Hilarious in Hindsight/Literature

"Don Cherry: "We thought of making it a blue fairy, but didn't want to offend anyone.""
 * In the first Discworld book, the heroes are surprised by a troll that appeared suddenly in their path, having been whisked away from its home in the mountains some thousands of miles away, in order to appear as a random encounter in the Dungeons and Dragons game of the Gods. While it was in reference to random Tabletop RPG encounters, the way it was described - a sound, the world looking 'strange' and a monster suddenly popping up - mirror exactly the random battles in most console RPGs. This was in 1983, three years before Dragon Quest or Final Fantasy, although Ultima III was from 1983.
 * Another Pratchett one in Carpe Jugulum: Having an Ax Crazy vampire parody Tom Cruise's character in Interview with the Vampire - funny; Reading this parody against Tom Cruise's current reputation? Hilarious.
 * Vlad is accused of only liking Agnes because he can't read her mind. Between that, and the odd amount of sparkling that goes on in Thud, there is much in the way of unintentional humor if you're at all familiar with Twilight or the Southern Vampire Mysteries, for that matter.
 * In Thief of Time there's a gentleman's club with a Rule 34. In this case, Rule 34 states that women cannot enter the club except at a certain time and date, which leads to members assuming any women they see inside the club outside of that narrow window of time must be figments of their imagination. The narration then notes that in Susan's case, with her strict schoolteacher outfit and black high heels, this could easily be the case.
 * The anti-war novels Jingo and Monstrous Regiment have echoes in conflicts that have broken out since they were published, but since "war is stupid, and all wars are stupid in much the same ways" is kind of the point, this is not surprising. Likewise with Making Money's jabs at the magical thinking inherent in economics.
 * Real life steals the plot!
 * The only logical conclusion is that Terry Pratchett is either clairvoyant or a time traveler (and he did steal Unseen University from Hogwarts!).
 * Word of God claims that "with amazing prescience, I saw no future in a series based around a college of magic and wanted UU to stabilise a bit to give me headroom for other stories."
 * Witches Abroad predates The Princess and the Frog, and is partially set in a combination of a Disney Princess city and The Big Easy(During Fat Lunchtime, no less) and with a frog prince. Also, Greebo always wanted to be ginger.
 * Witches Abroad also has a lot of odd similarities with Shrek 2, including the ruler who's only revealed to be a frog at the end, and the villain being a fairy godmother.
 * An early Watch book mentions that mass-circulation newspapers hadn't been invented yet in Ankh-Morpork, "leaving the public to fool themselves". Then Pratchett gets around to writing The Truth...
 * One of The Wee Free Men says he's "bigger on the inside" in a straightforward Doctor Who reference. Then, later on in the book, Tiffany comes across unnatural shadows that move around without any light source...
 * Also in that book is Tiffany rescuing someone from a dream, and being informed by said individual that they might still be trapped in a dream and be unable to tell the difference. The dream is populated by stuff from the dreamer's memories. Oh, and Tiffany was in said dream because she and the WFM wanted to steal something. Date of publication: 2003.
 * Neuromancer: "The sky above the port was the color of a television tuned to a dead channel". Some years after this was published, new television sets with sophisticated electronics began replacing "snow" on dead channels with a blank, sky-blue, screen.
 * Which is why, in Neil Gaiman's novel Neverwhere, he describes a perfectly clear sky as being the color of "a television tuned to a dead channel," in both a homage to Neuromancer and a nod to the changes in technology.
 * Speaking of Cyberpunk novels, it's hard to wonder if Neal Stephenson is a dead-on prophet when reading the descriptions of the "Metaverse", considering how many MMORPGs it resembles... then again, this may be a "Which came first" kind of situation.
 * The intro can by now be interpreted as at least 4 types of sky. Overcast (the intended), a clear black sky, a rainbow, and a clear blue sky.
 * Another interpretation would be a black sky with enough ambient light from surrounding structures/buildings/etc. to make it appear to be luminescent at the edges, much like a CRT that is on but does not have any input (like at a command prompt).
 * It came out over a decade before the Metal Gear series became popular. Reading it today, the inclusion of a genetically enhanced super ninja named "Hideo" is pretty funny.
 * A children's educational book in The Knowledge series called Crashing Computers, published in 1999, talks about policy discussions on the 10 Downing Street website and makes a joke about paying kids to go to school. A few years later, the Government created the Education Maintenance Allowance, paying some 16-18 year olds to go to school.
