In the novel Jumper, the main character drops a terrorist from the World Trade Center. He catches him before the man can die, but still... 9/11, anybody?
Early on in The Catcher in the Rye, the main character Holden quips "This is my people shooting hat. I shoot people in this hat." This was a harmless bit of sarcasm for decades until the book became associated with John Lennon's assassin and John Hinckley, attempted assassin of Ronald Reagan, respectively.
This happens in (of all things) Dave Barry's Guide to Guys. While talking about a mechanic he knew who was deeply into fireworks, Dave writes, "If those radical Muslim fundamentalist terrorists had had Ed on their team in 1992, the World Trade Center would now be referred to as the World Trade Pit." This was probably funnier in 1995, when the book was written, before a pair of precision-aimed airplanes created a World Trade Pit. Hey, those skyscrapers collapsed all the way down — and had underground levels and a subway connection. Their footprints are now filled by two sunken pools with water fountaining down the sides, an enduring memorial to where the Twin Towers once stood.
Another moment based around the same event: The movie Big Trouble, based on another of Dave Barry's books, was one of several that had their release delayed because of 9/11, due to the plot involving hijackers breezing through airport security. With a bomb. And the Air Force being sent to shoot the hijacked plane down. Did we mention that it was scheduled for release on Tuesday, September 11th, 2001?
Dave predicts the future again, albeit on a smaller scale, in his 1991 book Dave Barry's Only Travel Guide You'll Ever Need. He talks about how on a road trip through South Dakota, there was a hyped store called "Wall Drug", advertised on the side of the road for hundreds of miles on billboard after billboard ("153 miles to go", "146 miles to go", etc). His wife, Beth Barry, wanted desperately to go there, but he drove right past it, much to her chagrin. At the end of the story, he laments jokingly, "You know how certain incidents become permanent sore points in a marriage?...That's the status that the Wall Drug Incident has achieved in our marriage... If she ever files for a divorce, this is the first incident she'll mention to the lawyer." Dave must have a jinx or something, because they divorced in 1993. Whether she did, in fact, bring up "The Wall Drug Incident" to the lawyers in unknown.
There's the scene towards the end of the fourth Hitchhiker's book, So Long and Thanks For All the Fish, in which Marvin reads God's Final Message To His Creation ... which turns out to be 'We apologize for the inconvenience'. Given Douglas Adams' sudden death from a heart attack, leaving the sixth book unfinished (now being written as a posthumous sequel called And Another Thing... by Eoin Colfer), that message takes on a whole new meaning.
From Dirk Gently's Holistic Detective Agency is the line, 'I think a ghost is someone who died either violently or unexpectedly with unfinished business on his, or her - or its - hands. Who cannot rest until it is finished or until it is put right'. Between the unfinished nature of The Salmon of Doubt and the author's own dissatisfaction with the Downer Ending of Mostly Harmless it seems terribly apt.
There is also a bit in the same book about Dirk and the police officer experiencing 'a chill as the dead man's voice filled the room' while listening to an answering machine message. Not too bad... except when the author reads those lines on the audiobook.
His final Hitchhiker's Guide book Mostly Harmless introduced The Guide Mark II, an effectively omniscient and omnipotent version of The Guide, existing singularly in the entire multiverse. (The rest of this entry is a spoiler for Mostly Harmless, a Funny Aneurysm Moment, and Fridge Brilliance all rolled into one. You have been warned.) The device is revealed as a Vogon plot to destroy Earth once and for all, and prevent its resurrection in any parallel universe by the expedient of collapsing quantum timelines so that its final destruction is truly final. Anyone that The Guide Mark II can use to further its goals will think their life to be going swimmingly, until the Guide has finished using them, at which point they'll probably be killed. The author's most spectacular example is Agrajag the Ever-Murdered, who trapped Arthur Dent before Arthur Dent visited Stavromula Beta (actually Stavro Mueller's "Beta" nightclub) and ducked an assassin's bullet which slew Agrajag yet again. This ensured that Arthur Dent would survive anything the universe threw at him until this event happened. This was orchestrated by The Guide Mark II to ensure Arthur Dent was on Earth when it actually blew up. Did The Guide Mark II ensure Douglas Adams would complete and publish this, and then ensure Douglas Adams would not alter the fate of Earth?
