History FunnyAneurysmMoment / WebOriginal

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* A few hours after the ''Columbia'' disaster, the Associated Press website had an article on its return. The article described the events of the Columbia's safe landing and the happy comments of the crew in detail. It is unknown whether the false details were placeholders meant to be replaced after real details were learned or outright fabrication. Either way, the article was pulled so fast that its head spun.
* A What Would Tyler Durden Do thread [[http://www.wwtdd.com/post.phtml?pk=2268 published in 2007]] simply stated, "I predict Jett Travolta will die in the bath and be found by his caretaker at the end of 2008 due to Scientology. So sayeth the crystal ball."
* [[http://www.overheardeverywhere.com/archives/002023.html This]] Overheard Everywhere quote, posted in December of 2007.
** And now [[http://www.overheardeverywhere.com/archives/000630.html this one]] too.
* Woot.com's deal of the day for April 4, 2009, was for a set of four solar-powered lights; the product description began "What if the end of the world was tomorrow? Well, it probably wouldn't matter, because there would be no one left to notice." Their product descriptions are usually odd snarky things like that... but ''later that very same day'', North Korea launched a rocket over Japan, an action which many nations condemned as long-range missile testing and "provocative." Not quite TheEndOfTheWorldAsWeKnowIt, thank goodness, but at the time it was a little scary.
* On radio sites DigitalSpy and elsewhere, people were speculating that Dave Berry would be the future breakfast show presenter on 95.8 Capital Radio London and that there would be 100% national Capital Radio. The first one came true, and a backlash occurred. It's safe to say people would rather have a presenter who was "in touch" with their audience, like Simon Nicks, aka [[KnownOnlyByTheirNickName Nicksy]], Darren Spence, Wayne Tunnicliffe, Jacqui Blay or Rick Vaughn, '''not''' a celebrity who they can't relate to (and the fact Jacqui provides MsFanservice [[EvenTheGirlsWantHer for everyone]] too, helps).
* Depending on your opinion, this may also qualify as HilariousInHindsight too: the endless promotion for a then-unknown Music/{{Kesha}} on [[http://www.key103.co.uk Key 103 Manchester]], a British radio station's web site. Bizarrely, she was listed on the regular presenters' list too... although not now!
* Shellyfae's page on modelmayhem.com (possibly {{NSFW}}), and her Website/{{Twitter}} feed, is incredibly hard to look back at now.
* During the ''Podcast/RiffTrax'' commentary of ''Film/Terminator3RiseOfTheMachines'', either Mike Nelson or Kevin Murphy makes an offhand comment about Creator/HeathLedger dying of a drug-related matter. Although this was released back in 2006 while he was still alive, anyone who's heard it after the unfortunate events of January 2008 when Ledger died of a sleeping pill overdose has to just cringe.
* Website/{{Facebook}} had one which concerned ''the site itself''. The fact that someone registered the domain in March 2002 is one such thing, even though the content was not social networking, it was just domain-parking.
* Speculation about GMG Radio being taken over and Real Radio being rebranded as Heart and Smooth Radio rebranded to Gold is no longer comedy for people on media websites, ''especially'' now [[http://www.guardian.co.uk/media/2012/jun/12/gmg-receives-offers-radio-business this headline has happened]]. [[HopeSpot One can only hope UTV takes over them]], as Creator/GlobalRadio [[IdiotBall would have a monopoly on the UK radio market]]. Many jokes about Clear Channel[=/=]Creator/IHeartMedia are now HarsherInHindsight themselves, well, [[ValuesDissonance to British people in the media anyway]].
* The ''Franchise/{{Pokemon}}'' fan trailer ''Pokémon Apocalypse'' depicted a DarkerAndEdgier version of the Pokémon universe, and was released as a parody in late 2010. The parody lost all its humor on October 8, 2012, when PETA protested ''VideoGame/PokemonBlack2AndWhite2'' with a Flash game called ''Pokémon Black and Blue''; depicting Pokémon fighting back against their abusive trainers. The game has been met with resounding criticism from fans and the video game community.
* [[https://www.youtube.com/watch?v=Mcq87E0wzhM This]] 2007 parody video called "Elmo upsets Little Miss Shy", later renamed "Elmo becomes a molester", in which [[Series/SesameStreet Elmo]] tries to take [[Literature/MrMen Little Miss Shy]] home to supposedly molest her and eventually gets pissed at her. It's not funny now thanks to the fact that Elmo's puppeteer, Kevin Clash, resigned after being accused of having sexual relationships with underaged boys.
* In the [[WebVideo/BadMovieBeatdown Film Brain]]/Welshy crossover review of Texas Chainsaw 3D, a joke is made repeatedly throughout the video about Welshy being sad and angry that Matt Smith left Doctor Who. Due to time related to editing the video, it wouldn't be put up until mid-February. Two weeks before the video went up, Creator/JewWario killed himself, which changes the context of the comments about the people you love leaving you.
* ''WebVideo/{{Retsupurae}}'' made fun of a series of old video game reviews, [[https://www.youtube.com/watch?v=5s0lzbCK9f8 one of which]] included the reviewer's bizarre suggestion that Lara Croft from ''VideoGame/TombRaider'' should have a dramatic plotline where she gets breast cancer. Some years later, Creator/AngelinaJolie got a preventative double mastectomy for fear of breast cancer. The riff also has this unfortunate line:
-->'''slowbeef:''' Y'know, that's really what ''Tomb Raider 3'' needed: more double mastectomies.
* In 2007, the ''Franchise/StarWars'' wiki declared that only the movies and the [[WesternAnimation/StarWarsTheCloneWars animated series]] were canon. Fans of the [[Franchise/StarWarsLegends EU]] rejoiced that this was an April Fool's Joke. 7 years later, Lucasfilm, to guarantee a clean slate for their future films, made the same announcement--but this time, they [[Franchise/StarWarsExpandedUniverse weren't joking]].
* Episode 32 of LetsPlay/HatFilms' podcast Hat Chat was named after (and had a long segment related to) a Russian space experiment on the impact of zero-gravity on geckos having sex. During the segment, they joked the geckos would probably all die horribly. The satellite eventually returned with all occupants having frozen to death. This is perhaps HilariousInHindsight now that Smith owns three geckos.
* Jeff Zanini's ''Twisted Toonz'' panels (in which voice actors read movie scripts as characters they voiced and celebrities that they can impersonate vocally, switching off after every scene) had, as a running joke, Creator/JessHarnell do a Creator/BillCosby impersonation. You should know the drill by now. He later did the impersonation during a ''Film/{{Ghostbusters|1984}}'' read, but was a lot more negative in its purpose.
* In the first episode of Creator/TotalBiscuit and Jesse Cox's Terraria LP, started in 2011, Creator/TotalBiscuit refers to the Wooden Hammer as being "worse than cancer". Three years later, Creator/TotalBiscuit would be diagnosed with colon cancer, which would cause his death in 2018.
* Creator/TheFineBrothers' "College Kids React to Music/XXXTentacion" video was posted about a week before the rapper's murder in June 2018 and the internet's [[Administrivia/RuleOfCautiousEditingJudgement semi-divided]] reaction to it. Granted, it was a request by commenters who had no idea that would happen, but...
* WebOriginal/TheRealJims posted [[https://youtu.be/9rnDSz-FSF8 his "60 Second Simpsons" review]] of ''WesternAnimation/TheSimpsons'' episode [[Recap/TheSimpsonsS6E14BartsComet "Bart's Comet"]], which featured the song "Que Sera, Sera" by Creator/DorisDay on May 9, 2019, four days before she passed away at age 97, with [[https://youtu.be/rhMvSWyeDnY TheRealJims posting in his "Extra Seconds" follow-up]] that the timing between his reviews and her death was shocking.
* There is an entire account on Website/{{Twitter}} entitled “Poorly Aged Things” that is devoted to posting this kind of content.
* On October 30, 2020, Nicki Swift's [=YouTube=] channel added a video titled "[[https://youtu.be/oc97DWWgxt4 This Is Why We Never See Sean Connery Anymore]]", which detailed Creator/SeanConnery's last years as an actor, ending with "Enjoy your retirement, [[Film/JamesBond Mister Bond]].". The very next day, Connery passed away at age 90.
* Hollie Bennett of WebVideo/PlayStationAccess left the channel in January 2019 to join the PR team for ''VideoGame/Cyberpunk2077''. This was when ''Cyberpunk'' was still the cool upcoming game that everyone was excited about, instead of the infamously janky mess that was released in December 2020.
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* [[http://www.somethingawful.com/d/comedy-goldmine/jokes-with-realistic.php This]] AntiHumor article is unpleasant, especially since the current Pope has been (as of this writing) alive and Pope-ing for over half a decade.

