* Because a major plot point in episode "The City of New York vs. Homer Simpson" had their car being parked on the World Trade Center's plaza, several syndicated stations refused to air it after September 11th for a time. Lines like "They put all the jerks in Tower One!" didn't help. After 9/11, the writers on the DVD commentary did say they felt bad about that joke in hindsight.
** They lampshaded it when they returned to New York a decade later:
-->'''Bart:''' Come on, Dad, you'll love New York now that your two least favorite buildings have been obliterated: Old Penn Station and Shea stadium.
-->'''Homer:''' Lousy, outdated relics...
* Another 9/11 Aneurysm Moment: the episode where Bart, Milhouse, Nelson, and Ralph become a boy band had a scene where a missile from an aircraft carrier blasts the MAD Magazine building. While "City of New York vs. Homer Simpson" can be forgiven since it was the 1990s and no one even dreamed of that ever happening (except in action movies), the boy band episode aired in February 2001, seven months before the 9/11 attacks would go from being "Ha, ha, ha," to "O.M.G., TooSoon!" One of the writers pointed this out on the DVD.
* If the New York episode is the TropeCodifier for the show, the Season 5 episode "$pringfield" is a close second. In this episode, which aired in 1993, two NoCelebritiesWereHarmed versions of Siegfried & Roy perform an act with white tigers riding unicycles. The act goes horribly wrong when one of the tigers attacks one of the two illusionists. A decade later, a white tiger actually did attack Roy during one of their shows. This moment was lampshaded on DVD commentary and declared the "greatest prediction ever made by ''TheSimpsons''," though the writers also pointed out that the tiger attack was bound to happen sooner or later, considering how she was treated.
* In the Season 10 episode "Sunday, Cruddy Sunday" (which aired after the 1999 SuperBowl), Nelson asks if the postman has ever gone on a rampage and killed people. The postman remarks that the disgruntled mailman stereotype is a thing of the past. Skinner then replies, "I'm glad I work in an elementary school!". This episode premiered when the trend of kids going ballistic and opening fire at their schools was a hot topic, and with one of the most infamous school shootings of all -- UsefulNotes/{{Columbine}} -- taking place just a few months after it aired, the joke's darkness gets blacker and a lot more tasteless -- and thanks to the Sandy Hook Elementary School massacre in 2012 (which has been reported as the worst school shooting since the Virginia Tech massacre in 2007), the joke is '''''still''''' in bad taste. And if you're British, it's an ''especially'' massive TooSoon or DudeNotFunny because of the Dunblane school massacre (in which a gunman entered a school and shot 16 children, one adult and then himself, which happened 3 years before the episode aired).
** Most likely intentional, given that the earliest school shooting in US History happened in 1764. Perhaps what makes this joke in bad taste isn't the fact school shootings happen, but the fact that they are becoming much more common?
* In the closing credits of the clip show "All Singing, All Dancing", Snake is heard shouting "Stop the music!", and he fires his first gunshots as Phil Hartman's name comes up. Four months after it first aired, Hartman was shot to death by his wife in a murder-suicide.
* There's also the scene in "Marge vs Singles Seniors Childless Couples and Teens and Gays" where Bart wants to watch a TV show where Steve Irwin gets mauled to death by an animal (although it is a crocodile that kills him on ''TheSimpsons'').
* There's that episode guest starring Creator/MelGibson (season 11's "Beyond Blunderdome"). He was complaining that people like him too much (even going as far to say he never gets pulled over by the cops), and ends up creating a movie so controversial that everyone hates him. Funny how life imitates art, no?
** Funny Aneurysm Moments have also occurred with other celebrity guests starring on the show, whose later careers took a turn for the worse, causing their once innocent guest appearance to leave a bitter aftertaste. Some examples: Creator/MichaelJackson (after the 1993 and 2003 allegations of child abuse it may be a bit discomforting to see him interacting with Bart and Lisa in their bedrooms, while Homer and Marge are still asleep), cyclist Lance Armstrong (back when he had a guest spot on the show he was still the cycling champion, but now after his doping scandals his guest appearance feels very undeserved), British Prime Minister TonyBlair (should a politician who contributed to a senseless war in Iraq be joking with The Simpsons in an episode?),...