The Great Pacific War by Hector Bywater has a major one of these because, even though it was written in 1925 and is set in 1930-1933, it contains a Japanese surprise attack on Pearl Harbor.
Robert Jordan of The Wheel of Time fame's biography stub in most of his books included a line that he intended to keep writing "until they nail his coffin shut" — and so he did, since he passed away in September 2007, leaving the last book unwritten.
There was also a joke among certain internet fansites that goes along with the stub stating something similar to that. Thus, some people initially thought that Jordan's real obit was a joke.
This is an odd, creepy sort of subversion- he meant that the last few times he included it. He knew his health was on the decline but stayed at work until the end. He went out of his way to make sure there were enough notes for somebody else to finish Wheel of Time if he didn't quite make it. Brandon Sanderson was chosen to finish the final book.
Like with any author of a long series of DoorStoppers, there were plenty of jokes about Jordan dropping dead before finishing the series. They all became suddenly much less funny when he was diagnosed as fatally ill.
From Animorphs: in #46, Marco gives a rant on the state of events. Tobias concurs with an unintentionally sad comment.
Tobias: Marco has a point. Particularly Americans. I mean, we've got no enemies at sea, not many on land, and those aren't exactly real scary. The country's just not ready for war. Maybe it's arrogance, maybe a combination of things, but the average person on the street just doesn't think another World War is possible.
In book 37, the Animorphs hijack a (private) plane and fly it into a large building full of Yeerks. Remind you of something?
Also his first book under the Bachman pseudonym Rage, which was about a boy shooting students and teachers at school. King pulled the book out of print because of Real Life school shootings, when copies of the book were found amongst the gunmen's possessions.
In the "appreciation by Maurice Sendak" that accompanies the Yearling edition of The Phantom Tollbooth, Sendak notes how the monsters and obstacles in the book are "prophetic and scarily pertinent" to modern living and how Juster's "allegorical monsters have become all too real".
Christopher Brookmyre's book A Big Boy Did It and Ran Away describes an attempted terrorist attack on the 6th of September 2001. While the book was published on October 4th of the same year, the writing took place before the events of September 11th. To make this even more cringeworthy, the tagline of the book was "Terrorism, it is the new Rock'N'roll". Needless to say that some re-wrapping was needed after that. Brookmyre's universe tends to incorporate real-world events into the canon established by his previous titles; thus, more recent titles, such as 2008's A Snowball in Hell, consider the unfortunate co-incidence of timing and the resultant impact this has on the characters involved.
Also, in his first book, Quite Ugly One Morning, a character reflects that a doctor character who has quietly been killing elderly patients for years (and who is finding it hard to tell which of the doctor's patients have died naturally and which were murdered, or even for how long this has been going on) whose death toll is in the double if not triple figures is the worst serial killer in British history. And then, just two years later...
While editing her Kiesha'ra series, Author Amelia Atwater-Rhodes had a webcomic series called ihme* (Short for I Hate My Editor), which parodied the events of Kiesha'ra. It delved into possible alternative skylines, freely played with flanderization, and makes humorous events out of what would actually be traumatic and disastrous in the series' canon.
Lords and Ladies has a segment where Esmeralda Weatherwax, strongest and most focused of witches, thinks she is losing her mind, remembering parts of the house that she doesn't have. In light of Sir Terry's... embuggerance, that was painful to read.
In Masquerade and The Truth, several characters agree that multiple exclamation marks are a sign of a diseased mind. In Thud!, the text uses them for Vimes's Punctuated! For! Emphasis! moment. As said above, Terry Pratchett later announced he had Alzheimer's, making reading the latter passage nearly physically painful. There are also the passages in Small Gods where Om worries about losing his memories (again), how it would feel to have the knowledge drain away and how a part of him would be there, helpless, as he dwindled. The despair of the Great God takes on an even more moving and depressing tone in light of the above.
