* ''DrHorriblesSingAlongBlog'': The titular Dr.Horrible is in love with Penny, but is to afraid to talk to her. When he finally does, she gets swept off her feet ''by his enemy''. Then he learns that not only has Captain Hammer slept with her, but that he's only staying with her because ''Dr.Horrible wants her''. Then, at the end he accidentally [[spoiler: kills her]]. No wonder he seemed so depressed in the final song.
* Some of the more dystopic and CrapsackWorld settings hosted in AlternateHistoryDotCom may count. And then there's ''AWorldOfLaughterAWorldOfTears.''
** Such as the worst of them all, [[http://www.alternatehistory.com/foralltime/ ''For All Time''.]] This series delights in dragging things downward every five minutes. D-Day fails, Stalinists take over most of Eurasia, nuclear weapons are used like hand grenades, and the USSR-PRC war kills over 600 million people. When ''Canada'' is sufficiently militaristic and paranoid to have its own H-bomb program and the 1980 US Presidential Election is between [[http://en.wikipedia.org/wiki/Jim_Jones Jim Jones]] and [[http://en.wikipedia.org/wiki/Charles_Manson Charles Manson]], you know the world isn't doing so well.
* MarbleHornets shows this quite well. Basic story is a guy named Jay (or possibly J) decides to help a friend, Alex Kralie, by watching types of a movie Alex was making but scrapped. Ok so far. J soon notices...let's just say odd things in the tapes. Kinda bad but not horrible. Next thing J knows, he's being stalked by the same thing Alex was stalked by, and being attacked by a mysterious masked man (who turns out to be [[spoiler: his friend Tim]]). J decides to put this all behind him, but he receives a tape from someone in which he finds Alex has started a new life...only for the very thing chasing him to appear right at his house just because his girlfriend found a camera with a tape from the movie on it. J rushes to his friend's rescue, only to wake up in a strange town [[spoiler: "with no memory of the past 7 months."]] Oh and also shortly after finding someone who has had similar things happening to her, she disappears and J is attacked by the Masked Man again, forcing him to flee his hotel. So pretty much J's entire life has been ruined [[ForWantOfANail just because he wanted to help a friend out.]] Friendship can kinda suck that way, can't it? [[spoiler:Then he finds out his "friend" is a crazy murderer.]]
* ''{{Literature/Worm}}'' starts off with a severely bullied and lonely [[SociallyAwkwardHero young girl]] who has gained power over bugs at some point and seeks to find escape from her horrible life by becoming one of the city's many superheroes. Somewhat fittingly she shows interest in '[[LampshadeHanging turning negatives into positives]]' when she heads out on her first ever costumed excursion and singlehandedly defeats a well armed gang and one of the strongest supervillains in the city, then attempts to infiltrate a gang of supervillains. Good start, right ? Well, then [[spoiler:she starts BecomingTheMask, a {{Kaiju}} attacks her city, a superhero, a group of serial killers, her own boss and an EldritchAbomination all try to kill her (and, in some cases, more or less everyone around), her SecretIdentity is revealed, new Kaijus start to appear and accelerate the [[ApocalypseHow world's progressive destruction]], and finally [[SufficientlyAdvancedAlien Scion himself]] decides that helping humanity is boring and starts [[OmnicidalManiac killing everyone in the multiverse]].]] So... yeah, things go pretty downhill [[EarnYourHappyEnding before getting back to "not so bad"]].
** [[spoiler: In the words of one of the comments of the second-to-last chapter, "Honestly though this series has to be tied with When They Cry for the title of “It Got Worse- The Series”."]]
* WebVideo/TheNostalgiaCritic's issues with his job. By January 2012, he was willing to kill WebVideo/ThatSciFiGuy for planning to do a review of the same thing he was.
** At least in ''WebVideo/ToBoldlyFlee'' he [[spoiler: AscendedToAHigherPlaneOfExistence, saving reality in the process]]. But oh wait! Turns out [[spoiler: his ascension trapped him in a kind of purgatory (the show ''WebVideo/DemoReel'') where he was stuck as a terrible film maker, who was also a former child actor whose mother committed suicide. And now he's back reviewing]].
* The Wiki/SCPFoundation has strict orders to destroy SCP-523 if an [[ApocalypseHow end-of-the-world]] scenario occurs because the sole ability of 523 is to make ''everything worse'' -- which would be bad enough on its own, but it's ''also'' proportional to how bad the situation was in the first place.
* Basically every one of ''TheOnion'''s Digital Studios Series ends up along this route:
** ''WebVideo/SexHouse'': Starts as a parody of reality shows such as ''TheRealWorld'', [[spoiler: very quickly turns into what some commenters referred to as a possible Hell scenario, locking them in the house and watching them slowly mentally and physically decay without food or outside interaction save for motivation to have them have sex while America watches]], and [[TakeThat ends as a parody of reality shows such as]] TheRealWorld.
** ''Lake Dredge Appraisal'': Starts as a parody of auction-type public television shows, and [[spoiler: compiles troubles on the host until finally revealing a strange ''Literature/ThePictureOfDorianGray''-style dredge of him, painted 600 years prior, and suggesting further injury to him]].
** ''Horrifying Planet'': well, this nature show just stays bad, as its point is to declare nearly everything in nature to be a horrifying disaster. [[spoiler:In the final episode the narrator suggests to purify Earth by pouring copious amounts of bleach on everything, as the planet is better off completely dead]].
** ''Onion Talks'': A ''TED Talks'' parody, with two or more incarnations featuring DiabolusExMachina endings for no particular reason.
** ''Porkin' Across America with Jim Haggerty'': A traveling show where regular ''Today Now!'' host Jim Haggerty goes across America sampling pork dishes. This one rather quickly went south, with him putting the show above most of his family, setting divorce procedures in play from the first stop, as everyone else he knows outside of work [[spoiler: leaves him or dies, and he suffers debilitating injury necessitating porcine transplants until he starts to become more pig than man]]. All in front of the cameras. [[spoiler: Ends with a temporary revival of ''Today Now!'', with Tracy and a new male host reporting on "The Human Pig". Also somewhat subverted in that Jim/The Human Pig turns out to be quite happy with his new life and family]]
** The only current exception is ''Life Hacking with Drew Cleary'', which is on hiatus or ended without anything going badly for the host, but which has already included an episode on how to kill yourself.
* In 'The Camping Webisode' of ''DSBTInsaniT'', the groups campsite gets destroyed, which sucks. Then [[KnightOfCerebus Killer Monster]] shows up...
* In ''WebVideo/TribeTwelve'' Noah meets up with the Order, a cult that worships [[TheSlenderManMythos the Slender Man]] as a diety. After pissing them off and letting slip the names of his informents (the ''WebVideo/DarkHarvest'' guys who brought him there), the cult is about to kill him to ensure his silence. How could it get any worse? [[OhCrap Slendy himself shows up.]]