for everyone. But a special one is the team's plan not only failing to kill Sarda, but also making him even more evil and hate-filled than before.
And things just keep going wrong. First they have to fight the strongest sage in the world, then they have to fight the strongest sage in the world who just absorbed all the power of the 4 elements, then they have to fight the strongest sage in the world who just absorbed all the power of the 4 elements, plus all the evil of the 4 fiends and twice the evil of Black Mage, who just dropped their levels down so far Red Mage can't even cast spells any more, and transformed into the incarnation of chaos itself.
Concession: both Artie's current life and Joel's childhood. Artie's father died of cancer and his mother killed herself after Artie was diagnosed with the same type of cancer. He seemed to get better, then the cancer spread to his brain. He suffered blackouts which he thought were the result of the tumour, but were actually the work of Joel, who had decided Artie needed to be disposed of before his latent powers became a threat to Joel's own powers. He woke up from one of these blackouts to discover he had had sex with a ten-year-oldhypersexualtransgender child. He attempted to have a relationship with Kate, only to discover she actually was a paedophile and was in fact sleeping with the same child, among others. She broke up with him, but gave him money for the operation he needed, during which he was attacked by Joel on the spiritual plane. He tried getting help from elsewhere, but broke a major taboo of his new friends' society by impregnating one of them (they're dolphins and are forbidden to interbreed with land-dwelling species), and was apparently involved in the fire which burnt their whole city down. Joel, meanwhile, watched his twin sister murdered by his older brother when they were very young, and their parents assumed Joel had done it. He was put in an asylum, where he was sexually abused by a doctor and released back into the outside world while still unstable. His father then left the entire company to his older brother, leaving Joel with nothing, which started him planning an elaborate plan to destroy the company.
However, it is revealed that Joel's brother didn't do anything (most likely), and most certainly isn't evil, and Joel caused all this suffering for nothing. Wahee. But, at least things are getting better for everyone still alive, and with only four comics to go at the time of this edit, looks like things can't get worse.
For a while in Sluggy Freelance it looked like the "bROKEN" Story Arc was going to end with Zoe and Riff Trapped in Another World, and Torg having to find a way to bring them back. Then we see the world Zoe and Riff got sent to and discover Zoe died from her injuries moments after arriving, while Riff (believing Zoe's death to be his fault and that the genocidal dictator of this new dimension is his Alternate Universe self) willingly consigned himself to an eternity of drug-induced amnesia.
This is apparently what happened in the most recent arc of Ansem Retort. What happened specifically hasn't been revealed, only one line gives us an idea:
Riku: Shit be fucked!
Subverted. They saved the day, got everything to work according to plan, and ended on a high-note by psyching out their friends. Quite characteristically.
Unsounded s Duane Adelier was born into a low ranking family in a relatively low ranking caste, confronted an important politician, lost a promotion, found himself set upon by hired thugs in a dark alley with his young daughter, drugged, arm broken, skull smashed in, only to feel one last surge of adrenaline long enough to watch his daughter accidentally impaled by a sword. As he's slipping away and enters limbo, he watches her cross into the afterlife but has the door slammed before he can enter, and is dragged back into his dying body only to have his eyes gouged out. After these events, a currently unknown process occurs that binds his soul to his now dead body giving him not only a classic zombie horror hunger, but full sentience as he feels himself decompose and loose all his natural senses, ability to speak, and most of his soft tissue over a year until he composes mechanical and magical replacements for sight, speaking, and hearing. Six years after the fact he's a skeleton of his former self and still tethered to his desecrated corpse. The only reason he won't commit suicide is because his religion forbids it.
During "Hivebent", Karkat is left gaping in horror after Eridan pulls a FaceHeel Turn, knocks out Sollux and murders Feferi and Kanaya before leaving to join Jack Noir. Finally, he is contacted by his missing friend Gamzee, who informs him that he has apparently seen the light and is on his way to kill all the remaining trolls.
Gamzee: WELCOME TO THE DARK CARNIVAL, BROTHER. honk.
It turns out, Kanaya is back from the dead, and is now a vampire. And Terezi is without any methods of contacting anyone else, and in the last known area of Kanaya. Oh, and Equius is of no help against Gamzee, since Gamzee has the blood of royalty, and Equius personally believes that he must be indited into such a role. So, yeah. Things aren't good in the world of Homestuck.
Vriska Is backstabbed because her fighting Noir would get everyone but herself killed, and is arguably permadead because of future!Slick's hatred of clocks. Rose leaves Dave behind to deliver the Tumor herself, and is confronted by Diamonds Droog in the process. Bec Noir, in addition to possibly blowing up the universe as the Critical Event, could have been entirely avoided if Karkat was more careful, and Lord English is ALREADY HERE.
Jade is blown up by a mountain of shaving cream (she gets better), Noir destroys two universes, which ends up fueling the tumor, all of the exiles save for PM and WV (who is healed later) are murdered, with two beheadings, a classic chest stabbing, and getting uranium ripped out of one's stomach (it was healed), and Doc Scratch has been fooling everyone all along. The tumor doesn't destroy the Green Sun, it creates it.
Lord English then takes a more active role and starts killing people left and right. He murders the author. Then he visits a dream bubble and destroys the souls of everyone in the afterlife.
Bittersweet Candy Bowl: Had an incentive chapter called "Disaster Dominoes". The title was rather apt. The main comic gets pretty dark in sophomore year, with things continually getting worse between Mike and Lucy.
Played for Laughs in Questionable Content. Cosette asks out Marten (who works at the library), only to be turned down because he has a girlfriend. Embarrassed, she flees to a nearby coffee shop and tells the barista about it... only to discover that this is Dora, Marten's girlfriend. Once Marten and Dora make up after a short argument, they go out to dinner... and Cosette is their waitress.
Dora: Talk about shitty timing.
Freefall: The early colonization of the planet Jean was one crisis after another, starting with the first factory ship arriving damaged and the second not arriving at all.
Florence: What happened to the damaged factory ship? ABY 2: The beach head crew tried to repair it. That's how it went from damaged to severely damaged.