In "Game of Flags", Star complains that her mother, Queen Moon, was allowed to join the game of Flags when she was Star's age, and Moon replies "I did a lot of things you won't be doing." Fans speculated that Moon was a Former Teen Rebel, until the season 3 episode "Moon the Undaunted" revealed Moon became queen at a young age when her mother was killed by Toffee, then a rogue monster soldier, during the signing of a peace treaty. Not only that, Moon was driven to make a Deal with the Devil with Eclipsa, Queen of Darkness in order to learn a dangerous dark magic spell in order to defeat Toffee and put a stop to his rebellion.
Most of The Boondocks episode "Thank You for Not Snitching" follows the militarization of a Neighborhood Watch group that targets young black children. Considering what happened to Trayvon Martin, this makes the episode harder to watch.
One of the stations in the New New York tubeway system was given as "J.F.K., Jr. Airport". After the real-life John F. Kennedy, Jr. died when his private plane crashed, the line was replaced with "Radio City Mutant Hall".note Though the original line can still be heard on the full-episode animatic that appears on Futurama volume one DVD and on the UK airings.
The line in the first episode about the Stop & Drop Suicide booths being "Americans' favorite suicide booth since 2008" becomes a bit wince worthy in light of 2008's economic meltdown and the invention of an actual suicide machine in the same year.
In the pilot, Fry's reaction to realizing that his parents and everyone he's ever known died hundreds of years ago is a triumphant "Ya-hoo!" As the series continued, episodes such as "The Luck of the Fryrish," "Jurassic Bark" and "Game of Tones" explored Fry's relationships with the family he left behind and showed how profoundly he, and they, were affected by the loss, leading to the show's most infamous Tear Jerkers.
In "The Lesser of Two Evils", the main characters visit a theme park modeled on 2000s New York. There's a brief scene where the stock market drops from about 11,000 to 7,200, similar numbers to the real life 2008 crash.note Fortunately, it jumps right back up to 11,000, and all the stockbrokers who jumped to their apparent deaths float back up into the building via jetpack. Considering that the scene was supposed to be a "distorted history" take on the crash that started the Great Depression; that makes this a sort of bizarre life imitating art imitating life.
There is a not-so-untrueUrban Legend about a King of the Hill episode and a Columbine survivor who was hiding during the shooting and wrote a love note she intended to give to a friend after realizing how close she was to dying, but the friend turned out to be one of the perpetrators. "Wings of the Dope," the episode with Buckley's angel, aired two weeks later and watching it helped the girl realize she didn't need permission or approval from anyone to mourn her loss (or the loss of what could have been had she spoken up sooner). In the episode, when Hank is tired of everyone talking about the angel and tries to get Luanne away from him, he says:
"I'm sure with his help you'll do just fine. You'll pass the test and he'll have finished his good deed and there'll be no need for him to come back to Earth again. And if you do see Buckley's angel again, it will actually be an evil angel of death."
In another episode "That's What She Said"note With guest star Ben Stiller, Hank's co-worker makes inappropriate jokes and remarks in the workplace, much to Hank's chagrin. The episode, which aired in 2004, might be a little cringy to watch now in light of the #MeToo and #TimesUp movement which both deal with sexual harassment and toxic workplaces.
In the episode "Happy Hank's Giving", Hank packs a smoked turkey in a box which is mistaken for an explosive by the bomb squad and blown up. Considering that the episode aired two years before 9/11, the episode might be uncomfortable to watch.
The Sam & Max: Freelance Police episode "Fools Die on Friday", originally aired in 1997, is about a terrorist who hijacks an aircraft and almost crashes it into a tall structure in New York City. Of course, the aircraft is a blimp, the terrorist is just a mildly insane loser, and the crash (into the Statue of Liberty) is averted. But the overall plot and dialogue still parallel 9/11 enough that it makes the episode harder to laugh at. The episode was not shown on Gametap when they began streaming the series in 2006, but it is fully present on the DVD release.
