[[caption-width-right:350:...no matter how hard you mistakenly press the brake pedal.]]

Funny Aneurysm Moments that don't have their own categories yet.


* [[https://www.youtube.com/watch?v=MxJDobrrOYA The commercials]] for the Ayds appetite-suppressant candy (which, yes, died slowly during the 1980s because of the rise of AIDS combined with its unfortunately similar name. Back then the disease was called "GRID", short for Gay Related Immune Deficiency before it was renamed in the 80s).
--> "Thank goodness for Ayds!"
--> "Why take diet pills when you can enjoy Ayds?"
--> "[[WesternAnimation/SouthPark I lost weight because I have aides, and I think every obese person should have aides.]]"
** It gets even worse when you hear about the mad scramble the company made to save the brand -- they tried renaming it "Aydslim", only to find that in those early days, AIDS was known as "the slim disease" in some parts of Africa due to weight loss being one of its side effects. They also tried renaming it "Diet Ayds" to no avail.
* [[http://www.youtube.com/watch?v=c7d85T4OfqA Commercials]] for ''health insurance'', of all things, hosted by the late Billy Mays.
* In 1997, Sarah Ferguson appeared in a commercial for Weight Watchers where she was being hounded by reporters, and she says, "Losing weight can be harder than outrunning the paparazzi!" A few weeks later, her sister-in-law Diana (former Princess of Wales) had a run-in with the paparazzi that ended poorly.
* On September 11, 2001, NBC showed a [=McDonald=]'s commercial with the slogan "We love to see you smile." ''Right after that, Series/{{Today}}'' began their coverage of the 9/11 attacks.
** And also before that ad, Ross' Emergency Wardrobe 911 ad.
* [[http://1.bp.blogspot.com/_Me-BvCb5gYk/TQY-KoLuyzI/AAAAAAAACCc/MmQcL_dONaM/s1600/image001.jpg A 1979 ad]] [[http://www.snopes.com/rumors/photos/pia.asp for Pakistani International Airlines]] has the shadow of a jetliner over the Twin Towers. After 9/11/2001, it gets another whole new and way darker meaning.
* BP's advertisements for the Gulf Coast.
* Toyota's slogan "Moving Forward" has become a lot more uncomfortable ever since the [[http://en.wikipedia.org/wiki/2009Ė2010_Toyota_vehicle_recalls 2010 recalls]], since people have reported that their Toyota vehicles accelerate suddenly and uncontrollably, and don't respond to the driver pressing the brake pedal.
* In 1968, London Weekend Television was due to start broadcasting. During the final weekend of their predecessor ATV London's broadcast, they ran a [[http://www.transdiffusion.org/tools/playmedia.php?file=/smallscreen-audio/233.mp3 short trailer]] with a letter giving a positive review of the programming for the upcoming first weekend. The announcer noted that the letter "seem(ed) a bit premature", and indeed it was ó the first weekend (and several more afterwards) ended up being wiped out by [[UsefulNotes/TVStrikes strike action]].
* [[http://www.youtube.com/watch?v=X5zbEsQYMb0 A 2000 Super Bowl ad]] has a presenter who mentions how "in 2004, the tide was turned against AIDS", in 2006 ("two years later", according to the ad), there were "great strides against cancer, and most notably, a "remarkable breakthrough against spinal cord injuries", which featured the CG-enhanced Creator/ChristopherReeve [[CrowningMomentOfHeartwarming walking]] [[CrowningMomentOfAwesome onstage]]. Sadly, Reeve would die in 2004, as would his wife Dana from lung cancer (despite being a non-smoker) in 2006, and we haven't seen so much progress in all those areas.
* An ad for bendable eyeglass frames that aired until fall of 2001 showed a metal skyscraper ducking out of the way of an oncoming airplane.
* A 2009 [[http://www.youtube.com/watch?v=OC8XG9QR0AE commercial]] for the MTV Video Music Awards features Music/TaylorSwift singing about the 2009 VMAs and how good it will be, including the line "There'll be no teardrops on my guitar." At the actual show, Music/KanyeWest [[JerkAss happened]] ...
* There used to be a chain called Chapter 11 Bookstores with the motto "Prices so low, [[TemptingFate you'd think we'd go bankrupt!]]". Which, yes, they later did.
* There was a funny [[http://www.youtube.com/watch?v=nrkUMjoXWdY&feature=share commercial]] in 2008 where [[TeensAreMonsters Chavs]] are destroying Britain and a family takes shelter to watch TV without any worries. Fast forward to 6 August 2011, and the London tragedy, and this isn't a laughing matter anymore.
* In late 2011, one of the ads in the long-running Ashton Kutcher Nikon Coolpix campaign featured the man using his camera to seduce a bunch of women and lead them up to his hotel room. Around that same time, his marriage to Demi Moore was dissolving thanks to a very public affair.
* Mattel Electronics' [[http://www.youtube.com/watch?v=0rnRRph4bcE commercial]] for ''VideoGame/BurgerTime'', which ends with Mr. Hot Dog saying "We are ''closed'' now!" as he slams the window shut on the drive-thru, came out months before Mattel Electronics closed down.
* A 1980s lamb [[http://www.youtube.com/watch?v=Tt1YV9Bj72c commercial]] has a woman turning down the opportunity to have dinner with Creator/TomCruise because her mum was cooking a lamb roast that night. Nowadays, it seems like a perfectly rational decision.
* Target has a couple of instances.
** [[http://www.behance.net/gallery/Target-Pharmacy-dir-Mike-Mills/1268579 These pharmacy ads]] would be a little more convincing if they didn't look so much like ''Series/{{Dexter}}''[='s=] [[http://www.google.com/search?um=1&hl=en&biw=1280&bih=827&tbm=isch&sa=1&q=dexter+ads&aq=f&aqi=g1&aql=&oq= ads]] minus the blood.
** In 1997, Target tried to push a snowman by the name of Snowden as their official mascot for Christmas. Snowden had two holiday specials, one [[RecycledInSpace on ice]] in live action and another in stop-motion, before being retired after the 1999 holiday season. The name Snowden is more commonly associated with a wanted ex-CIA agent who exposed top secret NSA information to Americans.
* During the '00s, Washington Mutual ran a series of ad campaigns focused on how great it was for its bold new business practices that were so great for consumers, like loans for borrowers that other banks considered risky. The campaigns featured [=WaMu=]'s hip spokesman contrasted against a bunch of old and stodgy executives from their competitors, all of whom would declare that [=WaMu=]'s new innovation [[ItWillNeverCatchOn would never catch on]]. Then [=WaMu=] went bankrupt...because of loans to risky borrowers.
* Apple's '1984' advert, depicting IBM as a 1984-esque Big Brother figure, while these days, Apple are HUGE champions of Digital Restrictions Management and locking down devices so users can't use devices they own to their full capability. In addition, Apple banned Website/TheBestPageInTheUniverse from being viewable from Apple Stores and on Apple offices' networks, which Maddox speculates was due to his [[http://www.thebestpageintheuniverse.net/c.cgi?u=iphone anti-iPhone page]].
--> [[{{Irony}} "Yes, the company that once alluded to an Orwellian future with controlled media, is now controlling media."]]
* Commercials for Breyers ice cream used to feature kids having trouble [[UnfortunateIngredients reading the ingredient labels of competitors]], struggling to pronounce things like "polysorbate 80" and "mono and diglycerides", but can easily read the much simpler list of Breyers' ingredients containing things like milk and natural vanilla. However, Unilever has been cutting costs in the brand, so it features those same ingredients nowadays and is even marketed as [[LiteCreme "frozen dairy dessert"]] due to the use of the cheaper skim milk and whey (a byproduct of cheese) instead of whole milk and cream.
