With the series being a Long Runner, it’s no surprise that a timeless show like The Simpsons can have many hilarious moments through its time. But then there are these moments that doesn’t quite hit the same amount of hilarity when viewed today.
- "Bart vs. Thanksgiving" :
- Lisa makes a diorama of important women, including Marjory Stoneman Douglas. She tells Maggie that "you probably haven't heard of her." After the 2018 shooting at Marjory Stoneman Douglas High School, most of America became familiar with that name.
- Earlier in the episode, a balloon of Bullwinkle deflates during the Thanksgiving Day parade and Homer makes light of the situation, three years after the episode aired, a Sonic the Hedgehog balloon collided with a lamppost and a police officer during the Macy's Thanksgiving Day Parade which resulted in minor injuries. Since then there have been numerous incidents involving balloons due to high winds and size-related issues
.
- In "Bart Gets Hit by a Car", which first aired in 1991, Bart is told by the devil he's not due to end up in hell until the next time the Yankees win the pennant (their last World Series appearance at the time being in 1981). The Yankees won the pennant in 1996, which could mean Bart's had a short life.
- The ending of "Principal Charming" gets even more depressing knowing that not only would Seymour's other major love interest, Edna, would eventually marry Ned Flanders before passing away, but Patty has since come out of the closet, meaning they'll never get back together.
- In "Brush with Greatness", as Ringo Starr is responding to fan mail from the 1970s, he says, "I don't care if it takes me another 20 years. I'm going to answer every one of them." In October 2008, Starr announced he'd no longer accept any more fan mail.
- "Stark Raving Dad":
- From the song "Lisa, It's Your Birthday", the lyric "The training wheels come off your bike, you start to notice boys you like" became a bit awkward after the Michael Jackson trial where he was accused of child molestation.
- The whole episode has Michael Jacks—sorry, "John Jay Smith"—voicing the big, bald white mental patient who thought he was Michael Jackson can be uncomfortable to watch because of all the scenes of the guy hanging out with underage kids (Bart and Lisa).
- At the beginning of "Bart's Friend Falls in Love", Milhouse's Magic-8 Ball responds to Bart asking if he and Milhouse will be friends when they're old men, or even after leaving high school, solely in the negative. Since then, several episodes set in the future have shown Bart and Milhouse sharing precious few scenes together (and barely even talking to each other during those scenes), implying they really did drift apart over the years.
- "Lisa the Beauty Queen":
- A scene, 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. 20 years later, Australia was plunged with two fatal accidents with theme park rides. In 2014, an eight-year-old Malaysian girl was thrown off a ride and killed at the Royal Adelaide Show. Two years later, four people were killed in a collision on the Thunder River Rapids Ride at Dreamworld. Poor safety was blamed for both incidents.
- The episode has Lisa rebel against Laramie Cigarettes despite sponsoring the "Little Miss Springfield" beauty pageant because she doesn't want to be the symbol for them and give other kids the idea that smoking is good and "Homer The Moe" has a scene where Homer puts a cigarette in Lisa's mouth and lights it. "Smoke On The Daughter" negates her good intentions in the former and make the joke from the latter tough to watch by having Lisa smoke and the episode ends without her quitting. She instead takes nicotine patches.
- In "Mr. Plow", Homer imagines getting hired by then-President George H. W. Bush to deal with protestors outside the White House, with Homer saying "Mr. President, those young people are about to get a dose of reality" before plowing down protestors with his plow truck. In August 2017, a white supremacist march in Charlottesville ended with a white supremacist plowing down counter-protestors with his car, killing one person and injuring at least 19 others.
- In "Lisa's First Word", Bart spent the entire episode resenting Lisa because he felt that his parents were disregarding him as she was getting all the attention. Eventually, he is about to run away until Lisa says her first word, "Bart". Then comes "Lisa's Sax" where Bart being disregarded by his parents as Lisa gets all the attention is exactly what happens. Taken even further when Marge eventually admits she sees all of her children as Replacement Goldfish, making Lisa a serious case of the Middle Child Syndrome.