 * Some countries (e.g. Finland) had student benefits years before 1999, so it's more of a case of Hilarious When Put Into Multinational Perspective.
 * Dave Barry's Book of Bad Songs cited "All By Myself" as a member of the bathetic "you-don't-love-me-so-it's-time-to-jump-into-the-bathtub-with-an-electrical-appliance genre". The movie Me Myself I used the song for that exact dramatic situation.
 * Also, this book was published well before Emo became popular...
 * The book L.A. Confidential features the death of a down and out prostitute named Kathy Janeway. The creators of Star Trek: Voyager probably didn't have this in mind when naming their show's captain, but the name was removed from The Film of the Book nonetheless.
 * The original name of the character was Elizabeth Janeway. That had to be changed after the producers learned that a rather strident (and litigious) professor shared that name. They then went with Nicole, which went out the door when Canadian actress Genevieve Bujold walked off the production. Katherine was a last-minute choice.
 * In the 1998 Star Trek: The Next Generation/X-Men crossover novel Planet X (which is not a fanfic but rather an officially published, authorized, but noncanonical novel) Captain Picard meets a holodeck simulation of Professor Charles Xavier and is astounded by how similar he looks to him. Two years later the first X-Men film came out, casting Picard actor Patrick Stewart as Professor Xavier.
 * In Charles Stross' The Atrocity Archives, written in 1999, the author was looking for an obscure terrorist who was none the less likely to strike on American soil. In the book this terrorist gets his occult weapon mass destruction from Saddam, and is based in Afghanistan. Originally the terrorist in question was, you guessed right, Osama Bin Laden. The book was published in late 2001 and his publisher suggested he change this to some other terrorist who is still obscure, which Stross did.
 * In The Hitchhiker's Guide to the Galaxy, a Someone Else's Problem field is set up to stop people noticing a spaceship parked at Lords' Cricket Ground. A couple of decades later, they built this.
 * Holy pants, it's Wallace's smile!
 * Another example: at the beginning of the first book a demolition foreman is described as being a descendant of Genghis Khan to set up an amusing aside where he has visions of his ancestor's life. Later, it was discovered that 0.5% of the world's male population are indeed descended from Genghis Khan.
 * In Michael Crichton's 1994 novel Disclosure, discussing a computer help program:

""It's just a city, the whole thing, one big, huge, really big city. It's all city.""
 * Hey! Listen! (Press C^!) Some people might not get this one if they don't hover the links.
 * You could also go for that great Microsoft innovation, the Office Assistant, aka that annoying f-ing paperclip.
 * In the fourth Harry Potter Book, Mad-Eye Moody  repeats "Constant vigilance!" over and over. When this first came out, it seemed outdated. After 9/11, similar lines said by various officials were so pervasive that this line can now be viewed as prophetic dark humor.
 * When Dumbledore and McGonagall left Harry with the Dursleys as a Door Step Baby in the first book, McGonagall said "This boy will be famous. There won't be a child in our world that won't know his name." Indeed, there probably isn't. She also mentions that "there will be books written about him". No way THAT one wasn't intentional.
 * In the fourth book, Cedric earns the nickname of "Useless Pretty-Boy Diggory". Considering who plays him in the movie (and said actor's further roles)...
 * For years, various well-meaning parents have demanded that the Harry Potter books be banned because of the books' obvious Satanic undertones. My Immortal makes all of this hilarious.
 * From Harry Potter and The Philosopher's Stone: "... the Weasley twins were punished for bewitching several snowballs so that they followed Quirrell around, bouncing off the back of his turban." Remember how this book ended?
 * At the end of Prisoner of Azkaban, Snape flies into a rage and the Minister of Magic says to Dumbledore - "Fellow seems quite unbalanced...I'd watch out for him if I were you, Dumbledore" Possibly the only time Cornelius Fudge displayed sound judgment.