* [[https://www.youtube.com/watch?v=jJ3rndjje30 This ad for MLB 12: The Show]] depicts the Chicago Cubs winning the World Series and all of Chicago celebrating, even the Pope himself, before eventually cutting to a sobbing Cubs fan in his room with a [=PS3=] controller. In 2016, the Cubs finally made it to the World Series, only to choke against the Cleveland Indians in Game 7 (they still won, however).
* A Federal Express ad features Steve Irwin dying of a snake bite because he used the wrong service to deliver the antidote. Granted, it wasn't a snake that ended up killing him, but still...
* A 2010 Creator/{{ESPN}} "This is Sportscenter" ad featured mild-mannered Dwight Howard getting the story on how Superman saved Hannah Storm from a coffee machine that caught on fire (the joke, of course, being that Superman is Dwight Howard's alter ego). In December 2012, Storm received severe facial and upper body burns after a gas grill's propane tank exploded in her face.
* Subway had a mobile game called [[http://www.deathandtaxesmag.com/260300/jared-pants-dance-subway-website/ Jared's Pants Dance]] marketed for kids, which becomes a very unfortunate name in light of Subway's promoter, Jared Fogle's convictions of child pornography possession and sexual abuse of minors.
** On the same vein, Subway's slogan of "Eat Fresh" gets a whole other meaning following Jared's scandal.
-->''[[https://www.youtube.com/watch?v=J9JVOiD4o0w Eat Fresh, just umm.... Not Too Fresh]]''.
* In 2008, Greyhound pulled a series of bus ads, one of whose slogans was "There's a reason you've never heard of bus rage." The ads were pulled after Vince Li, in the midst of a psychotic break, attacked and decapitated fellow passenger Tim [=McLean=].
* ''Every'' commercial featuring a product endorsed by Bill Cosby (especially Jell-O and Coca-Cola) has become this due to his numerous rape allegations. Any commercial where he appears with children is especially cringe-worthy.
** Here's [[https://www.youtube.com/watch?v=afN4ib6JAy4 one]] with Creator/LindsayLohan.
* A 1996 [[https://www.youtube.com/watch?v=GPRscxQZs8E Snickers commercial]] shows a football player taking a big hit and subsequently thinks he is Batman. Pretty funny at the time (to be honest, still funny today), but since then there have been a ton of studies and examples of the damage that can be done to football players (''all'' football players, regardless of type) by repeated head injuries.
* Nike ads featuring double amputee sprinter Oscar Pistorius with the tagline "I am the bullet in the chamber" became unfortunate after Pistorius was charged with shooting his girlfriend.
* Actor James Garner did a commercial for the [[https://www.youtube.com/watch?v=hPT4tJFgRTA National Beef Council]] back in 1987, extolling the virtues of beef while simultaneously rejecting the vegetables on his steak kebabs. One year later, he underwent quintuple bypass heart surgery, and eventually died of a heart attack in 2014 at age 86. One risk factor for clogged arteries and heart disease is a high diet of red meat.
* [[http://www.youtube.com/watch?v=bnhBxOQOMAI This]] commercial for Snickers, featuring a man dressed as a cartoon dog getting cranky at people at the amusement park, becomes this after a 2013 incident where a similar situation happened with a man dressed as Cookie Monster in Times Square.
* The Marlboro Man. [[http://en.wikipedia.org/wiki/Marlboro_Man#Controversy There are, so far, at least four reasons why Marlboro cigarettes are occasionally called "cowboy killers."]]
* This [[http://youtu.be/JDor3S-0KGs?t=8m34s Wendy's snippet from 2002]] (taken from a ''WebAnimation/NextGPoop'' special) was Dave Thomas's last appearance before his passing. [[AnyLastWords His last words? "See you later."]]
* [[http://www.youtube.com/watch?v=o6E9s-KZlOo This Iran Air spot from 1978]] (third spot in compilation) fits taking into account [[UsefulNotes/{{Iran}} considering the Iranian Revolution the following year]] and especially the Iran Hostage Crisis that began in November 1979.
* [[https://www.youtube.com/watch?v=EVVFiuksLc4 Verizon FiOS]] began airing a series of ads in which a fictional network had to choose whether to send former Pittsburgh Steelers quarterback and real life {{Creator/FOX}} sportscaster Terry Bradshaw and a little girl. The girl gets the information in real time (using FiOS, of course) and gets the call; forcing Terry to watch at home. The spot took a swerve into this trope when Bradshaw was unable to go to UsefulNotes/SuperBowl XLVIII because his father had died.
* This [[http://www.youtube.com/watch?v=hU5N2SrEaZI]] eerily ironic Driving PSA with James Dean from the 50s.
* [[http://youtu.be/WPkByAkAdZs This 2013]] Audi commercial featuring Creator/LeonardNimoy and his [[Franchise/StarTrek Spock]] successor Creator/ZacharyQuinto racing to a golf club in different cars. At one point, Nimoy feigns weakness by coughing uncontrollably, repeating Spock's last words from ''[[Film/StarTrekIITheWrathOfKhan Star Trek II]]''. The following year, Nimoy got diagnosed with COPD (chronic obstructive pulmonary disease) due to years of smoking, which ultimately killed him in 2015.
* Rolf Harris starred in a series of ads in 2000 for milk, starring as an animated version of himself. What was the tagline? ''The White Stuff.'' And some ads featured some unintentional innuendos as well. Needless to say, they become beyond painful to watch after his allegations of child molestation.
* Back when Enron was viewed as a thriving corporation, they released a series of commercials with the theme [[http://www.youtube.com/watch?v=pboh1SFk6TM "Ask Why?"]] Years later when Enron suddenly went Bankrupt shocking the country, the United States government asked them why? They got their answer when they discovered years of corporate fraud.
* Sony started a line of TakeThat posters towards Microsoft after noticing the poor reception following the UsefulNotes/XboxOne's initial reveal. One of these claimed "The only red ring is the circle button," a jab at the UsefulNotes/Xbox360's infamous Red Ring of Death issue. Launch day arrives, and... [[http://www.gamezone.com/news/2013/11/15/new-claims-of-ps4-s-red-line-of-death-beginning-to-pop-up Well, let's just say things couldn't be more ironic.]]

[[folder:Comic Strips]]
* A minor one. In ''ComicStrip/CalvinAndHobbes'', Calvin discusses how gross sliced lunch meat is (such as saying the skin is plastic) and that apples are dyed and waxed to enhance their appearance, but you're basically eating a candle. Apples are actually waxed with "food grade shellac" (which is the stuff found on some insect carapaces)... but instead of it being for appearance it's to help preservation.

* The June 1993 ''Disney Adventures'' cover featured Music/MichaelJackson carrying a delighted Pinocchio (his favorite Disney character, according to the magazine) on his shoulders. Two months later, Jackson was first accused of child molestation and in the years to come his Neverland Ranch would be compared to Pleasure Island, where young boys were free to play but had to pay a horrific price for their fun -- including at his 2004-05 trial on a second set of charges. Similarly, all the "Pied Piper of Pop" accolades that flew around him in TheEighties turned sour in the wake of the accusations, as people remembered [[Film/InvasionOfTheBabySnatchers what happened to the kids he enchanted]]. (A ''Cracked'' back cover in '93 spoofed this with Jackson as "The Pied Piper of Encino".)
* Charb, cartoonist and editor in chief of the French satirical magazine ''Charlie Hebdo'', published a drawing on January 7th 2015 on the magazine's Twitter, titled "Still no terrorist attack in France", in which a terrorist said "[they] had until the end of January for the wishes." [[http://www.theguardian.com/world/live/2015/jan/07/shooting-paris-satirical-magazine-charlie-hebdo A few hours]] [[TearJerker later...]]
* Nintendo Power's Player Pulse section in volume 72 (May 1995) featured a list of "Top 10 Crime Games". #10 was "Super Bomber Man 3: The World Trade Center". Let that sink in for a moment...