- In "Homer's Triple Bypass" After Homer briefly dies of a heart attack, Mr. Burns decides to send a consolation ham to Marge in response (which ends up reviving him). The joke would become less funny thirteen years later when after Chris Candido's ultimely death, TNA refused to pay out his last check to his long-time girlfriend Tammy Lynn Sytch and eventually sent her a consolation ham instead.
- Also the cops busting into the wrong house isn't so funny anymore as the issue of people getting killed during no-knock warrants on the wrong house (e.g., the 2020 case involving Breonna Taylor) has become more prevalent in recent years and controversial enough that some states are outlawing the practice of no-knock warrants altogether. Then there's the line in the COPS: In Springfield theme song, "Whether in a car/Or on a horse/We don't mind/Using excessive force", which, thanks to heightened concern over police brutality (especially when it happens to minority suspects), would be considered in poor taste.
- In Season 5's "$pringfield", which aired on December 16, 1993, two No Celebrities Were Harmed 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.
- The Season 5 episode "Lisa vs. Malibu Stacy" has a scene where Grandpa admits to stealing Andy Griffith's medication for a heart condition while the latter, who's in character as Matlock, is being rushed to the hospital in an ambulance next to the bus Grampa is in. On July 3, 2012, Andy Griffith died of what was later determined to be a heart attack.
- "Bart of Darkness": Bart worrying that Maude might be dead doesn't seem so funny now that Maude really is dead.
- In "Fear of Flying", Homer didn’t want Marge to go to therapy because he thought it would turn her against him. In "Specs in the City", he finds out that she is in therapy and he is her biggest complaint.
- In "A Star Is Burns", the crossover episode with The Critic 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 Take That! 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 a similar vein, "Thirty Minutes Over Tokyo" featured Allen doing an embarrassing Japanese commercial prompting him to lament "What did I do to deserve this? ...oh, right".
- In the Season 7 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.
- An example that happened quickly after it came out: in "Team Homer" Homer is shown having stolen the Academy Award for Best Supporting Actor given to Dr. Haing S. Ngor for The Killing Fields. Only a month after it first aired, Dr. Ngor was murdered, which would imply Homer killed him for it. In syndication and on the season seven DVD set, the scene was changed to show the Oscar being the one given to Don Ameche for Cocoon, who had died a few years earlier, but of natural causes.
- Seeing what a cool, heroic guy that Jebediah Springfield, the town's founder, is portrayed as in "The Telltale Head" is this after his true identity is discovered in "Lisa the Iconoclast": as a conman and a scoundrel who tried to kill George Washington.
- "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 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 both US viewers and UK viewers after a Massachusetts high school teacher was stabbed to death in October 2013 at the hands of a student. As for UK viewers, a teacher was stabbed to death by a student during a lesson in April 2014.
- One poster in Nelson's room has the caption "Bomb the Arabs and take their oil," which is pretty much what the War in Iraq in 2003 was accused of being about. This idea wasn't exactly going out on a limb in the late 90s, but it still is an unintentional sting.
- The subplot with Homer and the "Happy Dude" autodialer becomes much more prophetic with the rise of robocallers and spambots affecting telephones in the 21st century.
- In "The Twisted World of Marge Simpson", at a Springfield Isotopes game, Springfielders are so angry at Mr. Burns "winning" the raffle that they start throwing Marge's pretzels at him, littering the field and hurting Whitey Ford. During a 2001 NFL game with the Jacksonville Jaguars vs. the Cleveland Browns, the NFL referees controversially overturned a potentially game-saving play for Cleveland, making Cleveland fans so angry that they threw bottles and other objects at them with numerous injuries, leading to the game being dubbed "Bottlegate".
