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 Travyon Martin, this all the more charged and slightly hard to watch.
In Futurama, one of the stations in the New New York tubeway system is 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" (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 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. (Fortunately, it jumps right back up to 11,000, and all the stock brokers 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.
In The Beast With a Billion Backs, Colleen, voiced by Brittany Murphy, is the only person in the universe to stay in heaven with Yivo.Beast With A Billion Backs was the last time Brittany Murphy did voicework on an animated show (besides her role as Luanne Platter on King of the Hill) before she died in December 2009.
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.
Godzilla: The Series has two. As if seeing the standing WTC towers in numerous background shots wasn't depressing enough as it was.
Randy Hernandez's line "Who's been playing dominoes with the World Trade Center?" in the episode "Future Shock" straddles between this and Harsher in Hindsight, due to having time traveled to a Bad Future.
"Metamorphosis" featured a giant centipede-cicada hybrid being on top of the Sears Tower (before the rename to Willis Tower), forcing Godzilla to bring the skyscraper down. The way how it collapses is eerily like that of both WTC towers collapsing in on themselves.
From Family Guy: "Road to Rhode Island" originally had a scene that depicted Osama Bin Laden getting past airport security by singing showtunes after Stewie did the same thing. Amazingly enough, this episode was produced and broadcast before September 11th, 2001, when few people knew who Osama bin Laden was and even fewer knew he would orchestrate an attack using commercial airplanes. The scene was removed from future airings of the episode and even from the DVD release, although it showed up on a later "best-of" DVD note The "Freakin' Sweet" DVD set. (One could also interpret this as Hilarious in Hindsight; but given the removal of the scene, it seems to belong here.) The worst part is that the show's creator, Seth MacFarlane, was supposed to be on one of the planes that hit the World Trade Center, but was lucky enough to miss it due to oversleeping from a hangover, his agent giving him the wrong flight information, and deciding to wait for another flight (until he saw the crash on the news).
Adult Swim reran an episode where Mayor West laughs uncontrollably for about a minute straight at the name of the character Boner from Growing Pains. That's all fine and good, until you realize that they aired said episode 2 days after Andrew Koenig, the actor who played Boner, killed himself.
In one episode, a Cutaway Gag had Bobby Brown and Whitney Houston sitting in bed and asking each other simultaneously if they want to smoke some crack. Owing to Houston's drug-related death in 2012, it's just not funny anymore.
The Cutaway Gag concerning Katie Holmes escaping Tom Cruise's manor. It becomes a little awkward after their divorce in 2012 (though given rumors that the marriage was a sham to cover up Tom Cruise's alleged homosexuality, this might be Hilarious in Hindsight in a sick way).
The gag from "Blind Ambition"note The episode where Quagmire saves a woman from dying of a heart attack while Peter goes blind trying to swallow the most coins so he can get into the Guinness Book of World Records where Peter tries to do good by dressing up as "Gary the No-Trash Cougar" and threatens kids at a school with a gun has now become yet another sick Seth MacFarlane joke thanks to the Sandy Hook elementary school massacre in Newtown, Connecticut on December 14, 2012. See also: Joe pointing a shotgun at a group of kids staring at him though his window as seen on the Christmas Episode "Road to the North Pole."
In "The Tan Aquatic with Steve Zissou", when Stewie thinks he's dying, he tells Brian to write down his final words. Instead, he draws a picture of himself hanging from a tree because he was bored and didn't feel like bowing to Stewie's whims. "Brian and Stewie" later revealed that Brian has been contemplating suicide for a long time because he feels like no one cares about him. In some viewers' eyes, this turns the visual joke from a warped one to a cry for help.
In 2013's "Turban Cowboy", one cutaway has Peter drive a car through the Boston Marathon, leaving injured, bloody bodies on the ground behind him, and is then praised for winning the race. Less than a month after it aired, the real Boston Marathon was attacked with explosives, creating a scene similar to the one in the show. Between that gag and the episode's plot of Peter joining a terrorist cell, the episode was yanked from Hulu streaming and has become the first Family Guy episode to air once before getting banned (as opposed to what happened to "When You Wish Upon a Weinstein," where it was banned for a time, then aired on TV, and "Partial Terms of Endearment" where it most likely will never air in America at all, but it does have a DVD release and people overseas have seen it).
"Save the Clam" opens with Horace pitching for Peter's softball team and being killed when a line drive is hit right back at him and strikes him. Two days after the episode first aired, Toronto Blue Jays pitcher J. A. Happ was seriously injured under very similar circumstances.
"Road to the Multiverse" ended with Human!Brian getting hit by a car and killed. This happens to the main universe Brian in "Life of Brian" and now he's Killed Off for Real.