* A lot of the earlier episodes had verbal jokes and sight gags depicting Homer as a monkey (and often being called a "big ape" due to his crass behavior and informed ugliness). These stop being funny with the episode "The Color Yellow," which reveals that one of Homer's ancestors was a black slave (and for the uninitiated, "monkey" is [or, at least, has been] used as a racial slur against black people).
** Then there's the line in "Weekend At Burnsie's" when Homer (who's been smoking medicinal marijuana after getting pecked in the eyes by crows) states that he can go up to The President and "...blow smoke in his stupid monkey face, and he'd be sitting there ''groovin'' on it!" This episode was written and premiered around the time that GeorgeWBush was U.S. President (and there were a lot of jokes about GeorgeWBush looking like a monkey because of his big ears and simian-looking face). These days, with [[BarackObama a black president]], that line comes off as horrifically racist (and it doesn't help that Obama himself has large ears as well).
** Homer sees a movie called "Hail to the Chimp" at the drive-in theater on the season nine episode "Dumbbell Indemnity." Very HilariousInHindsight during the "Dubya" Bush era; totally racist in the Obama era.
* The climax of "Deep Space Homer", with fears of the shuttle burning up in reentry, is wince-worthy in light of how the Space Shuttle Columbia burned up in its reentry in 2003.
* In "Lisa's Date With Density", Lisa asks Milhouse to send Nelson a love note from her, but Nelson is led to think the note's from Milhouse himself. Cut to Milhouse being led away in a stretcher to an ambulance (with the paramedics telling Lisa that Milhouse can't hear her -- not because he's dead, but because his ears are packed with gauze). It really stops being funny after the highly publicized rash of suicides and murders from bullying, especially anti-gay bullying. The setup of the scene is horrifyingly very similar to the murder of Lawrence King in 2008.
** The same thing applies to the flashback of "Bye Bye Nerdie" where a school-aged Homer is shown beating up a school-aged Smithers (who, in later episodes, was established to be gay and not just have a man-crush on his boss like in the early episodes) who's wearing a pink shirt and shorts to the tune of "Kung-Fu Fighting." [[ValuesDissonance These days, Homer would have been expelled for doing that]].
*** Due to the rise of youth violence (including bullying and suicides from teens who have been harassed), episodes like "Bart the General", "Bye Bye Nerdie", "The Boys of Bummer" and "Lisa's Date with Density" (though just the "note" scene as detailed above) will come off as very disturbing in a world of concerned parents and ostracized children who are or have ever been the target of a bully (though Marge stuck up for Bart in "Boys of Bummer and "Bart the General" did address bullying and violence in a serious manner at the end).
**** And also from "Lisa's Date with Density", Nelson's version of "Joy to the World" (where a teacher suffers a gruesome death by the kids' hands) becomes much, MUCH less funny to UK viewers in light of [[http://www.mirror.co.uk/news/uk-news/ann-maguire-teacher-stabbing-leeds-3479750 a teacher being stabbed to death by a student during a lesson]] in April 2014.
* In "Homer Defined", Magic Johnson "pulls a Homer" by tripping while trying to dunk and ending up in the adoring arms of a swarm of cheerleaders. Less than a month after the episode aired, Johnson announced he was HIV positive, which he got from sleeping around with many women.
* The season five episode "Lisa vs. Malibu Stacy" has a scene of Grampa stealing Andy Griffith's pills (and Andy Griffith in an ambulance next to him being rushed to the hospital for a heart condition), became significantly less funny after Andy Griffith's death on July 3, 2012, even less so now that it has been determined that his death ''was'' caused by a heart attack.