* [[https://www.youtube.com/watch?v=P6uTKPwVnNI This]] video by Videogamedunkey, the fake quote from WebVideo/JonTron ("Fuck you dunkey, I do not watch your videos because you are black") has become uncomfortable, considering [=JonTron=]'s disasterous stream with Destiny in which he talked about how he believed black people committed more crime and sympathized with those who want preserve a white majority in the United States.
** This also taints a great deal of [=JonTron=]'s episodes, most especially "Food Games," which outright depicts Jon owning a slave named Grimbo.
* During [[https://www.youtube.com/watch?v=lc_kTEHAkNM this]] video, Food Games Part 2, [=JonTron=] talks about how the game seems to depict a post apocalyptic New York, but that Trump Tower seemed to still be standing, prompting him to say "Oh god, this is the alternate universe where Trump wins, isn't it?"

* Creator/LittleKuriboh followed a SugarWiki/{{Heartwarming Moment|s}} (the proposal video) with a SugarWiki/{{Funny Moment|s}} ([[WebVideo/YuGiOhTheAbridgedSeries Tristan]]'s jab at said video)...and sent them both into a worse place when he announced he and Safty would be getting an annulment. He talks about it [[http://littlekuriboh.livejournal.com/112889.html here]] on his livejournal account.
** Another joke that has become uncomfortable is Yami Bakura being confused by the gaydar on his Millennium Ring being triggered by Creator/KevinSpacey, who he says is "straight as a die." It's far less funny as of 2017, when Spacey came out of the closet amid actor Anthony Rapp accusing Spacey of molesting him at age 14; to a massive public backlash that led to many creators and productions cutting ties with Spacey as a result.
** His entire parody of [[Anime/NeonGenesisEvangelion Cruel Angel's Thesis]] where he [[WhatMeasureIsANonBadass constantly mocks Shinji]] for being "gay" and "whiny" is pretty difficult to watch after Little Kuriboh opened up about his depression in real life.
* When WebSite/SFDebris was commenting on the episode of ''Series/StarTrekVoyager'' "Meld", there is a scene where, after mind-melding with a sociopath, Tuvok needs to test his self-control. He does this by spending a few moments with a holographic Nelix. SF Debris comments on this, "Doesn't this say a lot? What will be most likely to drive myself into a homicidal rage? Seeing my children get killed? Watching my wife get raped? [[Film/StarTrek2009 The destruction of my home planet?]]" We know now that [[spoiler: Vulcan getting blown up does tend to drive Vulcans mad with rage.]]
** Chuck has done jokes about Captain Picard having a HilariouslyAbusiveChildhood and in particular one reference to him being attacked by his drunken father. Sadly, ''Series/WhoDoYouThinkYouAre'' revealed that Creator/PatrickStewart actually ''did'' have an abusive father, lending an uncomfortable unintentional RealitySubtext to the whole thing. Acknowledged in his review of "[[{{Recap/StarTrekTheNextGenerationS4E4SuddenlyHuman}} Suddenly Human]]", where Chuck makes another joke about Picard's abusive parents [[OurLawyersAdvisedThisTrope while subtitles clarify that]] [[IAmNotSpock jokes about Picard are not about Patrick Stewart]].
* Creator/CharlieBrooker's old 2001 Zeppotron site [[http://www.zeppotron.com/unnovations/archive.html Unnovations]] has proved eerily prescient (please note these were not serious in any way):
** It's only a matter of time before someone uses [[http://en.wikipedia.org/wiki/Augmented_reality augmented reality]] to create a [[http://www.zeppotron.com/unnovations/scumbgone.html Scum-B-Gone Poverty Concealment Helmet]]. Today [[http://unlogo.org/ logos]], tomorrow, anything you want!
** This is the really scary one. We now ''have'' a [[http://www.zeppotron.com/unnovations/factoid_blaster.html Celebrity Factoid Blaster]] - it's called "Twitter on your mobile phone".
* ''Series/BigBrother 13'' US is probably the most slanted season in ''Big Brother'' history, with twists that obviously benefit the veterans (All fan favourites) and safeguards in the form of competitions they've already played in left and right, as well as the most ''obviously'' slanted challenge for [[CreatorsPet Brendon]] to return to the game. After a sudden flip around causing one of the fan favourites to be voted out, a bunch of people on sites begun to think about how the producers would bail out the two remaining veterans, resulting in one user making [[https://www.youtube.com/watch?v=N-zWvFGg3ck&feature=channel_video_title this video]] making fun of how they assumed production worked. This became worse when you consider within a week...almost all the events described to slant the season happened in the most blatantly contrived bailout in ''Big Brother'' history. Among these...Pandora's Box offering $5,000 to Porsche, restarting the duo twist, conveniently pitting Jordan and Rachel (The remaining veterans) with each other, and a literal ''copy'' of the first Head of Household competition (That Rachel won) for the veto. But with a different prop. One almost wonders if they got the idea for it after watching that video!
* [[http://forums.somethingawful.com/showthread.php?threadid=2875010 A SomethingAwful thread]] entitled "tim russert is the most handsome man on television" was posted on June 13th, 2008 as a joke topic. ''Barely'' three hours later the news broke that Tim Russert had passed away. Needless to say it surprised everyone, and it's become a minor [[MemeticMutation meme]] that if someone dies, the topic will have a title similar to "[Person] is the most handsome man on television".

* Also, in December 2010, someone ([[NoNameGiven whose name was never revealed]]) wrote on Website/{{Twitter}}: "predictions for 2011... Twitter will be super-regulated #ladygaga". This may have been considered funny/highly speculative at the time, but not now that the [[http://en.wikipedia.org/wiki/2011_British_privacy_injunctions_controversy 2011 Twitter gagging order row]] has happened, and it's definitely uncomfortable to read, particularly as this got quoted around a few football forums too.

* On an automotive blog, someone wrote an article entitled "Fifty Shades of Grey" - which was a TakeThat at some well-known automobile manufacturers, and the Chinese automobile industry. Now, though, with Literature/FiftyShadesOfGrey out in novel form, the title of the article seems less funny than originally.
* The photoset of [[http://www.buzzfeed.com/bwgan/otters-who-look-like-benedict-cumberbatch-lpl Otters Who Look Like Benedict Cumumberbatch]] went viral in April 2012. August 28, 2012, the featured species was declared extinct, and every single repost of those photos became an inadvertent memorial to the Japanese River Otter.

* One episode in the WebVideo/GameGrumps playthrough of Mega Man 7 has Jon mocking Proto Man's vaguely sinister sounding hints (ex. Asking Mega Man to [[PyroManiac burn down a forest]] to find a hidden passageway), and Jon creates the dialogue "Mega Man, I need you to gun down a school full of elementary school children." A lot less funny after the [[http://en.wikipedia.org/wiki/Sandy_Hook_Elementary_School_shooting Sandy Hook Elementary School shooting]] in Newtown, Connecticut, four months after the episode's release.
* The April 9, 2013 edition of ''Blog/WhatIf'' had as its topic [[http://what-if.xkcd.com/40/ "Am I right to be afraid of pressure cookers? What's the worst thing that can happen if you misuse a pressure cooker in an ordinary kitchen?"]] Barely six days later, [[http://en.wikipedia.org/wiki/Boston_Marathon_bombings somebody used a pair of pressure cookers filled with nails and ball bearings to bomb the Boston Marathon.]]
* In Website/TheEditingRoom's "abridged script" for ''Film/HarryPotterAndTheOrderOfThePhoenix'', Harry jokes about his "uncle" not being in the next movie thanks to a heart attack. The actor playing Vernon Dursley, Richard Griffiths, died from complications of heart surgery at the age of 65.

* An [[http://muesproductions.com/2014/04/04/hulk-hogan-vs-ultimate-warrior-rope-break/ episode]] of Creator/MarcMues' show "Rope Break" had him and Dillon commentating on a match with Wrestling/HulkHogan vs. Wrestling/UltimateWarrior, while Dillon makes some inflammatory comments towards the latter. It was released only four days before Warrior's death.