In South Park, considering how badly Chef had a bridge dropped on him after his voice actor, Isaac Hayes, left the show two months after a stroke and an episode mocking Scientology (and someone - not him - told the powers that be that it was due to their mocking religion, when everyone would know they would put two and two together and know they meant Scientology), it was that much more disconcerting to find out that Hayes died on August 10, 2008. What's even worse is that on the official 2008 South Park Calendar, the month of December has Chef on fire on the bridge just after it was struck by lightning with the quote "Oh my god! They Killed Chef!" underneath.
The entire episode "The Jeffersons" (and the lines from the black man on "The Mexican Staring Frog of Southern Sri Lanka" who kept telling Jesus that Michael Jackson is still a beloved entertainer, despite being branded as a Memetic Molester), which brutally spoofed Michael Jackson, considering the death of the pop idol and how all the jokes about Michael Jackson being a child molester fell out of favor when he was acquitted in 2005 and when he died in 2009. Considering all the crap he got for his alleged crimes both in real life and on other TV shows that make jokes about Michael Jackson being a child molester, South Park actually had a shocking amount of sympathy for him on the episode "The Jeffersons" as a Man Child who acted this way to make up for the childhood he never had (and Kyle calls Michael out on acting like a kid when really he should be caring for the child he has).
"Butters' Very Own Episode" ends with Gary Condit, JonBenet Ramsey's parents, and O.J. Simpson being called out for being murderers who lie through their teeth and (in the second case) are playing the victims on top of that. Not nearly as funny and biting now that the Ramseys and Condit have been confirmed as innocent people Convicted by Public Opinion, and too late for Patsy Ramsey (who died of ovarian cancer) at that. And especially after O.J.'s book If I Did It.
The episode "Scott Tenorman Must Die", aired in 2001, has a scene where Scott finds a human finger in his bowl of chili (that turns out to be the finger of one of his parents, whom had been used as the secret ingredient of the chili Cartman cooked). Four years later, a woman named Anna Ayala claimed that a human finger was found in her bowl of Wendy's chili, but it turned out to be a hoax.
And for an in-universe example of this trope, the revelation in the Wham Episode "201" completely twists the climax of "Scott Tenorman Must Die" around in a new light. For those who wonder: Cartman's true father and Scott Tenorman's father are the same. Meaning that Cartman killed his own dad and thus that his his victory in "Scott Tenorman Must Die" was a retroactive Pyrrhic Victory.
In 2004's "Passion of the Jew," Mel Gibson is shown as a deranged man who goes after Stan and Kenny for hating Passion of the Christ and ends up making a fool of himself in front of everyone in town (even going so far as to act like Daffy Duck, back when he was a screwball). In 2006, Gibson was pulled over for drunk driving, and while being arrested he made anti-Semitic remarks and insulted a female officer by calling her a misogynistic name. Now in 2010, he's been taped making racial and sexist slurs and screamed at his wife while threatening her, in a way that is scarily similar to his insane depiction. Though this probably actually makes this episode even funnier, but it makes you wonder if the South Park creators knew something the audience didn't at the time.
The season five episode "Proper Condom Use" has parents pushing for sex ed to be taught to the younger grades. How young? Try "kindergarten" (which Chef finds appalling, as he believes that kids should be kids and not worry about sexual matters until they find out about it for themselves). It was just a joke about how insane the need for teaching sex ed to younger children can be pushed...until some schools actually proposed having sex ed classes for 1st and 2nd graders, though this is arguable, as the sex-ed proposed for grade schoolers is more centered on child molestation and what to do if you or someone you know is being sexually molested.
This school made condoms available to elementary students of all ages, but they are required to talk to a nurse first (despite opposition from some of the school committee who didn't want that requirement).
The episode "You're Getting Old" reveals that all of Randy's Crazy Awesome antics in the later episodes were literally nothing but the antics of a bored, bitter family man trying desperately to give his joke of a life some substantial meaning.
In the Season 8 episode "Red Hot Catholic Love", Cartman discovers that you can eat in reverse by sticking food up your ass and shit out your mouth. This catches on with the rest of the adults and they all adopt this method (around the same time that they become atheist to avoid going to church so their children won't be in danger of being molested). Twelve years later, during its 2012 Halloween episode, Tosh.0 unveils, as is usual for the show, a Real Life video of a man puking into a toilet, and crap comes out his mouth.
In "Volcano", Jimbo says that because lawmakers are making it harder to hunt animals, hunters pretend to act like the animals pose a threat to them as an excuse to hunt. This becomes cringe-worthy after the shooting of Trayvon Martin and the George Zimmerman trial put Florida's controversial "Stand Your Ground" laws (harming/killing someone if you feel poses a threat to you) into the national spotlight.