The episode "Unrestrainable Trainable" has Captain Hero investigate the city under attack from a giant midget (which later turns out to be his inbred son), with one of the evidence of destruction being a giant reservoir of banana pudding being drained. Bill Cosby is seen standing over it, saying that he's just another unemployed sexual predator without it. Then theres the episode Foxxy and the Gang Bang/Toot Goes Bollywood, where Toot challenges Foxxy to stop having sex and viceversa. In Foxxys plot, she tries to find out the reason for her heavy sexual appetite, and tracks it back to memories of Fat Albert and the Cosby Kidsexpies sexually assaulting her when she was young, later turning out that the memories were fake and implemented by Wooldoor. The accusations of sexual assault against Cosby make these jokes not so funny.
When Steve Irwin gets tail-whipped by Medusa, he rips his heart out and puts it back in, saying "What a stinger!" This is now seen in bad taste due to Irwin's real-life death after being stung in the heart by a stingray.
Siegfried getting attacked and killed by the tiger in Penn & Teller vs. Siegfried & Roy match became less funny when Roy was mauled by the tiger in Real Life.
Avatar: The Last Airbender: The season 3 episode The Ember Island Players, about a Fire Nation play about the cast, which is about as hilarious a warping of reality as the Unalaq play. Then came The Movie, where pretty much everything the actual Gaang had a "No. Just... No" Reaction to in the play was true of the movie's portrayal. The movie goes on to be considered In Name Only, universally reviled by fans, got a lukewarm reception at best by non-fans, derailed the lot of the cast's careers, and put a hitch in the 3D revival with it's last minute conversion and the Razzies that it won for it.
This ad for◊ Clarence is a lot less funny after the creator was fired from Cartoon Network over allegations of sexual assault. However, the episode where this scene came from, "Slumber Party", did eventually air unaltered.
The Wild Thornberrys contains an episode where Eliza meets a pack of wolves in Yellowstone National Park. Eliza claims that there has never been a single human in North America killed by a wolf. The deaths of Kenton Joel Carnegie and Candice Berner, who were both killed by wolves in North America (Carnegie was Canadian, Berner was American), make this quote hard to stomach.
Season 1's "Call of the Cutie" sees Scootaloo tell Diamond Tiara and Silver Spoon they're "stuck being stuck up". "Crusaders of the Lost Mark" reveals Diamond Tiara's mother is practically abusing her to act like a proper 'rich pony', which basically translates into being a stuck up snob to anyone beneath her, meaning Scootaloo was more right than one would think.
The Season 1 episode "Over a Barrel" has Fluttershy's memetic statement of her desire to be a tree. In Season 7's "A Health of Information", she is one of the victims of the "Swamp Fever" disease which ends with turning into a tree.
Happened with the Season 2 episode "Hurricane Fluttershy". Fluttershy pretends to be sick to get out of training, painting spots all over her body and calling her ailment "pony pox". In Season 7's "A Health of Information", the same colored spots turn out to be one of the symptoms of the aforementioned "Swamp Fever" disease.
The Scootachicken jokes which originated in Season 1's "Stare Master" became considerably less funny when it turned out that in Season 4's "Flight to the Finish", Scootaloo has trouble flying in canon and Diamond Tiara and Silver Spoon tease her for it.
A lot of the various Spike gags became somewhat sadder in hindsight after "Equestria Games" revealed he has serious self-esteem issues.
The episode "Amending Fences" does this to the very first episode. The Establishing Character Moment of Twilight brushing aside a party invite to focus on her studies with Nightmare Moon's imminent arrival? Turns out the party that she was invited to was for an old friend of hers named Moondancer, and by snubbing it and moving to Ponyville without even saying goodbye it effectively ruined the entire pony's life. Moondancer's scene where she breaks down delivers a tear-filledreason you suck speech is easily the most heartrending thing the show has ever produced.
Season 5's Do Princesses Dream of Magic Sheep? had Big Macintosh turning himself into an Alicorn princess during the Dream Sequence. It was seen as nothing more than a funny gag at the time... then later that season, Brotherhooves Social reveals that Big Mac developed an inferiority complex as a result of Applejack becoming a hero of Equestria and being adored by his baby sister Apple Bloom, while he was ignored. This puts his dream in a very different light.