- Over the closing credits of "All Singing, All Dancing," Snake fires his gun several times to make the theme music stop. The first shots coincide with the appearance of Phil Hartman — who was shot to death by his wife in a Murder-Suicide a few months later. (On the DVD commentary for this episode, everyone present goes suddenly silent when this happens.)
- 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 "Viva Ned Flanders", the people running away from the dust cloud after Mr. Burns' casino gets demolished, looks eerily similar to the cloud caused by the collapse of the Twin Towers, two years after the episode was aired.
- In the Season 10 episode "Sunday, Cruddy Sunday" (which aired after 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. Principal Skinner then replies, "I'm just glad I work at 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 — Columbine — taking place just a few months after it aired, the joke's darkness gets blacker and a lot more tasteless.
- In "Beyond Blunderdome" guest star Mel Gibson is genuinely shocked when audiences react badly to the ultra-violent climactic bloodbath ending to his remake of Mr. Smith Goes to Washington. A few years later, Gibson's life and career would spiral out of control when he couldn't cope with general audiences reacting badly to his very bloody 2004 Crucifixion film The Passion of the Christ, seriously damaging his reputation in the process as he suffered a serious nervous breakdown complete with alcohol relapse and the end of his long standing marriage to Robin Moore.
- 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.
- 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 police helicopter did just that in Scotland.
- From seasons 1 to 19 the show would always have an intro before the couch gag consisting of Homer pulling his car to the driveway and almost gets run over when Marge pulls up to the driveway. Not so funny anymore when Marge really did hit Homer with her car in "Brake My Wife Please".
- "Marge vs. Singles, Seniors, Childless Couples and Teens, and Gays":
- There's a scene 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 of Springfield going anti-kid, Moe flips the backwards "R" of the Toys R Us logo forward while a mob of children look on in horror. In 2018, Toys R Us went out of business (though they've managed a small-scale comeback in Macy's stores since).
- At one point, Lindsey Neagle says that children are keeping television from pushing the envelope when it comes to sex and violence. Barely a month after the episode premiered, Janet Jackson's infamous "wardrobe malfunction" occurred during the Super Bowl XXXVIII halftime show, leading to a major FCC crackdown and a debate over the amount of perceived "indecent" content coming from Hollywood.
- Dr. Hibbert's whole situation of being the anti-Cliff Huxtable in light of the Real Life sexual crimes that Bill Cosby has been accused of doing, especially in "On a Clear Day I Can't See My Sister", where Hibbert makes a reference to dealing with a sexual harassment lawsuit.
- At the end of "Goo Goo Gai Pan", Selma says she'll bring Ling back to visit China when she's a spoiled American teenager. Come "The Changing Of The Guardian" where Selma and Patty have done the opposite of spoiling Ling forcing her to do various activities (lasso, art, playing music) at once and tell Homer and Marge not to compliment her so as not to make her lazy.
- 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.
- In "The Monkey Suit," Chief Wiggum busts into the school to arrest Lisa for illegally teaching evolution, and when she questions why he arrested her, Wiggum says that they only have enough manpower to enforce the most recently enacted law, which is when the camera shows Snake going on a shooting spree, and Wiggum trying to ignore it. Although it was played for Black Comedy, it becomes terrifying in the light of future mass shootings, including the one in Stoneman Douglas High School in Florida in 2018, and the one in Uvalde, Texas in 2022, where the local law enforcement failed to act due to being ordered to stand down and await further instructions by their respective commanding officers.
- 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 (Homer then mocks him for the bracelet before finding out it's the number for a doctor). In 2017, an allergic toddler died when his preschool allegedly forced him to eat a grilled cheese sandwich.
- 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 Color Yellow", which reveals that one of Homer's ancestors was a black slave.note
- In the Flash Forward episode "Holidays Of Future Passed", Ned Flanders is revealed to have married the ghost of Maude Flanders, his deceased wife, after Homer somehow got Ned's second wife, Edna Krabappel, killed. While clearly meant to be a Call-Back to how Homer got Maude killed, it becomes much harder to watch two years later after Edna was retired from the show following the death of her voice actress, Marcia Wallace. Edna was later revealed to have died, but the exact circumstances surrounding her death are never explained, possibly because of this episode.