* Creator/AlexDay and WebVideo/{{Charlieissocoollike}} were at one point as thick as thieves, with many jokes about how they would be married together and inseparable. By 2014, the latter publicly ended their friendship in disgust at the former's actions.
** On a similar note, the song "Mrs Nerimon", written by Kristina Horner, was a song about how she wanted to be married to him and spend the rest of their lives together. In 2014, it became apparent that Alex had not only been emotionally manipulative to her, but had also been abusive to some of his other girlfriends in various ways. This was all on top of the revelations that Kristina had been emotionally and sexually abused by one of her ex-boyfriends, Luke Conard.
* In one Creator/AchievementHunter Let's Play, the team was playing ''VideoGame/RainbowSixVegas'' and the crew began wondering if Tom Clancy was still alive or not. Ray looked it up and found out that, yup, Tom Clancy was still alive. About an hour after the video was posted, Tom Clancy was declared dead. Of course, this lead to a lot of funny Website/YouTube comments on the video declaring that Geoff, who was a ''horrible'' shot that game, killed Tom Clancy.
** This trope happened so much that the gang actually discuss this. Jack Patillo attempts to invoke this when playing the various ''VideoGame/{{Worms}}'' games by naming his worms after unpopular political figures, but after awhile, they come to the conclusion that it only works ''if'' they're discussing someone unintentionally.
** Ryan Haywood's TokenEvilTeammate and "secretly creepy" shtick was often PlayedForLaughs until in 2020, it was revealed that he was being inappropriate with multiple female fans, and was fired by Rooster Teeth after compromising material of him leaked online, leading to the allegations.
* In TheStinger of ''Franchise/StarWars in 3-D!!!'' by WebVideo/MatthewSantoro, a fan commenter asks Matt, "You like [[Music/TheBeatles the beatles]] right?". He turns around and looks at his posters of Music/TheBeatles, and when he turns back to face the camera, he has Beatle hair and gives the commenter a thumbs up. This is PlayedForLaughs. It became less funny when Matt revealed that he actually isn't a big fan of Music/TheBeatles, and that the posters belonged to Marci, his then-girlfriend, whose relationship with Matt ended not too long before Matt revealed that the posters weren't his.
* In ''WebVideo/TenLittleRoosters'' episode 6, Miles finds what appears to be a mocap video of what he calls "dot sex" [[spoiler:(It's actually Adam being strangled and his futile fight to save himself)]]. As he does, Miles walks away in shame and proclaims "You're a sick, sick man, Creator/MontyOum." A month later, Monty ''would'' be sick... and pass away.

* In September, comedy group Cyndago uploaded a video entitled "WATCH CYNDAGO DYE!"[[note]]later retitled "We Dye Our Hair!"[[/note]]. Just one week after the video was uploaded, Cyndago member Daniel Kyre committed suicide.

* In a 2014 video, toy reviewer [[https://www.youtube.com/user/glennwebman69 Glenn Webb]] made a joke about using a Comicbook/{{Magneto}} action figure to short out his grandpa's pacemaker when he was a kid. In August 2016, Webb died in his sleep from heart failure caused by undiagnosed myocardial fibrosis.
* On December 20th, 2016, the {{WebVideo/Cinemasins}} spin-off channel Music Video Sins released their "sinning" of Wham!'s "Last Christmas". George Michael passed away on Christmas Day 2016, only 5 days later.
** Jeremy’s comments about Avicii in the “I Took A Pill In Ibiza” sins become a lot harder to swallow after the “Wake Me Up” DJ died by suicide in 2018.
* ''WebVideo/EpicRapBattlesOfHistory'''s "Hitler vs. Darth Vader" and "Clinton vs. Trump" battles both became this to the series' creative team after the 2016 presidential election. Not only did they stop performing the Hitler battles during their 2017 tour, the series went on an extended hiatus due to the current US political climate.

* On May 10th, 2020, Youtuber Corey La Barrie posted a short vlog titled [[https://youtu.be/Ehq4QaNcKzc "Deleting This Video in 24 Hours"]]. In it, he talks about his 25th birthday celebration that day and how he and his friends "might get a little drunk". The next morning, the video was still up...because Corey had been killed by his drink-driving friend, fellow Youtuber and tattoo artist Daniel Silva, who had crashed a car in which he was a passenger.

* [[https://images.app.goo.gl/Pam1kkRNhbDHBjaq8 There was a meme]] around December 2019-January 2020 joking that various disease outbreaks in the 1720s, 1820s, and 1920s hinted at another outbreak coming soon. The UsefulNotes/COVID19Pandemic would arrive only a few months later.
* For many years, a popular New Year's Eve meme read something like "When someone asks me what it will be like in (X amount of years from 2020) and I say "I dunno, I don't have 2020 vision"". At last, 2020 arrived...and it brought such sheer insanity -- including Australia being on fire, followed by California and Colorado-- that it's possible almost ''no one'' will [[TraumaCongaLine be mentally unscathed from it]].
* Before ''Film/AvengersEndgame'' with its spoilers came out, a [[https://www.youtube.com/watch?v=rakCDfjmG5U 2018 fan video]] had Tony Stark ending up in ''The Good Place'' world where Michael tells him he suffered an UndignifiedDeath after Thanos did the first Snap that make everyone laugh. [[spoiler:Michael remarks that Tony has a record of sacrificing himself for the greater good, so he's obviously in The Good Place. Tony figures out he's in the Bad Place and uses [[TooKinkyToTorture demon tortures to wind down from a lifetime of stress]]. Hilarious and awesome? Yes. It becomes a TearJerker when in ''Avengers: Endgame'', Tony sacrifices his life to save everyone, human, alien and magical being alike. The [=YouTube=] comments don't help. You've earned your spot in ''The Good Place'', Mr. Stark.]]

** Speaking of Billy Mays YTP's, "Mark3611's" video, "[[https://www.youtube.com/watch?v=gdxRowVtVho Billy Mays Sells Zorbeez in a Bad Mood]]", throws in a final joke by overlaying Billy saying "A year's supply of powder!" with an image of cocaine and a razor. Well, given the results of a [[http://www.cnn.com/2009/SHOWBIZ/TV/08/07/florida.mays.cocaine/ certain autopsy...]]
** [[https://www.youtube.com/watch?v=CCrh4tUwytQ A]] WesternAnimation/TheLandBeforeTime Youtube Poop by Creator/JitteryDragon has one. In a moment when Ducky dies, a title card pops up with a picture of her in black and white which says "Ducky... She died for your sins" which is funny... that is until you realize that her original voice actress, Judith Barsi, was murdered by her father a few months before the first movie was released.
** [[https://www.youtube.com/watch?v=lthpiHT7ggA Mako Explores His Sexuality]] had [[WesternAnimation/TheLegendOfKorra Amon]] announcing that he'll call upon Obama to shut down the government...a year before the actual shutdown.
** The [=YTP=] "Shiteo Games" (a parody of the song [[SoBadItsGood "Video Games" by Black Out Band]]) ends with the lead members running off to their house to play video games.....only for a missile to suddenly explode on them. The lead singer of the band, Hunter Watson, later died in a car crash at only 20 years old.

* For a time, WebVideo/TheTourettesGuy videos were considered a Funny Aneurysm ''series'' after news about its star's death appeared in August of 2007. About two years later, it was then revealed that the Tourettes Guy was [[HesJustHiding in prison the whole time]], and a new video was released in late 2009 following his release from prison.
** Also, the line "When I die and go to heaven and see God, I'm gonna say...... shit" became ''a lot'' more relevant after said death rumors.
* While the first WebVideo/PotterPuppetPals short, "Bothering Snape," came out a few months after ''Literature/HarryPotterAndTheOrderOfThePhoenix'' was released, "Bothering Snape" can seem disturbing if you watch it after having read the scene in the book where James (Harry's father) and his friends bully Snape just for kicks (basically, the exams are done and Sirius is looking for some fun, and they decide to go mess with Snape who is just reading over his test). It makes Harry's "Let's go bother Snape" seem disturbingly like his father's bad side (although Harry in those shorts ''is'' generally more arrogant and more cruel than he usually is in the books).

* [[https://www.youtube.com/watch?v=5xniR1GN69U the seventh episode]] of ''asdfmovie'', while still hilarious, has a lot more jokes about death and suicide than previous entries. A month after it was released, [[https://www.youtube.com/watch?v=Ds8sSeJtwYs the creator admitted he had been suffering from depression]] and that it may have been subconsciously influencing those jokes, though luckily he emphatically denied wanting to commit suicide.
** This is also one of the main reasons the original "Crash Zoom" was canceled. After the Sandy Hook shooting, a crazy person breaking into a school and killing children was a lot less funny, for some reason.
** In asfmovie10, LetsPlay/JackSepticEye appears in a sketch as a character who tries to tell another character not to jump to their death, then pulls out a camera and tells them to jump so he can record it. LetsPlay/JackSepticEye later tweeted a warning about a Logan Paul video featuring the corpse of someone who committed suicide.

