Hilarious in Hindsight/Other Media

Commercials

 * The "Phones-4-You" ad campaign goes from being a mildly successful attempt at Memetic Mutation to being pretty hilarious once you've played Metal Gear Solid 4: Guns of the Patriots, where the weapons merchant has a hand-gesture catchphrase for the slogan 'EYE HAVE YOU'.
 * It is generally quite hard to deliberately engineer a Hilarious in Hindsight moment, as it's all too easy to be offensive or to simply pander to an obvious in-joke. For a master class in doing it right, step forward the late, great British comedian Bob Monkhouse. Four years after his death in 2003, with thanks to modern digital wizardry, he appeared on television in an advert suggesting the wisdom of being tested for prostate cancer, cracking jokes about it being an even bigger killer of men 'than (his) wife's cooking!' so that the viewer doesn't end up 'as (he) did' - spoken while appearing standing beside his own actual tomb-stone.
 * At the time it aired, a McDonald's commercial featuring N'Sync and Britney Spears playing "spin the bottle" had a rather light-hearted punchline, whereby the bottle stops on Justin Timberlake, not Britney. A few years later, Lance Bass came out as gay, and it gives the ad a whole new meaning.
 * The Big Boss Grill.
 * A drug PSA showed Pee-wee Herman (Paul Reubens) talking about how dangerous crack was. Reubens would later go on to play a drug dealer in the movie Blow. Then again, he had already been in some Cheech and Chong movies, which are about drugs.
 * After an Encyclopedia Britannica commercial had its run, they decided to make a direct follow-up to it. And the very first line said was, "Remember me?" To add, both were made by Stan Freberg, who was the voiceover talent. The onscreen talent? Freberg's son.
 * The "Lex Luthor stole [[media:40cakes_4996.jpg|forty cakes]]" meme takes a new meaning with an UK advert for Innocent Smoothies, and the bakery's name.
 * A 1996 This is Sports Center ad featured Karl Ravech and Keith Olbermann interviewing former Senator Bill Bradley for a job. The last line of the commercial has them questioning whether he'd spoken in front of an audience. Bradley says he gave the keynote address at the Democratic National Convention. Olbermann replies, "We meant a large audience." One that a decade later he himself would try to tap.
 * T-Mobile made a series of anti-AT&T commercials, very closely modeled after Apple's infamous "I'm a Mac and I'm a PC" ads. Mere months later, T-Mobile was almost absorbed into AT&T.
 * Alltel Wireless also ran a series of ads spoofing their competition, with takeoffs of AT&T, Verizon, T-Mobile, and Sprint "employees" featured (and the Verizon character often the butt of the jokes) -- until merger talks between Alltel and Verizon heated up. The Verizon character was quietly dropped late in the campaign -- shortly before Alltel itself was dropped into Verizon.
 * Lebron James appeared in a State Farm commercial where he dreamed of playing for the Cleveland Browns. The team they were playing? The MIAMI Dolphins.
 * Sega Saturn vs. "Plaything". The Console Wars would determine which one was worthy. It was the Playstation.
 * An article on X-Entertainment points this out about a Reese's Pieces commercial starring an alien.
 * Sega's very attack-oriented advertisement campaign with arrogant claims and insults directed at Nintendo in The Nineties led to many instances of this trope:
 * The Game Gear commercials poked fun at the Game Boy's graphical limitations. Everyone forgot about the Game Gear's existence before Nintendo even announced the Game Boy Color.
 * "Genesis does what Nintendon't." One decade-and-a-half later, Sega decides to release a special version of the Genesis with Wii-mote inspired controllers.
 * "Genesis does what Nintendon't" doesn't mean anything anymore now that the Wii's Virtual Console service has Genesis games. A few years later, the Nintendo 3DS is announced to have plans for Game Gear games on its own Virtual Console in addition to Game Boy and Game Boy Color games, furthering the effect.
 * Also, one infamous Sega CD commercial has become this. "You still don't have a Sega CD? What are you waiting for, Nintendo to make one?!"
 * This 2014 Turbo Tax features a man being told about his work clothes counts tax-deduction thanks his job as a circus clown. It’s actually a bit for funnier when you learn Bjorn Ulvaeus did the same thing due to Swedish tax during the  1970s allow such  work-only costumes to counted as tax-deduction if they were embarrassing to be street legal. . However, Ulvaeus did study both business and law; both  came in handle in the early 2000s due to a tax dispute. The case was dismissed in 2008 by the county administrative court after they agreed Ulvaeus didn’t own any money thanks to how the laws were written.
 * In this advert for a cable company, a young boy is watching a program about dinosaurs when he decided to see if he could find some fossil. Fast forward to April, when a Chilean boy went to go exploring with his family, he found fossils of a previous unknown species of dinosaur.