 * Combined with the movie, Harry Potter and The Deathly Hallows Part 1 has a mixed-income wedding where commoner Bill Weasley (handsome but disfigured by a werewolf's claws) marries the (presumably) wealthy Fleur Delacour, who is wearing an Alexander McQueen-inspired dress. There's a featured wedding guest in yellow, meanwhile there's dark doings involving terrorists and secret missions in the background (that ultimately succeeds, and the defeated foe is given a swift, unceremonious burial) that quickly overshadows the happy occasion. Less than a year after the movie's released, Prince William (handsome but prematurely balding) marries wealthy commoner Kate Middleton, who wears an Alexander McQueen dress while the Queen wears a cheerful yellow ensemble (wait, The Queen in yellow?). Meanwhile, there's a secret mission to take out Osama Bin Laden (who is killed and quickly buried at sea) that knocks the royal wedding off the news cycle (at least until the newlyweds visit California).
 * In the second book Ron suggests that It turns out
 * In a case of either this or a Funny Aneurysm Moment (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. 10 years later, guess what Robin Williams decided to nickname his penis (and name a trope in the process)?
 * In The Fountainhead, one of the characters walks past a movie theater advertising a cheapened version of Romeo and Juliet: "Bill Shakespeare's immortal classic! But there's nothing highbrow about it! Just a simple love story. A boy from the Bronx meets a girl from Brooklyn. Just like the folks next door. Just like you and me." Ayn Rand wrote this description long before West Side Story. Shakespeare wasn't highbrow in Shakespeare's day, either.
 * Dave Barry Slept Here uses the word "befriend" in talking about the United States using Gunboat Diplomacy to establish relations with Latin American countries.
 * The book White Oleander has a passage where the protagonist's racist foster mother calls Oprah a "nig-nag". When Oprah selected the book for her Book Club, she quoted the passage for her audience, then described her call to the author. "Hello, this is the fat nig-nag calling." (Beat.) "'Ohmigod, Oprah!'"
 * In the original Shrek picture book, there's a scene where the title character has a nightmare about being beloved by children.
 * In Good Omens: "She wanted a change. Something with openings. She quite fancied herself as a newspaper journalist." Let's just say that whatever the state of the newspaper industry was in 1990, well, It Got Worse.
 * Before the invention of Internet memes, there were two points in The Thrawn Trilogy where Admiral Ackbar brings up traps. In the first book, told that smugglers suspect that alliance with the New Republic is a trap, he says "Because of me, no doubt." Later he says "It appears to be a trap."
 * And in the X Wing Series, years before Ric Olié's "Coruscant. The whole planet is one big city", newbie Tatooine pilot Gavin Darklighter has a Narm Charm moment.

""Maybe the rain had something to do with why you lost your memory," Deena offered. "A torrential rainstorm. A car speeding down Mulholland Drive. There was a crash, the squealing of brakes, and then...”""
 * In The Space Traveler's Handbook, published in the 70s but set in 2061, the second US space colony is called the Richard Nixon. This is indicated to have been a very popular choice.
 * A book of very serious, scholarly articles published in the New York Times in the 1950s had an interview with a Russian scientist just after Sputnik went up. He detailed a whole plan for how he thought humanity would expand into space, landing on the moon "Perhaps as early as the year 2000."
 * In the Malazan Book of the Fallen books Midnight Tides and Reaper's Gale (the latter published in 2007), one plot thread is Tehol Beddict's plan to destroy the economy of Lether by exploiting everyone's greed. Considering how much of the 2008-2009 economic unpleasantness was caused by unsustainable and shortsighted investment and lending makes it even better.
 * Julie Kenner's 2000 novel The Cat's Fancy is about a cat who becomes human in order to marry her owner. She shows up in her owner's house seemingly with amnesia, and he and others try to find out who she is, in a plot already reminiscent of a movie that would come out a year later... but then we get this line:

""The ambassador ventured to frame excuses by saying that the vanity of nations was a matter of little consequence; that Holland was proud that, with such limited resources, she had maintained her rank as a great nation, even against powerful monarchs, and that if a little smoke had intoxicated his countrymen, the king would be kindly disposed, and would even excuse this intoxication.""
 * At the beginning of The Hobbit (published in 1937), Thorin describes the mark Gandalf had left on Bilbo's door as indicating a burglar looking for work. "You can say 'expert treasure hunter' instead of 'burglar' if you like. Some of them do." Nearly sixty years later, gamers who played the US release of Final Fantasy VI met one such individual.
 * In the 7th Everworld book, Senna Wales decides to stab a Coo-Hatch alien to death with a knife, for no apparent reason, and then acts coldly unmoved by what she did. When the others question her as to why she had suddenly gone Ax Crazy, she laughs ruefully, shakes her head to herself and replies, "Had to be! There was no avoiding it ... Not over the long haul." In the eleventh book, Senna suddenly goes psychotic and becomes a evil maniac, presumably for plot purposes.