* The ''WebVideo/BadMovieBeatdown'' and ''WebVideo/ToddInTheShadows'' crossover review has Matt panicking at the sight of Todd, mistaking him for a "hoodie", which may have been partly due to him being of [[AmbiguouslyBrown unclear race]]. This took a dark twist after the Travon Martin case

* ''Website/{{Cracked}}'':
** As part of "Batman Week", they had a live action/animated video called [[https://www.youtube.com/watch?v=rVp_pXTCRU4 "Fuck Batman"]] that featured at the end of it a few dead bodies (some penguins, but one human) splattering blood in the shape of the Batman logo. Worse still, the video was made in advance and put out the same day as news of the Aurora, Colorado theater shooting (which occurred during the premiere of ''Film/TheDarkKnightRises'') circulated.
** The article [[http://www.cracked.com/article_25085_5-movie-scenes-that-aged-in-unexpectedly-horrifying-ways.html "5 Movie Scenes That Aged In Unexpectedly Horrifying Ways"]] is about scenes in films that have been subject to this trope.
* During [[{{LetsPlay/Chuggaaconroy}} Chuggaaconroy's]] Let's Play of ''VideoGame/{{Super Mario Sunshine}}'', a fair amount of humour came from how the game screwed him over, whether it was the time he had a power outage whilst recording, or the difficulty with the watermelon stage, or how frustrating the game was in parts. It became a lot less funny however, when (during his LP of ''[[VideoGame/TheLegendOfZeldaMajorasMask Majora's Mask]]'') {{LetsPlay/Chuggaaconroy}} revealed that during the LP of ''Sunshine'' he'd been suffering from a {{Creator Breakdown}}, and was [[StepfordSmiler trying to hide it]].
** On a more meta note, his Creator/BillCosby impressions from his earlier Let's-Plays (and that one episode of ''VideoGame/MarioParty4'' on LetsPlay/TheRunawayGuys) have fallen in immensely bad taste in light of Cosby's ongoing rape scandal and subsequent court case, which made Chugga's impressions of the guy go from comical to cringeworthy.

* ''Podcast/TheWorstIdeaOfAllTime'':
** Jokingly invoked in the parody commentary for ''Film/BatmanAndRobin'', where, while in-character as director Creator/JoelSchumacher and writer Akiva Goldsman, the guys brought up the fact that Music/RKelly contributed to the film's soundtrack. They jokingly noted that Kelly was still a respected and well-liked singer during the late 90s, and that all the disturbing details about his personal life and sexual misconduct made it difficult for the movie to secure a rerelease to celebrate its 20 year anniversary.
** In the parody commentary for ''Superbabies: Film/BabyGeniuses 2'', Tim Batt jokingly claimed that Scott Baio has a close relationship with American law enforcement because he's been arrested so many times. The following year, former child actress Nicole Eggert alleged that Baio molested her on the set of ''Series/CharlesInCharge''.

* ''WebVideo/HonestTrailers'' released their ''Film/{{Taken}}'' trailer that joked a little about how the film made Europe look dangerous and said the message it sent was "don't go to Europe" (while showing a skyline shot of Paris of all places) on January 6th 2015. The "Charlie Hebdo" shooting happened on January 7th, and an even worse terror attack struck the city on November 13th, killing over 100 people.
** While on Webvideo/ScreenJunkies, they celebrated 5 years of the channel with "Top 10 WORST Screen Junkies Show Moments!!". At the time, it was just SelfDeprecation on OldShame. But two weeks later, channel creator Andy Signore - who of course, is on the video - [[RoleEndingMisdemeanor was fired for sexual harrassment]], something much worse than whatever happens. To make it worse, #1 opens right away with host Hal Rudnick asking the cast of ''Film/{{Anchorman 2|TheLegendContinues}}'' to sit on his lap... no wonder it was [[MissingEpisode erased]] once the channel broke the silence that followed the dismissal.
** The roast of Captain America features an example that doubles as this and HilariousInHindsight: a joke made at the expense of Black Widow is that the host can "imagine doing that leg-scissoring thing to Thanos and he just throws you into the sun." In ''Film/AvengersInfinityWar'', not only does Thanos throw a moon at the Avengers during the battle on Titan, [[spoiler: but Black Widow actually turns out to be one of the few ''survivors'' of the film's final battle]].

* ''Podcast/MyBrotherMyBrotherAndMe''
** One episode featured a brief bit involving a Robin Williams impersonation which ended in an implied suicide. This episode was released shortly before Williams's death by suicide. The podcast's creators expressed regret over this bit, and removed it from the version of the episode currently available on the show's feed.
** Another episode had a bit where Travis jokingly suggested that Creator/KevinSpacey was being forced to make terrible movies like ''Film/NineLives2016'' because someone was using damaging information to blackmail him. The following year, Spacey was outed as a sexual predator who was accused of having harassed numerous young men, including ''Series/StarTrekDiscovery'' actor Anthony Rapp, who claims he was only 14 when Spacey tried to seduce him.

* Towarda the end of [[https://youtu.be/y1wITenLaUs this]] WebVideo/ShaneDawson video guest starring Music/ChristinaGrimmie , the latter sweetly claims she's part of Shane's "fan army". Shane jokingly replies, "You're the one with the gun who doesn't know how to use it. You're just shooting everywhere and people are dying." This former burst of BlackComedy became horrifying after Christina was gunned down during a meet-and-greet in 2016.
** In a "get-to-know" video posted by Grimmie, she said that her mother initially didn't want her to post videos because she was afraid "some creepy man would come and hunt her down." [[AdultFear She was right.]]
* In May 2017, WebVideo/RhettAndLink released [[https://youtu.be/W8tDvR_fFIc "Does Music Make Food Taste Better?"]], guest starring Mike and Chester of Music/LinkinPark. Chester committed suicide barely two months after the episode was posted, making his cheerful, goofy appearance here seem much more like the mask of a StepfordSmiler. Possibly the eeriest bit is this line, sung while R&L are eating ramen:
--> I'm one noodle closer to...death.
* This one’s either this or HilariousInHindsight: The WebComic/CyanideAndHappiness Short “Hello Youtubers” shows a vlogger recording (and then presumably posting) the moment she learns her father died in a car accident. The {{Stinger}} has her filming an “unboxing” video of her dad’s coffin. Some commenters were worried that at the rate teenage Youtubers were going, it would be predicting the future. With the highly controversial Creator/LoganPaul video of him filming a dead body in Japan’s “Suicide Forest”, that future seems to have arrived.
* In [[WebVideo/BrowsHeldHigh Kyle Kallgren]]'s review of Andy Warhol's ''Vinyl'', he explained how the acting was bad because the actors were all "dragged there, tired and confused" with little direction and no compensation, before adding: "By the way, [[WebVideo/ToBoldlyFlee the fourth year shoot]] was fun." This is a lot harsher after a number of former Channel Awesome reviewers alleged mistreatment by management in 2018, which was backed up by Doug in his commentary where he talked about having a breakdown and making everyone miserable while he forced himself to keep going.
* [[WebVideo/TheMusicVideoShow The Music Video Show]] had many [[TakeThat Take Thats]] directed at Scott Stapp that become less funny in the midst of Stapp becoming penniless in real-life.
** EVERYTHING in season five through seven after [[https://youtu.be/OfByCu4kEIQ this video]] was released and revealed that the host had depression during season five and tried to kill herself years earlier. It especially makes [[https://vimeo.com/275056580 Episode 113]] a bit hard to watch.
** Season five is a Funny Aneurysm SEASON twice so when, during a livestream, she admitted that she was suicidal while making said season. She said that if she didn't finish the season before a due date, she would kill herself.
** The season four [[https://www.youtube.com/watch?v=Ejp0WvGGBGs trailer]] has the line, "This season is gonna suck,isnt it?" Turns out this was the LAST season of the show she was happy doing.
** During an early season four episode, the host pulls out a life size cardboard cutout of Terry Crews and kisses him, saying "he can be used...any place...any time." A month later, Crews revealed that he was groped by a male Hollywood executive which was during the sexual assault scandals.

* Creator/MaxLandis' tribute to Wrestling/TripleH, ''Wrestling Isn't Wrestling'', [[CrossCastRole cross-cast]] women as Hunter and all of his partners and enemies. The tribute provided humor when it premiered, but allegations of Landis abusing and harassing women now makes it harder to watch so many work for him. It really doesn't help that the first such allegation came from Creator/AnnaAkana, who portrayed Wrestling/{{Batista}} in ''Wrestling Isn't Wrestling''.
* After Heidi O'Ferrell divorced WebVideo/ProJared due to him allegedly cheating on her, Jared's rating for the Intec Interact in his "WORST CONSOLE EVER" video- a "broken marriage out of 10"- became used against Jared a ''[[MemeticMutation lot.]]''

* Not a real-life occurrence, but {{WebVideo/Vinesauce}} Vinny managed to accidentally foreshadow an in-game tragedy of his own making when he played ''{{VideoGame/Minecraft}}''. After building a snowman only to have it immediately [[DeathByIrony die from being snowed on]], he played it off by noting that having pets is "investing in sadness." Two of the most famous moments in the series would end up being the times he tried to adopt actual pets--Ziggy the cat and then the parrots John and Michael--only to have them get killed in [[ArtificialStupidity similarly dumb]] but much less funny ways before he could get them home. The parrots were a double case because they were named after John Cleese and Michael Palin from the ''Series/MontyPythonsFlyingCircus'' sketch about a dead parrot.