One episode has a banner advertising the New York City Marathon, which Jay later runs in, with the slogan "It's More Fun to Run When it's Not From a Gun". Terrorism at a marathon was unthinkable until the Boston Marathon bombing in 2013 that left three dead and more than two hundred and fifty injured, making this one hit a bit close to home.
Jokes about Doris' smoking habits are this ever since her voice actress, Doris Grau, died in 1995 from respiratory failure. A notable one is when she blows a smoke cloud of an evil figure telling her that her time is coming soon.
There's more than one joke at the expense of Dudley Moore and his apparent drunkenness and resemblance to his Arthur character. Two years after the show ended, he was diagnosed with progressive supranuclear palsy, a disease in the same family as Parkinson's.
The episode "The Menace of Maninsuit" (first aired in 2004) had Dodgers fight the titular kaiju on the Japan-like planet of Nippono in a mecha, who eventually crashes into a nuclear power plant and comments on how it's a bad idea to have one near the ocean. The 2011 Tohoku earthquake and tsunami, along with the subsequent Fukushima nuclear disaster, show how it's a bad idea.
"Samurai Quack" has one gag where Dodgers carves his way through countless robots, but pulls back from striking a human because he can't get away with that with a Y7 rating (a jab at how Samurai Jack got away with plenty of violence because it was directed towards robots and not organic beings). Then Season 5 of the latter show aired, it is no longer rated Y-7, and Jack brutally slashes the throat of one of the (very human) Daughters of Aku, whom he had assumed was just another one of Aku's robotic minions.
Likewise, Achoo's (Aku's) spoof of Darth Vader's iconic We Can Rule Together scene doesn't sound as hilarious when the 9th episode of Season 5 had shown that the daughters of Aku being the ''literal'' Daughters of him.
In a bad naming coincidence, the organization which the protagonists of Archer work for is named ISIS, the International Secret Intelligence Service. Among other things, they have engaged in counter-terrorism and espionage, unintentionally racking up high body counts and causing international incidents. The group is a parody of intelligence agencies, and allows the writers, usually through Lana or Mallory, to give their opinions on the fubared nature of covert geopolitics, and the horrible things that happen when said politics go wrong. Unfortunately, in early 2014, an organization known as ISIS, the Islamic State of Iraq and Syria, rose to prominence, the result of several geopolitical disasters in the Middle East. Among other things, they have engaged in terrorism and mass murder, purposefully causing an international incident and racking up a high body count. The trouble caused by the real life ISIS has led to the creators to drop the name from the sixth season onwards.
One of Zurg's lines in the Buzz Lightyear of Star Command episode "Stranger Invasion" suddenly gets very disturbing after seeing Toy Story 3, when Andy's toys come very close to being burned alive in an incinerator.
Zurg: And if I may remind you, no gianttrash compactor! When heroes fall in, they always have enough time to figure a way out! Make it an incinerator!
In Rugrats episode "Reptar 2010" has Imagine Spots where Reptar versions of the kids tear up New York City, the last one having Phil and Lil tear up two buildings that resemble the World Trade Center.
The episode "Let Them Eat Cake" is set during a wedding, during which Stu sees that Chas is crying and tells him, "Get ahold of yourself, Charles. It's just a wedding." Fast-forward to "Mother's Day" and we learn that Chas is a widower. What previously seemed like a good-natured joke about how sensitive Chas is has become downright tragic; there's a chance he was in fact weeping as he thought of his deceased wife.
The relationship between demon dragon and Big Bad Shendu and his son Drago in the final season of Jackie Chan Adventures starts carrying more weight when the real Jackie Chan became estranged from his own son Jaycee, which culminated in Jaycee being arrested for drug possession, which in the People's Republic of China could have given him the death penalty. The relationship between the cartoon Chan and his niece Jade falls into this as well, and the strainedrelationship between Shendu and his ownsiblings has the possibility of qualifying. All of these may be Harsher in Hindsight instead.
The short "Magic Time" features expies of Sigriend & Roy who mistreat their animals and wind up getting attacked by them at the end. Six years after it aired, Roy Horn got attacked by one of his own tigers.
Jokes towards 90s celebrities didn't exactly age well, particularly this line.