** In the March 2012 issue, Chris Slate said something among the lines of "The world hasn't ended yet, but until it does, we'll be covering the hottest games throughout the year." The magazine ended in December that year.

* October 23, 1872: Unusual one from the US election ó the legendary cartoonist Thomas Nast published in Harper's Weekly a [[http://nastandgreeley.harpweek.com/subpages/cartoon-1872-largeB.asp?UniqueID=38&Year=election cartoon]] featuring newspaper publisher Horace Greeley, then running for President, being carried back into his home like a corpse. One week after the cartoon was published, Greeley's wife died. On November 29, Greeley himself died.
* Much of the early career of UsefulNotes/RichardNixon was impacted by Nixon's involvement in [[{{Scandalgate}} the Watergate scandal]].
** One [[http://www.livingroomcandidate.org/commercials/1952/nixon-on-corruption#3953 1952 campaign ad]] features Nixon (shortly after being named UsefulNotes/DwightDEisenhower's running mate) has then-California Senator Nixon hammering away at the corruption that had plagued the administration of outgoing President UsefulNotes/HarrySTruman.
** Not long after being named the Republican Vice-Presidential candidate; a corruption scandal threatened to sink Nixon when he was accused of having a slush fund, with the scandal being serious enough to lead to his potentially being dropped from the ticket. Nixon then took to television to deliver what became known as the [[http://www.americanrhetoric.com/speeches/richardnixoncheckers.html Checkers speech]] (named after the name of a dog given as a gift for Nixon's young daughters that Nixon emphasized they were keeping), and the controversy saved his career after it was revealed he was in the clear[[note]]It was later revealed that the campaign of Democratic Presidential nominee, Illinois Governor Adlai Stevenson II, had a ethically questionable "miscellaneous" fund account of his own[[/note]].
** Following his narrow defeat for the Presidency in 1960 by UsefulNotes/JohnFKennedy; Nixon decided to run for Governor of his native California against incumbent Democratic Governor Edmund "Pat" Brown[[note]]father of current Governor UsefulNotes/JerryBrown[[/note]]. One of Nixon's campaign ads touted him as a man of integrity; complete with a [[https://www.youtube.com/watch?v=ltD5knypEWk still shot of evangelist and close friend Billy Graham]].
* Just after the completion of his victory speech in 1988, Creator/{{CNN}} anchor [[https://youtu.be/LAAdN4o4QMw Mary Alice Williams said of]] President-elect UsefulNotes/GeorgeHWBush "There's a man who keeps his promises."[[note]]Williams was referring to Bush closing his speech by saying "Thank you New Hampshire", itself a reference to Bush promising to say that if he was elected President following Bush winning the New Hampshire primary after coming in 3rd place behind Kansas Senator Bob Dole and longtime ''Series/The700Club'' host Pat Robertson in the Iowa Caucus[[/note]]. Two years later, Bush would break a [[https://youtu.be/0MW44jsYi0g more important promise]][[note]]"Read my lips, no new taxes[[/note]], which played a major role in his going down to defeat in 1992.
* Prior to the 2000 U.S. Presidential Election, Dave Barry wrote a column talking about the election results, with blanks left for the winner. The joke was supposed to be that he couldn't be bothered to stay up late on election night to find out the results and asked the editor to fill it in later. However, due to the Florida recount controversy, the election ended up not being decided until over a month later.

[[folder:Professional Wrestling]]
* At the WWF's 2nd Annual Summer Slam in 1989, one of the matches was a six-man tag; Wrestling/{{Demolition}} (Axe & Smash), joined by Wrestling/HacksawJimDuggan, vs. The Twin Towers ("African Dream" [[Wrestling/OneManGang Akeem]] & Wrestling/BigBossMan), joined by Wrestling/AndreTheGiant. Before the match began, cameras showed a young audience member holding up a posterboard sign reading "DEMOLITION WILL TOPPLE THE TWIN TOWERS," illustrated with a drawing of two leaning skyscrapers.
* On the 8/9/1997 Edition of [[Wrestling/WCWMondayNitro Nitro]] the Wrestling/{{n|ewWorldorder}}Wo ran an angle where they called Wrestling/{{Sting}} down from the rafters (as he'd been doing for some time at that point). However, Sting came down way too fast and crashed at ringside. Hogan and the rest of the boys start selling it like the man was really hurt. They gathered around him, called for help from the back, brought a stretcher down...and then they revealed that it was a dummy, and pulled it into the ring to mock Sting and have Hogan beat "him" in a match. Wrestling/OwenHart would die from a rappelling stunt gone wrong two years later.
* It was a long one but when Wrestling/KevinSullivan divorced from his wife Nancy, it had sprung up from an affair she and Wrestling/ChrisBenoit had while they were touring together as part of an angle Sullivan had booked while working in WCW. The joke was Sullivan had "booked his own divorce" by having them travel together to maintain {{Kayfabe}}. This led to their marriage, which unfortunately led to Nancy Benoit's death in 2007 when her husband murdered her, their son, and finally himself, which rendered the original joke pretty tragic.
* Part of Wrestling/StoneColdSteveAustin's FaceHeelTurn in 2001 included him mistreating his wife and manager, Debra [[http://www.youtube.com/watch?v=syUz3kd9DRk]]. This happened little more than a year before Stone Cold was arrested for domestically abusing her.
* Wrestling/CMPunk's IWA M-S "feud" with Wrestling/MattSydal and [[Wrestling/HunterJohnston Delirious]] at one point involved Punk screaming Sydal's [[ItsOkayIfItsYou maybe]] girlfriend and Delirious's TranslatorBuddy Wrestling/DaizeeHaze needed a "[[HollywoodThin sammich]]". While this would lead to Haze getting some humorous retribution on Punk, her entire involvement is less funny when one knows anorexia eventually forced Haze into retirement.
* At ''ECW One Night Stand 2005'' during the Wrestling/MikeAwesome (who was reviled by ECW fans for jumping to WCW without warning, while he was still the [[http://www.wrestling-titles.com/us/ecw/ecw-h.html ECW World Heavyweight Champion]]) vs. Wrestling/MasatoTanaka match, Wrestling/JoeyStyles commented, "Suicide dive by Mike Awesome, and it's a damn shame he didn't succeed in taking his own life!" In February 2007, Mike Awesome committed suicide.

* Frank Kramer of [[http://www.fhfshow.com/ Frosty, Heidi, and Frank]] fame has had a long career's worth of jokes mocking the ideas of love and monogamy. In late 2017, however, he claimed to begin seeing a therapist about his "intimacy issues" as he called them. In their [[https://www.fhfshow.com/b/MeToo/71731475749561781.html October 24th, 2017 broadcast]], inspired by the rising #metoo movement, Frank admitted for the first time ever that he was molested as a young toddler, and had the realization that this might be where his intimacy problems stem from. His history of jabs at love and marriage is considerably less funny now, knowing where it's supposedly coming from.
* [[http://www.youtube.com/watch?v=2p6cerxq4rk&feature=player_embedded Gordon Ramsey asks Irish Broadcaster Gerry Ryan]] if he's had his heart checked. Ryan died of an apparent heart attack sometime afterwards.
* An episode of ''Radio/ImSorryIHaventAClue'' from 1995 where, after they both try to speak at once, Creator/WillieRushton says to Barry Cryer, "No, you go first, you're likely to die sooner than me". Willie Rushton died the next year.
** During a game of predictions in 1986, Willie predicted -- to much laughter -- that one of the sad events he foresaw for 1996 was his own death that January; he died in December.
** In 1995, Tim Brooke-Taylor predicted that a 2010 Radio Times would include a listing for "I'm Sorry I Haven't a Clue with Humphrey Lyttelton, Barry Cryer, Graeme Garden, and Tim and Samantha Brooke-Taylor." Willie, the only one of the regulars left out, died the next year, while the others were all alive up to Humph's death in 2008.