* The WebVideo/RyanGeorge video [[https://www.youtube.com/watch?v=mtCgnz-Jxnw "Nobody Cares About Game Show Hosts"]] features Creator/AlexTrebek mistaking contestants' responses on ''Series/{{Jeopardy}}'' as questions about his well-being, and then sobbing when he realizes nobody's actually checking up on him. A few months after the video came out, Trebek revealed he had Stage IV pancreatic cancer, and in his memoir, he described the psychological issues that came with his cancer treatment, including crying jags and suicidal ideation. Many more people were concerned for Trebek's well-being after hearing that. He died 18 months later.
* ''WebVideo/{{Phelous}}'':
** All of the jabs between Doug and Phelan in crossovers and such are not as funny now since the latter left Channel Awesome on less-than-friendly terms.
*** After hearing about some of the unpleasant things that have gone on behind the scenes leading up to Phelous' departure from Website/ChannelAwesome, as well as his general displeasure with ''To Boldly Flee'', a lot of his [[TakeThat Take Thats]] directed towards the film, WebVideo/TheNostalgiaCritic, ''WebVideo/DemoReel'', Creator/DougWalker and so on seem less like friendly jabs and a lot more pointed and acidic.
*** In the ''Film/ChildsPlay2'' crossover with Critic, Critic shamelessly whores out ''WebVideo/SuburbanKnights'' and when Phelous calls him out on it, he says “it's either that or another midroll” before grinning and cutting to commercial. Cute, but not so much [[http://imgur.com/a/K8Xe4 after chatlogs were revealed]] of Rob telling Lupa off for “too many midrolls”.
*** In the aforementioned ''Film/ChildsPlay2'' crossover, Phelous says he hasn't seen such fake special effects since ''WebVideo/{{Kickassia}}''. Critic retorts that special effects in ''WebVideo/SuburbanKnights'' were even worse... [[DontExplainTheJoke because Phelous did them]]. After [[http://phelous.tumblr.com/post/108013883721/goodbye-farewell-and-amen-ca Phelan revealed]] part of the reason he left Channel Awesome was because the site's management was accused him of "half-assing" the effects in the anniversary movies behind his back, it's rather uncomfortable to watch.
** All of the crossovers starring Phelan, Allison and Creator/BradJones are more likely to become uncomfortable to watch since the latter two are no longer on speaking terms with each other after the aforementioned "Not So Awesome" document came to light. Brad went so far as to ''mock'' Allison's struggles with depression in a later ''Cinema Snob'' video, which probably makes it even worse.
** During his review of the ''Series/NinjaTurtlesTheNextMutation'' episode "Turtles' Night Out", Phleous mocks a scene of Michelangelo condemning drug use. Mikey's VA, Creator/KirbyMorrow, died as a result of substance abuse. Phelan later included a dedication to Morrow in the credits for his review of "Unchain My Heart, Part 3."

* WebVideo/FilthyFrank:
** The many scenes with Pink Guy having seizures become rather uncomfortable to watch when we learn George has a medical condition that he's had since youth that '''causes''' seizures.
*** Also, there's a line in Pink Guy's [[https://www.youtube.com/watch?v=NXWcl1gKjPg "Big Mama"]] rap that states, "And when I'm not on my pill / my brain deteriorates and I go ''insane''."
** The song "Nickelodeon Girls" describes that rough sex with singer Ariana Grande will "put her in a coma" and "put her in a coffin." Consider the fact that this was before the attack on her Manchester concert. Though she wasn't hurt physically, she was extremely broken up about the victims.
*** It also doesn't help that Pink Guy coughs up blood on posters of various Nickelodeon actresses throughout the video.
*** The insistance in the chorus that Creator/DanSchneider is "ruining his business" by not putting hot girls on the channel is also harsher after Nickelodeon fired Schneider in 2018, with unconfirmed theories that it may have been due to the long-standing rumors of his pedophilia.
* In the third edition of "Things I Am not Allowed to Do at the ''WebOriginal/ProtectorsOfThePlotContinuum''" was the line "I will not unleash [[Series/StarTrekVoyager macroviruses]] in HQ". Three guesses (and the first two don't count) what the League of Mary Sue Factories unleashed in Headquarters over a year later, with massive loss of life.
* ''[[http://www.newgrounds.com/portal/view/212859 Cancer's Passion]]'', a short cartoon on ''Website/{{Newgrounds}}'', features a hotdog vendor whose mother is in a cancer clinic, with her death at the end serving as part of the punchline. The hotdog vendor's voice actor lost his real life mother to leukemia less than two years after the cartoon was made.
** ''[[http://www.newgrounds.com/portal/view/136826 Fun With Suicide]]'' by the author Livecorpse is much darker in retrospect as he committed suicide several months later. Even moreso by the fact that one of the options is "SuicideByCop", considering that he was on the run from the police when he died.
* When news came out in 2018 about Creator/JewWario having sexually assaulted people, leading to many of his scenes becoming uncomfortable in retrospect:
** Particularly the RunningGag of his huge bulge in ''WebVideo/SuburbanKnights'' and how all the women fawn over him.
** In the Reloaded DVD extras, a joke about Creator/JewWario showing his penis equaling a "gross out shot fatality" seems far harsher with the revelation that Jew Wario was fired from Channel Awesome for committing sexual assault.
* WebVideo/TheAngryVideoGameNerd example: In the NES ''Franchise/{{Superman}}'' review, he makes a big deal about how part of the plot of the game involves Clark being sent to investigate an unexplained drop in stock prices, and how it was a ludicrous element to include in a superhero game. Funny then. Cringe-inducing for anybody with a 401(k) in the wake of the stock market dropping 1,000 points over the course of thirty minutes.
** The review of ''Action 52'' and ''Cheetahmen'' became this as of August 2012, when a Kickstarter project to get a completed version of ''Cheetahmen II'' was posted to James' Website/YouTube channel, and subsequently got a huge amount of backlash.
** The review of ''Franchise/{{Transformers}}'' on UsefulNotes/{{Famicom}} featured a RunningGag of James using the hot sauce endorsed by Billy Mitchell; remarking on his world record high scores for ''VideoGame/PacMan'' and ''VideoGame/DonkeyKong''. Mitchell would later be stripped of said records after it was discovered that he had achieved them by using emulation instead of the original arcade hardware.
* Speaking of the Cinema Snob, Creator/BradJones is a big fan of ''Tequila and Bonetti'', a short-lived show starring an NYPD officer who moves to California after accidentally killing an innocent, unarmed black kid. While reviewing the first episode, Brad got sorta-serious for a moment and said "It would be ''very'' hard to do this show nowadays," in reference to the spate of high-profile instances of police shooting unarmed black people in TheNewTens.
* During a late night chat on Creator/LordKat's livestream (circa September 2010), a conversation between [[WebVideo/TheSpoonyExperiment Spoony]], WebVideo/SeanFausz, and Skitch was interrupted by a sudden ''THUD'', after which Spoony's line went quiet.[[note]](He later explained that he dropped his laptop and ran out of the room because his dinner had caught fire on the stove.)[[/note]] After about five minutes of silence, Skitch jokingly speculated that Spoony had "dropped dead from a heart attack"; Sean replied, "Oh, well. [[SiblingTeam Miles]] will find him and give him a eulogy." A little over a month later, Spoony started having fainting spells and ended up making numerous trips to the hospital...because of a previously unknown heart condition. Ouch.
** Also in Spoony's Deadly Premonition LP he gives the line "I think my heart's about to explode!"
*** And again way back in his ''Terror TRAX: Track of the Vampire'' audio CD review where Spoony offhandedly joked about having a heart condition.
** And again involving Spoony: anything involving his now ex-girlfriend Scarlett. Poor guy has had a rough time of it...
*** Particularly awkward is the [=SGC=] 2010 [[https://www.youtube.com/watch?v=B2gLG_b9zOI&feature=mfu_in_order&list=UL Q&A Panel]] where he informs the crowd that "there would be no website without Scarlett", joking that he needs to keep her happy because "if she gets mad, everything's goin' down!" After the pair broke up, The Spoony Experiment nearly ''did'' go down: Noah fell into a deep depression, and announced that he wasn't in the frame of mind to produce any videos in the foreseeable future; there was no new content on the site for nearly three months, during which Noah contemplated leaving internet reviewing permanently.
** In his review of the ''Make My Video'' games, Spoony jokes about bringing medication with him because the games are so bad, he's afraid of having an insanity attack. Numerous other reviews make jokes about having mental breakdowns or taking "crazy pills" (in fact, it's something of a RunningGag). As of June 2012, Noah's been diagnosed with [[http://en.wikipedia.org/wiki/Bipolar_II_disorder Bipolar II disorder]]....
** The first part of the 2012 Channel Awesome Anniversary ''WebVideo/ToBoldlyFlee'' made jokes about The Nostalgia Critic only calling the other reviewers to fire them, featured the line, "The Spoony One must not return", and has an entire plotline about [[WebVideo/TheSpoonyExperiment Spoony]] being possessed and initially mistaken for insane by the others. A few months after filming wrapped (but before the special was released, so that everybody in the audience is aware of this), Noah Antwiler was suspended from the TGWTG over recent bad behavior, then left the site for good (of his own accord), and shortly afterwards was diagnosed with bipolar disorder. He seems to take it with humor, though. It's also worth noting that they actually averted it in one case: originally, when the Nostalgia Critic called Film Brain, Film Brain would've said, "I promise not to do another crossover with Spoony!" This was meant to reference the negative reaction certain fans had to their crossover review of the live-action ''Tekken'' movie. However, given what had just happened with Spoony, this line was cut out of fear that it would be seen as a reference to the events.
*** ''WebVideo/ToBoldlyFlee'' is loaded with these given the numbers of falling outs and resignations that followed it's completion. [[WebVideo/LukeMochrieAndTheInners Kinley Mochrie]] in particular gives a speech about how the members of TGWTG are a family and that internet video critics need to stick together; just a few months later, she was gone from the site.
** Spoony used to use SuicideAsComedy. Then one of his fans committed suicide...
** Narrowly averted in Spoony's review of ''Film/TheBarbarians''. Spoony see had originally planned to do the review in his Ultimate Spoony character, except the real Wrestling/UltimateWarrior died the day before Spoony was going to begin filming. The review treats the movie as a parting gift from Warrior and Spoony reviews it as himself.
* Speaking of Funny Aneurysms regarding Channel Awesome movies, try watching [[https://www.youtube.com/watch?v=qjmPCVMd8HA this exclusive episode]] of WebVideo/AskThatGuyWithTheGlasses included on the ''WebVideo/{{Kickassia}}'' DVD, where Ask That Guy (who, remember, is played by Doug) rants about how the site doesn't like any of the producers, even the ones in the movie.
* WebVideo/{{Jacksfilms}}:
** In [[https://www.youtube.com/watch?v=RlhZuZOYawE "Your Grammar Sucks #20"]], WebVideo/{{Tobuscus}} is called "an awesome raper". In 2016, [[http://www.nydailynews.com/entertainment/youtube-star-toby-tobuscus-turner-accused-alleged-rape-article-1.2596563 Toby was accused of rape by his ex-girlfriend]].
** In 2011, Jack released [[https://www.youtube.com/watch?v=5yrSwhBK6ak WTFRussia]] -- a parody of Creator/FPSRussia in which Jack is fatally shot with a Nerf gun by fellow [=YouTuber=] Olga Kay, who runs off in shock. Nearly two years later, Keith Ratliff, a member of the [=FPSRussia=]'s production team, was found shot dead in his own gun store.
* Every so often, Website/{{the Onion}}'s satirical stories get unsettlingly close to reality:
** [[http://www.theonion.com/content/node/30940 This article]], posted four years before the fact, is about the ''real'' Michael Jackson whom everyone loved in TheEighties -- as opposed to the UncannyValley resident the world knew for so long -- being found dead in his home. Interestingly, that came true in more ways than one -- not only was MJ found dead in his home, but it was ''at that moment'' that people started thinking of him as the MJ everyone loved again.
** Another Onion article dated [[http://www.theonion.com/articles/bush-our-long-national-nightmare-of-peace-and-pros,464/ January 17, 2001]] featured the headline "Bush: 'Our Long National Nightmare Of Peace And Prosperity Is Finally Over'". The article itself only goes downhill from there.
** Also, check the date on this one: [[http://www.theonion.com/articles/stunned-nation-mourns-as-french-stewart-survives-p,3367/ Stunned Nation Mourns As French Stewart Survives Plane Crash]], especially harsh as several celebrities actually did die in the attacks.
** Maybe not as harsh as these other ''Onion'' examples, but [[http://www.theonion.com/articles/top-halloween-costumes-women-1834,7171/ this old Stat Shot]] is becoming less and less funny and more prescient now that we live in a world where the [[http://www.buycostumes.com/Sesame-Street-Cookie-Monster-Sexy-Female-Adult-Costume/69931/ProductDetail.aspx "Sexy Cookie Monster Costume"]] exists.
** This [[http://www.theonion.com/articles/earthquake-sets-japan-back-to-2147,2240/ Onion article]] isn't quite as funny in the wake of the 2011 earthquake and tsunami in Japan.
** The day before the Empire State Building shootings, the Onion published "Nation Celebrates Full Week Without Deadly Mass Shooting." [[http://www.theonion.com/articles/nation-celebrates-full-week-without-deadly-mass-sh,29293/ It was promptly updated]].
* A meme on 4chan is to post a picture of a living star, pretending them to be dead with the text "Goodnight, sweet prince". The most famous is the one on the [[http://www.encyclopediadramatica.se/Goodnight_Sweet_Prince right...]] Another example now appears on the page as of the death of David Bowie.
* The cinnamon challenge, for a while, was one of the most popular, hysterical memes to do on [=YouTube=]. But it's a little unsettling to laugh at them since [[http://www.dailymail.co.uk/news/article-3182227/Four-year-old-Kentucky-boy-killed-inhaling-cinnamon-kitchen-cabinet-family-home.html a four-year-old boy choked to death on cinnamon]], proving that consuming raw cinnamon ''is'' very dangerous.