"A Quake, A Quake" is pretty funny, but the end line (which references the then-recent Lebanese Civil War) takes on a new Oh, Crap! meaning after 2006 and especially 2020:
"We want to find some peace and quiet, so we're moving to Beirut"
The episode "Plane Pals" has an in-flight safety film that pokes fun at various potential in-flight disasters. A few years after the episode aired, one such scenario came true:
"Welcome to Air Pacific, the Jolly Airline. Our deluxe 757 is equipped with a number of safety features to use in case of an emergency, such as our fuel tanks explode, and we crash like a fiery ball into the sea."
"Potty Emergency" has a scene where Wakko tries to use the women's restroom at a movie theater due to the men's room being out of order and gets kicked out. The controversy over transgender people and gender-specific bathrooms in the mid-2010s makes this moment cringe-worthy.
A dropped pilot for Constant Payne has a scene where the daughter squeezes a balloon plane in between two buildings, shattering the windows. This came out in 2001 and is a theory for why the pilot didn't pass (though in reality, it was because the creator was pushing for unionization in the animation industry).
Moral Orel's early episodes in general. The show got considerably darker around the middle of the first season and put a lot of focus on how miserable most of the main cast are. A lot of these traits (Clay's drinking, Blobert'a Stepford Smiler tendencies, etc.) are still present in the early episodes though. They're just played for laughs and not explored very deeply. Making those scenes a little cringe-worthy if you watch them after you've seen season 2 and especially season 3.
Uncle Grandpa had a gag in "Pizza Eve" involving an awards show where Uncle Grandpa wins every single award. The gag ends with Uncle Grandpa telling the stars of the other Cartoon Network shows that they're not getting picked up for another season. Not long before this episode aired, it was established that no new Uncle Grandpa episodes would be made anymore and the crew had already been fired. Whoops.
In Disney's 1925 Alice ComedyAlice's Egg Plant, Alice has trouble filling out an order of eggs when a Bolshevik chicken heads her hens on a strike. In 1941, the Disney studio would undergo a crippling strike, which Walt Disney, in his 1947 testimony to the House of Un-American Activities Committee, blamed on Communist sympathizers.
The Transformers: At the end of "Only Human", which takes place in the then-future year 2006, "Old Snake"* who is all but stated to be a future version of Cobra Commander laments that "they simply don't make terrorists like they used to..." as the episode's villains are taken away. Even beyond 2006, real life has proven that they do make terrorists like they used to.
Kaeloo: Like most comic reliefcartoon characters, Stumpy the squirrel is often made fun of by other characters or placed in dangerous or unpleasant situations for the audience's amusement. The Season 3 premiere revealed that he's genuinely hurt by this, because it makes him feel like his friends don't care about him enough to help him out of bad situations or treat him with respect and love.
At the end of "The Flood", as floodwaters surround PS 118, Principal Wartz stands on the roof of the school singing, "Way down yonder, in New Orleans..." This became a lot less funny after Hurricane Katrina caused extensive flooding and damage in New Orleans in 2005.note Hurricanes have flooded New Orleans multiple times, the most recent pre-Katrina occurrences being in 1940, 1947, 1965, and 1969. The joke post-Katrina is pretty much the same amount of Funny Aneurism as it always had been, it's just that the target audience's shallow reference pool now contained an event that had occurred during their lifetime.
In "Helga on the Couch", Mr. Simmons gets nervous when he learns that the school psychologist will be observing his class, stuttering and asking for reassurance that she will just be observing the students, and not him, the teacher. While this is a moment played for laughs when the viewer is a child, as an older viewer who knows about Mr. Simmons being gay he was likely still in the closet and worried that the school psychologist would see through him and expose him, which could have disastrous backlash from the parents whose children attends P.S. 118.
In "Curly Snaps", Curly loses his mind because he feels like he isn't respected by the other students and teachers, locks himself in the principal's office, and assaults people with dodgeballs. The episode aired half a year before the Columbine High School Massacre, when such behavior would be considered way less funny. There's also the fact that if Curly pulled something like this the 2010s, with the many controversial "Zero-Tolerance" policies and extreme rules in place at schools, this kind of behavior would likely have the police called.