** Willie often complained about the "___'s Ball" games full of punning names about various subjects. At his last ISIHAC recording, the chosen subject was "Undertaker's Ball," full of puns about death and burial.
** One of the small number of old episodes that have been released on CD (in 2006) includes a round where the teams had to guess who a famous celebrity was by asking questions about him/her. Unfortunately, one of the celebrities they had to guess was Creator/JimmySavile.
* On an episode of ''Radio/FibberMcGeeAndMolly'' from March 20th, 1945 where Fibber is trying to fix the radio, Molly says "I hope you fix it in time for Roosevelt's next inauguration!" UsefulNotes/FranklinDRoosevelt died 23 days later.
* In one early episode of the ''Radio/BobAndRay'' show, Ray explains that he was off yesterday due to 'a sharp pain in my lower back', joking to the effect that since he's in radio, he didn't know if it was a cold (ie., a kidney infection) back there or a knife. In hindsight... he's evidently joking about a very early symptom of the kidney failure that would kill him years later.
* The special 25th anniversary edition of ''Radio/ImSorryIllReadThatAgain'' in 1989 ended with David Hatch reading the credits and finally saying "I hope to see you all again in 25 years' time", to laughter and cheers from the audience. All the original performers were (and as of 2015 are) alive 25 years later -- except David Hatch.
* Anything said about GMGRadio's portfolio and Real Radio becoming Heart (a Creator/GlobalRadio brand) online now seems uncomfortable to read rather than comedy; given that their Christmas Day schedule is only 4 hours (6am-10am) local this year, compared to previous years, all due to syndicated programming. However, Real Radio still retains its "wacky DJ" personality which Heart ''does not'' have.
** Now it has started to come true, and a severe backlash was seen at Radiotoday.co.uk about this.
* The week before he suddenly died of a brain anyeurism, radio DJ Kidd Kraddick did a segment called "Deathbed Confessions", where he imagined what he would say to his radio cohosts when he was on his deathbed.
* 97.7 HTZ-FM (a rock station in St. Catharines/Niagara Falls, Ontario) DJ "Iron Mike" Bensson died of cancer in early November 2013. The fact that he received his nickname "Iron Mike" due to his perfect nearly-20 year daily broadcast track record, hosting shows even through sickness and tragedy, makes his death a cruel irony. His last few shows, where he broke the news of his cancer, are especially tough, hearing him talk about how he just wants to keep working, as Iron Mike has gone through illness before, and he will again...
* One of the {{Running Gag}}s on Radio/CarTalk, established in the show's early years, was that Tom could never remember the previous week's [[OnceAnEpisode Puzzler]]. Tom eventually developed Alzheimer's disease.

[[folder:Real Life]]
* The crew of the Apollo 1 took [[http://i.imgur.com/vA1GUM7.jpg this]] mock portrait, jokingly praying to the untested craft. It becomes a lot less funny when they all burned to death inside it during a routine test.
* At the 2005 MTV Video Music Awards Show, which aired on August 28, Eva Longoria joked about a ďsmall hurricaneĒ. Well, that hurricane, which got Miami at the time, happened to be named Katrina and New Orleans suffered her wrath a day later.
* Herbert Viana, the lead singer of the Brazilian band Paralamas do Sucesso, finished an interview in 2001 by saying all he had bought a new plane, and all he wanted to do was fly (he was a pilot). Months later, he crashed the plane into the sea, in an accident that left him paralyzed from the waist down, and killed his wife.
* [[http://upload.wikimedia.org/wikipedia/commons/e/ed/New_Hampshire_quarter%2C_reverse_side%2C_2000.jpg The New Hampshire state quarter]], initially circulated in 2000, depicts The Old Man of the Mountain, which was a state landmark. Three years after the quarter was released, the Old Man naturally collapsed.
* Every joke about Dick Clark's eternal youthfulness has suffered from this since Clark's stroke in late 2004, which rendered him...somewhat less youthful.
** Now even less funny come 2012, since Clark has passed away of a heart attack.
** Still, one could look at it as it taking a massive stroke for Dick Clark to age, which is a lot more than it takes most people to move past appearing young.
* On November 24, 1958, at a Friars' Club roast in Los Angeles for Creator/LucilleBall and [[Series/ILoveLucy Desi Arnaz,]] after comedian Harry "Parkyakarkus" Einstein [[note]]the father of Creator/AlbertBrooks and Bob Einstein, better known as "Super" Dave Osborne,[[/note]] suffered a heart attack and slumped into Milton Berle's lap, emcee Art Linkletter asked Tony Martin to sing a song in order to lighten the mood. He selected "There's No Tomorrow" (sung to the melody of "O Sole Mio"), and sadly, Harry Einstein died soon afterwards, with Tony Martin serving as a pallbearer at his funeral.
* From "The Good War" -- the massive set of WWII-based interviews by historian Studs Terkel (the brackets are part of the title, by the way): The interviewee, Maurice E. Wilson, talks about an apparently white man called Robert Brooks in his unit whom Wilson often called Nig on account of his features and hair. After Brooks died, it emerged that he was black and had lied about his race (he was pale enough to pass for white) to get into a white outfit.
* Jim Fixx, the guy who made jogging popular, died of a heart attack while he was jogging. This looks ironic on the surface, but the heart problem was known, and was actually the reason Fixx took up jogging. It likely extended his lifespan.
** Similarly, James Rodale - a writer and publisher who advocated for organic foods and healthy living in such publications as ''Prevention'' magazine - died of a heart attack at 72 while appearing as a guest on ''The Dick Cavett Show''. Just minutes earlier, Rodale had predicted he would [[TemptingFate "live to be 100"]].
* Providence radio DJ [[MeaningfulName Doctor Metal]] of the hard rock station WHJY threatened not to go see Metallica play during the summer (even though he supported them on the air since they were still in the underground) if their new album wasn't good. He then qualified the statement by saying he doesn't know what'll happen and he could be dead by then. Shortly after that, Doctor Metal died in the Station nightclub fire in Rhode Island in February 2003. Oh and that next album, ''St. Anger''? It was almost universally hated by Metallica fans upon its release.
* [[https://www.youtube.com/watch?v=_ykJaN0Q9PI In a documentary about countries that aren't internationally recognized]], the crew's translator talks to the Russian peacekeepers in South Ossetia, and says that, if fighting begins, they will take off their peacekeeper badges and help fight for South Ossetian independence. Three years after the documentary was filmed, fighting ''did'' break out in South Ossetia...
* There is a show on the History Channel called ''Wild West Tech'', hosted by DavidCarradine. A 2005 episode featured him detailing the differences between two ''noose'' knots. It gets better. At the end of the segment, he signs off: "Don't try this at home." The reruns since 2009 are...uncomfortable.
* When Dr. Guillotin presented his killing machine to French Convention (the ruling body during the Revolution), he joked: "With this machine, I could cut your heads off, and you wouldn't notice!". Most members of that Convention were later executed by guillotine, though not Dr. Guillotin himself.
** Even worse, that part about "you wouldn't notice?" Later testing with the guillotine during the Reign of Terror suggests that '' the head stayed alive for some time after being sliced off'', and modern research has confirmed that from the perspective of the brain, the only difference between decapitation and sudden cardiac arrest is that there is no possible way to reverse decapitation. It is well known that cardiac arrest victims remain conscious for twelve seconds before collapsing, and the same can be said for victims of decapitation.
** Though however long it took, it was still far faster, more dignified and probably less painful than strangulation by [[FairForItsDay short-drop hanging]], which had been the normal method for ordinary people until then. Other western nations solved this in the early 19th century with the invention of the long-drop gallows, calculated to each victim to kill as fast as possible... by what is in all intents and purposes decapitation without breaking the skin.[[note]]The long-drop, along with the way the noose is placed, is designed so that the sudden stop at the end wrenches the neck enough to snap the spine. It still takes a bit to actually die, but since you're likely paralyzed and unconscious, you're not likely to be suffering.[[/note]]
* After a would-be terrorist tried igniting a bomb in his shoe in 2001, some comedian quipped, "...so now the government is looking in people's shoes. Thank god he wasn't trying to light a bomb in his crotch." [[http://en.wikipedia.org/wiki/Northwest_Airlines_Flight_253 Yeah...]]