Fan Works

 * The AMV Anime Academy Heroes had Edward Elric piloting a Gundam. Then, the director of Fullmetal Alchemist went on to direct Mobile Suit Gundam 00.
 * The first line of the first Kirk/Spock fic is "Shut up. We're by no means setting a precedent." Of course, K/S went on to spawn Slash Fic as a genre, setting quite possibly the most important precedent in the history of fandom.
 * An infamous and NSFW Homestar/Strong Bad slashfic, somewhat infamous within the fandom, was reputedly written before the "Long Pants" email.
 * In the Final Fantasy VIII fic "Phantom Dreams", there's a joke about Zell's hair looking like a chocobo (and that's why Seifer called him a chicken) which was merely painfully unfunny until Final Fantasy XIII gave us a character with a chocobo living in his hair.
 * In 2004, a furry-based anthology comic featured a mini-comic involving a lapine boy band who turns out to be secretly gay behind the scenes. Obviously, it's meant to parody the rumors of homosexuality within real boy band members at the time, but with the aforementioned coming out of Lance Bass and the outing of Ricky Martin (though many don't know he was a part of Menudo), you've got to wonder if the creator knew something we didn't. And, to make things even more hilarious, one of the band members in the comic is even named "Rickay"!
 * On 23 July 2010, a Power Rangers fanfic called "Mythic Rangers" was started, with one character named Hector. On 5 August, the names of the cast for the new 18th season of the franchise were leaked... the new green ranger is played by Hector David Jr. While the fanfic contains some deliberate Power Ranger references, this one was not intended.
 * In 2006, a Tekken story based off the Super Sentai franchise, Tekkenshu Sentai Shinkenger, was written and published on various websites. Two years after the fanfic was finished, cue Samurai Sentai Shinkenger; this is even funnier due to all the times Chiaki/ShinkenGreen is shown playing Tekken 6: Bloodline Rebellion.
 * You Got Haruhi Rolled is a Haruhi Suzumiya Crack Fic which has been running for over a year now, since before the preview to the tenth novel was even suspected, let alone released. In a chapter from before the preview, Kuyou Suou, who could not talk without ridiculously-long pauses between words, is suddenly able to speak articulately and chew out the characters who made fun of her speech issues. Guess what happens in the tenth novel?
 * A Harry Potter fanfic titled Gears of Potter had Marcus Fenix and Dominic Santiago from Gears of War team up with Harry Potter and his friends. Then EA Games released the video game adaptation of Harry Potter and the Deathly Hallows, which was basically Gears of War with MAGIC SPELLS.
 * A Final Fantasy XIII post-game fanfic written in June 2010 called New Dawn has Lightning, feeling empty and unfulfilled though happy her friends and family are doing well, go off on her own as if beckoned to go on another journey. Late that year, the Episode One novellas were released and the next month after, Final Fantasy XIII-2 is announced. What do they portray? Lightning, feeling empty and unfulfilled though happy her friends and family are doing well, go off on her own as if beckoned to go on another journey.
 * Early in Hogwarts Exposed Jamie unveils her pet, a robot unicorn with the power to chase away bad dreams.
 * In a Darths and Droids comic released in 2009, Made Windu says his apartment blew up. (It didn't in the Attack of the Clones movie.) Roll in Star Wars the Clone Wars episode 2x20, released in Spring 2010, and his apartment blows up.
 * An Dragon Ball Z and Anne Frank crossover fanfic, "Until The End of Time", had Adolf Hitler going Super Saiyan. Cue The Legend of Koizumi and the "Legendary Super Aryan".
 * In a Castlevania fanfic called Castlevania: Wisps of Dracula, Simon's son was "dead of the skick". While a slight spelling error, it becomes a very funny joke to Super Sentai fans when considering the Skick Tribe.
 * In the Katawa Shoujo fic "From Shizune's perspective," which was published before the full game was released, Shizune is surprised to find out that Emi is a lesbian, and Shizune says that "The track team captain being a lesbian is the sort of thing high school students would talk about," but that she gets left out of the loop because of her deafness. In Emi's route, while Emi is heterosexual, it turns out that the track team captain Hisao assumed was a romantic rival is gay, and Hisao appears to be the only one who knows of the captain and yet is unaware of his sexuality.

Magazines

 * The Mario Vs. Wario comics printed in Nintendo Power shortly after Wario's debut in Super Mario Land 2: 6 Golden Coins said that the reason for Wario's grudge against Mario was when they were playing cowboys as kids, he got to be sheriff only once. Ten years later, the GBA game Wario Ware Inc.: Mega Microgame$ features a hidden version of Nintendo's arcade game Sheriff with Wario taking over the title role. Wario also gets to be a sheriff in Mario Party 2.
 * Another Nintendo Power example: when Lucario was suggested as a playable character in Super Smash Bros. Brawl in the letters to the editor, it was juxtaposed with a suggestion of Dora the Explorer and laughed off by the responder. Later along the line, Lucario was announced as a playable character. (Sadly, Dora didn't make the cut.)
 * During the early days, the Player's Pulse section once featured a topic of the issue being the most infuriating gaming moments for players. One such player ranted about something involving his sister, and ended his post with "God must be a girl!" Two decades later...
 * And a decade after that we got another example of a universe's God being female.
 * A fan letter published the December 1991 issue' detailed a fantasy game system which would come bundled with a game "better known as Super Mario Bros. 24", but would actually have the title of Super Mario Galaxy.
 * Another letter in the mid-90's had someone writing in about how awesome a game set in a courtroom would be, which the editors replied would've been a stupid idea. Capcom, apparently, was reading that letter, and came with the Ace Attorney series.
 * Electronic Gaming Monthly made an April Fool's Day joke about a code to get play as Sonic and Tails in Super Smash Bros.. Melee (even photoshopping an extremely convincing pic). Come the Wii generation and Brawl, Sonic (but not Tails) joins the cast of playable characters.
 * An article in Mad magazine included various predictions about what would happen in the Star Wars series after The Empire Strikes Back. Among them, Luke Skywalker would discover in the final movie that his father was actually The Force. It turned out the writers were only one generation off.
 * Their Return of the Jedi parody made fun of the scene where Luke reveals to Leia that they were twins, by also claiming that Threepio was his brother. Once again, fast forward to 1999 and Episode I, and he's right (From a Certain Point of View).
 * When they did their parody of Batman Returns in 1992, one of the background sight gags was that the newsboys reporting on the Penguin's good publicity were the dancing ones of Newsies, which arrived a few months prior to the Batman sequel and was a notorious flop. That Disney musical ultimately found a cult following, but what makes the joke funnier now is that Christian Bale played the youthful hero in it.
 * An old issue which was "concerned" with the population explosion suggested that, to prevent "young folks" from having children, people should give them a robotic dummy baby in order to convince them they can't be parents. Which is exactly what they're handing to teenage girls (and sometimes boys) in high schools across the nation today.
 * The magazine had this parody ad for Cadillac back in 1960, showing a woman wearing an emblem of the car like a necklace to show off her status symbol. Who knew rappers would adopt the same style decades later?
 * An early 70's issue of Cracked magazine predicted youth culture 30 years later pretty well