Snuff is even worse for this. In Thud the multiple exclamation marks tend to be used with precision. In Snuff... less so. And other aspects of the style and technique show similar changes.
It's not as horrible as Sir Terry's current condition, but descriptions of the lack of rain in The Last Continent hit a little too close to home in certain parts of Australia of late. Like the towns that are completely out of water. Some inhabited places in Australia have not seen rain in six years.
Jingo was written in 1997 and, in addition to parodying Lawrence of Arabia, it contained a number of satirical observations on mindless patriotism and xenophobia against Arabs. Reading it after the start of the Iraq/Afghanistan wars in the 2000s feels a bit awkward in how accurate it gets.
In Guards! Guards!, Vimes nearly panics when he sees Constable Carrot is about to try and arrest the Patrician, Havelock Vetinari, for a minor traffic violation. Near the end of Jingo, several books later, Vimes is tasked with arresting Vetinari on charges of treason, for turning Leshp over to the Klatchians without consulting the guilds or the nobles, and Vimes has a whole dramatic Inner Monologue about how leaders can't be placed above the law. It somehow manages to be Hilarious in Hindsight at the same time when Vetinari insists that he be placed under arrest, including "being run out of town on a rail" and all that, and the whole business with Leshp turns out to be part of his plan.
In Grendel by John Gardner, the work ends with the words, "Poor Grendel's had an accident. So may you all." Eleven years later, Gardner died in a motorcycle accident (days before his wedding, no less).
Gaudy Night (1935), one of Dorothy L. Sayers's Lord Peter Wimsey novels, features a scene where a few of the characters discuss politics. An ex-soldier who served under Wimsey, and is now working as the college porter, makes an approving offhand mention of Hitler doing "interesting social experiments" in Germany. There are also some mentions of German policies by the dons, especially the Nazi idea of keeping women “in their place”. note If you follow these references carefully, you’ll find that Sayers was (presciently) using lack of disapproval of the Nazis as an indication that a character is either naïve, or opposed to Harriet’s (and Wimsey’s, and clearly Sayers’s) position on gender relations.
In The Girl Who Kicked the Hornet's Nest from Stieg Larsson's The Millennium Trilogy, there is an incident where a newspaper editor drops dead of a heart attack at his desk. It's very difficult to read the passage for anyone who knows how Stieg Larsson died.
In addition, upon (the possibly Jewish) Gatsby's death from a madman, the narrator ends the description of the scene with "...and the holocaust was complete."
Fitzgerald seems to be astonishingly unlucky with these. In The Beautiful and Damned, Anthony meets a disagreeable character who happens to be Jewish:
I detest these underdone men, he thought coldly. Boiled looking! Ought to be shoved back in the oven; just one more minute would do it.
In Albert Camus' The Plague, Tarrou says, "In fact one might go farther; have you ever heard of a man with cancer being killed in an auto smash?" Camus had a life-long struggle with Tuberculosis. He died in a car crash.
An In-Universe one in the original Starship Troopers novel: Johnnie Rico and his campmates had been joking about the 31 capital offenses in the Terran military, which they called "crash landings". When it came out that one of his comrades was facing a possible crash landing, he finds the jokes of old a lot less funny.
In a case of either this or Hilarious in Hindsight, depending on how you handle your childhood memories being perverted): In 1971, Roger Hargreaves started the Mr. Men book series, the third of which was titled "Mr. Happy". The titular character was a very happy little yellow man. Ten years later, guess what Robin Williams decided to nickname his penis? (And his action became aTrope Namer.)
The last word that Will Rogers wrote before he died was the word "death".
