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The Simpsons really suffers from this one… to the point, an entire page was done just on the series alone.

  • 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, it wasn't shown much in syndication after September 11th. 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.
  • 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 for having an episode that now appears dated due to a tragic event, the boy band episode aired in 2001 -- February 2001 -- seven months before the destruction of a New York City tower would go from being "Ha, ha, ha," to "Too Soon!" One of the writers pointed this out on the DVD.
  • If the New York episode is the Trope Codifier for the show, the Season 5 episode "$pringfield" is a close second. In this episode, which aired in 1993, two No Celebrities Were Harmed 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, though the writers pointed out that the tiger attack was bound to happen sooner or later.
  • Another Simpsons episode, "Team Homer", had Homer possessing an obviously stolen Academy Award from Haing S. Ngor of The Killing Fields, with Ngor's name crossed out and Homer's written in. The joke lost all its humor only a month later when Ngor was fatally shot. A viewer not knowing that the episode came first might conclude that the show was implying that Homer had killed him for the award. In syndication, the scene was reanimated so that way the Academy Award Homer stole was really from Don Ameche. Ameche had died a few years earlier, but of natural causes.
  • Then there's "A Streetcar Named Marge", where Marge performs in a musical version of A Streetcar Named Desire that features an entire song about what a hellhole New Orleans was. Even when it originally aired, it was controversial -- Hurricane Katrina made matters worse.
  • Bart complaining about Generation X in 1996's "The Day the Violence Died":

  "We need another Vietnam to thin out their ranks a little."