Poetry

 * The poem For Heidi with Blue Hair by Fleur Adcock seems uncomfortable now considering it mentions "twittering", which to today's audiences, has different connotations than it did at the time of publishing...
 * Longfellow's The Jewish Cemetery at Newport which discusses the plight of the Jews, ends with the stanza "But ah! what once has been shall be no more! / The groaning earth in travail and in pain / Brings forth its races, but does not restore, / And the dead nations never rise again." He did not foresee the creation of the modern State of Israel.

Politics
"I don't think there will be a woman Prime Minister in my lifetime."
 * The Official Monster Raving Loony Party had a policy of passports for pets. Guess what was actually introduced in 2001.
 * In 1973, Margaret Thatcher said the following:


 * Chris Rock starred in a movie called Head of State, in which his character runs for the (2004) Presidency as a long shot and wins. Fast forward to 2008.
 * The Gettysburg Address, possibly the most famous speech in U.S. history and the only one that American students are likely to have to learn by heart, includes the line, "The world will little note nor long remember what we say here."
 * There was a report in a newspaper from the 1930s in which a spokesman for Nazi Germany accused Britain of oppressing its colonial subjects. Another paper of roughly the same vintage had a report detailing economic deals the Nazis had made with the Kingdom of Yugoslavia which were being enthused about by the German economics minister at the time. His name: Dr Funk.
 * There is a history documentary, made during the Cold War, in which a famous historian says "[The Berlin Wall] now separates Germany, a country that will probably never be united again." The documentary was made in 1988...TheGreatPoliticsMessUp at its finest.
 * Anyone remember the much-memed quote from Ted Stevens about the internet being "a series of tubes"? Now take a look at the dozens of "_____Tube" sites online (YouTube, XTube, FilesTube, etc). And people say that Al Gore invented the internet!
 * Former Arkansas Governor Mike Huckabee has often been quoted as saying, "There were three heroes in Arkansas: Jesus, Elvis, and FDR, not necessarily in that order." Now someone by the name of Elvis Presley is running for Governor of Arkansas.
 * In 1845, the Anti-immigrant Nativists in the US formed the (White) Native American Party.
 * This interview on the controversial CBC television show This Hour Has Seven Days is particularly hilarious for a number of reasons if you know your Canadian history. To explain/ruin the joke for the rest of you:
 * Sometime in the 1890's, president Stephen "Grover" Cleveland once met a young toddler. Cleveland said to him "I’m making a strange wish for you, little man; a wish I suppose no one else would make. I wish for you that you may never be President of the United States." The toddler's name? Franklin D. Roosevelt!
 * Something similar occurred in Canada about a decade later, when Prime Minister Wilfrid Laurier was touring Western Canada. In one town, he stopped to chat with a little boy, and the kid eventually excused himself because he had to finish his paper route. That little boy was one John George Diefenbaker, who would himself run the country from 1957 to 1963.
 * King Ludwig II, ruler of a then-independent Bavaria, was so obsessed with building castles that the kingdom began drowning in debt. His nobles eventually got so fed up that they deposed him before he could bankrupt the country. Today, those castles bring in huge amounts of tourist revenue to the local economy.
 * Communist leader Santiago Carrillo had the nickname of Juan Carlos I of Spain picked out before his reign even began: "The Brief". 35 years later, Santiago is no longer leader of the Communist Party in Spain, but Juan Carlos is still King.
 * In 2007, Senator Larry Craig was arrested in a men's room for allegedly engaging in lewd conduct toward another man, who ended up being an undercover cop. Several websites began playing a clip from 1998 during the Lewinsky scandal in which Sen. Craig referred to President Clinton as a "naughty boy."
 * In response to his opponent Dwight D. Eisenhower putting out the first political TV ads, Adlai Stevenson stated "presidential campaigns will eventually have professional actors as candidates."
 * In 1980, the famous French humorist Coluche joked about the left-wing party rising to power in 2012. The man died in 1986. Comes 2012, and France elects a left-wing President after ten years under right-wing governments.