** LarryTheCableGuy also once made a similar joke about a "panty bomber" which was made similarly unfunny by the same incident.
* Captain Morgan rum is named for privateer Henry Morgan, who died of liver failure from drinking too much rum.
* The name "Hiroshima" translates literally as, and uses the characters for, "Spacious Island". As seen [[https://upload.wikimedia.org/wikipedia/commons/a/a0/Hiroshima_aftermath.jpg here]], World War II left it a little ''too'' spacious.
* When Creator/SandraBullock appeared on Creator/DavidLetterman to promote ''Film/TheBlindSide'', the music they played when she walked out was "I Wish That I Had Jessie's Girl."
* According to his childhood friend Asher Wright, [[http://en.wikipedia.org/wiki/Nathan_Hale Nathan Hale]] had a mole on his neck and as a boy he was teased about by other boys who said it meant he would be hanged. One day he and Asher were out sailing and a storm blew up. Nathan laughed and said cheerfully, "Don't worry, I know I won't be drowned today. I'm going to be hanged, you know."
* Inverted with Serene Branson's infamous mess up as she was reporting the Grammys. At the time people were worried she'd had a stroke but it turned out it was just a migraine so it became ok to laugh at the incident. There's even a remix of it on Youtube.
* When Amy Winehouse was a guest on ''Series/NevermindTheBuzzcocks'' some of the jokes told by Simon Amstell included: "you want us all to sit here while you drink yourself to death?" "This is not a popquiz anymore, this is an intervention. [...] We used to be close, what happened?" Amy's response? "She's dead, let it go Simon"
** Also on ''Series/MockTheWeek'' a Kevin Bridges during the segment ;Scenes We'd Like To See' came up with this:
--> Dear Ms Winehouse, congratulations on turning 100, best wishes, the Queen.
** On Creator/PattonOswalt's blog in 2007, in a gag list of his top five albums from the year he includes "Remembrance: The Amy Winehouse Box", giving Island Records credit for "embracing reality and preparing for the inevitable."
* [[Music/TheMonkees Davy Jones]] quipping "You know I used to be a heartthrob, now Iím a coronary" in [[http://nj.broadwayworld.com/article/BWW-Interviews-Hey-Hey-Its-The-Monkees-Davy-Jones-20110825 an interview]] in August 2011.
* Helen Keller, who lived during the first half of the 20th century, owned a dog named Kamikaze. That was a pretty beautiful name for a dog back then, as it's Japanese for "Divine Wind"... except thanks to UsefulNotes/WorldWarII most people who hear "kamikaze" think of suicide bombers.
* One of the most famous letters written by Klemens von Metternich (1773-1859) says this : "My life has coincided with a wretched epoch. I came into the world too soon or too late (...). I ought to have been born in 1900 and to have had the twentieth century before me." Of course Metternich couldn't know that people born at the beginning of the 20th century had to witness far worse than the Revolutions that made him so bitter.
* One passenger on a Malaysia Airlines flight [[http://news.yahoo.com/passenger-posted-joke-plane-disappearing-boarded-jet-223807473.html joked about his plane disappearing]] on Twitter before it was shot down over Ukraine.
* [[http://www.bbc.com/news/technology-28970473 This report]] about a gamer who's raided by the police, all because of someone making a hoax phone call to the police. Any comment about overzealous homeland efforts is summed up as the now-idle game suddenly blurts out [[VideoGame/CounterStrike "TERRORISTS WIN"]].
* Kate Upton said in a 2014 interview regarding her not doing nude shoots: ď...with social media and the Internet and not so great blogs and the attention like that, I donít think that my pictures would be received in the way that Iíd want them to be received. Thatís why Iíve stayed away from them.Ē Not long afterwards, on Labor Day a hacker got hold of and released private pictures of herself, Creator/JenniferLawrence and other ladies... suffice to say she was right.
** During his performance of his song "We Saw Your Boobs" at the Oscars, Creator/SethMacFarlane sang "...but we haven't seen Jennifer Lawrence's boobs at all." Well, thanks to a perverted cybercriminal, now we have.
*** "My [=iCloud=] keeps telling me to back it up, and I'm like, I don't know how to back you up. Do it yourself." [[Creator/JenniferLawrence So spoke guess who.]]
* At the 1994 Academy Awards, when Creator/TomHanks won the award for Best Actor in ''Film/{{Philadelphia}}'', he thanked his gay drama teacher in his acceptance speech. Unfortunately, Hanks was unaware that the teacher was still in the closet, [[NiceJobBreakingItHero and it got him tons of unwanted attention about his sexual orientation by mainstream media]]. [[RippedFromTheHeadlines This inspired the plot]] of the 1997 film ''Film/InAndOut''.
* ''[[UsefulNotes/BritishNewspapers The Guardian]]'' published a letter from a reader wishing she could be out of the country to avoid the inevitable frenzy come the demise of the Queen Mother, but realising it wasn't the kind of thing one could plan in advance. It was published in the March 30 2002 edition, and you can probably guess where this is going...
* There once was a time when TV presenter Creator/JimmySavile acting goofy and silly was considered to be all in good fun. Even when he grabbed women and children or made DidIJustSayThatOutLoud comments which shocked, surprised and embarrassed people, everyone assumed them nothing else but innocent jokes. After his death, when he turned out to have been a gigantic sex offender of minors, all these antics have become HarsherInHindsight. It has gotten to the point that all his memorials, statues, archive footage, pictures, fundraising organisations,... have been now been effectively removed, destroyed or disbanded, making him an UnPerson at this point.
* After the Columbia space shuttle broke up during re-entry, one of the items recovered in the debris field was [[http://www.nasa.gov/columbia/media/Media_Resources_Archives.html the videotape that was being recorded in the cabin as they were re-entering]] (this was standard procedure on shuttle flights). The final critical minutes were missing (presumably because the outer layers of the tape on the take-up reel were damaged), but fifteen minutes into the recording, as the glow of the plasma caused by atmospheric re-entry becomes visible through the cabin windows and lights up the interior, Pilot Willie [=McCool=] says, "This is amazing, it's really getting fairly bright out there", and Commander Rick Husband jokes, "Yeah, you definitely don't want to be outside now"... A few minutes later they were.
* UsefulNotes/{{California}} is officially nicknamed the "Golden State", after the Gold Rush of the mid-19th century. In TheNewTens, California was hit by the worst drought in its recorded history, and one widely-adapted water conservation measure is watering lawns less frequently, allowing them to turn a little brown, or "golden" as many [=PSAs=] put it--[[http://www.cityofsacramento.org/City-Manager/Media-Releases/Gold-is-the-new-green "Gold is the new green!"]] In other words, California is the "Golden State" for different reasons today.
* In an interview with ''GQ'' in 2007, Creator/HaydenPanettiere stated "You canít schedule rehab for me... I think Iím going to be one of those boring girls." In 2015, she ''did'' go into rehab for postpartum depression.
* The city of Brussels started a campaign named [[https://www.youtube.com/watch?v=ZsHYK1eMs2E #callbrussels]] in January 2016, to reassure potential tourists of how safe and welcoming the city was and to downplay the then-recently issued terrorist threat alert, [[https://en.wikipedia.org/wiki/2016_Brussels_bombings two months later]]...
* In February 1959, Music/WaylonJennings lost a coin-flip to Music/BuddyHolly and was forced to take a bus to Minnesota whereas Buddy took a plane. Before leaving, Holly joked "Well, I hope your ol' bus freezes up.", to which Jennings joked, "Well, I hope your ol' plane crashes." Tragically, the plane did crash, killing Holly and everybody else aboard. [[PartingWordsRegret Jennings was haunted by those words for the rest of his life]].