 * Made even funnier since Senna can see the future in visions, talks about her "destiny", and is Dangerously Genre Savvy. Given Senna's sense of humor, she had obviously guessed what was going to happen.
 * In the 9th book, Senna also recites a list of reasons why the adventure must not end with her death. Perhaps a certain Magnificent Bitch had some awareness of the fourth wall.
 * The title of the book The BFG by Roald Dahl has taken a new, wonderful meaning.
 * The Iron Dream is a Norman Spinrad book, essentially taking the racial ravings of Adolf Hitler, taking them to the logical conclusion by having this Hitler be obsessed with the purity of the human genome rather than the human race. Thirty five years later, we learn that the only "pure" humans on the planet are those whose ancestors stayed in Africa, while all others mated with neanderthals.
 * In the second Maximum Ride book, a kid at Disneyland mistakes Ari for Wolverine. Then Disney bought Marvel...
 * In The Catcher in The Rye, Holden says that if he ever gets drafted, he'll volunteer to sit on a nuclear bomb as it is dropped. Twelve years later...
 * During the climax of Ramona and Her Father, a strange man in a restaurant asks Ramona if she's been good to her mother.
 * During the climax of Adventures of Huckleberry Finn, an old woman rambles on about, ending every sentence with 'says I'.
 * The Serpent and the Rainbow is the autobiographical non-fiction account of Harvard ethnobotanist Wade Davis' journey to Haiti to investigate a mysterious drug being used to turn people into the zombies. The book was notable for its respectful treatment of Haitian and voodoo culture and included several passages that condemned the way voodoo is sensationalized by Hollywood. It was adapted by Wes Craven into a horror film that epitomizes everything that Davis condemns in these passages.
 * The Dale Brown novel Edge of Battle has a part where someone is telling a Russian commando to speak No Russian. Complete with said Russian supposed to be pretending to be from elsewhere as part of a False-Flag Operation.
 * Edward Gorey's first book, The Unstrung Harp came out in 1953. In one scene, the main character goes driving near a town named Something Awful.
 * Among many other bad translations in the infamous Portuguese-to-English phrasebook "O Novo Guia da Conversação em Portuguez e Inglez" (also known as "English As She Is Spoke") was its translation for "Cômô dizeís ôu díz Vm?": "What you say?"
 * Speaking of that, at one point in Lord of the Flies Piggy says, "What You Say?
 * In The Phantom of the Opera, the Narrator refers to Christine's first abduction (the one where she disappeared for two weeks) as "not the infamous abduction" which everyone has heard of. In context, this refers to how famous her second abduction became in the news in-universe, but the story is so famous now through Popcultural Osmosis that this clarification seems to be Leaning on the Fourth Wall.
 * Sinclair Lewis' 1947 novel Kingsblood Royal features the Sant Tabac, a racist secret society fronting as a cigar club. Flash forward 50 years to the height of the cigar craze, when such clubs were all the rage.
 * In the Book of Exodus, God lets Aaron speak for his brother Moses because the latter stutters when he speaks. Come 1998, Dreamworks Animation decides to adapt Exodus into an animated film, and who do they cast as Aaron? Jeff Goldblum.
 * In the novel Hannibal they have an early scene where Mason Verger pumps Paul Krendel on info about Clarice Starling. They come to the point where he mentions that Clarice has a female roommate, and Krendel casually speculates that the pair's relationship is sexual in nature. At the time the book was written it was a quick Establishing Character Moment to show us that Krendel is a creep, but then a certain someone decided to finally come out of the closet, and it reads quite differently.
 * In The Honor of the Queen, one enemy officer is criticized for trying to rely on weight of fire rather than proper timing to overwhelm Honor's defenses, which looks odd in light of the Macross Missile Massacres of later books.
 * In The Short Victorious War, the idea of battle-cruisers trumping ships of the wall, even in a missile fight, is dismissed as impossible. Wait a minute...
 * In Crown of Slaves,  claims that the only two things she would be good at are being a housewife or a queen. Guess what...