Professional Wrestling
""...by God Lita's here. Jerking Edge off... the ladder!"."
 * In Adam "Edge" Copeland's autobiography, On Edge, there is a picture captioned, "One of the best ways of getting heat from the crowd is to spear Lita". A year or so later, his affair with Lita was exposed... yeah, he did get a lot of heat for "spearing" her (Lita got more, though).
 * Also at Wrestlemania X-Seven, Edge and Christian, The Dudley Boyz, and the Hardy Boyz took part in TLC2. Lita ran in to assist the Hardys by pulling Edge off a ladder, to which Jim Ross called on commentary


 * Also in the same vein, in 2003 the WWE tried an all-Divas trading card set: WWE- Divine Divas. Card number 82 in this set: "Double Trouble- Lita & Edge."
 * All Lita stuff aside, towards the end of Edge's book, he said that he thinks he's headed for a heel turn, and states that while he's okay with that, he works better as a face. In the best way possible, he was wrong...oh god, he was wrong.
 * During Jeff Hardy's first stint in TNA, his entrance video contained the words "See You In The Future." Fast forward years later, and Jeff is now back in TNA.
 * This editor's school filter has a lazy habit of labeling anything "inappropriate" that they don't feel like giving a specific category to as "R-rated." I couldn't help but laugh when I saw that WWE's official website had been blocked as such. No points for guessing who the WWE champion was at the time.
 * During the annual WWE show in Iraq in 2003, Stone Cold Steve Austin actually gave John Cena the Stone Cold Stunner after being unimpressed with his "You Can't See Me" taunt. This was before Cena was made the top face of the company as Austin had been in the late 90's; the event has become both funnier and much more symbolic in hindsight.
 * Edge seems to get a lot of these as he cut a promo shortly after winning the 2001 King of the Ring where he took down Billy Gunn, claiming he failed to get over after he won the 1999 KOTR and went on to say "If in two years I'm not WWF Champion you can just shoot me because I promise not to 'Billy Gunn' this account". In two years Edge would get a broken neck and be out of action for over a year and would struggle as a babyface before being turned heel and get paired with Vickie Guerrero in a storyline and although he became WWE Champion several times he never won it cleanly. To top that when he returned in 2010 as a face he effectively bombed and the crowd turned on him at his Wrestlemania 26 match with Chris Jericho thus forcing the creative team to turn him heel again. Fate doesn't like to be tempted, Mr Copeland.
 * And speaking of which, at the end of Edge's book, he said he worked better as a face than a heel. From 2004 onward, we discovered that he was wrong.
 * Pete Rose appeared at Wrestlemania XIV, XV, and 2000 (aka XVI) and was beaten up by Kane at the first two events (he was given a stinkface in the third). In his first appearance, which was held in Boston, he insulted the Boston Red Sox (whom his team, the Cincinnati Reds, had beat in 1975 to win the World Series) and said the Red Sox couldn't win a World Series and mocked the Curse of the Bambino (before Kane came out and destroyed him to cheering from the crowd). Two World Series wins for Boston later...who's laughing now, Pete?
 * And the nickname of the Cincinnati Reds in the 1970s was the Big Red Machine, which became Kane's nickname in his first run.
 * Triple H vs. Ultimate Warrior at Wrestlemania XII, Currently Triple H is one of the main eventers in the WWE and in order to kick out of the Pedigree Triple H's finisher you need written permission from Triple H. During this match Triple H used the Pedigree on the Ultimate Warrior and Warrior just stands up from it like it's nothing. If this were to happen in current WWE the career of the wrestler would possibly be on life support.
 * That's also cause Warrior has a tendency to Won't Work On Me opponents' offense, especially their finishers.
 * Again concerning Triple H, the end of an old theme song of his finished with the snarky remark, "Who's sleeping with who around here?" Guess who married the boss's daughter.
 * While in WCW, Steve Austin suggested that he started a feud with Hulk Hogan by proclaiming "Steveamania" was bigger than "Hulkamania." It was dismissed as silly. A few years later, Austin went to the WWF and proved Steveamania was in fact bigger than Hulkamania.
 * Triple H: "The Game". Ric Flair: "The Dirtiest Player In The Game". And then they teamed up in Evolution...
 * Deliberate homage, "The Game" is wrestling, Ric's bragging about being the biggest cheater, and Trips (who is a gigantic Flair mark) talked about how people said they were students of "The Game" but he was "The Game".
 * When the rumors of Sting facing The Undertaker at Wrestlemania was gaining traction on the internet, this fake poster was floating around for said match to the tone of The Joker's Dark Knight poster. Approximately, 5 months later and this is Sting's current gimmick....
 * On the edition of Smack Down prior to the 2009 edition of Bragging Rights John Morrison had a confrontation with his former partner The Miz, mocking RAW and its recent parade of guest hosts, by saying it had become a "poor man's Saturday Night Live" and asking "who's next, Big Bird?". Fast forward two years and The Muppets hosted RAW on Halloween.
 * Which contained another hilarious hindsight moment; Edge had at one point called Sheamus Beaker. So come The Muppets hosting, Beaker and Sheamus meet backstage, who tells Beaker he can't make it to the family reunion.
 * In a backstage segment with Trish Stratus, Melina said if she beat her "wouldn't that be a kick in the head?". I think this needs no explanation.
 * Brock Lesnar returns... only in WWE 12. Not!
 * Just before Tough Enough season 5 premiered, contestant Ariane Andrew said in her promo "I am the next WWE Diva". She would be eliminated on the very first episode but then it became even more hilarious when she was signed anyway and also became the first of the contestants to debut on WWE TV in a regular role and make it to WrestleMania.
 * It becomes even funnier when, as of mid-2012, WWE actually released Andy Leavine, who did win that season.
 * This promo for the 2000 King of the Ring. Who is the superstar that stars in the commercial? Triple H. What is one of his current monikers?
 * During her commentary on RAW Feb. 3, 2014, AJ was asked on who would be given a chance at her Diva Championship. AJ states she would give it to the “two cute blondes that was dancing earlier”, reference to Summer Rae and Emma. Fast forward to March 24th of the same year when Vickie Guerrero ordered AJ into a battle royal for the Divas Championship at Wrestlemania, which includes… Summer Rae and Emma. Considering how AJ was to the other divas lately since becoming a champion, it let’s you about how karma is the real BITCH.
 * In June, 18, 2012 episode, AJ Lee shows up during a match featuring Daniel Bryan and Kane up, dressed as the latter. This causes Kane to take interest while Bryan yell at him to get back before the  team that were up against, who were also distracted, took advantage of the matter. The funny part one of them  ended marrying AJ in 2014.

