%% Since all actors and creators are mortal, if someone mentions death or plays a character who dies, and then die themselves,
%% that's not a "funny aneurysm" moment unless there's some connection to the circumstances of the death which was originally played for laughs.
%% As uncomfortable as it might be, the World Trade Center appearing in a work made prior to 9/11 is not an example of this
%% unless there is some sort of reference of the towers being attacked.
%% Image removed per Image Pickin' thread: http://tvtropes.org/pmwiki/posts.php?discussion=1469745368043832400
%% Please start a new thread if you'd like to suggest a new image.
Being a LongRunner, ''WesternAnimation/TheSimpsons'' have many hilarious moments through its time. Nowadays, however, some of the past episodes aren't so funny anymore when viewed today.

* One of the last scenes of "[[Recap/TheSimpsonsS12E14NewKidsOnTheBlecch New Kids on the Blecch]]" depicts the ''MAD'' building being blown up after (almost) publishing an unflattering satire of Bart, Milhouse, Nelson, and Ralph. This episode aired seven months before 9/11, and that scene ended up getting cut in some syndicated broadcasts for a while as a result. Also in January 2015, the headquarters of French satirical magazine Charlie Hebdo were attacked by terrorists for publishing a satirical image relating to Islam.
* In Season 5's "[[Recap/TheSimpsonsS5E10Springfield $pringfield]]", which aired on December 16, 1993, two NoCelebritiesWereHarmed versions of Siegfried & Roy perform an act with a white tiger riding a unicycle. The act goes horribly wrong when the tiger attacks both illusionists due to the mistreatment that she has suffered. A decade later, a white tiger actually did attack Roy during one of their shows. The DVD commentary declared it 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 "[[Recap/TheSimpsonsS10E12SundayCruddySunday Sunday, Cruddy Sunday]]" (which aired after UsefulNotes/SuperBowl 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. Principal 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. The Sandy Hook Elementary School shooting on December 14, 2012 and seemingly one a week in recent years would make this line even more tasteless.
* There's a scene in "[[Recap/TheSimpsonsS15E8MargeVsSSCCATAG 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. On September 4, 2006, Irwin died when a stingray pierced his heart.
* During the montage where every child... friendly thing in town gets destroyed, we have kids morning the Toys "R" Us sign having its [[TheBackwardsR backwards R]] flipped forwards. Come March of 2018, and the company is on the verge of going out of business, starting with all its British stores closing down.
* The series' monkey/ape references can be considered this for the following reasons:
** A lot of the earlier episodes had verbal jokes and sight gags depicting Homer as a monkey. In addition, he was often called a "big ape" due to his crass behavior and informed ugliness. These stop being funny with "[[Recap/TheSimpsonsS21E13TheColorYellow The Color Yellow]]", which reveals that one of Homer's ancestors was a black slave.[[note]]For the uninitiated, "monkey" is a racial slur towards black people.[[/note]]
** There's the line in "[[Recap/TheSimpsonsS13E16WeekendAtBurnsies 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 line would be considered horrifically racist during the presidency of Barack Obama.[[note]]It doesn't help that Barack Obama himself had large ears as well, not to mention that he actually did smoke marijuana in his college days.[[/note]]
** Homer sees a movie called ''Hail to the Chimp'' at the drive-in theater in the Season 9 episode "[[Recap/TheSimpsonsS9E16DumbbellIndemnity Dumbbell Indemnity]]." This scene would become very racist in the Obama era.
* The Season 5 episode "[[Recap/TheSimpsonsS5E14LisaVsMalibuStacy Lisa vs. Malibu Stacy]]" has a scene where Grandpa admits that stole Andy Griffith's pills while the latter, who's in character as Series/{{Matlock}}, 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.
* "[[Recap/TheSimpsonsS8E7LisasDateWithDensity 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.[[note]]Not because he's dead, but because his ears are packed with gauze.[[/note]] 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.
** Nelson's version of "Joy to the World" (where a teacher suffers a gruesome death by the kids' hands) becomes ''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.
* During the end credits of the clip show "[[Recap/TheSimpsonsS9E11AllSingingAllDancing All Singing, All Dancing]]", Snake fires his first gunshots when Creator/PhilHartman's name comes up saying, "Yo! I told you to stop the music, dudes. I'm serious!". Four months after it first aired, Hartman was shot to death by his wife in a murder-suicide.
