Being a LongRunner, ''WesternAnimation/TheSimpsons'' have many hilarious moments through its time. Nowadays, however, some of the past episodes [[FunnyAneurysmMoment aren't so funny anymore when viewed today.]]

* A major plot point in the episode "The City of New York vs. Homer Simpson" involves Homer's car being illegally parked at the World Trade Center's plaza. When Homer arrives at the World Trade Center, there are several gags making fun of the towers and the people inside them. The most notable is someone in Tower Two saying, "They put all the jerks in Tower One!" Following 9/11, several syndicated stations refused to air the episode for a time. In the DVD commentary for the episode, the writers did express regret for doing this.
* In "New Kids on the Blecch", the episode where Bart, Milhouse, Nelson, and Ralph become a boy band, there is a scene where a missile from an aircraft carrier blasts the MAD Magazine building. One of the writers pointed this out in the DVD commentary. Given the terror attack on the headquarters of French satirical magazine Charlie Hebdo in January 2015, the ending where the MAD Magazine headquarters is blown up could easily be seen as this as well. It didn't help that Sky 1 aired this episode ''a week'' after the attack.
* In Season 5's "$pringfield", 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 both 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 ''The Simpsons''," 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 [[SuperBowl Super Bowl XXXIII]] on January 31, 1999), 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. Thanks to the Sandy Hook Elementary School massacre in 2012, the joke is ''still'' in bad taste.
* There's a 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 (albeit by a crocodile rather instead of a stingray).
* 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.[[note]]For the uninitiated, "monkey" was, and still is, used as a racial slur towards black people.[[/note]]
** 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!" These days, with [[UsefulNotes/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 in the Season 9 episode "Dumbbell Indemnity." Very HilariousInHindsight during the "Dubya" Bush era; totally racist in the Obama era.
* The Season 5 episode "Lisa vs. Malibu Stacy" has a scene where Grandpa admits that stole Andy Griffith's (as Series/{{Matlock}}) pills while Griffith is in an ambulance next to him being rushed to the hospital for a heart condition. This became significantly less funny after Griffith's death on July 3, 2012. Furthermore, it was determined that his death ''was'' caused by a heart attack.
* 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.
* 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.
** Also, when the family bashes Lisa for her activism, Homer says that whey can't watch Creator/{{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.
* In the end credits of the clip show "All Singing, All Dancing", Snake is heard shouting "Stop the music!", and he fires his first gunshots as Creator/PhilHartman's name comes up. Four months after it first aired, Hartman was shot to death by his wife in a murder-suicide.
* In "Burns, Baby Burns", Homer and Larry tried to hide inside an AbandonedWarehouse , 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.
* "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''.
* 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). Simon was diagnosed with terminal cancer in early 2013 and died two years later.
* 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 stepdaughter Soon Yi. Things got worse, when in October 2013, his adopted daughter, Dylan, alleged he sexually abused her twenty years earlier.
* 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 "Treehouse of Horror IX" there 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 "Brother's Little Helper", then-single season home run record holder Mark [=McGuire=] showed up when Major League Baseball was found to be using spy satellites to collect marketing data on Springfielders. His offer to tell everyone the "terrifying truth"[[labelnote:*]]or hit a few dingers[[/labelnote]] is now incredibly awkward seeing as how he and other major hitters of that era were all using various steroids to improve their performance. It's also poignant seeing as how at the time the fans were in fact content to see him "hit a few dingers".
* A scene in "Lisa the Beauty Queen", normally cut out for syndication, shows Otto operating a faulty rocket ride and after causing it to spin faster at Bart's request, one of the rockets falls off and crashes into the school. Not that funny anymore after the Royal Adelaide Show of 2014, where an eight-year-old Malaysian girl was thrown off a ride and killed due to poor safety.
* In "Lisa's Sax", Marge asks Bart if she can read him ''Curious George and the Ebola Virus'', which was a joke about its outbreaks in the early 1990s. This joke is less funny now considering the ''Literature/CuriousGeorge'' books take place in the U.S., and there have been many outbreaks of the virus in the U.S. in 2014.
* In "The Old Man and the 'C' Student", released in 1999, there's a reference to Russia's then recent [[https://en.wikipedia.org/wiki/1998_Russian_financial_crisis currency crisis]] with a Russian Olympic Committee representative panicking as the rouble collapses to 1000 to the dollar in just a few minutes. Come 2014 where [[http://www.bloomberg.com/news/2014-11-07/ruble-set-for-worst-week-since-1999-amid-ukraine-oil-pressures.html the rouble suffered a collapse just as bad as the one in the late 90s]] due to falling oil prices.
* The scene in the 1999 episode "Monty Can't Buy Me Love" depicting billionaire Arthur Fortune knocking out Muhammad Ali in the present day was always in rather bad taste, given the man was by then significantly crippled by Parkinson's disease. It has only become more uncomfortable in the years since, as Ali becomes more and more frail.
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