* ''Machinima/RedVsBlue'':
** In Episode 50 of ''The Blood Gulch Chronicles'', published in 2005, Church attempts to save Captain Flowers from a heart attack in his sleep by giving him an injection. It turns out, however, that the injection had aspirin in it, which Flowers was allergic to, and was what actually caused his death. In 2015, Creator/MontyOum suffered an allergic reaction during a routine medical procedure and died ten days later. Once you notice the similarities, it's hard to find the scene anywhere near as funny as it was before.
** Most of the second half of Season 4 and all of Season 5 portrays Church as on the verge of reaching his RageBreakingPoint as he struggles to keep Blue Team at least ''partly'' functional despite the world seeming to fall apart around them. This is largely [[PlayedForLaughs Played For]] BlackComedy at the time, but ''The Project Freelancer Saga'' would later reveal that [[spoiler:the Alpha [=A.I.=] was successfully tortured past the brink of insanity multiple times by having him be ForcedToWatch as the people he cared about most died horribly and he was told that it was [[ItsAllMyFault all his fault]]. So in essence, Church is pretty much going through his worst possible nightmare all over again throughout the last portion of ''The Blood Gulch Chronicles'' - and he ''doesn't even realize it''.]]
** In ''Reconstruction'' Delta tries and fails to reassure Church by saying "I believe that Agent Washington's sanity is well within acceptable deviations, for now." Well, by the end of ''Recreation'', [[spoiler:"now" is officially [[FaceHeelTurn over.]]]]
** In ''Recreation'', when Simmons and Lopez are "discussing" whether or not Donut is the real Donut or not, Lopez says they should shoot him anyway. [[spoiler: Donut is shot and seemingly killed three episodes later.]]
** In ''Revelation'', Tucker tells Tex and Church not to come and ask the other Blues or the Reds for help if they die again, as they usually do, when they go to the Freelancer base on Sidewinder. [[spoiler:A couple episodes later, the Meta stabs a two-foot spike into Tex's helmet.]]

* In the wake of the Aurora, Colorado movie theater shooting, the "Slipping" scene in ''WebVideo/DrHorriblesSingAlongBlog'' is pretty uncomfortable to watch.

* Website/CollegeHumor:
** [[https://www.youtube.com/watch?v=gPYromrN7OI This video]] after Steve Jobs' 2011 passing.
** Similarly, the scene in [[https://www.youtube.com/watch?v=dhyLXlEti6s this video]] when the Genie from ''WesternAnimation/{{Aladdin}}'' tries to drown himself becomes pretty harsh after [[Creator/RobinWilliams the dude who voiced the original Genie]] committed suicide.
** In [[https://www.youtube.com/watch?v=V7eO-HO7GLI this video]], titled "Stop Saying "It Ruined My Childhood."", one of the self-entitled fans is played by Creator/KellyMarieTran, who would later be the target of racist attacks via social media by the very people the video is lampooning, over her role in the ''Franchise/StarWars'' sequels.
* Even on Wiki/ThisVeryWiki, there's one. The fact that one of our tropes is called {{Macekre}} seems very irreverent now that Carl Macek is dead.