Radio

 * An episode of Saturday Night Fry (1988) included a sketch where Stephen Fry went on a night out in London. At one point he goes to the theatre: "I spent a thoroughly enjoyable time watching Simon Gray's The Common Pursuit. Half way through the interval, I realised I was supposed to be performing in it." This was eight years before he abandoned the West End production of Simon Gray's Cell Mates, something he's made jokes about since.
 * In the same radio show, he also said the word "iPhone". That's right. Stephen Fry claimed the iPhone.. in 1998. See here.
 * Early on in this podcast of a 4e D&D game, one of the players goes off on a tangent about a "Rat King", an urban legend about a monster rat that is formed when the population of rats is so dense that they fuse together. Guess what they run into later on in that session...
 * Two Words: Schrödinger's Gun.
 * In the early 2000's, BBC Radio DJ's Mark Radcliffe and Marc 'Lard' Riley used to broadcast sketches featuring two naff club singers with the names Skel Nonch and Erk Dre who specialised in 'Cumbrian Tight-throated Singing'. One of the items of clothing the duo sported, a symbol of their terminal out-of-touch naffness, were trilby hats...
 * In August 2001, an episode of Old Harrys Game featured Satan showing Professor the truth behind his image of England. This included a cricket match which turned out to be fixed by the bookies. It was rebroadcast in September 2010, while this was still in the news.
 * In the first series of You'll Have Had Your Tea: The Doings of Hamish and Dougal, in 2002, reference is made to the Red Hot Chilli Pipers. When first broadcast, it was a simple pun on the Red Hot Chili Peppers. Repeated later, it sounds like a reference to the actual Red Hot Chilli Pipers, who formed in 2004.

Sports

 * Brazilian example: sports manager Vicente Matheus was known for his "brilliant" phrases, among them "I'd like to thank Antarctica for the Brahmas they sent us". Well, in 1999 (2 years after his death) both breweries merged...
 * Another, which might not count: basketballer Rafael Araújo (who even played some time for the Raptors) was known in Brazil as Baby. Then for numerology, he decided to rewrite his nickname as... Bábby. Yes.
 * A television ad proclaiming American Football quarterback Eli Manning to be "Unstoppable" became hilarious as he had two of the worst games in NFL history, then became funny in an ironic sort of way when the same player had an uncharacteristically great run in the playoffs, and then...
 * A T-Mobile ad which took several moments from everyday life, replacing the word "goodbye" with the word "hello", featured a Brett Favre press conference, spoofing his recent retirement: "After seventeen seasons, it's time for me to say... hello." By the time the commercial made it to air, Brett Favre had already stated his desire to play another season.
 * It's become even more hilarious since Favre has retired AND unretired again. He's retired again now, but who knows if it'll stick.
 * In an Adidas soccer ad during the 2006 FIFA World Cup, a shot by England midfielder Frank Lampard hit the goal line and was counted as a goal despite arguments from Oliver Kahn (star goaltender for Germany). Four years later, Lampard shoots a similar shot against Germany, but it doesn't count despite evidence showing the contrary.
 * Even funnier is England's 1966 World Cup Final win over West Germany, where Geoff Hurst scored a goal that didn't actually cross the line (though it was due to the match officials not being able to speak the same language. FIFA wasn't as smart then than is is now).
 * Given Helio Castroneves indictment for tax evasion there's something cruelly amusing about his trademark victory celebration of climbing up race track debris fences/prison fences.
 * Terrell Owens, after Dallas's early playoff exit, tearfully defended Tony Romo, saying "That's my quarterback". Next season, Owens accused Romo and tight end Jason Witten of conspiring to keep him out of the offense.
 * A baseball manager once said of weak-hitting pitcher Gaylord Perry that "a man would land on the moon before he hit a home run." He was right... by about 15 minutes. Perry did the deed on July 20, 1969, shortly after Apollo 11 landed. Snopes couldn't quite verify the quote, however.
 * Huh huh huh, "Gaylord"...
 * Everybody found Michael Phelps's insanely large diet surprising, to say the least (12,000 calories a day?). Then that photo of him using a bong showed up...
 * Now he's always in Subway commercials advertising a meal that (in the commercial) comes with BAKED chips. It's a lame joke, but someone HAD to have thought that one out.
 * During the Week 5 NFL on NBC pregame show during the 1995 season, following a "News and Notes" segment that included a story on efforts to re-introduce instant replay to the NFL (this was midway through the period where replay was dropped thanks to lengthy delays). While the other panelists were making their comments and when it came to NASCAR owner and former Washington Redskins head coach Joe Gibbs, Gibbs quipped that the interest in reviving instant replay was "...too late for Mike (Ditka) and I". The modern challenge format of instant replay was introduced in 1999, in time for Mike Ditka's final season as New Orleans Saints head coach, while Gibbs got to use it during his four-year return to the Redskins between the 2004 and 2007 seasons.
 * During the lead-up to the 1988 World Series opener between the Oakland Athletics and Los Angeles Dodgers; much had been made of Kirk Gibson not being likely to play due to a nagging leg injury. Following the National Anthem performance by 1980s teen pop star Debbie Gibson, NBC pregame host Bob Costas commented that, "The Dodgers have Debbie Gibson. If only they had Kirk Gibson". Late in the game, of course, Kirk Gibson would hit the famous game-winning homer (his only at-bat during the series) while limping his way through the bases.
 * In the acclaimed 1993 documentary Baseball the Red Sox and the White Sox both had "and they never won a World Series again" after respectively selling Babe Ruth to the Yankees and the Black Sox Scandal. They did win, eighty-something years later (Red Sox in 2004, White Sox one year later).
 * In the 2006 NFL Draft, the first pick was held by the Houston Texans. There were three pretty big names in the draft: Vince Young (who'd just led the University of Texas to a stunning national championship), Reggie Bush, and Matt Leinart (who both played for the then-dominant University of Southern California). Instead, they chose to draft defensive end Mario Williams, and were roundly criticized by everyone. The funny part comes five years later: Leinart's a backup, Bush's team has all but severed ties with him, and Vince Young's team's owner has gone on record as saying he won't be back next year. Meanwhile, Mario Williams has gone on to be one of the game's better linemen.
 * The Miami Heat were doomed to this with all of their pre-season theatrics from Lebron's "Decision" to a smoke-machine-included press conference to announce the big three to them predicting they would win "three, four, five, six..." championships. All they had to do to avoid the ridicule was win the first one. Too bad the Dallas Mavericks had other plans.
 * After the Dallas Mavericks won the NBA Championship, they went on The Late Show With David Letterman to read the Top Ten for an evening - "Top Ten Perks of Winning the NBA Championship". The #1 entry via Dirk Nowitzki was "finally, I'm gonna get my shot with a Kardashian sister!" That next offseason, Khloe's husband Lamar Odom was traded to the Mavs. Dirk's prediction may come true...
 * In 2008, NASCAR driver Clint Bowyer claimed that "Michael Waltrip is the worst driver in NASCAR, period." In 2012, he's racing for Waltrip's team.
 * In the 1995 post-season of the Premier League, Manchester United sold three of their starting players - Paul Ince, Mark Hughes & Andrei Kanchelskis - and proceeded to replace them with three of their youth team; Paul Scholes, David Beckham & Nicky Butt, also bringing Gary & Phil Neville into the squad aswell. In their first game of the 95/96 season, United lost 3-1 to Aston Villa, prompting Match of The Day pundit Alan Hansen to declare "You don't win anything with kids." Come the end of the season, United won the Premier League & the FA Cup.

