%% 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 "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 "Homer Defined", Magic Johnson "pulls a Homer" when he slips on a wet spot during a breakaway, loses control of the ball which goes off the referee's head and into the basket. He ends up in the adoring arms of four cheerleaders. Less than a month after the episode aired, Johnson announced he was HIV positive, which he got from sleeping with numerous women.
* In Season 5's "$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 "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 would make this line even more tasteless.
* 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. On September 4, 2006, Irwin died when a stingray pierced his heart.
* In the 1999 episode "Homer to the Max", Homer mentions that networks like animation because they don't have to pay the voice actors squat. Flanders then shows up with [[TheOtherDarrin a new voice actor]] (Karl Wiedergott) in order to illustrate the joke. In Spring 2015, Creator/HarryShearer, Flanders' regular voice actor, temporarily left the series following a contract dispute before the issue was resolved a couple of months later.
* 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 the episode "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 "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 "Dumbbell Indemnity." This scene would become very racist in the Obama era.
* The Season 5 episode "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.
* "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 "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.
* "A Totally Fun Thing 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 "The Simpsons 138th Episode Spectacular," the original three ''Simpsons'' showrunners-cum-creators are [[SelfDeprecation Matt Groening]] (depicted as a gun-crazy redneck), [[BitingTheHandHumor James L. Brooks]] (depicted as being very fat, very rich, and the winner of several awards), and [[TakeThat 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 "A Star Is Burns", the crossover episode with ''WesternAnimation/TheCritic'' that Matt Groening hated, there is 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.
* In "Lisa the Iconoclast", the historian at the Springfield Historical Society holds Jebediah Springfield not as a "minor patriot" but along the ranks of Thomas Jefferson and even Woody Allen. Apart from Allen's aforementioned fall from grace, Thomas Jefferson's public reputation has taken a hit in recent years for his support of states' rights and his ownership of slaves (something at odds with his liberalism).[[note]]Jefferson is nonetheless still highly regarded between scholars, not least for being one of the "Founding Fathers".[[/note]]
* The "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 "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=] 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 "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 "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 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.
* A scene in the 1999 episode "Monty Can't Buy Me Love" depicting billionaire Arthur Fortune proudly knocking out a retired Muhammad Ali. 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 "Homer vs. Patty and Selma", Homer dreams his financial worries will be over with an invention of his that fits in the palm of one's hand and everybody has at least one. This description fits that of the "fidget spinner", invented by a destitute woman. She didn't get to enjoy from the profits as she was too poor to have the patent renewed (and even if she had been able to afford to get it renewed, it would've expired in 2014), and she's ''still'' penniless.
* In "I've Grown A Costume on Your Face" from 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.
* The "Treehouse of Horror XIX" segment "How to Get Ahead in Dead-vertising" has Homer killing celebrities for corporations wanting to use their image, among them Music/{{Prince}} and Neil Armstrong. Not as funny following their actual deaths in April 2016 and August 2012, respectively.
* In "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.