* [[WebAnimation/ZeroPunctuation Yahtzee]] did a completely fake joke review of ''VideoGame/DukeNukemForever'' a while after said game was cancelled. Fast forward a few months, and the review has been voted the #1 fan-favorite. A few days afterward, ''DNF'' was announced to be UnCancelled at PAX 2010, and would come out to overwhelmingly negative reviews (with it really saying something when [[CausticCritic Yahtzee]] actually ''tried'' to list some positives of the real life game when he actually reviewed it).
** Additionally, Yahtzee gave an overall positive review to Creator/{{Telltale Games}}' ''VideoGame/TheWalkingDead'', but snarked at on how it would likely end with the typical BittersweetEnding of a ZombieApocalypse story where the survivors end up rebuilding civilization. The actual game ends on [[spoiler:an infamously [[TearJerker heartbreaking]] DownerEnding which has [[KidHero Clementine]] forced to kill her ParentalSubstitute [[ICannotSelfTerminate at his own urging]] as all of their friends have either been EatenAlive or have disappeared, with the last shot of the game being Clementine nervously walking across a field on her own as the sun sets and there's no one left to help her]].

* [[https://www.youtube.com/watch?v=ROMCPCBgsU0&feature=related This]] ''VideoGame/SuperSmashBrosBrawl'' [[WebAnimation/BowsersKingdom Parody video]] from Dec 22, 2007 has one [[VideoGame/SuperMarioRPG character]] comment at 1:15 "If I'm somehow not in this game, I'm blowing up Japan." kinda awkward considering the earthquake they had in 2011.

* WebAnimation/DickFigures has the episode "Pleasure Cruise", where Red and Blue are having a vacation on a cruise ship and they end up trying to save it and the passengers from a terrorist who plans to blow it up after being mistakened for secret agents. Although they defeat the terrorist, the bomb blew up before they could act, causing the ship to sink. On Jan. 13, 2012, the ship Costa Concordia has been grounded with several dead and missing. The episode was uploaded on Youtube at Jan. 12.

* WebAnimation/EddsWorld had a joke about Tom getting cancer in the future because of a laser he got hit by. It's lost some of its humor as the real life Edd has died because of cancer.
** It's not the only one about him. In ''[[WebAnimation/ASDFMovie THE TWENTY MINUTE ASDFMOVIE]]'', an angry potato tells the "I like trains" kid, "I am an angry potato and I hope you get cancer!" Edd Gould voiced the "I like trains" kid.

* In one of the fastest cases of this (it was funny for at most ''eight hours''), ''WebAnimation/{{Spill}}''[='s=] audio review of ''Film/TheDarkKnightRises'' starts off with the crew joking about critics being killed at the film's premiere. Then [[http://theweek.com/article/index/230875/the-dark-knight-rises-massacre-in-aurora-colorado-4-takeaways the Aurora, Colorado massacre]] happened
* ''WebAnimation/HomestarRunner'' isn't immune:
** In the Strong Bad Email Specially Marked, Strong Bad suggests the viewer tries cereals with certain sound effects, one of those is "gunshots in a crowded mall" this joke aged terribly with the Westroads Mall Shooting of 2007, and the many other shootings committed in malls in the US.
** In the Strong Bad Email [[Recap/StrongBadEmailE167TheMovies "the movies"]], there is a RunningGag involving turning off your bazooka before the movie starts. This is significantly less funny in the wake of the Aurora, Colorado movie theater shooting at the midnight premiere of ''Film/TheDarkKnightRises''.
*** Made even worse by the fact Strong Bad, who got annoyed and blew up the theater near the end of the e-mail, was once ComicBook/TheJoker for Halloween. Shortly after Aurora, James Holmes dyed his hair green and claimed he was The Joker.
** Near the end of "Fall Float Parade", a giant Marshie Balloon feebly controlled by The Cheat rams into the platform where Marzipan and Coach Z are reporting. This became less funny when three days after the cartoon was posted, a UsefulNotes/MacysThanksgivingDayParade balloon accidentally slammed into a streetlight, injuring two people.
*** In a similar vein, three years later a balloon version of Keith Haring's "Figure With Heart" [[http://youtu.be/4lnBDODCC2I?t=1h14m19s bumped into the booth where the hosts were broadcasting from]]. No one was injured, though, and they were quick to make jokes about it afterwards.
** "Best Caper Ever", which is about Homestar floating on an ice floe through the Arctic as Strong Bad and The Cheat try to remember what happened, came out February 9, 2009, one day after 134 people were rescued from a freeflowing sheet of ice that broke off into Lake Erie. Because of this, the page title of the cartoon was "Total Coincidence! Not Intentional!".
** The Strong Bad Email [[Recap/StrongBadEmailE187WinterPool "winter pool"]] is about [[ItMakesSenseInContext filling up a pool with red gelatin.]] Unfortunately, it also contains a FanDisservice joke about attracting "oiled-up Bill Cosby" that's a lot less funny after his sexual abuse allegations and subsequent trial.

* The second episode of ''WebAnimation/SuperFreakinParodyRangers'' features Blue Ranger Willy getting replaced by his brother Billiam, who is an over-the-top CampGay stereotype. Years later, David Yost (the original Blue Ranger) revealed he's gay and the reason he left the show was due to excessive gay bashing. Suddenly, Billiam feels even more wrong.

* WebAnimation/Kitty0706's video ''Mass Defect'' has a joke in it called, "[[http://youtu.be/V46KYxFav24?t=13m38s Take cancer and die]]." The joke now becomes horrendously unfunny because WebAnimation/Kitty0706 has passed away from leukemia.

* In 2006, ''WebAnimation/{{Arfenhouse}} 6'' took a crack at rogue security software (ala [[https://en.wikipedia.org/wiki/WinFixer WinFixer]]) with a scene where the movie is briefly hijacked by a (clearly fake) scareware virus posing as an antivirus program. Fast-forward to 2015: Adobe Flash, the program used to animate ''Arfenhouse'', is revealed to be so full of security vulnerabilities that tech experts are calling for it to be retired for good and all

* ''WebAnimation/{{RWBY}}'':
** Jaune's ButtMonkey antics take on a whole new light after we find out near the tail end of Volume 1 that he has no prior training and cheated his way into Beacon.
** Also in Volume 1, Jaune makes a [[GallowsHumour suicide joke]] about his predicament at school to Pyrrha. [[spoiler:Later on, Pyrrha dies in battle against Cinder and Jaune develops a [[DeathSeeker genuine death wish]].]]
** In the first episode of Volume 2, during [[MundaneMadeAwesome the most epic]] FoodFight ever put to animation, Weiss is slammed into a wall and Ruby hams up her "death" and says PleaseDontLeaveMe. [[spoiler:Fast forward to Volume 5, Jaune ends up in the same place saying it to Weiss and this time she is dying for real. Thankfully she gets better.]]
** Nora's BigEater tendencies, usually played for comedy, take a darker turn in Volume 4 [[spoiler:when we learn she was once just a StreetUrchin who spent many days scavenging in the trash for food and came close to starvation more than once. No wonder she takes nearly any opportunity to eat her fill as a young adult...]]
** In Volume 3, Ironwood and Qrow's argument ends with Ironwood declaring he'd shoot Qrow if he was one of Ironwood's men, and Qrow humorously retorting that he'd shoot himself if he was one of Ironwood's men. In Volumes 7-8, it becomes clear that Ironwood was not joking. [[spoiler:He [[KickTheMoralityPet shoots Oscar]] for trying to talk him down from abandoning Mantle, and he shoots Councilman Sleet for [[DisproportionateRetribution objecting to martial law]]. The only reason he doesn't shoot Marrow for [[BrokenPedestal refusing to support him any more]] is because Winter quickly disarms and arrests Marrow before Ironwood can fire, thereby saving his life.]]
* ''WebAnimation/RWBYChibi'':
** In "Mortal Frienemies", [[BelligerentSexualTension Qrow and Winter's bickering]] causes Ozpin to lament that "flirting used to be a lot less destructive in my day". Volume 6 of the series proper reveals that's because flirting was never the part of a relationship Ozpin had the difficulty with. [[spoiler:[[BigGood Ozpin]] and [[BigBad Salem]] were originally married until it collapsed in a terrible fight that accidentally killed their children; the world has been subject ever since to a SecretWar between two immortals who [[ForeverWar cannot permanently defeat the other]], making it the longest, bloodiest and most destructive divorce in Remnant's history.]]
** In "Mysterious Red Button", Neo chooses to fall into a trap that Roman accidentally falls into, proclaiming via sign that he's an idiot, but he's ''her'' idiot. [[spoiler:Her subplot in volume 6 of the series proper involves her seeking revenge for Roman's death because he was the only person in her entire life who ever cared about her.]]

* The infamous Pablo is one of the most well-known skits of the [[LetsPlay/VanossGamingAndCompany Vanoss crew's]] many sessions for being a joke that straight-up ''obliterates'' the line. For those who don't know, Craig "Mini Ladd" Thompson, back when he was part of the crew, made a [[https://www.youtube.com/watch?v=xHWN_E7wVJk video in 2014]] where he was telling the others a story (with a bad accent) about Pablo, a Mexican Mario knock off who, in a surprise twist added at the end, was a pedophile. Things took a surprisingly dark turn, when, in June of 2020, Mini was accused by two people of sending them inappropriate messages while they were underage and he was in his twenties, to which Craig tweeted out admitting his behavior. This made the Pablo bit much harder to stomach, and it has not gone unnoticed; many fans have commented on the original Pablo video lampshading that the joke aged ''very'' poorly.
** Similarly, [[https://youtu.be/_aMz67unx2k?t=479 this roast by Wildcat]] (who was mocking Minecraft-uploading [=YouTubers=] who were accused of sexually inappropriate behavior towards minors), became much harder to stomach after the above accusations.

