Harsher In Hindsight / Stand-Up Comedy

• George Carlin spent the first ten minutes of his 1999 special, You Are All Diseased, by mocking airport security, emphasizing the unlikelihood of a terrorist attack, how he finds terrorism "entertaining", and how everyone needs to settle down and enjoy life. Needless to say it wasn't so entertaining after 9/11 happened.
• In 1990, Brazilian magazine Casseta Popular (whose members would be part of the comedy group Casseta & Planeta) did a satirical analysis of each team/country on the upcoming FIFA World Cup. Yugoslavia's one said there was no joke to be told as it was an unremarkable and "meh" country. One year later...
• An oft-repeated Billy Connolly routine from the '90s onwards revolved around his visit to the doctor for a prostate exam. In 2013 he was diagnosed with prostate cancer. Luckily he was eventually given the all-clear.
• Jason Cook in the emotionally charged climax to his stand-up show "Joy" does a list, the "5 worst things to happen to the Cook family" topped at #1 by his Dad's death to cancer. he then presents a new list: "5 people who should have died of cancer instead of my Dad". #2 was originally Jade Goody, who, during the tour, died of cancer. It was changed, but the audience is informed of this change, hence Liverpool making the list twice.
• In a particularly horrifying example, British magician and comedian Tommy Cooper had a heart attack and collapsed live on stage, being broadcast to millions across Britain. As this was not out of character for his act, the audience started laughing, only to lapse into horror as they realized it wasn't an act. After seeing that, watching old recordings of his act can be pretty painful.
• Bill Cosby:
  • One track on his Himself album is titled "Kill the Boy". It begins with Bill's wife telling him to go upstairs and kill their son. Not so funny Ennis Cosby's was murdered on January 16th, 1997. He also made a remark about his daughters killing his son. Something like: "The boy is eleven. I don't think he'll make it to twelve. His sisters will kill him."
  • Sending a Drugs Are Bad message is good... until people discovering you were drugging and raping women.
  • The many rape allegations against Cosby that led to his prison sentence makes his Spanish Fly routine, all about his desire to slip the drug into women's drinks, very uncomfortable. Plus, it appeared in an album called It's True! It's True! (and let's not delve into how Bill Cosby Talks to Kids About Drugs is now hypocritical)
  • In November 2013, Bill Cosby did his first standup special since Bill Cosby Himself called Far From Finished. A year later, countless rape allegations against Cosby began coming to light, and with the swift backlash against him, Cosby's career may indeed be finished.
  • In light of those rape allegations and his subsequent conviction, the numerous times in his career where Bill talked about sex, like giving The Talk to his daughters, have also become this trope.
• Rodney Dangerfield made a statement to his fan club before going into surgery saying "If all goes well, I will be out in a couple weeks. If not, a couple of hours." He would die from complications from that operation within a few weeks. Lightened by the fact that the statement was so typical of his style of humor, and that he might have thought the irony funny.
• At WrestleMania V there was a segment where comedian Morton Downey, Jr. kept blowing cigarette smoke in Roddy Piper's face. At one point Downey even said, "That's good for you. That's healthy. Look, you can live as long as I have." Morton Downey, Jr. would die on March 12, 2001 from lung cancer.
  • Invoked twice here. Downey died at age 68. Piper didn't make it that far, dying on July 31, 2015, aged 61.
• During Jeff Dunham's All Over the Map tour/special in 2014, Malaysia "asked" Jeff not to use Achmed the Dead Terrorist, one of his most popular characters. To get around this, he instead used "Jacques Merde^note Jack Shit, the Dead French Terrorist". Given the terrorist bombings in Paris in 2015 and onwards, this has become a lot more.... Awkward.
• After the 2017 Best Picture Oscar mix-up, Billy Eichner tweeted “If anyone in the In Memoriam is still alive, please let us know!” Turns out someone was: The name of late costume designer Janet Patterson was shown alongside a picture of producer Jan Chapman, still very much alive and not happy about the error.
• Jeff Foxworthy:
  • When the Atlanta Olympics were announced, Jeff Foxworthy had a several minute set about how Georgia would inevitably screw it up. Then there was a bombing.
  • In 1998, he had a joke where he was discussing Red Necks' love of commemorative plates, and NASCAR, referring to a "Legends of NASCAR" plate with Dale Earnhardt. Foxworthy's redneck says "That's Dale Earnhardt, he wasn't in a wreck or nothin', that's just catsup on the plate". Three years later at the 2001 Daytona 500, Dale Earnhardt was killed in a crash.
• All the drug addiction jokes directed at Greg Giraldo (which he was always a good sport about, even making a few himself) at the Comedy Central roasts and on his Comedy Central Presents episodes became a lot more uncomfortable when he died of a prescription drug overdose.