Then of course there's the Looney Tunes short "Often an Orphan," where Charlie Dog dramatizes how claustrophobic city life is, and ends this by screaming that the towers are falling. Now, there's no denying that this has become an aneurysm moment thanks to the September 11th attacks, but it wasn't specified what kind of towers were falling (on top of that, The World Trade Center towers weren't around in the 1940s. Groundbreaking started in 1966, construction of the first tower was from 1968-1970 and construction on the second tower was from 1969 to 1971. Even though five other lesser-known towers were constructed between 1980 and 1987, the Twin Towers themselves weren't opened until 1973 and stayed there until that fateful day in 2001).
Plus, the infamous Milli Vanilli episode. The scandal broke out two weeks after the episode aired, causing their songs to be removed from later airings and home video releases.
In a 1999 episode of Batman Beyond titled "Mind Games", Terry/Batman is receiving some history tutoring from Maxine. Trying to remember the presidents:
Terry McGinnis: Ford, Carter, Reagan, Bush, Clinton... I don't know.
Maxine Gibson: Come on. Clinton was the fun one, then came the boring one.
Terry McGinnis: They're all boring.
This probably still counts as a "Funny Aneurysm" Moment with maybe a dash of Hilarious in Hindsight, but there were quite a few gags and references in other shows between the years 1998 and 2000 about how Al Gore would immediately follow Bill Clinton in the Presidency and be considered a boring president.
The New Scooby-Doo Movies: Special guest voice Mama Cass helps the gang solve a mystery in an abandoned candy factory. A majority of the jokes are about her weight. This becomes icky when one recalls that Cass Eliot died of obesity-related causes. The gag about her having to eat her way out of a room filling with candy (pretty damn crass in itself) is worse given the persistent rumor that she had died choking on food.
In one episode of Extreme Ghostbusters, there's a fog monster that the heroes are trying to destroy. During their Hard Work Montage, it cuts to clips of the fog monster eating different landmarks of New York. One of them is the World Trade Center. Bonus chill points because the fog monster rises from the ground as a dark roiling mass, making it look like the buildings are being consumed by smoke.
In one episode of Hey Arnold!, as Arnold tries to teach a held-back student named Torvald math, he tells him how math is important and that without it, you might have trouble with things like pluses and minuses. This cuts to an Imagine Spot of an adult Torvald at Wall Street pressing a minus button on a computer, causing the world economy to crash. With the 2010 flash crash in which a mysterious force caused the market to drop 600 points in five minutes, and recover within 20 minutes, it brings to mind fears of a real-life economic collapse.
Helga's home life was once considered funny in a dark way as it showed that the family was falling apart ever since her sister Olga left home for college (her father became a jerk, her mom gave up on being a parent and began drinking "smoothies" to forget). "Helga on the Couch" showed that Helga has been neglected for years and had to walk to preschool by herself because her parents were too busy listening to Olga's piano playing.
Inverted in the pilot episode of Drawn Together. Comedy Central initally didn't want Toot Braunstein to cut herself, as they felt that the gag was too tasteless. A year before the show premiered, an episode of The Real World: San Diego revealed that Frankie Abernathy was a cutter. Because of its relevance, the scene was left in the show.
For the same reason as the Family Guy Whitney Houston gag, an American Dad! gag on the episode "Francine's Flashback," where Stan brings Whitney Houston (as voiced by Debra Wilson from MADtv) over to sing Francine's favorite song "The Greatest Love of All" note Though a later episode revealed that Francine's favorite song is Prince's "Little Red Corvette", which Houston refuses to do — until Stan offers her a bag of crack cocaine and she sings, "No matter what they take from me/They can't take away my dignity!" before diving for the bag and missing, which is then followed by Francine throwing the crack out the door and telling Houston to fetch it like a dog. Because of Houston's death, that scene is edited out in reruns, but has returned sometime later.
Some of us gave nervous laughs when in 2007 Lite Brites of the "Mooninites" Ignignokt and Err were placed around Boston in a Viral Marketing scheme and mistaken for bombs (which caused the episode titled "Boston" to be banned indefinitely). Six years later when bombs did explode at the Boston Marathon, no one was laughing (and the Banned Episode will still never get shown).
Plus, the second president of Cartoon Network left following this incident, which influenced a restructuring of the network that spawned what could be considered Network Decay.
In Celebrity Deathmatch, 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 in bad taste due to Steve 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.
In 1991, NBC's Saturday morning cartoon lineup included the new series Space Cats. Each episode ended with a Spoof Aesop, the first one being "Don't watch cartoons. They will rot your brain." Another character whispers "Don't say that! We'll lose our jobs!" A year later, Space Cats and all other NBC Saturday morning cartoons were gone, having been replaced by the live-action teen sitcoms like Saved by the Bell and City Guys (and later still, those would be replaced with a Saturday edition of Today and local programming).
Adventure Time: When Ice King was first introduced, his patheticness and total inability to get anybody to love him were quite amusing. With the reveal in season 3 that the Ice King is a normal man whose cursed crown cost him his love and his memories you're more likely to want to give him a hug.