Tabletop Games

 * In Mekton: Operation Rimfire, one of the characters had a girlfriend called Maria who was brainwashed and given an alternate identity. Especially given that it's a mecha game, the similarities to a plotline in a certain anime series are amusing.
 * There is a certain Call of Cthulhu (tabletop game) scenario called "Final Flight", in which the characters are on a plane with a disguised serpent person. To make it obvious: There is a motherfucking serpent man on the motherfucking plane.
 * In the Dungeons & Dragons 4th edition Player's Handbook, a section on why you'd want both melee and ranged weapons says: "When the flying monster makes its getaway, you don't want to be hurling insults at it." The Player's Handbook 2 released the Bard...which can kill enemies by insulting them.
 * An old Dragon Magazine article discussed ways to avert the Aerith and Bob trope in a campaign, advising DMs about how to establish consistent cultural motifs for character and place names. The article's title? "What Do You Mean, 'Jack the Samurai'?"
 * From the Pokémon Trading Card Game we have Double Rainbow Energy.
 * In the Yu-Gi-Oh Card Game, there is a pseudo-God Card named "Thor, Lord of the Aesir", who is listed as a Beast-Warrior-Type. Furries will get a kick out of this, due to an infamous parody picture that had floated around years back of Anubis, lamenting his change from God of the Dead to furry sex symbol, with Odin (Thor's father) comforting him by telling him Thor "wasn't spared, either", a reference to near-life sized horse dildo created during the time. To clinch the hilarity, Thor is a Synchro monster, which requires a Tuner monster called "Guldifaxe of the Nordic Beasts" to bring out. Guldifaxe, in case you're wondering, is a horse.
 * Speaking of Yu-Gi-Oh and furry internet memes, one popular meme is that Krystal can't have her sandwich. In the card game, there's a Fusion monster called Sanwitch who, at present, is very hard to get out - its Fusion Materials and most of the alternative ways of bringing it out are either banned or limited to one per deck. So Krystal can't have her Sanwich.

Technology

 * Possibly this article about an early beta of Vista, depending on your sense of humor.
 * At the advent of computers it was declared by Thomas J. Watson that there would never be a market for more than five computers in the entire world.
 * Conversely, Danny Hillis talks about the first computer conference he went to, where he proclaimed that the market for microprocessors would be in the millions. One wag asked, "What, will there be a computer in every doorknob?" Flash forward to Danny Hillis returning to the same hotel, where the room keys had been replaced by keycards. There was a computer in every doorknob.
 * This video of one of Steve Jobs's keynote speeches. Him explaining the "Megahertz Myth" is so much funnier when Apple switched to Intel in 2005...
 * The Take Thats at Intel in Apple's old "Snail" and "Toasted Bunnies" ads as well.
 * [[media:iPAD.png|This]] iPod parody. Two years later...
 * This 1972 photo of a "Super Airbus."