• Tom Green's line of "if I get lucky/I'll get a disease!" from his 1999 novelty single "Lonely Swedish (Bum Bum Song)" came back to bite him big time when less than a year later, he was diagnosed with testicular cancer, which abruptly ended his popular MTV comedy program. He was able to successfully beat the disease, but he admits to no longer finding that line funny.
• Rolf Harris:
  • In Roy Chubby Brown's 1998 show Chubby Goes Down Under and Other Sticky Regions, Brown jokes about Harris' songs being about sex ("Tie Me Kangaroo Down Sport"? What's all that about? "Two Little Boys"? Dirty bastard"). Barely a decade later, Harris was revealed to be sexual predator.
  • Bernard Manning even took a shot at him that proved quite prophetic.
  Two Little Boys, dirty fuckin' bastard.
• Mitch Hedberg
  • His album Do You Believe in Gosh? has Mitch receiving answers to his questions from an audience member, Phil, before he asks them with this following conversation:
  Phil: Downhill!
  Mitch: Hey, Phil, which way is my career going?
  • Another album Mitch All Together has a bit where he jokes about someone asking him "where do you see yourself in five years?" He died less than two years later.
• Bill Hicks was a very, very heavy smoker, who habitually tore the filters off his Marlborough Reds before smoking them and joked about going through "two lighters a day" in his act. One routine had him confessing his failure to quit, which is greeted with ecstatic cheering from the audience. He turned this into a joke too. "Bill's gonna kill himself, WOOOH! Bill's gonna lose a lung, YEEAH!" He didn't lose a lung, but did die from aggressive pancreatic cancer at the age of 32. So, err, yeah.
• When you consider that comedian Richard Jeni was diagnosed with clinical depression and killed himself two years after his last HBO stand-up special, A Big Steaming Pile of Me, watching it is like watching a videotaped suicide note with a laugh track. Of course, this is a risk with any comedian who talks about their married and/or personal life, really.
• In his routine at the 2003 Melbourne Comedy Gala, Jimeoin joked that Steve Irwin was dead, saying, "You wouldn't be surprised if he was... attacked by a crocodile." Come 2006, a lot of people were surprised to hear Steve Irwin was attacked and killed by a wild animal (though it was a sting ray, not a crocodile that killed Irwin, it's still fairly upsetting — and not at all surprising — that Steve Irwin would die at the proverbial hands of an animal).
• Sam Kinison had several:
  • He did a rant about how people overreacted to drinking and driving. His untimely death was caused by some drunk asshole crashing into his car, and Kinison reportedly had drugs in his system at the time, making his advocacy of drug use darkly ironic.
  • The "driving to Barstow" bit on Have You Seen Me Lately eerily echoes the time and place of Kinison's death, in a car crash in the California desert.
  • Related to Californian deserts, the 2010s droughts lead many people to compare the state to Kinison's famed "YOU LIVE IN A FUCKING DESERT!" routine.
• In a bit about bicyclers in New York in 1997, Denis Leary joked that the last person to get a ticket for speeding in New York was a guy who crashed his plane into the Empire State Building in the 30s. Four years later, the joke became a bit awkward...
• In his 2017 special Hitler's Dog, Gossip and Trickery Norm Macdonald does a lead in to a joke where he mentions the two leading causes of death are heart failure and cancer. This is sad to watch now, as Macdonald died from cancer 4 years after the special was filmed. (As well as having been already diagnosed with cancer years earlier, which he hid from almost everyone until his death in 2021.)
• In the 1960s impressionist Vaughn Meader recorded two comedy albums entitled "The First Family Vol. I" and "The First Family Vol. II" poking fun at then White House occupant John F. Kennedy. When he was assassinated, nobody could bear to see Meader perform his act and all unsold copies of his records were destroyed and both albums remained out of print until the turn of the millennium (when they were released on CD).
• Patton Oswalt: In one of his comedy specials, Oswalt jokes about how difficult it is to write edgy comedy now that he's so happily married. A few years later, his wife died suddenly, and he followed up with a comedy special in which his grief plays a large role.
• Joan Rivers:
  • On August 28, 2014, Joan Rivers joked at a stand-up performance that she could "go any day now". Just hours afterward, during what was supposed to be a minor throat surgery, she suddenly stopped breathing and was placed in a medically-induced coma. She died a few days later.
  • Before she passed away, she was set to do a UK tour called "Before They Close the Lid".
• In his 2008 comedy special Kill the Messenger, Chris Rock joked about Senator John McCain's presidential campaign, saying about his time as a POW during the Vietnam War, "I don't wanna vote for nobody who got captured, I wanna vote for the motherfucker that got away." In 2015, then-nominee Donald Trump attacked McCain's service, saying "I like people who weren't captured." McCain was so incensed by Trump that when he died in 2018, he specifically prohibited then-President Trump from attending his funeral.