At the end of Emily Neville's It's Like This, Cat, troubled college drop-out Tom decides to enlist in the Army for three years as a way of getting his life back on track, finding stability and, with some luck, making money to continue his education and marry his girlfriend. He even speculates that he'd be drafted in a year or two, anyway, but seems very convinced, and no one contradicts this, that he can be stationed in New York throughout his three years of service. Well, the book was published in 1963, and guess what happened in 1965...
Not as bad as most of the things on here, but bad enough. In 1973, one year after the last Apollo moon mission, Carl Sagan wrote a book showing one of the landing sites on the moon with the caption "The party is over and the guests have gone home." Nobody has been back to the moon since.
Saki's story "The Unrest-Cure" involves a practical joker in pre-WWI England (near Saki's "present day") convincing a sedate gentleman that he's planning to "massacre every Jew in the neighborhood." The gentleman exclaims that it will be "a blot on the Twentieth Century!" but the story ends with the century "unblotted." Later on, the century got good and blotted.
Prior to the release of the fifth Harry Potter book, a filk of "Cell Block Tango" from Chicago that contained various fans' predictions on who would die in that book was posted on the Harry Potter Filks website. The irony of the filk lies not so much in the fact that the character that did die in that book was not among those listed, but that two books later, three of the ones listed did after all. Read at your own risk if you haven't finished the series yet.
Another Potter one: Back in Phoenix, Moody goes on and on about the possibility of death while flying to Headquarters, and is told nobody is going to die, and the whole thing is played for laughs. Guess what happens in Hallows while flying to HQ? Yeah.
Early in HBP, Ron and Harry are talking about hoping that the new DADA teacher, Snape, will succumb to the trend of DADA teachers leaving after only one year. Harry flippantly says something along the lines of "I'm hoping for another death". Well, Snape certainly leaves the post after another death...
Ron very often predicted future events with his jokes—more often than not becoming these.
Almost every scene with Sirius and Dumbledore.
Especially then scene with the Mirror of Erised in the first book. Warm pair of socks, anyone?
And, with Fred. "When I get married, I won't be bothering with any of this nonsense. You can all wear what you like and I'll put Mum in a full Body-Bind Curse until it's over." Except, he doesn't get married, does he?
Same with Cedric "That'll be something to tell your grandkids Ced. You beat Harry Potter!"
Everything Amos Diggory says to or about Cedric involves him living to a ripe old age. One can only assume Rowling did that on purpose.
In Goblet of Fire "If the Hogwarts Express crashed tomorrow and George and I died, how would you feel knowing the last thing we heard from you was an unfounded accusation?" As of Deathly Hallows, jokes about Fred dying are rather unfortunate...
Even worse, the last thing Fred heard from Molly before he died was her yelling at him for letting Ginny come to the battle... not exactly an unfounded accusation, but close enough.
For that matter, later on in Goblet of Fire, Fred and George temporarily grew long white beards when their attempt to fool Dumbledore's Age Line with an Aging Potion backfired. That's the closest Fred ever got to true old age...
One that wasn't even funny in the first place: Order of the Phoenix has Molly trying to face a boggart, which keeps turning into the corpses of her children. She sobs that she thinks of them dying all the time, and worries that it'll happen before they can reconcile with Percy. So of course, when Percy shows up for the Battle of Hogwarts in the next book, he makes amends to his family and fights alongside them... and then Fred is killed.
After the anthrax scare following 9/11, it's more than likely that more than a few insensitive fans have made at least one inappropriate joke about Rita Skeeter sending prank mail infested with anthrax spores to Hermione (kind of like that one "curse mail" incident from Goblet of Fire).
Near the end of Prisoner of Azkaban, while Snape is in a rage about the escape of Sirius Black, Fudge comments to Dumbledore that he seems quite unstable and that the Headmaster should watch out for him.
In Harry Potter and the Chamber of Secrets, they're trying to figure out who Tom Marvolo Riddle is and why he won an award for Special Services to the School, and Ron jokes that it is because he killed Moaning Myrtle. At the end it is revealed that Tom Marvolo is Lord Voldemort, and he did in fact murder Moaning Myrtle when he opened the Chamber of Secrets. It is also shown that he he turned in Hagrid for the murder. It is taken Up to Eleven in the penultimate book when it's discovered that he used Myrtle's death to create one of his horcruxes!