Theater

 * Beatrice's line, "No, not till a hot January" in Much Ado About Nothing sounds somewhat ridiculous to anyone in the Southern Hemisphere (except maybe Antarctica). It's even funnier, and maybe a little less ridiculous, when you realise she's talking about getting along with Benedick.
 * And the play was set in Sicily, which has a typical Mediterranean climate, so it's really just a Did Not Do the Research.
 * The entire "We Need a Little Christmas" number in Mame. The entire point of the scene is that the characters are at such a low point in their lives that they decide to cheer themselves up by starting their Christmas decorating early, even though, to quote the lyrics, "it's one week past Thanksgiving Day now". Now that retailers have extended the holiday season to well before Thanksgiving, it's hard to see how Mame and co. are rushing into things; if anything, they're dogging it.
 * Early on in Act II of Iolanthe, the Fairy Queen sings of Captain Shaw (London's fire chief at the time and a Big Name Fan), and in the premiere she stretched out her arms towards him. A few years later, Shaw was mixed up in a messy adultery scandal.
 * Nick Jonas playing Marius opens up an entire can of recursive funny at Eponine's expense. The first is, obviously, her Stalker with a Crush status making her the original Jonas Brother fangirl; the second, she has a crush on her brother. (For those of you not in the know, Nick Jonas originally played Gavroche in Les Mis.)
 * In Bell, Book and Candle, Shep refers to himself as having been "bewitched" -- "I didn't say I meant it literally." Guess what Fantastic Comedy Bell, Book and Candle inspired?
 * In Sweeney Todd: The Demon Barber of Fleet Street, Mrs. Lovett calls the title character "Mr. T." Pity the fool...
 * Towards the end of Rosencrantz and Guildenstern Are Dead, there's a lot of talk about being, or not being, On A Boat.

Other Examples
""I'll limit myself to observing that with the increasing popularity of vampires, we're on the verge of the unicorn syndrome all over again. If it hasn't happened already, in a few months look for airbrushed posters of sad vampires in Wal-Marts everywhere, and in a decade look for female college students saying to each other 'Were you into vampires when you were nine? Me too! We were such dorks!""
 * From Lore Sjoberg's Online Book of Ratings written in 1998:


 * ... nailed it (well, aside from being about ten years off), didn't he?

"It follows from such a view that psychology may be an interim science destined to wither away as neurology advances. I think this is about as imminent as the withering away of the Soviet dictatorship but I would not deny the possibility. -- Roger Brown, Words and Things, 1958"
 * The Barney the Dinosaur scene in this mock Watchmen: PG Version trailer can easily become this if you read the Dark Fic Day of the Barney (Or a plain old Funny Aneurysm if the fic gave you Nightmare Fuel.).
 * This page on a wrestling website lists various disturbing search terms that have lead people to pages on that site. One of them is "Cowboys Humping".
 * There's a similar one in an episode of South Park, where Cartman talks about artsy "movies about gay cowboys eating pudding".
 * This Chris Benoit action figure, which changes his expression from nice guy to screaming angry bastard, is funny for the wrong reasons.
 * A 1995 issue of Odyssey Magazine had an article titled "A Note From The NASA Administrator". The accompanying photograph showed the author of the article, then-administrator Daniel Goldin, and astronaut Charles Bolden talking to schoolkids about space exploration. In July 2009, Bolden was appointed as... NASA's Administrator.
 * In the 1997 movie October Sky, one of the men who helps the boys build their rockets is named "Mr. Bolden". And he's black, too.
 * There was a Tolkien/Harry Potter joke in Russian from 2005, which said "I already know what will happen in book 6: Well... off by one book.
 * This Entertainment Weekly story mused about the possibility of Paula Abdul dancing with Fred Astaire after seeing Elton John playing with Louis Armstrong for Diet Coke. Well, it wasn't Fred, but it was close enough...
 * One wonders if that writer has ever played Super Castlevania IV...
 * One Nickelodeon special from January 2004, just after the Spirit and Opportunity rovers landed on Mars, featured two celebrities having five minutes to build any sort of contraption out of some random materials on a table. One guy made a very dumpy-looking car-like thing out of straws and gum, with waffles for wheels. When the host asked him what it was, he said "A Mars rover." "Do you think this thing could really go to Mars?" "This is the one that's been having problems." (Spirit had a computer problem at the time.) During this exchange, the thing starts to fall apart. Flash forward six years, and Spirit and Opportunity are still roving, despite being made to last only 3 months.
 * In 1977, long before the book Night at the Museum was ever published, a commemorative book from the Smithsonian opened with an essay titled "I Wonder What Happens At Midnight", about everything in the museums magically coming to life after closing time. In 2008, Night at the Museum 2 came out, with that exact premise.
 * The USAF revealed in January 2010 through Jane's that they are modding Sidewinders for air-to-ground usage. Funny how all those arcadey flight-action titles like Ace Combat, Afterburner etc. had us using ersatz Sidewinders for multirole purposes well before this, eh?
 * There is a Social Psychology textbook written in 2008 which contains the following line: "More than anything else, the celebrity power of Tiger Woods is based on his athletic performance, his youthful charm, and his winning smile." A perfectly reasonable statement at the time of writing. Now? Yeah...
 * On the subject of academic writings...