** Also, when the family bashes Lisa for her activism, Homer says that whey can't watch {{FOX}} anymore because [[BitingTheHandHumor "they own those chemical weapons plants in Syria"]]. This becomes less funny after Syria used chemical weapons on their own citizens.
* A gag in "The Monkey Suit" has Snake shooting people from atop the Kwik-E-Mart became much more grim in 2011, when a gunman opened fire and killed six people (and severely wounded Senator Gabrielle Giffords) outside of a Safeway store in Tucson, Arizona.
** There was a similar gag to that on the season five episode "Homer the Vigilante," only it was Apu shooting a man who was trying to enter the Kwik-E-Mart. Back then, it was supposed to be a reference to what Korean store owners did during the L.A. Riots in the mid-1990s.
* In "Burns, Baby Burns", the news shows a computer simulation of Homer walking out of the Aztec Theater and shot to death by the cops. It's a lot less funny thanks to that Aurora, Colorado theater shooting in July 2012.
** Also in that episode, Homer and Larry tried to hide inside [[AbandonedWarehouse an abandoned building]], only to learn [[SubvertedTrope it was no longer abandoned]], making Homer say "D'OH! Stupid economic recovery!" It really stops being funny after the 2008 recession.
* In the episode "Brawl in the Family" the Republicans meet to talk about what to cut from the budget. Krusty mentions cutting PBS funding because "[[SesameStreet those lousy Muppets]] are taking up his airtime". It stopped being funny when Mitt Romney announced he would cut PBS's funding if elected President, and Big Bird appeared in an Obama ad (after news hit about his appearance on ''SaturdayNightLive'') attacking Romney for it. It's now HilariousInHindsight since Obama got re-elected.
* In "The Day the Violence Died", Bart and Lisa complain about Generation X during the Schoolhouse Rock parody, with Bart commenting that "We need another Vietnam to thin out ''their'' ranks a little." We did get another Vietnam, only it's called "The Second War in Iraq" (the one started in 2003).
** Ditto Moe's line on ''Homer's Phobia'':
-->"Used to be if you wanted to make a boy into a man you'd send him off to war. But there aren't even any wars anymore; thank you very much, Warren Christopher!"
** Made somewhat less tasteless in that the Iraq War did not prompt drafting, the main distinction between Vietnam and successive US conflicts, but still, Vietnam and the second Iraq war were wars that were controversial because of the vague reason for fighting it.
* "A Totally Fun Thing Bart Will Never Do Again" centered on Bart sabotaging a cruise ship so his cruise vacation can last forever, which leads to disaster. In February 2013, a similar situation happened to Carnival Cruise Line's ''Triumph''.
* An in-story example: in the episode "Homer Loves Flanders", Bart [[FalseReassurance says that its because of genetics that Homer is a loser]] (with Bart yelling, "D'oh!" [[FridgeHorror after realizing that the "being a loser based on genetics" theory applies to him too]]). Four years later, we got "Lisa the Simpson", an episode which confirms that [[UnfortunateImplications Simpson males get dumber as they grow older (while the women still stay smart)]](though that was later contradicted in the episode "HOMR" where it's revealed that a crayon lodged in Homer's brain is the real reason for his stupidity).
** The "The Simpson males are stupid losers because of their genes" fact becomes even more cringe-worthy after a later episode [[UnfortunateImplications revealed that one of their ancestors was black]].
* In the episode ''See Homer Run'', Rainier Wolfcastle (''The Simpsons'' {{Expy}} of Arnold Schwarzenegger), in a stump speech, mentions that he is among other things, a womanizer. Years later, we have Arnold Schwarzenegger divorcing Maria Shriver because Schwarzenegger cheated on her and had an illegitimate son.