• Jimmy Savile:
  • In 1987, Scottish comedian and magician Jerry Sadowitz made a joke about Savile during his show at the Edinburgh Festival The Total Abuse Show, which became the album Gobshite. The Savile joke was te reason the album was pulled.
  My mate reckons Jimmy Savile's a paedophile. Rubbish, he's a child bender. The reason he does all that charity work is so he can gain public sympathy for when his fucking case comes up.
  • In July of 2008, he joked that Robert Novak contains "the cure for the cure for cancer"... the week before he was discovered to have a massive brain tumor which ultimately killed him a year later.
• Hungarian comedian Gergely Szőllősy-Csák's standard self-deprecating stand up acts, in which he constantly poked fun at his lanky physique, often joking that he looked like someone suffering from a deadly disease, became pretty unsettling after he died in June 2014 due to a bacterial infection.
• Christopher Titus's first two stand-up specials^note Norman Rockwell is Bleeding and The 5th Annual End of the World Tour (and the original first episode of his sitcom Titus) both have bits in which Christopher gushes over how wonderful is girlfriend Erin is (especially compared to the briar patch of psycho-bitches he dated in the past, including the abusive Noelle, who, like Titus's violent, manic-depressive schizophrenic mom, had a high IQ, was said to be beautiful, and often snapped and abused Titus for little or no reason). Fast forward to Love is Evol and Neverlution, in which Titus and Erin (renamed "Kate" or referred to as "my ex-wife" for legal reasons) are divorced and Erin turns out to be no different than the psycho-bitches Titus dated — in fact, Erin was worse: She cheated on Titus with two men (one of which was a 60-year-old man who was richer than Titus), stole her children's college money so she could get plastic surgery, drank excessively, tried to kill Titus in front of his daughter, goaded him to kill himself just like his mom and sister, and committed perjury in court by claiming that Titus was abusive just so she could take him for everything he had^note California is usually a "no-fault divorce" state, meaning that if a couple divorced, everything they own is automatically split down the middle. However, if one spouse claims that the other abused him or her and/or their children, then everything the abuser has becomes property of the one who claims abuse. The only good thing to come from this is that Titus now has a girlfriend (Rachel Bradley) who actually loves him and who comes from a functional family.
• Robin Williams:
  • In his 2002 comedy special Live on Broadway, Robin Williams mocks the French for their supposed outrage about Lance Armstrong winning the Tour de France bicycle race despite the ravages of cancer: "'He is on chemicals!' 'It's chemo-therapy, you little toad-suckers!'". Though in 2012, it was determined that Armstrong had used performance-enhancing drugs in his victories, and he got stripped of all his titles.
    • During the same special, Robin discusses the heightened security following the September 11th attacks, and how such measured singled out Muslims and Middle Eastern people in a "totally random" manner, adding "every Black and Hispanic man in the room is going, 'Thank you, God! Oh, yes, we're off the list, motherfucker, yeah!'" As it turned out, both Black and Hispanic people wouldn't be any less discriminated against, as the September 11th attacks also led the US government to establish the Immigration & Customs Enforcement (ICE) agency, which would more aggressively scrutinize immigrants, especially those from Mexico and Latin America, leading to the 2018 scandal where ICE forcibly took the children of immigrants and refugees from their families to detention centers; and Police Brutality against Black people increased in the years that followed, leading to massive international protests against policing after George Floyd's murder by police officers in 2020.
  • His final comedy special, Weapons of Self-Destruction in 2009, has gotten uncomfortable since his suicide in August 2014. First of all, the title, Weapons of Self-Destruction, has taken on a whole new meaning. Second, in the special, Robin shared a humorous story about his GPS mistakenly telling him to turn while crossing a bridge, saying "No can do, HAL... Not that depressed, really."
• The Whitest Kids U' Know: The Russian Roulette skit involves Trevor Moore roping up the rest of the group into playing the game, eventually killing himself. On the night of August 7, 2021, Moore would accidently kill himself by jumping off his balcony while drunk.
• In a few episodes of the podcast U Talkin' U2 to me?, the hosts Scott Aukerman and Adam Scott make several comments about the "death" of comedian Harris Wittels. They were jokingly referring to him as dead, since in a previous episode he had expressed his dislike for the band U2, the subject of the podcast and favorite band of the hosts. Wittels in reality died of a drug overdose a few months afterward. A new listener could easily mistake the order of events, as Aukerman and Scott, in their typical very dry sense of humor, even discuss how sad his "funeral" was.

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