- "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.
- The episode has Bart hijacking the ship's public address system with a movie clip that causes everyone to believe that there is a worldwide pandemic and that ships cannot head towards land, stranding the passengers in the middle of the ocean in miserable conditions. Fast-forward to 2020, the novel coronavirus outbreak leads to a real life worldwide pandemic, and in one famous case during the early days of the outbreak, the Diamond Princess cruise ship that took a stop in China was left to wander around in the sea unable to dock at any country's ports for fear some of the passengers onboard may be infected. They were eventually allowed to dock in Japan, with the whole ship locked down, all the passengers kept in quarantine, and several passengers and crew members did test positive for the virus.
- Another Flash Forward episode, "Mr. Lisa's Opus", has an older Bart making a crack that Lisa has "a voice that would make a rhino want to shove its horn in a socket", to which Lisa responds by reminding him that rhinos are extinct. Come March 20, 2018 when the northern white rhinoceros was declared functionally extinct with the death of the last male of the subspecies.
- "I do not thank you and I will not come again." Apu has been Put on a Bus.
- While Homer is an Alcoholic Parent, the episodes "You Only Move Twice" and "Co-Dependents' Day" subvert the idea of Marge becoming one herself, with the latter dealing with Marge drinking excessively with Homer after they tour wine country and going to a clinic to dry up, only to realize that it was her enjoyment of time with Homer that was motivating her drinking and that she has no real desire to drink at all outside of those specific circumstances. However, by the Season 30 premiere "Bart's Not Dead" she reveals that she really has begun to secretly drink wine to cope.
- In "Diatribe of a Mad Housewife", Lisa's locked-up teen libido urging her to, among other things, "binge and purge." Lisa actually develops an eating disorder in the following season's "Sleeping With the Enemy," and it's implied that these struggles will follow her into her adulthood.
- Season 17's "Homer's Paternity Coot" became more winceworthy in light of the Oceangate Submersible tragedy. in which 5 lives were lost on a tourist trip to the wreckage of the Titanic. The episode features a storyline where Homer goes on a deep-sea excursion with the man who he believes to be his real father in search of a priceless treasure at a shipwreck and ends up stuck. there's a scene where it shows the oxygen in the sub depleting and Homer losing consciousness, which was feared to be happening to the passengers on the doomed submersible for four days (they had 96 hours worth of oxygen onboard) until it was later announced that the submersible had actually imploded.
- In an even more eerie coincidence, Season 9's "Simpson Tide" was produced by Mike Reiss, and features Homer and several other characters being trapped on a damaged submarine. Reiss was a passenger on the doomed submersible in 2022.
- In season 10's "Monty Can't Buy Me Love", Mr. Burns goes to Jerry Rude's radio show expecting a straightforward interview but is unaware that Jerry is really a Shock Jock similar to Howard Stern, and is subsequently humiliated instead. Less than a week after this episode aired, Dana Plato appeared at The Howard Stern Show and was subjected to mockery by callers, and despite Howard's defenses, she was so badly shaken that she killed herself the following day.
- In "The Sound of Bleeding Gums", Homer tells Lisa that only losers watch broadcast television, while looking at the viewer. This episode would end up being a series low in the ratings, being the first to get less than a million viewers. Seems like Homer was right about that.
- In "The Italian Bob", the Simpsons travel to Italy, where they meet Sideshow Bob, who's serving as mayor of an Italian village and introduces them as honored guests. However, Homer makes rude facial expressions and hand gestures to some Italian people, prompting Lisa to say "Dad, don't act like Mussolini.", to which Homer says "Oh, I thought I was doing Donald Trump.". In 2016, Trump got in trouble when his presidential campaign's Twitter page retweeted a Mussolini quotation.