"Robinson: They want to change the name from "Shoeless Joe." Kinsella: Oh that's alright, that wasn't even my title. That was the publisher's title. Robinson: What was your title? Kinsella: "Dream Field.""
 * This troper was reading a book on Italian politics written shortly after the election of Berlusconi which referred to him as 'a breath of fresh air after so many years of sleaze and corruption'. It's true that Italy doesn't have the most admirable past, but that description of Silvio is definitely hilarious now he's on trial for both sleaze AND corruption.
 * Matthew 25:8-9, more and more "funny" from World War II to this day.
 * Bob Saget and his remark about how Full House "gave him Tourette's" does count.
 * Ever heard of the flappers? ("Modern" feminist women from The Roaring Twenties?) Hard to take them serious since a certain webcomic popularized the term "fappers" for something completely different...
 * In this 1997 interview, the reference to Tom Cruise at the very end is pretty hilarious in retrospect. So is the earlier part about how good she is at picking projects, considering that she hasn't had a major starring role since that interview came out.
 * From 1989 through 2004, Disney/MGM Studios in Orlando, Florida had an attraction called The Magic of Disney Animation which had a short film at the beginning called Back To Neverland (not to be confused with Disney's direct-to-video Peter Pan sequel Return To Neverland), starring Robin Williams and the late Walter Cronkite. In it, Robin is a huge fan of Peter Pan and actually becomes an animated Lost Boy, and he defeats Captain Hook with a little help from both Tinkerbell and his quick improvisational comedy skills. Doubly hilarious in hindsight in that not only would he later get a chance to really show off his improvisational skills in a full-length Disney film, but first he would also get the chance to actually be Peter Pan himself (courtesy of Steven Spielberg and TriStar Pictures).
 * In 1989 palaeontologists chose the name Revueltosaurus for a new species of dinosaur discovered in Revuelto Creek, New Mexico. Years later, it was determined that the partial skeleton used to describe this species was actually a mix of bones from different animals and that the most of them probably belonged to a basal crocodilian, not a dinosaur. It just happens that "revuelto" is Spanish for "messed up".
 * In 2008, BP sent an angry email to the activist organization known as The Yes Men, complaining about usage of their trademarks in a half-finished parody website run by the group. In their response, the Yes Men argued that "BP does every bit as much damage to this planet as does Exxon" and deserved a fully realized parody site. Two years later...
 * This 1835 British children's book says about the Chinese, "It is from China that we obtain tea and silk, and fine muslins." Little more than a century later...
 * In Mayan mythology, Quetzalcoatl is portrayed as a "feathered serpent," which is also what his name means in the Nahuatl language. Millennia later, paleontologists discovered that theropod dinosaurs, among the largest reptiles that ever lived, were feathered.
 * Walt Disney saw Pollyanna make less money than expected, and commented, "I think the picture would have done better with a different title. Girls and women went to it, but men tended to stay away because it sounded sweet and sticky." Decades later, Disney executives would use the exact same logic to justify the retitling of one of the CGI films, which came off the heels of another underperforming film with a "girly" title.
 * Seth Meyers at the 2011 White House Corespondents' Dinner making jokes about Osama Bin Laden. Little did anyone who wasn't Barack Obama or a member of his staff know that the very next day...
 * The joke in question is at 2:05 in this video of Seth's standup. Note Obama's reaction to the joke: in retrospect, his face seems to be saying "That joke is going to be even funnier in about 48 hours."
 * In what may be an amazing example, on the DVD commentary for Field of Dreams, director Phillip Alden Robinson shared that while making the movie based on W.P. Kinsella's novel "Shoeless Joe," the studio decided to change the name of the film to its eventual title: "Field of Dreams". Robinson, upset, called Kinsella to tell him the news, not telling him the new title, and had this conversation:


 * Here is James Rolfe's "Angry Batman" comic, which was created in the early 2000s. Not too far off from what Frank Miller would give us years later.
 * This Rosie O'Donnell doll made by Mattel from the 1990s (around the time of her talk show and massive popularity), which depicts her as Barbie's best friend. In 2002, Rosie would come out as a lesbian, adding a whole new level to their "partnership".
 * The asteroid Antiope was discovered in 1866, and named after one of two characters in Greek mythology with that name (there's some dispute about which one). Fast forward to 2000, when it was discovered that Antiope is in fact a double asteroid (two pretty equally sized bodies orbiting a point between them), and it takes on another dimension.
 * In the wake of the August 2011 liberation of Tripoli, Libya comes this story of one rebel's trophy from the conflict... a hat..
 * The "Bucket Filling" concept. Any Homestuck fan will be able to tell you why this is hilarious.
 * Clinton wasn't the first President to not inhale. All of Reagan's cigarette ads qualify (and a lot of other tobacco product ads on the subject of inhaling.)
 * Loki from Norse Mythology is a jotun, or troll. During the the age of the Internet, the term "troll" took on a whole new meaning: a person who sows chaos and discord (sometimes For Great Justice, sometimes For the Lulz), which is Loki's raison d'être. But wait, it gets better: trolls are known for "flaming" others, and guess what color Loki's hair is? Here's a hint: one of his kennings is "Flame-Hair." Bow before your god, all ye Internet trolls.
 * One of Thor's kennings is "Troll-Basher." What do administrators use to get rid of pesky trolls? The banhammer, of course!
 * This PvP Online comic from almost ten years ago.