->''"During the 40-minute speech, [[UsefulNotes/GeorgeWBush Bush]] also promised to bring an end to the severe drought of war that plagued the nation under [[UsefulNotes/BillClinton Clinton]], assuring citizens that the U.S. will engage in at least one Gulf War-level conflict in the next four years. ‘You better believe we’re going to mix it up with somebody at some point during my administration. … Unlike my predecessor, I am fully committed to putting soldiers in battle stations. Otherwise, what is the point in even having a military?’"''
-->-- [[https://politics.theonion.com/bush-our-long-national-nightmare-of-peace-and-prosperi-1819565882 “Bush: ‘Our Long National Nightmare Of Peace And Prosperity Is Finally Over’”]], ''Website/TheOnion'' headline, '''January 17, 2001'''

!!Web originals with their own pages
[[index]]
* FunnyAneurysmMoment/TheNostalgiaCritic
[[/index]]

* Creator/LittleKuriboh followed a SugarWiki/{{Heartwarming Moment|s}} (the proposal video) with a SugarWiki/{{Funny Moment|s}} ([[WebVideo/YuGiOhTheAbridgedSeries Tristan]]'s jab at said video)...and sent them both into FunnyAneurysmMoment when he announced he and Safty would be getting an annulment. He talks about it [[http://littlekuriboh.livejournal.com/112889.html here]] on his livejournal account.

* ''Series/BigBrother 13'' US is probably the most slanted season in ''Big Brother'' history, with twists that obviously benefit the veterans (All fan favourites) and safeguards in the form of competitions they've already played in left and right, as well as the most ''obviously'' slanted challenge for [[CreatorsPet Brendon]] to return to the game. After a sudden flip around causing one of the fan favourites to be voted out, a bunch of people on sites begun to think about how the producers would bail out the two remaining veterans, resulting in one user making [[https://www.youtube.com/watch?v=N-zWvFGg3ck&feature=channel_video_title this video]] making fun of how they assumed production worked. This became a FunnyAneurysmMoment when you consider within a week...almost all the events described to slant the season happened in the most blatantly contrived bailout in ''Big Brother'' history. Among these...Pandora's Box offering $5,000 to Porsche, restarting the duo twist, conveniently pitting Jordan and Rachel (The remaining veterans) with each other, and a literal ''copy'' of the first Head of Household competition (That Rachel won) for the veto. But with a different prop. One almost wonders if they got the idea for it after watching that video!

* Shellyfae's page on modelmayhem.com (possibly {{NSFW}}), and her Website/{{Twitter}} feed, are one entire FunnyAneurysm moment.

* Speculation about GMG Radio being taken over and Real Radio being rebranded as Heart and Smooth Radio rebranded to Gold is no longer comedy for people on media websites, ''especially'' now [[http://www.guardian.co.uk/media/2012/jun/12/gmg-receives-offers-radio-business this headline has happened]]. [[HopeSpot One can only hope UTV takes over them]], as Creator/GlobalRadio [[IdiotBall would have a monopoly on the UK radio market]]. Many jokes about Clear Channel[=/=]Creator/IHeartMedia are now a FunnyAneurysmMoment themselves, well, [[ValuesDissonance to British people in the media anyway]].

* The ''Franchise/{{Pokemon}}'' fan trailer ''Pokémon Apocalypse'' depicted a DarkerAndEdgier version of the Pokémon universe, and was released as a parody in late 2010. The parody lost all its humor on October 8, 2012, when PETA protested ''VideoGame/PokemonBlack2AndWhite2'' with a Flash game called ''Pokémon Black and Blue''; depicting Pokémon fighting back against their abusive trainers. The game has been met with resounding criticism from fans and the video game community. Also qualifies as HarsherInHindsight.

* Purposely {{invoked}} on WebVideo/AtopTheFourthWall in a storyline where Linkara found out [[spoiler:he was turning evil]] and a series of flashbacks to old comedic moments from the series shows evidence of him [[spoiler:becoming aggressive and egotistical to dangerous levels]].

* WebOriginal/TheRealJims posted [[https://youtu.be/9rnDSz-FSF8 TheRealJims his "60 Second Simpsons" review]] of ''WesternAnimation/TheSimpsons'' episode [[Recap/TheSimpsonsS6E14BartsComet "Bart's Comet"]], which featured the song "Que Sera, Sera" by Creator/DorisDay on May 9, 2019, four days before she passed away at age 97, with [[https://youtu.be/rhMvSWyeDnY TheRealJims posting in his "Extra Seconds" follow-up]] that the timing between his reviews and her death was shocking.

* On October 30, 2020, Nicki Swift's [=YouTube=] channel added a video titled "[[https://youtu.be/oc97DWWgxt4 This Is Why We Never See Sean Connery Anymore]]" about Creator/SeanConnery's last years as an actor, ending with "Enjoy your retirement, Mister Bond.". The very next day, Connery passed away at age 90.

* The WebVideo/RyanGeorge video [[https://www.youtube.com/watch?v=mtCgnz-Jxnw "Nobody Cares About Game Show Hosts"]] features Creator/AlexTrebek mistaking contestants' responses on ''Series/{{Jeopardy}}'' as questions about his well-being, and then sobbing when he realizes nobody's actually checking up on him. A few months after the video came out, Trebek revealed he had Stage IV pancreatic cancer, and in his memoir, he described the psychological issues that came with his cancer treatment, including crying jags and suicidal ideation. Many more people were concerned for Trebek's well-being after hearing that. He died two years later.

** "Mysterious Red Button" Neo falls into a trap after Roman, proclaiming via sign that he's an idiot, but he's ''her'' idiot. [[spoiler:Her subplot in volume 6 of the series proper involves her seeking revenge for Roman's death because he was the only person in her entire life who ever cared about her.]]

** In "Mortal Frienemies", [[BelligerentSexualTension Qrow and Winter's bickering]] causes Ozpin to lament that "Flirting used to be a lot less destructive in my day." Volume 6 of the series proper reveals that's because flirting was never the part of a relationship Ozpin had the difficulty with. [[spoiler:[[BigGood Ozpin]] and [[BigBad Salem]] were originally married until it collapsed in a terrible fight that accidentally killed their children; the world has been subject ever since to a SecretWar between two immortals who [[ForeverWar cannot permanently defeat the other]], making it the longest, bloodiest and most destructive divorce in Remnant's history.]]

** "Mortal Frienemies" sees Ozpin laments upon seeing [[BelligerentSexualTension Qrow and Winter's bickering]] that "Flirting used to be a lot less destructive in my day." Volume 6 of the series proper [[spoiler:reveals that flirting with Salem wasn't Ozma's problem, it was the split as one: he and [[BigBad Salem]] were husband and wife and two: their current feud is effectively a protracted, bloody, global divorce that resulted in the deaths of their kids and by extension, Summer, Pyrrha, Roman, and Hazel's sister, as well as until voulme 7 opened with the reveal she was rebuilt, the dismantling of Penny.]]
** "Mysterious Red Button" Neo falls into a trap after Roman, proclaiming via sign that he's an idiot, he's ''her'' idiot. [[spoiler:Her subplot in volume 6 of the series proper involves her seeking revenge for Roman's death.]]
** [[spoiler:The mere existence of Mike and Marty, two Grimm who can talk, are this after volume 7 revealed that this is canon to the main series and played as horror.]]

** In Volume 3, an argument between Ironwood and Qrow ends with Ironwood declaring he'd shoot Qrow if he was one of Ironwood's men, and Qrow humorously retorting that he'd shoot himself if he was one of Ironwood's men. In Volumes 7-8, it becomes clear that Ironwood was not joking. [[spoiler:He [[KickTheMoralityPet shoots Oscar]] for trying to talk him down from abandoning Mantle, and he shoots Councilman Sleet for [[DisproportionateRetribution objecting to martial law]]. The only reason he doesn't shoot Marrow for [[BrokenPedestal refusing to support him any more]] is because Winter quickly disarms and arrests Marrow before Ironwood can fire, thereby saving his life.]]

** In "Heroes and Monsters" Roman rants to Ruby about how bad men like him will always survive... and promptly gets eaten by a griffon, allowing her to go on to save her friends. Three seasons later, [[spoiler:Neo resurfaces, obsessed with getting revenge for Roman's death. It turns out their relationship was not strictly professional- Roman was Neo's only friend and without him her life has gone to hell]].