* The "Phones-4-You" ad campaign goes from being a mildly successful attempt at MemeticMutation to being pretty hilarious once you've played ''VideoGame/{{Metal Gear Solid 4|GunsOfThePatriots}}'', where the weapons merchant has a hand-gesture catchphrase for the slogan 'EYE HAVE YOU'.
* It is generally quite hard to deliberately engineer a HilariousInHindsight 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, [[https://www.youtube.com/watch?v=quxOMX1jl1w 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, [[http://www.youtube.com/watch?v=w61vieuH1kw a [=McDonald=]'s commercial]] featuring Music/{{NSYNC}} and Music/BritneySpears 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 [[VideoGame/MetalGearSolid Big Boss]] [[http://www.youtube.com/watch?v=FqLZkZEYKHo 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.
* DavidKaye. ''WesternAnimation/BeastWars'' Megatron. Enzyte commercial announcer. Enzyte was charged with fraud.
* After an ''Encyclopedia Britannica'' [[http://www.youtube.com/watch?v=vO2D_sxXAWM commercial]] had its run, they decided to make [[http://www.youtube.com/watch?v=Hxwin9XFbnQ a direct follow-up to it]]. And the very first line said was, "[[VideoGame/MetroidOtherM Remember me?]]" To add, both were made by Creator/StanFreberg, who was the voiceover talent. The onscreen talent? Freberg's son.
* The "ComicBook/LexLuthor [[MemeticMutation stole]] [[http://static.tvtropes.org/pmwiki/pub/images/40cakes_4996.jpg forty cakes]]" meme takes a new meaning with an UK advert for Innocent Smoothies, which shows a [[http://www.youtube.com/watch?v=5hd_BmPfxIo&feature=player_detailpage#t=47s bakery named "Luthor's Cakes"]].
* A 1996 ''This is SportsCenter'' ad featured Karl Ravech and [[CountdownWithKeithOlbermann 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, [[AlternateCompanyEquivalent 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.
* SegaSaturn [[http://www.youtube.com/watch?v=Q-lCJr0yVo8 vs.]] [[PlayStation "Plaything"]]. The UsefulNotes/ConsoleWars would determine which one was worthy. It was the Playstation.
* [[http://www.x-entertainment.com/messages/629.html An article]] on X-Entertainment points this out about [[Film/ETTheExtraTerrestrial a Reese's Pieces commercial starring an alien]].
* {{Sega}}'s very [[TakeThat attack-oriented advertisement campaign]] with arrogant claims and insults directed at Creator/{{Nintendo}} in TheNineties led to many instances of this trope:
** The Game Gear commercials poked fun at the UsefulNotes/GameBoy's graphical limitations. Everyone forgot about the UsefulNotes/GameGear's existence before Nintendo even announced the UsefulNotes/GameBoyColor.
** "Genesis does what Nintendon't." One decade-and-a-half later, Sega decides to release a special version of the Genesis [[http://www.engadget.com/2010/02/02/sega-zone-the-genesis-with-a-wiimote-nobody-asked-for/ with Wii-mote inspired controllers.]]
** "Genesis does what Nintendon't" doesn't mean anything anymore now that the Wii's VirtualConsole service has Genesis games. A few years later, the UsefulNotes/Nintendo3DS is announced to have plans for UsefulNotes/GameGear games on its own VirtualConsole in addition to UsefulNotes/GameBoy and UsefulNotes/GameBoyColor games, furthering the effect.
** Also, [[http://www.youtube.com/watch?v=HCQRcinZYH8 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?!" Nintendo was actually the last console maker to get into using optical media (though despite a common misconception, Gamecube and Wii discs aren't [=CDs=]--they're more like [=DVDs=]).
*** In a way, Nintendo had the last laugh on this one. They actually did attempt to contract with Sony to develop a CD-ROM add-on for the SNES. The deal went sour, resulting in Sony developing the device into a [[PlayStation stand-alone console]] which went on to become a significant factor in Sega's exit from the console market altogether.
* [[http://www.youtube.com/watch?v=-adG9pcRhrA One old]] "Creator/CartoonNetwork Responds" bumper had them respond to a JimCarrey fan who asked them for a picture of him. They told said fan they'd never show anything with Jim Carrey in it. Fast forward to their shift to live-action programming, and they eventually would show both ''Film/TheMask'' and ''Film/HowTheGrinchStoleChristmas''.[[note]]They seem to at least vaguely remember said bumper, though - while [[{{Sequelitis}} terrible sequels to Jim Carrey movies which don't feature Jim Carrey in them]] are aired as often as anything else, CN's only shown ''The Mask'' and ''Grinch'' one time each.[[/note]]
** What's also damning about that ad is the majority of the characters listed in it are no longer shown on the network.
* Another [[https://www.youtube.com/watch?v=6juEOmOaYVk Cartoon Network]] promo. The time, early 2000s. Cartoon Cartoons Kings and Queens of the Network, Scrappy Doo and his fellow Hanna-Barbera cartoons forced out to be shown less in favor of Cartoon Cartoons. The time, early 2010s, Warner Brothers has released about half of their Hanna Barbera offerings to DVD, and very few of the Cartoon Cartoon offerings. One seems to sell so much better than the other, TakeThat Creator/CartoonNetwork
* Back when Enron was viewed as a thriving corporation, they released a series of commercials with the theme [[http://www.youtube.com/watch?v=pboh1SFk6TM "Ask Why?"]] Years later when Enron suddenly went Bankrupt shocking the country, the United States government asked them why? They got their answer when they discovered years of corporate fraud.