* Shortly before Creator/MarilynMonroe famously sang "Happy Birthday" to UsefulNotes/JohnFKennedy, presenter Peter Lawford jokingly called her "the late Marilyn Monroe" due to her reputation for tardiness. Three months later, Monroe would be dead.

[[folder:Theme Parks]]
* Ride/DisneyThemeParks
** A popular joke on the ''Jungle Cruise'' has the skippers advising parents "Watch your children, or the crocodiles will". In June 2016, a two-year-old boy was dragged into a lagoon and drowned by an alligator near Disney's Grand Floridian Resort & Spa, and the cruise skippers were told to never use the joke again.
** ''Universe of Energy'' at Epcot was once sponsored by Exxon, and while it discussed clean energy at length, it also ended with a long celebration of Exxon and their oil tankers. This...didn't go over well after a certain incident in Alaska, and the show was changed...
** ...into [[Ride/EllensEnergyAdventure a new show]] that might as well be renamed "I Love Fossil Fuels". It was probably [[HarsherInHindsight unfunny]] to start with, but people were apparently ''leaving the theater'' after the gas crisis and the show played even worse that before. It wasn't until 2017 when it ended.
** The part in ''The Enchanted Tiki Room (Under New Management)'' where Iago is charred by the tiki gods is slightly uncomfortable with a fire damaging the attraction in 2011. Though it could be HilariousInHindsight for those who [[ReplacementScrappy hated that rendition and preferred the original.]]

* Many Americans are familiar with Rollen Stewart, more commonly known as the "Rainbow Man" who attended many sports games from the 1970s and 1980s wearing a cute rainbow wig and carrying a sign that simply said "John 3:16." This caught the attention of the cameras, and sports fans from that time period watching games on television would invariably see Rainbow Man, guaranteeing him a positive place in American pop culture. That was, [[http://www.straightdope.com/classics/a971107.html until he was sentenced to life in prison in 1992 for kidnapping and terrorist threats]].
* All those highlight-reel moments of Dale Earnhardt's failures in the Daytona 500. Especially the last lap blow-out in 1990 that happened yards from where he crashed and died on the last lap eleven years later.
** Comedian Jeff Foxworthy had a joke where he was discussing Red Necks' love of commemorative plates, and UsefulNotes/{{NASCAR}}, referring to a "Legends of NASCAR" plate with Dale Earnhardt. Foxworthy's redneck says "That's Dale Earnhardt, he wasn't in a wreck or nothin', that's just catsup on the plate".
* In 2007, NASCAR driver Jeremy Mayfield was sponsored by 360 OTC, an over the counter prescription line for 10 races. This sponsorship takes on a whole new meaning considering his suspension from NASCAR for testing positive for methamphetamine, or his recent arrest for drug possession.
* Football manager Alan Pardew- who was out of work at that time- was censured for comparing a challenge by Michael Essien as a rape during the Chelsea vs Manchester City in March 2009. The player who was victim of that tackle? Chedwyn Evans who was imprisioned for a real case just 3 years later.
* Rob Moroso was named the 1990 NASCAR Rookie of the Year, despite dying in a DUI accident earlier in the season. The scary part to this is that his first sponsorship in a NASCAR race was Old Milwaukee beer! This is even more frightening if you consider that for the two races he was sponsored by Old Milwaukee, he was only 17!
* The development of Nomex firesuits in the 1960's for race car drivers was brought on by the deaths of three drivers due to fire, and the lackluster protection drivers were offered at the time. The first driver to die was a NASCAR driver by the name of Edward Glenn Roberts Jr. His nickname? "Fireball Roberts!" Guy really should've picked a better nickname....
* [[http://www.youtube.com/watch?v=PcFtcoo0ic4&feature=related This Subway commercial]] features an American football referee with a number 85 shirt admitting to missing a call. In 2008, referee Ed Hochuli admitted to missing a call to the San Diego Chargers coach, which ended up costing the Chargers the game. Hochuli's shirt number? 85.
* At the age of 25, college basketball legend "Pistol" Pete Maravich stated in an interview, "I don't want to play 10 years in the NBA and then die of a heart attack at 40." A leg injury necessitated his retiring from basketball after 10 seasons. And he died of a heart attack, at 40.
* In a 2006 Toronto Star interview, Then-Toronto Maple Leafs defenseman Wade Belak was asked where he'd be in 5 years, and jokingly replied "Dead". Belak commited suicide 5 years later, in 2011, and the interview was reprinted
* In a TakeThat to the accusations of rules violations regarding overseeing his players' academic progress that led North Carolina State basketball coach Jim Valvano to resign in 1990, he titled his autobiography ''Valvano: They Gave Me a Lifetime Contract, and Then They Declared Me Dead.'' The book came out in February of 1991. Valvano was diagnosed with cancer in June of 1992 and died less than a year later.
* Eugene Robinson was a longtime free safety who joined the Atlanta Falcons in 1998 after having appeared in the previous two Super Bowls with Green Bay. The morning before the 1999 UsefulNotes/SuperBowl (the third consecutive he appeared in), Robinson, who had been outspoken about his Christian faith, received the Athletes in Action Bart Starr Award for outstanding Christian character. That night, Robinson [[WhatAnIdiot got arrested for soliciting a prostitute who turned out to be an undercover cop]]. Robinson returned the award, but his distraction was made obvious when Bronco wide receiver Rod Smith burned him for an 80-yard touchdown pass near the end of the first half.
* In September 2009, troubled former NHL player Theoren Fleury began a much-publicized attempt at a comeback by signing a tryout contract with the Calgary Flames. On September 25, though making an admirable effort to return to the game after recovering from alcohol and drug addictions, he was released from his contract. Even worse for Fleury? An article about his comeback published by Canada's largest sports network TSN was titled "Snuffed Out." Given Canada's obsession with the game of hockey, this being just an oversight is... well, unlikely.
* French-Canadian UsefulNotes/FormulaOne driver Gilles Villeneuve called the Belgian Zolder circuit "a good killer" in an interview in early 1982. (meaning it would be extremely tiring in the hard-sprung cars of the time). He was killed in crash at that track later in the same year.
* Before the 1999 British Grand Prix, Martin Brundle on his gridwalk spoke to Damon Hill, and urged him to "Break a leg mate". Damon didn't, but Michael Schumacher did, literally.
* Jochen Rindt, upon winning the 1970 German Grand Prix at Hockenheim, claimed that his car was so easy to drive that a monkey could have won the race. 2 races later and Rindt was dead, having crashed the very same car.
** Rindt was advised a year before he died by his manager (one Bernie Ecclestone); "If you want to win, join Lotus. If you want to live, join Brabham". He joined Lotus.
* Murray Walker signed off the 1994 Pacific Grand Prix coverage by remarking how interesting the season was turning out, and told us to look forward to the next race at Imola where anything could happen. We soon found out what could happen.
** On the Eurosport coverage of the 2nd qualifying session at Imola, the commentators were joined by one of the team mechanics. The subject of Barrichello's accident the day before was brought up, and the mechanic went into a long spiel of how safe Formula One is now and how the cars protect the drivers so well. Before he had the chance to finish what he was saying, Roland Ratzenberger's shattered car, complete with fatally injured driver, popped up onscreen.
** 10 years before, Clive James narrated the official season review tape with his signature wit. After a start line shunt in which Nelson Piquet lost a wheel, narrowly missing Ayrton Senna's head, James remarked "Luckily, the flying wheel did not kill Senna this time". What was a little remark in 1984 now sounds so different post-1994.
* F1 journeyman Andrea de Cesaris had an unfortunate reputation for crashing often, gaining him the nickname Andrea de ''Crasheris''. Funny at the time, but now takes on a different meaning after he was killed in a motorcycle accident near his home in 2014.