In Sewer, Gas and Electric, a 20 Minutes into the FutureCyber Punk parody from 1997, the Empire State Building has been replaced by a mile-high skyscraper called the Phoenix. The original building had been destroyed by a colliding airliner. No longer funny in hindsight.
Given how the building had already had a plane crash into it in the past, it probably had this effect on some at the time it was written too.
Three Men on the Bummel by Jerome K. Jerome is a lighthearted Victorian comedy about a bicycle tour through Germany. The narrator laughs about the German love of order and deference to authority. The last chapter is extended chuckling about totalitarianism and authoritarianism: the German citizen will do anything the police tell him, makes the perfect soldier when you give him a uniform and march him into another country, and just might come into some trouble under a bad government.
Buzz Aldrin's novel Encounter With Tiber has a Space Shuttle failing to make orbit and crashing set within two years of the 2003 Columbia re-entry breakup.
This is more likely to be a reference to the Challenger disaster of 1986.
P. G. Wodehouse has one tucked away in Bachelors Anonymous. This book, written in the seventies, includes this throwaway joke:
Mr Llewellyn's plane was on its way. A complete absence of hijackers enabled it to reach New York...
In Wraith Squadron, Wedge Antilles beats one of his pilots in a race. She complains that he cheated, and he responds by laughing and saying
"When an Imperial laser cuts through your canopy and hits you, the energy will superheat the water in your tissues. They will literally explode. If there's enough of your X-wing to retrieve, they'll have to hose down the inside. When that happens, will you complain that the TIE fighter pilot cheated?"
"What will you say?"
"I won't say anything. I'll be dead."
And, in the climactic battle at the end, guess how she dies?
Well, it wasn't a laser... it was the Star Destroyer she was flying around inside of dropping onto the moon and self-destructing.
The Star Wars Expanded Universe is fond of these. Mostly they deal with Han and Leia's children. First there was Luke's vision of them. The Jedi Academy Trilogy gave us Jacen Solo holding off Exar Kun's minions. Then there was Master Ikrit's view that Anakin Solo would become the greatest Jedi; he gets Killed Off for Real in the New Jedi Order. More recently, we had Young Jedi Knights have Jacen say "What's the difference between a Jedi Knight and a Jedi Master? Ask me in about twenty years!" Nearly twenty years later, he's a Sith Lord.
In the novel Good Omens, first published in 1990, has a bit that is now not so funny to read anymore... Remember the Horseman of the Apocalypse, Pollution? His favorite disaster was an oil spill? Causing mayhem, destruction of life, and disaster for years to come? Yeah... Ouch.
Though in all fairness, the novel could've been written in the aftermath of or inspired by the then-recent Exxon Valdez oil spill (occurred in 1989), which was until 2010 the worst oil disaster the United States had ever seen, with "destruction of [wild]life" being constantly reported on in the news and "disaster for years to come" predicted by all the experts.
An off-handed joke about even a demon not being cruel enough to turn someone into Freddie Mercury is now a lot less funny, knowing that at the time, he was dying a slow and painful death of AIDS. At the time of the book's publication, there were rumors that he had contracted the disease, but he had repeatedly denied them. The truth came out a little over a year later, shortly before his death.
In the book, Pollution replaced Pestilence, who retired in defeat after the invention of antibiotics. Fast forward 25 years, and we have scientists worrying about world-wide flu pandemics, there was a big ebola outbreak killing tens of thousands that was barely kept from spreading to the rest of the world, an entire generation (and their young children) are dying of AIDS in Africa, and we are confronted with an increasing number of multiple-drug-resistant strains of bacterial diseases like tuberculosis. And there havsn't been any real breakthroughs in finding new antibiotics in ages.