* In "Brush with Greatness", Music/RingoStarr says that he'll take his time to answer every piece of fan mail that he didn't get to answer (including Marge's, which included a painted portrait of Starr). These days, this comes off as either confusing (for anyone who hasn't seen the early episodes of ''TheSimpsons'' in the 1990s and now are discovering them on DVD or the Internet) or depressing, as Ringo announced in 2008 that he's not accepting fan mail anymore.
* On the season seven clip show episode "The Simpsons 138th Episode Spectacular," the original three ''Simpsons'' showrunners-cum-creators are Matt Groening (depicted as a gun-crazy redneck), James L. Brooks (depicted as being very fat, very rich, and the winner of several awards), and Sam Simon (depicted as a frail expy of Howard Hughes in his later years). Sam Simon was diagnosed with terminal cancer in early 2013 and is slowly, but surely dying.
* In "Bart-Mangled Banner", [[Series/SesameStreet Elmo]] is shown in prison as a political prisoner. Eight years later, Kevin Clash (the puppeteer and voice actor for Elmo) was later accused of having sex with underage boys. The case was dropped and he wasn't imprisoned, but it definitely changes the context of the line, "Elmo went to wrong fundraiser."
* In "A Star Is Burns" (the ''Critic'' crossover episode that Matt Groening hated), there was a scene from Rainier Wolfcastle's horrible stand-up comedy movie where his Woody Allen "impression" is just Wolfcastle saying, "I'm a neurotic nerd who likes to sleep with little girls." Back then, it was a TakeThat at him marrying his step daughter Soon Yi. Things got worse, when in October 2013, his adopted daughter Dylan alleged he sexually abused her twenty years earlier.
** YMMV heavily on this, as Allen's son said that [[WomanScorned Mia Farrow]] coached Dylan into saying these things, but there is a [[http://www.huffingtonpost.com/danny-shea/heres-the-1993-woody-alle_b_4746866.html court document]] that allegedly shows that Woody was at the very least inappropriate with her (Dylan). [[RuleOfCautiousEditingJudgement It's a thorny issue, and let's just leave it at that.]]
** It also makes [[ShowWithinAShow the Krusty the Clown biopic]] from "Lisa's Sax", which parodied Allen and Farrow's marriage in one scene, a lot less amusing.
* A deleted scene from "Krusty Gets Kancelled" (which was later featured in "The Simpsons 138th Episode Spectacular") shows Krusty trying to sell a book featuring him in sexually explicit positions in an attempt to revive his show (in the wake of stiff competition). He makes the mistake of trying to sell said book during a taping of his show, where there are children present, and the FBI arrest him during the promotion. ("It's not really me; I used a stunt butt!") It was meant to be a knock on Madonna producing a similar book, as well as a joke about Krusty being a very pathetic showman/promoter. Almost 20 years after "Krusty Gets Kancelled" aired, British TV and radio host Jimmy Savile was posthumously accused of upwards of ''218'' cases of sexual assault, with allegations that he may have molested children during tapings of ''TopOfThePops'' and ''Jim'll Fix It'' (the latter was a popular kids show during the 70s and 80s). As a result, ''Jim'll Fix It'' is all but banned forever, and reruns of ''TopOfThePops'' featuring him are either banned or scrubbed to remove all traces of him. Whether it was funny or not in the first place, the scene is definitely more awkward now. (Note: few people outside the UK know who any of the disgraced BBC broadcasters from Operation Yewtree were - or how they manipulated people and got away with their abuses for so long - but this makes the joke particularly disturbing to UK viewers. The scene was based on Madonna, but this real life example of a depraved kid's show host renders this a funny aneurysm moment.)
* The "Treehouse of Horror XII" segment "Hex and the City" featured a helicopter crashing into Moe's Tavern, killing Lenny and Carl. Twelve years later, a [[http://en.wikipedia.org/wiki/2013_Glasgow_helicopter_crash police helicopter did just that in Scotland]].