* The BBC intro for the 2014 Japanese Grand Prix featured mock-ups of video games with the characters replaced with F1 drivers and team logos, complete with faux Japanese voiceover. Near the end, a driver is seen performing a Mortal Kombat style "Fatality" on another driver, with the voiceover stating "Say sayonara to your breakfast!". It would take on a darker meaning when Jules Bianchi suffered an accident in the race which would ultimately claim his life.
* A columnist writing for the ''San Jose Mercury News'' joked in his October 17, 1989 column that, as the two teams contesting the [[UsefulNotes/{{Baseball}} World Series]] were from California (San Francisco and Oakland), an "earthquake could rip through the Bay Area before they sing the national anthem for Game 3". The Loma Prieta earthquake, the most intense earthquake in California for 35 years and in San Francisco for 80 years, struck at 5:04pm that day... during the warm-up for Game 3.
* Declan Sullivan, a Notre Dame student, had a job filming the school's football practice from a hydraulic scissors lift. On an extremely windy day, he tweeted, ""Gusts of wind up to 60 mph. Well today will be fun at work. I guess I've lived long enough." During work that day, the lift collapsed and he died.
* "I will never have a heart attack. I give them." - George Steinbrenner
* "I probably won't be alive to see it (his record 88-game winning streak broken)" - John Wooden (Died June 2010, record was broken by The University of Connecticut Women's Basketball in December 2010.)
* "This is gonna be a spectacle. This is a great way to go out." - Dan Wheldon to ABC during pace laps of the final race of the 2011 UsefulNotes/IndyCar Series, commenting on the scale of the event and his shot at a $5,000,000 prize in Las Vegas. He would be killed from injuries sustained in a mass accident 11 laps into the race. I guess blunt force trauma from hitting your head on a fencepost wasn't the greatest way to go out, huh, Dan?
* Greg Moore, injured in the paddock following an accident on his scooter the day before the final race of the 1999 CART season at Fontana, gave an interview to ESPN before getting into his car. The reporter handed back to the commentators with the words: "Greg's ready to fly today". Just under an hour later, Greg's car became airbourne and hit a barrier. He was killed instantly.
* Penn State's venerable college football program was rocked in 2011 when allegations of child sexual abuse against former assistant coach Jerry Sandusky, spanning several decades, became public. Back in 2001 Sandusky had published an autobiography titled ''Touched: The Jerry Sandusky Story''.
* "Babe Ruth is 'dead' as far as the Yankees are concerned." Jacob Rupert October 22, 1935...13 years later that quote had a much sadder reality behind it.
* Before the 2013 Sprint All-Star Race and Coca Cola 600, Fox Sports devoted a large amount of time talking about their new camera that flies over the track. Around lap 122 of the Coca Cola 600, a cable on the camera broke, damaged a few cars like Kyle Busch and Marcos Ambrose, and led to a red flag to sort out the damage. This bragging is even worse in light of the fact that UsefulNotes/{{NASCAR}} has now banned these cameras from use at NASCAR events.
* Shortly after the law banning cigarette advertising on race cars in the United States was signed into law, Benny Parsons was discussing the matter, and stated at length that he supports Winston as the title sponsor of NASCAR's top series. This discussion takes on a whole different meaning after his death from lung cancer.
* UsefulNotes/AustralianRulesFootball: In 2013, Essendon's slogan was "Whatever it takes". Then news of the doping scandal broke.
* One of Tony Stewart's most infamous moments came at Bristol in 2012 when in a moment of anger after a wreck he got out of the car and threw his helmet at Matt Kenseth. It's a lot less funny since he hit and killed a driver who was confronting him in a sprint car race.

[[folder:Stand Up Comedy]]
* In [[http://www.youtube.com/watch?v=tqPCT9vwhdg this]] rare stand-up footage of Chris Latta (using his birth name Chris Collins), known for voicing Starscream and Cobra Commander, refers to himself as "a psychotic who managed to market his psychosis". He later died of cerebral hemorrhage.
* Creator/BillCosby:
** One track on his ''Himself'' album is titled "Kill the Boy". It begins with Bill's wife telling him to go upstairs and kill their son. Not so funny after Ennis Cosby's murder. He also made a remark about his daughters killing his son. Something like: "The boy is eleven. I don't think he'll make it to twelve. His sisters will kill him."
** [[RuleOfCautiousEditingJudgement Regardless of whether the allegations against Cosby are true]], the fact that they exist at all makes his [[https://www.youtube.com/watch?v=LAorIG6MZnc Spanish Fly]] routine very uncomfortable. Plus, it appeared in an album called ''It's True! It's True!''
** [[https://en.wikipedia.org/wiki/Bill_Cosby_Talks_to_Kids_About_Drugs Bill Cosby Talks to Kids About Drugs]].
* In the Creator/EddieMurphy standup special ''RAW'', the comedian talks about the problems with marriage. In one (extremely politically incorrect) part, he details how he would court and marry a poor impoverished African woman as opposed to an American one, as all American women are interested in are "half" of a man's net worth; but he notes that, in the US, the African woman would soon be interested in the same thing. Then in the movie ''Film/{{Coming to America}}'', Murphy plays a prince of an African kingdom who comes to America to find love because all of the women in his kingdom only want him for his status. In Real Life, Murphy married an American woman, who eventually divorced him, and fathered a child with a British singer (Scary Spice).
* Standup comedian Creator/LouisCK did a routine in his 2008 stand up special ''Chewed Up'' where he described his marriage as "almost done." Later that year, he and his wife divorced.
* An oft-repeated Creator/BillyConnolly routine from the 90's onwards revolved around his visit to the doctor for a prostate exam. In 2013 he was diagnosed with prostate cancer. Luckily he has now been given the all-clear.
* Before she passed away, Creator/JoanRivers was set to do a UK tour called "Before They Close the Lid".
* Creator/GeorgeCarlin:
** His HBO special ''You Are All Diseased'' was recorded in New York City in 1999. It began with a typically scathing routine on airport security being "a stupid idea" and "a waste of money." A couple years later were the 9/11 attacks, provoking sharply increased airport security.
** Carlin twice tried to name an HBO special ''I Kinda Like It When a Lot of People Die.'' The first one was renamed ''Complaints and Grievances'' due to the September 11 attacks. The second was renamed ''Life Is Worth Losing'' after Hurricane Katrina.
* Creator/PattonOswalt: In one of his comedy specials, Oswalt jokes about how difficult it is to write edgy comedy now that he's so happily married. A few years later, his wife died suddenly, and he followed up with a comedy special in which his grief plays a large role.

[[folder:Tabletop Games]]
* The core rulebook for Creator/WhiteWolf's ''TabletopGame/VampireTheRequiem'' includes, in a passage about storytellers embellishing the "dark and gritty" elements of the [[TabletopGame/NewWorldOfDarkness World of Darkness]], a description of the differences between the {{real world}} version of New Orleans and the World of Darkness version; this was an example for the book. The last paragraph detailed how the street level was just below the water level of the Mississippi River and that the water was held back by levies that were ill-kept. ''Vampire: The Requiem'' was first published in 2004, one year before Hurricane Katrina caused the canal levies in New Orleans to break and flood the entire city.
* A fairly (in)famous example would be the "[[http://www.cuttingedge.org/Terrorist_nuke.jpg Terrorist Nuke]]" card from Steve Jackson Games' 1995 CCG ''Illuminati: New World Order''. Granted, it's implicitly a bomb going off rather than an airplane crash, but '''they even got the positioning right'''.
* A RunningGag in the ''TabletopGame/{{GURPS}} Illuminati University'' setting involves the crushing amounts of debt racked up by students (to the point where the university often has claim to all future earnings from the student, assuming they let them graduate). Not nearly so funny since 2012.