The Tales of the City books have many of these. There's just something about cheerful, utopian gay-themed romantic comedies written in the 1970s.
Star Trek: Articles of the Federation ends up having one within the context of the wider Star Trek Novel Verse. The novel ends with a somewhat upbeat comment from President Bacco's Chief of Staff and prime supporter, Esperanza Piniero, pointing out that while the first year of Bacco's term has had its ups and downs, at least the Federation is still intact. Given that Bacco herself praised a former president earlier in the novel by stating that if you complete a term with the Federation still intact, you've done the job, this is somewhat heartwarming. Two months after this novel (In-Universe), cue Star Trek: Destiny. While Bacco continued to do a fine job through the apocalyptic mayhem of "Destiny" and its aftermath, the destruction in that trilogy does render Piniero's comment a bit painful.
In the second Temeraire novel, there's an amusing little subplot where Laurence hears about a nasty cold going around the English dragons, and many jokes are made about how dragons are such big babies when they're sick. Temeraire comes down with the cold, and it's played largely for laughs. In the fourth novel, it turns out that the "cold" is a form of dragon tuberculosis that's slowly and painfully killing every dragon in England. If they hadn't stopped at exactly the right port in Africa and prepared exactly the right mushroom for Temeraire on a whim, he and every other English dragon would have died. For that matter, since Temeraire was on his way to China when he came down with the "cold," all of the Chinese dragons would probably have died, too.
In the fourth book, there's also a throwaway line from Riley worrying about getting dragons out of the ocean and back onto the Allegiance: "What the Admiralty will say to me if I get a transport sunk in harbor on a clear day, I should not like to think." In Crucible of Gold, due to useless sailors getting drunk directly after a long, severe storm, the Allegiance sinks with only the worst sailors saved. Riley goes down with the ship trying to save it, and Laurence realizes that he'll be remembered as the captain whose ship sank on a clear day.
Reading Piers Anthony's references to his family life in his early works' Author's Notes, and especially the dedication to his daughter Penny, "Heaven-Cent", becomes a Tear Jerker when you know that Penny died of respiratory distress following brain surgery in 2009.
In-story example in Sarah Waters's Tipping the Velvet: a minor character chats up another by saying something along the lines of "Are you Sue Bridehead? I'm Jude Fawley" -a reference to Thomas Hardy's Jude the Obscure, then being serialised. Jude and Sue both end up having horribly unhappy lives. In context, it's a terrible line.
On the commentary for Fight Club, Chuck Palahniuk comments that a friend of his named Bob ended up getting testicular cancer after he'd written the book, "and so the irony of that was just crushing."
Listening to a certain children's story by Dick King-Smith is rather uncomfortable with hindsight. Renaming a cat you've found out is female? Okay, yes, female cats are called queens. the cat's a queen. So we get this line:
"Or Diana... That's what the Princess of Wales is called, she'll be Queen one day!"
In Suzanne Brockmann's The Unsung Hero, the main character, a Navy SEAL on medical leave, imagines reporting to his superior officer:
"Hi, I think I just saw the international terrorist that I spent four months tracking in '96 taking a cab out of Logan Airport. Yeah, that's in Boston, Massachusetts, that teeming hotbed of international intrigue...."
Funny in 2000, when the book was published. Much less funny a year later, when two killer planes took off from Logan on 9/11.
One edition of Uncle John's Bathroom Reader includes an article with a list of strange unofficial holidays. One of them is "No News Is Good News Day". Date: September 11. At first you might think it's just a bit of tasteless Black Comedy. But the copyright date is 2000.
In another edition, published in 2003, there's an article on humourous church bulletins. One of them is "Visitors are asked to stay seated until the end of the recession." Depending on your point of view, that's either this or Hilarious in Hindsight.
In Catherine Alliott's 1999 novel Rosie Meadows Regrets, the titular character is wistfully musing that her life would have been much better if she'd married someone else other than her alcoholic, bigoted, mentally abusive, uncaring and unsupportive husband. The celebrity she specifies? Mel Gibson. Hmm.