* In "Angry Dad: The Movie" from Season 22, Lisa says that she's seen all the {{Creator/Pixar}} films, "except for WesternAnimation/{{Cars}}", a reference to how the film was widely considered to be the studio's weakest film by the time the episode came out. Just a few months later, the sequel came out, immediately replacing its predecessor for that title by far for many people, becoming the first Pixar film ever to earn a "rotten" critical rating on RottenTomatoes.
* Viewed today without context, "Trash of the Titans" seems like a satire about the Tea Party, [[DoesThisRemindYouOfAnything as Homer goes around spewing angry rhetoric at a respected politician with little thought about how he'd do better if elected]], and after being elected, messes up so horribly everyone in Springfield hates him. Ray Patterson's lines "Nobody wants to hear the nonsensical ravings of a loudmouthed malcontent!" and "the American people have never tolerated incompetence from its elected officials." hit harder than ever in light of how badly-received the Tea Party-dominated US Congress has been, receiving the lowest approval rating ''of all time'' in 2013.
** On the upside, the episode is more relevant now than it was back then. Back when "Trash of the Titans" first aired, the episode was disparaged as being the harbinger of all the problems later ''Simpsons'' episodes would have: Homer being a jerkass who doesn't get his comeuppance, Homer taking on yet another new job, good plots getting tossed aside for yet another Homer adventure (the department stores coming up with fake holidays just to make money), gratuitous celebrity cameos (The completely unnecessary Music/U2 appearance), and [[GainaxEnding nonsensical endings]] (the entire town moving away and leaving behind a landfill). It still carries that problem today, but, with everything that's happened between then and now centering on the U.S. government and the state of the environment, it plays out more like a latter-day episode that, for all its flaws, actually has relevant satire.
* "Saddlesore Galactica" (which originally aired in February 2000) ends with UsefulNotes/BillClinton [[InsaneTrollLogic justifying the]] FamilyUnfriendlyAesop [[InsaneTrollLogic he gives to Lisa as being fitting, because, in his own words, "I'm a pretty lousy president"]]. As Mike Amato of Me Blog Write Good said, "it stings even more knowing [[UsefulNotes/GeorgeWBush who'd come after him]]". [[WordOfGod Even the writers]] acknowledged this in the DVDCommentary for the episode, saying "[[TakeThat we had no idea what was coming]]".
* Actually [[AvertedTrope averted]] regarding PhilHartman's last appearance. In Treehouse of Horror IX Troy [=McClure=] was supposed to host Snake's execution, but the scene was redone with Ed [=McMahon=]. The episode aired after Hartman was murdered and the crew didn't want his last role to revolve around death (especially since Hartman's kids may be watching).
** A straighter example from the same segment is the mention that one of the series also produced by "World's Deadliest Executions" was titled "Secrets of National Security Revealed." In 2013, Edward Snowden stepped down from the NSA after outing himself as the man who revealed the more controversial methods used to gain information at the NSA.
* In ''Holidays of Future Passed'', it's stated that Edna was killed (by Homer), and now Ned was dating Maude's ghost. With the passing of Marcia Wallace and Edna also dying, the joke stops being funny.
* The "Ode to Branson" song, which is all about celebrities who might be mistaken for dead, features the line "Charlie Callas doesn't sleep in the ground/Yes I'm still alive and I'm making my sounds!" Come 2011 and Charlie Callas really is sleeping in the ground/no longer alive or making his sounds.
** As of 2013, another person mentioned in the song, Bonnie Franklin, is no longer merely mistaken to be dead. And it'll only worsen as everyone else dies off.
* In "Brother's Little Helper", the revelation that Major League Baseball was spying on Springfielders has become less amusing after the full revelation of the NSA's spying on Americans in 2013.
* In "Rosebud" Mr. Burns wants The Ramones killed (He mistakes them for The Rolling Stones) after they insult him at his birthday party. This comes across as cringeworthy now that after Tommy Ramone's death, all the original members of the band have passed.
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