* Flying Buffalo thought it would be funny to pretend that one volume of their ''TabletopGame/GrimtoothsTraps'' series had been confiscated in a government raid (presumably so the carefully-unidentified agency could use those traps). Four years later, Steve Jackson Games was raided by the US Secret Service and ''TabletopGame/{{GURPS}} Cyberpunk'' confiscated. Sorta killed the joke, there (and Flying Buffalo's publisher apologized in the next reprinting of the ''Traps'' volume that had the fake raid story).

[[folder:Still Other Examples]]
* In January 2009, Cinema Blend did an article on the [[http://www.cinemablend.com/pop/The-100-Most-Likely-People-To-Die-In-2009-14401.html 100 People most likely to die in 2009.]] It said that Music/MichaelJackson would die of "the wind blowing him over". Other people on that list that died in 2009 are Ed [=McMahon=] and Ted Kennedy. Several other people on the list have since passed away, but they didn't die in 2009 (Gary Coleman, J.D. Salinger, Peter Falk, Senator Robert Byrd, Dick Clark, etc.)
* In the Podcast/RiffTrax of ''Film/BatmanAndRobin'', when Bane is charging through Arkham Asylum with Mr. Freeze's PowerArmor in a shopping cart, the joke that's made is "Just like Wal-Mart on BlackFriday." In 2008, a Wal-Mart employee was trampled to death on BlackFriday.
* 1976: A column by Mike Royko noted that some viewers were irrationally offended by the appearance of an elderly Mary Pickford on the Academy Awards telecast. He wrote: "If you turn your head away from Mary Pickford, and find it all so distasteful, then there's something wrong with you, kid, because it's perfectly normal. It happens to all of us, unless we croak first. We get old. Take Margaux Hemingway, the tall stunner who was on the show. One of these days she's going to wrinkle up, and maybe her teeth will fall out, maybe even her hair, and her knee joints will go crackety-crack. Is that too terrible to face -- Margaux Hemingway's knee joints going crackety-crack?" As it turned out, none of that happened to Margaux Hemingway; she died of a drug overdose at age 42.
* A video created for the 5th anniversary of the Spirit rover's landing on Mars used a song with the lyric "She's run aground, she's run aground." Shortly thereafter, Spirit got stuck in a sand dune and can no longer, um... rove.
* Actor CoreyFeldman has a tendency to make jokes about what a trainwreck his career is, the irony being that his friend CoreyHaim was doing even worse. And now he's dead...
* Observe [[http://gizmodo.com/5580239/bp-foresaw-its-doom-in-1970s-offshore-oil-strike-board-game this board game from the 1970s]], branded with BP's logo, all about managing an offshore oil rig.
* [[http://javidluffy.deviantart.com/art/FOP-The-Movie-156416135 This fan-made poster]] for a live-action ''WesternAnimation/TheFairlyOddParents'' movie is pretty hard to find funny now that the movie [[Film/AFairlyOddMovieGrowUpTimmyTurner finally got made]] after being on the [[DevelopmentHell planning board]] for a long time. Wiki/ThatOtherWiki claims that ''Wishology'' may have actually been originally planned as a cinema movie.
* On the first of March of 2011, adoptable pet website Chicken Smoothie released a line of adoptable dogs themed after Japanese woodblock prints, including the famous and iconic [[http://randomknowledge.files.wordpress.com/2008/05/the_great_wave_off_kanagawa.jpg "The Great Wave off Kanagawa"]], colloquially known as "The Tsunami." This ended up being the ''worst timing ever,'' after the [[http://en.wikipedia.org/wiki/2011_Sendai_earthquake_and_tsunami earthquake later that month]] ended up rocking Japan with its worst earthquakes and tsunami in more or less its recorded history.
* The Formspring Question of the Day on March 10, 2011 asked something to the effect of what you would do if you had 24 hours left to live. Unfortunately, that wasn't a hypothetical situation for many people...
* In the webcomic adaptation of ''Fanfic/ChristianHumberReloaded'', Normalman's AuthorAvatar appears in a cameo at the end of Part 1, talking about how he plans on writing a webcomic about Christian Humber Reloaded even if it humiliates the kid who wrote it. Vash himself responds by [[EvenEvilHasStandards saying that he "sound(s) like an asshole"]]. Not long into Part 2, the Humber family heard of the comic and complained, which resulted in Normalman [[OrphanedSeries stopping work on the comic]].
* This Jewish joke: Two ''shnorrers'' are standing at the roadside and watching some workers repair the street. One of them muses: "Today, we have a bad life... but soon, a MessianicArchetype will come, and then everything will be exactly the opposite." The other one thinks about it and states then: "You mean - we will repair the street, and they will watch us?"\\
Definitely becomes unfunny when you think about that some time after this joke was made, [[UsefulNotes/NaziGermany The Nazis]] made the Jews do all kinds of forced work, including street repairing, while Germans would oversee them.
* Canadian model Tanya Melissa Makse (whose profile can be found on a certain model website), mentioned on her official Facebook page about Wigan/Bolton/Bury council's planned budget cuts for 2011, speculating about them. The date?? ''April 2010''. Fast-forward to now, and it seems incredibly HarsherInHindsight, not to mention eerily prophetic.
** Although Tanya herself has become, ironically, [[GermansLoveDavidHasselhoff somewhat popular in Northern England]].
*** Incidentally, although her Facebook page ''still exists'', her modelmayhem.com profile [[MissingEpisode disappeared]] (but if it will return is another issue!)
*** Now she's back on modelmayhem.com, but as [[OverlyLongName Tanya Makse]], dropping her middle name.
* Possibly [[http://www.iwatchstuff.com/2011/09/george-lucass-1988-speech-about-preservi.php#disqus_thread this]] essay from George Lucas on preserving films.
* NEC never specified exactly what the name for its PC-FX stood for. One interpretation happens to be "Personal Computer - Future Unknown". It's no secret that they had no future with video game consoles, or even games themselves, after the system bombed.
* Google's Chrome browser's Incognito mode is designed to leave no local trace of your web activity once you exit it. One of the warnings about traces it cannot cover is "surveillance by secret agents". Edward Snowden's turned that fluffy bit of absurdist humor into rather [[BlackComedy dark commentary]].
* [[http://gamersgate.com/ Gamersgate]] is a UsefulNotes/DigitalDistribution website for PC games that was founded in 2004. 2014 brings us the [[{{Scandalgate}} Gamer]][[http://knowyourmeme.com/memes/events/gamergate Gate]] controversy. Gamersgate CEO Theodore Bergqvist had to put out a [[http://www.facebook.com/GamersGate/posts/10152439494828616 statement]] clarifying that the site had nothing to do with [=GamerGate=].
* In [[https://www.youtube.com/watch?v=5h5yPJ8s8IM this]] video, a man is frequently heard calling the coaster he's on a "Togo Death Machine" (TOGO was the name of the manufacturer). In Mid-2007, a woman was killed on that very exact ride when the trains derailed, and the park ended up closing later that year.
* David Gest, a music producer and celebrity contestant on numerous reality shows, was set to host a concert tour before he died in April 2016. The name of the tour, the ''David Gest Is Not Dead But Alive With Soul Tour'' was a humorous jab at a fellow contestant on ''Celebrity Series/BigBrother'' who thought he was dead. Worse is that the poster for said tour has David [[http://i.imgur.com/GynF0YL.jpg emerging from a coffin...]]
* The [[https://en.wikipedia.org/wiki/Verr%C3%BCckt_(water_slide) Verrückt]] water slide at the Schlitterbahn Kansas City water park in Missouri was billed as the tallest water slide in the world when it first opened in 2014, with its name being German for "crazy". After a ten-year-old boy was [[http://time.com/4444447/caleb-schwab-verruckt-water-slide-death/ decapitated going down the slide]] in August 2016, it's crazy for a whole different reason. It has been closed down indefinitely since then.