Sisterhood Series by Fern Michaels: In the book Fast Track, Jack Emery brags to reporters Ted Robinson and Joe Espinosa that the Post is going to be sold to a new owner. Joe turns green upon hearing this, because that means he and Ted could lose their jobs. At that point, it seemed like a brilliant and cool way to upset the apple carts of those reporters, who had been thorns in the Vigilantes' sides. Then, in a later book, Under the Radar, Ted explains to the Vigilantes why they can trust Joe. Joe is the only son out of eight kids. His father died early on, leaving his mother to take care of all of them. He's the youngest in his family. The family managed to get enough money to send Joe to college. He's the only one in the family to have a college education. Joe is a citizen of the United States, and he sends every cent of money he can back to his people in Tijuana. Joe cannot afford anything to live in except a one-room dump, and his immediate family has 37 members in it! Also, his family supports the Vigilantes quite strongly, and his salary combined with some other jobs he moonlights as help his family, but it's not nearly enough. His family is not lazy, but the economy in that area sucks. Boy, that not only explains why Joe turned green at the possibility of losing his job, but it makes Jack's bragging come off as a Kick the Dog moment!
No Country for Old Men by Cormac McCarthy: The novel takes place in 1980, and in it Ed Tom Bell mentions the recent murder of a federal judge in San Antonio, TX. He's referring to the murder of Federal Judge John Howland Wood, who was assassinated outside his townhouse by a contract killer named Charles Harrelson on May 29, 1979. In 2007, Woody Harrelson (yes, the son of Charles) would co-star in the film version of the novel.
Vlad Dracula and Elizabeth Bathory in Count and Countess, who write letters to each other across time and have been doing so since childhood. In this story, Elizabeth suffers from chronic epilepsy. When they are children, Vlad lists a number of ancient epileptics to try and cheer Elizabeth up about her disability. Vlad brings up Socrates, Caesar, and Alexander the Great. Elizabeth quickly retaliates with Caligula.
In one Warrior Cats book, the young blind apprentice Jaypaw is frustrated that one-eyed Brightheart is assigned to be his mentor (considering her to not be a "real" warrior), even more so when Brightheart announces that Longtail, a blind elder, is going to give Jaypaw tips on how to move around the forest without sight. Jaypaw irritably thinks "Sure, let's lump all the useless cats together and hope a tree falls on them!". A few books later, a tree falls into the camp, killing Longtail.
A Song of Ice and Fire: In one of Bran's chapters in the first book, he remarks that "Theon Greyjoy had once commented that Hodor did not know much, but no one could doubt he knew his name." The line appears to just be using Theon's Jerkassery to launch a humorous tidbit from Old Nan that his real name isn't even Hodor, it's Walder. In the fifth book, after Theon is tortured into insanity, he's forced to take on the name Reek. He can't even bear to think the name Theon until well into the novel, and doesn't say it aloud until his very last line.
James Patterson's I Funny, about a paraplegic middle-schooler who becomes a stand-up comic, is set very specifically in Long Beach, NY (a barrier island off Long Island). A month before its' publication date, Superstorm Sandy slammed that area.
Diana from GONE gives a reason you suck speech/comfort talk to Caine in the first book...
Diana: (In response to Caine's angst over his mother abandoning him) Wow, it's a shame dr.Phil isn't here. Look, she was probably just a messed up teenager then.
This was hilarious until the 4th/5th book, when Diana actually gets herself into this situation (teen pregnancy) with Caine. Only she's tortured by Drake for it goes insane from having to give birth in a mine whilst getting flogged and having horrible mind tricks played on her for hours.
The autobiography of former Penn State football assistant coach Jerry Sandusky, released in 2001, was titled Touched: The Jerry Sandusky Story. Needless to say, the title is now VERY disturbing in hindsight—see The Other Wiki for the gory details.