Early into "Who Do You Trust?", Clint taunts Tony for messing up his welcome speech to Carol, prompting Tony to mockingly threaten to fire Clint. Soon afterwards, Tony finds himself in a position where he must consider actually renouncing Hawkeye's membership, for possibly being a Skrull.
"Along Came a Spider..." has a gag in which Spider-Man tries to speak in a Badass Baritone, but fails so badly at sounding tough, S.H.I.E.L.D. agent Clay Quartermain asks, "What's wrong with your voice?" Before this episode aired, Marvel had the writers' first choice for Spider-Man's actor, Josh Keaton, dubbed over by Drake Bell, as synergy with Ultimate Spider-Man.note Never mind how many other characters sound and/or look completely different between the two shows... After the airing, cue peeved Josh Keaton fans decrying Drake Bell's performance as inferior, and questioning the need to change an already-animated Spidey's voice.
Xiaolin Showdown: In the episode "Enter the Dragon" one of Dojo's attempts to convince Omi to release him from the cage is by disguising as an older woman (among other things) and saying that he's Omi's mother, something he doesn't fall for, knowing that he's an orphan. Then comes the episode "Omi Town", which not only shows how serious his parental issues is, but falls for a real trap. When he thinks he finally found his true parents, they turn out to be robots built by Jack Spicer and made to look like Omi's possible relatives with the Moby Morpher.
Mixing with Harsher in Hindsight, The Real Ghostbusters episode Janine's Genie has a scene where mischievous ghosts hijack a passenger jet and the Ghostbusters narrowly prevent it from crashing into multiple buildings, including the World Trade Center.
The Powerpuff Girls: In "Powerpuff Bluff", a gang of impostors commit crimes dressed as the girls, leading to a scene where a SWAT team bursts into Pokey Oaks Kindergarten to apprehend them while firing their machine guns all over the place. After the 2012 massacre at Sandy Hook Elementary, this scene becomes much harder to stomach.
One of the recurring characters in the U.S. Acres segments of Garfield and Friends was Aloysius Pig, an Ink-Suit Actor version of comedian Kevin Meaney. In his final episode, "Kiddie Korner", the gang tries to find a wholesome nursery rhyme that won't offend him. During one part, Aloysius says "More death, to say nothing of high cholesterol!" in reaction to Orson showing him Humpty Dumpty. On October 21, 2016, Kevin Meaney died in his home of a heart attack, which is sometimes cause by a diet that's high in cholesterol.
In the Arthur Episode "Binky Barnes, Art Expert," Arthur and Buster tell Binky that the school burned down, to which he replies, "Wow, great!" Several seasons later, the episode "April 9th" aired, in which the school actually did have a fire (it didn't burn down, but was closed for a few weeks afterwards). Binky's reaction to that was...less enthusiastic.
Two newspaper gags featured in both "The Loudest Yard" (where one of the headlines is "Savino Indicted") and "Health Kicked" (with one of the headlines being "Savino Trial Takes a Turn");
Lincoln's attitude towards his crush Cristina in "Making the Case", such as attempting to kiss a picture of her and showing it his chest hair, when it's made clear she doesn't reciprocate his feelings and is so uncomfortable about it that she changes classes (or even schools);
And finally, Clyde's repeated cringeworthy pining after Lori. It's likely not a coincidence that this recurring gag was dropped after said firing.
The short-lived Comedy Central series Legends of Chamberlain Heights had a 2016 gag where NBA legend Kobe Bryant died in a helicopter crash. Come January 2020, this might be one of the worst non-9/11 example of this ever. Thankfully, the creators pulled all clips and encouraged the Internet to keep it buried.
Scooby-Doo has always had lots of jokes around Shaggy being addicted to some kind of drug, and Scooby Snacks containing (or being a metaphor for) some sort of substance, but they all took a sour note when it came out in 2016 that Bill Lutz, the original writer for the first season, was an alcoholic around the time of writing, and that the addiction was so bad, it broke up his marriage (his wife was alcoholic as well, but was able to recover), estranged him from his family, and caused him to die of liver failure only two years after the series premiered. One almost wonders if Scooby Snacks had a personal and not-so-innocent (and not-so-funny) connotation for him.