* [[http://www.youtube.com/watch?v=HJ2N0kZgOXY This 2007 Honda Civic Hybrid ad mocking the Toyota Prius "Yes" campaign]] is hilarious enough on its own, but not long afterwards, Honda reintroduced their Insight hybrid as a five-door hatchback which looked a hell of a lot like the car they were making fun of before.
* [[http://responsiblemarketing.com/blog/wp-content/uploads/2008/10/camel-moredoctors.jpg More doctors smoke Camels than any other cigarette]]
* In some old Windows 95 commercials (such as [[http://www.youtube.com/watch?v=Tw-GGT6900s this one here]]), Microsoft used a 2 by 2 grid of squares that were colored the same way as the Windows flag in order to demonstrate certain features, though it wasn't their official logo. 17 years later, Windows 8 shows up with a more tablet-oriented UI. [[http://i.s-microsoft.com/global/ImageStore/PublishingImages/logos/hp/logo-lg-1x.png Guess what their logo turns into?]]
* The Brazilian arm of Fiat made [[http://www.youtube.com/watch?v=ERDj5OKH0eI an ad]] related to the 2013 Confederations Cup, entitled "Come to the Street", described as "the biggest bleacher of Brazil". Given that at the same time [[http://en.wikipedia.org/wiki/2013_protests_in_Brazil huge protests emerged in the country]], the revolted people embraced it as an anthem. [[http://www.youtube.com/watch?v=i3lCMiUAJ90 "Come to the Street"]] became their motto (along with "The Giant Awoke", taken from [[http://www.youtube.com/watch?v=MLU95q0BgQA a Johnnie Walker ad]]) and was stamped and sung everywhere.
* Sony started a line of TakeThat posters towards Microsoft after noticing the poor reception following the XboxOne's initial reveal. One of these claimed "The only red ring is the circle button," a jab at the {{Xbox 360}}'s infamous Red Ring of Death issue. Launch day arrives, and... [[http://www.gamezone.com/news/2013/11/15/new-claims-of-ps4-s-red-line-of-death-beginning-to-pop-up Well, let's just say things couldn't be more ironic.]]
* Creator/SarahMichelleGellar did an ad for Burger King complaining that rivals do not have as much meat, she was about six at the time. Today [[PetitePride she has less meat]] than some girls at the same age she did the ad.
** Also, the rivals in Gellar's Burger King commercials included [=McDonalds=]. Thirty years later, Gellar would play an advertising executive on ''TheCrazyOnes''. Guess who [[UsefulNotes/McDonalds their first client]] was.
* In a Dutch ad for distance education service LOI, well-known lawyer Bram Mozkowicz is involved in a - very minor - traffic collision, and is stunned by the other party's legal knowledge. In 2014, an automobile police chase in Amsterdam came to an abrupt halt when the perpetrator's car crashed into Mozkowicz's Aston Martin, with Mozkowicz inside. (Thankfully, nobody was hurt.)
* [[http://www.youtube.com/watch?v=oRValgHDvxE A Singaporean ad]] about problem gambling which airs on [[WorldCup 2014 FIFA World Cup]] shows a group of children discussing who would win. It then cuts to a depressing shot of a sad young boy hoping for Germany to win, as his dad bet all of his son's savings on them. Well, depressing until hours later, when [[CurbStompBattle Germany beat Brazil 7-1]], and eventually winning the whole thing.
* In 2002, Creator/{{Nickelodeon}} ran a parody of ''WesternAnimation/FrostyTheSnowman'' with [[WesternAnimation/SpongeBobSquarePants Patrick Star]] playing the snowman. Three years later, ''The Legend of Frosty the Snowman'' comes out with Creator/BillFagerbakke, Patrick's voice actor, playing Frosty.
* During his time with the [[UsefulNotes/NationalBasketballAssociation NBA]]'s Charlotte Hornets, star power forward Larry Johnson did a commercial as part of the Converse "Grandmama" series where Johnson (as Grandmama) was stuck in [[https://www.youtube.com/watch?v=GT_3YaOQcXo three-point land and needed to get to the low post]]. Partly because of a 1993 knee injury, Johnson would later develop into a decent outside shooter for someone in his position; with his most famous individual play coming at the end of game 3 of the 1999 Eastern Conference Finals between the New York Knicks (which Johnson had joined in 1996) and Indiana Pacers when Johnson hit a three-pointer that became known as a "four-point play" due to Johnson being fouled and sinking the free throw for the winning points in the 92-91 victory en route to the last-seeded Knicks winning the series in 6 games and going to the NBA Finals.
* Similar to the Sega vs. Nintendo ads listed above, Apple once regularly ran ads such as [[https://www.youtube.com/watch?v=e6PoLiXCA40 this one]] making fun of the Intel processors used in [=PCs=] while touting the superiority of the [=PowerPC=] chips that Macs used. Fast forward to the mid-2000's, and Apple announces that they're switching their computers from [=PowerPC=] chips to Intel ones. From the start of the Intel transition to the present, Apple's promotional material has continuously sang the praises of Intel's [=CPUs=], [[NiceJobBreakingItHero which was somewhat necessary because of the rabid hatred for Intel that they had cultivated among their fanbase.]]
* A Geico commercial had the caveman playing against Brian Orakpo in Scrabble. The caveman's shirt resembled the colors of Tennessee Titans, who Orakpo would sign for next.