* "[[Recap/TheSimpsonsS23E19ATotallyFunThingBartWillNeverDoAgain A Totally Fun Thing That Bart Will Never Do Again]]" centers 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''.
* In the Season 7 clip show episode "[[Recap/TheSimpsonsS7E10TheSimpsons138thEpisodeSpectacular The Simpsons 138th Episode Spectacular]]", the original three ''Simpsons'' showrunners-cum-creators are Creator/MattGroening (depicted as a gun-crazy redneck), Creator/JamesLBrooks (depicted as being very fat, very rich, and the winner of several awards), and Sam Simon (depicted as a frail expy of Creator/HowardHughes in his later years). Simon was diagnosed with terminal cancer in early 2013 and died two years later.
* In "[[Recap/TheSimpsonsS6E18AStarIsBurns A Star Is Burns]]", the crossover episode with ''WesternAnimation/TheCritic'' that Creator/MattGroening hated, there is a scene from Rainier Wolfcastle's horrible stand-up comedy movie where his Creator/WoodyAllen "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 "[[Recap/TheSimpsonsS13E1TreehouseOfHorrorXII Treehouse of Horror XII]]" segment "Hex and the City" features 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 "[[Recap/TheSimpsonsS10E4TreehouseOfHorrorIX 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 "[[Recap/TheSimpsonsS11E2BrothersLittleHelper Brother's Little Helper]]", then-single season home run record holder Mark [=McGuire=] shows 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" or hit a few dingers is now incredibly awkward seeing as how he and other major hitters of that era were using various steroids to improve their performance. It's also poignant seeing as how, at the time, many fans were in fact content to see him "hit a few dingers".
* A scene in "[[Recap/TheSimpsonsS4E4LisaTheBeautyQueen 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 "[[Recap/TheSimpsonsS10E20TheOldManAndTheCStudent The Old Man and the "C" Student]]", which originally aired on April 25, 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 ruble 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 ruble suffered a collapse just as bad as the one in the late '90s]] due to falling oil prices.
* A scene in the 1999 episode "[[Recap/TheSimpsonsS10E21MontyCantBuyMeLove Monty Can't Buy Me Love]]" depicting billionaire Arthur Fortune proudly knocking out a retired UsefulNotes/MuhammadAli. This was already in rather bad taste, given that Ali was by then quite significantly crippled by Parkinson's disease.[[note]]This was just a few years after his emotional, shaky lighting of the 1996 Olympic torch.[[/note]] The gag became even more uncomfortable in the years that followed as Ali became ever-more frail before eventually dying from septic shock on June 3, 2016.
* In "I've Grown A Costume on Your Face" from "[[Recap/TheSimpsonsS17E4TreehouseOfHorrorXVI Treehouse of Horror XVI]]", Chief Wiggum becoming 'Jared from the Subway ads' and referring to himself (Jared) as 'sexually ambiguous' is a lot more uncomfortable since Jared Fogle's arrest for child porn possession.
* In "[[Recap/TheSimpsonsS18E7IceCreamOfMargieWithTheLightBlueHair Ice Cream of Margie (with the Light Blue Hair)]]", Homer forces a lactose-intolerant boy to eat an ice-cream bar, causing him to collapse as he tells Homer to call the number on his bracelet. In 2017, an allergic toddler died when his preschool allegedly forced him to eat a grilled cheese sandwich.
* In "[[Recap/TheSimpsonsS11E22BehindTheLaughter Behind The Laughter]]" the episode ends with a teaser for a "future" episode of ''Behind the Laughter'' featuring Huckleberry Hound admitting he is a closeted homosexual. Come 2018, the DC comic "Exit, Stage Left!: The Snagglepuss Chronicles" portrays Huckleberry Hound as a troubled gay man, and this is PlayedForDrama up until [[spoiler: he hangs himself after being arrested during a anti-gay raid]].
* "Lisa's Opus" has Bart making a joke that Lisa has "a voice that would make a rhino want to shove its horn in a socket", which Lisa responds that rhinos are extinct. Come March 20, 2018 when the last male northern white rhinoceros had died, making the subspecies functionally extinct.