The Moviegoer has a series of crippling Take That!'s against the entire 60's counter culture movement, except that the book came out in 1961 when those things hadn't become popular yet.
Futility, or the Wreck of the Titan was published in 1898 and was about an ocean liner called the Titan that sinks on its maiden voyage across the North Atlantic when it hits an iceberg. Fourteen years later, the RMS Titanic sank on April 14, 1912 and every circumstance surrounding the Titanic's sinking (number of lives lost, what started the sinking, lack of lifeboats, triple screw propellers, ship described as "practically unsinkable", ship length, and ship speed) matches something in the descriptions about the Titan, making this trope Older Than Radio.
Early in Shadow Kiss during the guardian practice exercise, Rose wants Dimitri to have the opportunity to show that he could be a badass Strigoi.
In Blood Promise, Rose notices that Sydney doesn't seem to eat much of her food, but doesn't think much of it, and actually steals some of her fries. It's later revealed that Sydney has fairly severe body issues.
Aleksandr Pushkin wrote various works involving or alluding to duels, the most famous being that in Yevgeny Onegin. He was actually killed in a duel in 1837.
Cinderella was finally identified when the prince fit the glass slipper on her foot. Several centuries later, the O. J. Simpson trial used a similar method (fitting a glove onto O. J.'s hand) to determine whether or not O. J. was guilty. Even worse, the saying "if the shoe fits" sounds eerily similar to a phrase used by one of O. J.'s lawyers: "If the glove doesn't fit, you must acquit." This could also be considered Hilarious in Hindsight depending on how you feel about Black Comedy.
Special Circumstances: In-Universe. At the beginning of Princess of Wands, Barbara's martial arts sparing partner says, after watching her warm-up exercises, that he was gay. She calls him on it, the narration commenting that he's married and has five children from two different marriages, and that "[i]f he was gay, it was a very closet condition." Fast forward to the end of Queen of Wands, when it's revealed that her husband, with whom she's had three children is having a homosexual affair.
Radar, who's black, getting a t-shirt with a confederate flag on it that says, "Heritage not Hate", was hilarious in Paper Towns, which came out in 2008. Fast-forward to 2015, the year the movie came out... and also the year when the controversy over the Confederate flag, and whether it stands for racism or not, has reached violent levels of protest and conflict. Suddenly the scene isn't so funny.
H.P. Lovecraft's horror writings weren't ever meant to be funny, but they were harmless thrills because of their obvious reliance of fantasy. Then you suddenly realise one day that that Cthulu and R'yleh work quite well as a metaphor for the "methane clathrate gun". note It's huge, it's been "sleeping" deep under the sea for countless eons, and when it rises, it will cause The End of the World as We Know It through runaway climate change and a mass extinction possibly as big as the "Great Dying" at the end of the Permian era. And there are many people (climate scientists) who really do have nightmares about it, and at least a few particularly pessimist dark-green activists have developed mental illness (depression) and even committed suicide.
Yet another 9/11 reference: Tom Clancy's 1994 novel Debt of Honor ends with a distraught Japan Air Lines pilot flying a 747 into the US Capitol building during a joint session of Congress, killing the President, most of Congress, the Supreme Court, and many others. Unlike the 9/11 terrorists, however, the pilot ensured that no passengers were on board (it was an empty ferry flight) and murdered his copilot prior to the attack so that he alone would bear the blame. The Capitol building was the most likely intended target of United Airlines Flight 93, which crashed in a rural Pennsylvania field instead thanks to the actions of its passengers and crew.
The Neanderthal Parallax: In the last book, Mary lists Bill Cosby as one of the men that isn't evil while she thinks about male violence. This was before the accusations against him were well known. It's especially ironic since she's a victim of rape, and this a large part of her character's arc throughout the books.
There is an off-hand remark in The Candidates (based on a true country) about Bill Cosby being a good rolemodel. The book was written in 2011, when Cosby was still considered to be the human embodiment of wholesomeness - you know, before fifty-odd women came forward to accuse him of having raped them...