 * In his non-Honor book The Excalibur Alternative, the end involves
 * In Alexandre Dumas's Louise de la Valliere, one of the sequels to The Three Musketeers, we have this paragraph in which a Dutch ambassador tries to apologize to the French king for injuries committed against him; it acquires a whole new meaning now with the Freestate Amsterdam stereotype:

"Were kisses all the joys in bed,
 * In Philip K. Dick's short story Stand-By, in the future setting, the most important TV news presenter is...a clown.
 * Atlas Shrugged has a passage that sounds just like the commonly parodied Master Card commercials: "The roast turkey had cost $30. The champagne had cost $25....[Several more examples]. But it was held to be unspiritual to think of money and what it represented." If it didn't predate the Master Card commercials by many decades, it would seem like the perfect setup for something like "Thanksgiving dinner with family was priceless" Or "Using the power of reason to produce wealth was priceless." Or "For Rearden's family, the opportunity to make him feel a sense of unearned guilt was priceless."
 * The first book of John Ringo's Posleen War Series, released in 2000, features Mike O'Neal, initially an NCO, using an experimental suit of Powered Armor with an AI named "Michelle" in it, part of a military unit that exclusively uses said armor. He and said AI are close friends. See also; Halo: Combat Evolved, featuring Master Chief Petty Officer John-117 and his AI best friend Cortana, member of the elite group known as Spartans. And yes, both types of armor have the Sticks to the Back trope
 * One 80's gamebook featured the player as a mage, leaving the reader to determine what type of magic they used. Each type of magic was assigned a colour. Of which there were five. Even better, they were white, blue, black, red, and green.
 * In the 1990 short horror novel The Langoliers by Stephen King one of the characters is trying to figure out what caused practically all the passengers of a cross country airline flight do disappear and while internally brainstorming considers the idea that someone filled the plane's luggage compartments with poisonous snakes before immediately dismissing it as ludicrous.
 * In The Princess Bride, the old Archdeacon, as part of Buttercup and Humperdinck's marriage ceremony says, "Mawidge is a dweam wiffin a dweam. (He was old and deaf and had a speech impediment.)
 * One part of Romance of the Three Kingdoms involves Guan Yu crossing five passes and slaying six generals, which sounds awfully like a videogame.
 * Similarly, Liu Biao has an advisor named Kuai Liang. That won't be too significant for most readers, but any Mortal Kombat fans are sure to get a chuckle out of it since Mortal Kombat 9 revealed (the younger) Sub-Zero's real name to be just that.
 * The book also features a Red Shirt named "He Man"--while the name is not pronounced anything like He Man and The Masters of The Universe, it's still funny to see him appear, make a Badass Boast, and then cut down without anyone batting an eye.
 * In A Wrinkle in Time, Meg Murry's father's mathematically-based nickname for her has a slightly different meaning to those who read the book after, say, 1984: "Megatron".
 * In the Sweet Valley High book Sweet Valley Saga Alice (the twins' mother) was engaged to Hank Patman (Bruce's father). When Sweet Valley Confidential comes out, guess who become a couple at the end of the book?
 * This couplette is from The Passionate Pilgrim, attributed to Shakespeare:

One woman would another wed."


 * In Lewis Carroll's 1872 novel Through the Looking-Glass, and What Alice Found There, one of the lines of his famous "Jabberwocky" poem mentions a "rath," which was defined by Word of God as "a sort of green pig." 137 years later, well...
 * Jacob Black has an older sister named Rebecca. Think about that for a second...
 * Try reading the Fablehaven books during the 2012 election and NOT laughing at Vanessa Santoro's surname, which is only 2 letters away from that of a certain Pennsylvania ex-Congressman who shall not be named.
 * At least one translation of Beowulf referred to 'great tracts of land'.
 * In the 1932 novel When Worlds Collide, the League of the Last Days picked a location in Michigan to build the space arks because of its geological stability; in another universe, so did a certain shower curtain company.
 * The 2008 Doctor Who Expanded Universe novel Ghosts of India has the Doctor trusting an alien on the grounds the alien is making tea, adding "The Daleks never made me tea."
 * The children's novel The Twenty-One Balloons has the protagonist landing on Krakatoa shortly before the fateful volcanic eruption. He meets a secluded society whose men are named "Mr. (letter)". This naming convention results in two Hilarious In Hindsight moments: 1)the first person the protagonist meets on the island is named Mr. F and 2) a later one named man on the island goes by Mr. T.