  • In another episode ("Homer's Phobia"), Moe complains that at one time, boys could be made into men by being sent off to war, but that there aren't even any wars anymore, "Thank you very much, Warren Christopher." Thank you indeed.
  • In the episode "Homie the Clown," Krusty asks his accountant if he delivered a thousand roses to (then-alive) Bea Arthur's grave. While death is inevitable, hearing that joke will make you cringe.
  • The Simpsons once used a joke where a gasoline station charging $1.40 and eight tenths a gallon was a discount gas place. Fast forward a decade, and that price really is a discount.
  • In You Only Move Twice, the Simpsons decide to just abandon their house because it's worth less than they owe on the mortgage. Twelve years later, the housing bust happens and this becomes common in Real Life.
  • How can anyone forget season six's "Bart of Darkness" where Bart thinks Ned Flanders killed Maude? Or season nine's "Realty Bites" where Marge worries that the Flanders' family is going to die after moving into an old house where an old murder occurred? Funny when they were first on -- not so much after Maude Flanders died on season 11's "Alone Again, Natura-Diddly." It's as if the writers planned it...but we know they didn't.
    • Also the scene from "The Springfield Connection" when Homer uses "Police Line: Do Not Cross" tape to prank Flanders about his family dying.
    • And in "I'm With Cupid", Ned admitting he probably takes Maude for granted is really sad since she would die only a year later.
  • In the Season 10 episode "Sunday, Cruddy Sunday" (which aired after the 1999 Super Bowl), 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!" followed by an awkward silence (though the awkward silence could be because no one laughed at Skinner's lame attempt at making a joke). 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.
    • This was made even worst following the Sandy Hook shooting in 2012.
  • In the closing credits of the clip show "All Singing, All Dancing", Snake is heard shouting "Stop the music!", and 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 the TV show).
  • There's that episode guest starring Mel Gibson (season 11's "Beyond Blunderdome"). He was complaining that people like him too much, and ends up creating a movie so controversial that everyone hates him. Funny how life imitates art, no?
  • In a 14th season episode ("Brake My Wife, Please"), there's a throwaway gag about oil spills threatening the gulf cost. As of July 2010...
  • 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 -- whether or not they actually have African heritage in their family background).
    • 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 George W. Bush was U.S. President (and there were a lot of jokes about George W. Bush looking like a monkey because of his big ears and simian-looking face). These days, with 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 Hilarious in Hindsight during the "Dubya" Bush era, absolutely racist in the Obama era.
        • One of the Halloween specials did a parody of King Kong with Homer as the titular character.
  • An in-story example: in the episode "Homer Loves Flanders", Bart says that its because of genetics that Homer is a loser (with Bart yelling, "D'oh!" 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 this. This particular Funny Aneurysm Moment is notable because it's one of the meaner cases of Cerebus Retcon.
  • And now all the nuke disaster episodes have been pulled off the air in Europe. They're anything but funny after what's just happened in Japan.
    • Apparently those nukes on Japan in WWII weren't so offensive, then...
  • Also, in the episode See Homer Run, Rainier Wolfcastle (in other words, 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.
  • This is more of a YMMV variation, but in the episode Sideshow Bob's Last Gleaming, we have Rupert Murdoch (or at least a lookalike of him) in jail with Sideshow Bob for an unspecified crime. Years later, Rupert Murdoch is facing charges for the FOX newsletter for wiretapping to get news, and was shut down.
  • The climax of "Deep Space Homer", with fears of the shuttle burning up in reentry, is winceworthy in light of how the Space Shuttle Columbia burned up in its reentry in 2003.
  • The scene where Krabappel confirms that Bart got an "A" on his United States map test, and also admits that she forgot to pull up the state map (thus causing all her students to get an A), is painful to watch years later with the cheating scandal going on in the various high schools across Georgia (granted, it probably wasn't intentional on Krabappel's part, but still...).
  • In the episode "The Cartridge Family" Springfield ends up having a lot of riots commencing due to the populace growing bored with a soccer game (a riot that was intensified by Groundskeeper Willie and some of his Scottish relatives), followed by the local government declaring martial law on the town (at least until the story shifts into Homer buying a gun and scaring his family with his carelessness). This becomes significantly less funny than it already was when you take into account the 2011 Great Britain riots.
  • Remember Blinky, the three-eyed fish that Bart and Lisa found near the nuclear plant on the season two episode "Two Cars in Every Garage, Three Eyes on Every Fish"? Turns out he's real (at least in another country).
  • It's either this or Harsher in Hindsight, but the plot of the episode "The PTA Disbands", where the school faculty are commencing a long strike period over low pay, even when Skinner made it clear that the lack of funds is because of the local economy and a raise in pay would mean higher taxes, is even less funny after the Wyoming Teacher's Union Strike and Britain's teacher's strike (both in 2011).
  • 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, since he's waving at him. 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). After the highly publicized rash of suicides from anti-gay bullying, the murder of Lawrence King, as well as the "gay panic defense", it's turned into this trope and/or Dude, Not Funny.
    • 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." These days, Homer would have been expelled for doing that.
  • In the audio commentary for "Bart Gets Famous", former writer Conan O'Brien expressed fear that his appearance on the show as a late night host would turn into a Funny Aneurysm Moment if his struggling talk show was cancelled before the episode made it through production and onto the air.
  • In "Homer Defined", Magic Johnson trips, scores, and falls into a group of adoring cheerleaders. Less than a month after the episode aired, Johnson announced he was HIV positive.
  • One episode had Lisa enter an American Idol expy with a little black girl as competition. The girl has an amazing voice and delivers a version of "Hush Little Baby" that has the audience singing along and clapping. Bart comments that she's "Like Whitney Houston brought back to life!" In light of her death, this line is a lot less funny.
  • In the segment "Life's A Glitch, Then You Die" from Treehouse of Horror X, when the Y 2 K bug takes over, Dick Clark, says "It's happening" and melts to reveal a robotic skeleton, referencing a joke about him being perpetually young. This became less funny in when Clark himself suffered a stroke on 2004 and even lesser after his death in 2012.
  • The "Ode to Branson" song features the line "Charlie Callas doesn't sleep in the ground, yes he's still alive and he's making his sounds!"
  • The "Treehouse of Horror XII" segment, Hex in The City, had Carl and Lenny getting killed after a helicopter crashes into Moe’s Tavern. Homer’s moaning for the lost is interrupted by Moe’s death and asking “When did that happen?” Twelve years later in 2013, ten people in Scotland were killed when a police helicopter met the same fate.
  • The scene in “Holidays of Future Past” where Homer explains how he killed Edna has been made more tasteless following the death of Marcia Wallace in 2013.
  • The 2008 Treehouse of Horror's second segment had the ghosts of various celebrities killed by Homer. Rip Taylor attacks Comic Book Guy, who says "you're not even dead!" Taylor replies "someone needs to check my apartment!" Amusing back then, but not so funny after Taylor died of complications from an epileptic seizure in October of 2019.
    • Homer also killed Prince and Neil Armstrong, who were still alive at the time. Armstrong died in 2012, and Prince died in 2016.
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