And this infamous strip, whose mockery of the bogus release date for Duke Nukem Forever was funny in 1999 when the game was a year and a half late, but only grew more so as the game grew two years, four years, eight years, nine years, only to loop back around to Hilarious in Hindsight when a demo of the game, now out of development hell, was released at PAX.
This strip became a lot funnier when a few years later Tycho actually did miss a portion of PAX due to the birth of his child.
This strip has a squirrel with a cigar and a T-shirt that says "Fuck you" getting turned down for Conker's Quest, for not being "accessible" enough to kids. Eventually, Conker's Bad Fur Day came out, and the squirrel probably would have fit right in there.
Another strip parodied the "progression" from Darth Maul's double-bladed lightsaber in The Phantom Menace and Anakin's dual wielding of lightsabers in Attack of the Clones with having characters draw quadruple, quintuple and septuple lightsabers...
David Morgan-Mar: This comic was published over 2 years before Episode III was released in May, 2005. Need I say anything more than "General Grievous"? I'm ready for those royalties, George.
A minor one, but the comic is currently (Oct 2010) on a Tue-Fri-Sun update schedule. Amber posted a comic with the tagline, "It's like a Friday cliffhanger, but on a Tuesday!" Then she got sick and couldn't update on Friday, so it was a Friday cliffhanger.
In a 1998 cartoon where Irwin ended up in the computer system of the space station Mir, he said at one point "I can barely believe this thing stays up." Two years later, the station was decommissioned, deorbited and burned up in the atmosphere. Now, if anybody had been onboard at the time, this would be a "Funny Aneurysm" Moment, but as nobody was...
In this 2009 Sunday strip, a Star Trek crossword has as #6 down, "Brain connection with fingers to face". The actual answer is Vulcan mind meld, but considering what Captain Picard is now famous for...
An Awkward Zombie animated short features the crew of the MythBusters attempting to build a cannon out of duct tape in order to fire a pig. While the "cannon made out of duct tape" sounds like a Flanderized "silly Mythbusters build," the Mythbusters did a "duct tape" special much later. And guess what they actually built?
Another Awkward Zombie comic has someone using a dog whistle that only Link can hear because he has huge ears; this was made before Twilight Princess.
This comic fits the trope in terms of the US release date of Professor Layton vs. Ace Attorney. In the comic, Apollo asks the judge for more chairs for the witnesses, who are all crammed into the one-person stand along with the defendant. In the aforementioned crossover, there's a long witness table in Labyrinthia's courtroom since you interrogate multiple witnesses at the same time.
The Order of the Stick: Early on, there is ambiguity as to whether Sabine is a demon or a devil. She is later revealed to be a succubus. This was before 4th edition.
And this 2001 strip wherein Torg and Riff need leiderhosen and pliers to party with Charlie Sheen, but Sasha tells them he's been sober for months, so they try to find Robert Downey Jr., a belt sander, and a Portuguese man-of-war. Over the next decade, guess which got his career back on track and which became a walking punchline?
In thisVirtual Shackles comic, one of the 'problems' the Kinect can't fix is the boy's ethnic friends. A month later, Gamespot reported that Kinect's facial recognition software has trouble with dark-skinned people.
Speaking of The Elder Scrolls, the troll alphabet is the Daedric one, only with the letters flipped upside down. Andrew has admitted that he just picked it at random from a website documenting fictional alphabets. It turned out to be a lucky pick - the Daedric alphabet is, in the games, used by the Dremora, a grey-skinned, horned, shaggy-haired Proud Warrior Race with a Fantastic Caste System who hail from Another Dimension. In other words...trolls.
Dave's mini-Coming-Out Story is both sad and an in-universe example of Hilarious in Hindsight, considering how Dave spent many years suffering from internalized homophobia due to his abusive, inscrutable, macho warrior of a brother (who produced gay puppet porn)... only to meet Dirk, the alternate universe counterpart of Dave's Bro, who is gay. Quote Dave:
DAVE: i think...
DAVE: there is a SLIGHT chance...
DAVE: i may be the biggest idiot in the world
DAVE: when it comes to understanding some things about my bro
DAVE: some pieces i never really put together
DAVE: about him
DAVE: until maybe literally right now
Somewhere in December, FPS Russia releases a video showing him wrecking havoc with an L85A2 rifle. A couple days later, Battlefield 3: Back to Karkand is released. Guess what is the name of the Assignment needed to unlock the L85A2?
Depending on your opinion, this may also qualify as a "Funny Aneurysm" Moment too: the endless promotion for a then-unknown Kesha on Key 103 Manchester, a British radio station's web site. Bizarrely, she was listed on the regular presenters' list too... although not now!
Sonichu mentioned that he had a dream of seeing his creator, Christian Weston Chandler, with long hair in the mirror in one issue. Needless to say, this ended up coming true. Also, an author's note in Episode 20 says "I would rather suffer a painful gender-change operation than ever be a homo."
A Running Gag in the script is Psycho Mantis' utter refusal to believe in the supernatural despite ample evidence to the contrary, up to and including the spirit of the Sorrow showing him the spirit world. In Metal Gear 4Psycho Mantis' spirit was forcibly implanted into Screaming Mantis and when Snake defeats the latter, the former's spirit manifests and is eventually banished back into the grave by the Sorrow's spirit.
The very existence of the webcomic Pokémon X is much funnier now that the newest Pokémon games have been revealed to be Pokémon X and Y.
This comic where Martin, Angus, and Faye discus Martin's comfort with his ex Dora dating Tai is a bit funnier now than it was at the time. Angus said to Faye, "I'm just saying, if you have to break up with me, at least leave me for a girl." Pintsize followed with "Leave him for a robot. A girl robot!" After Faye and Angus broke up, Faye's next romantic partner was Bubbles, who is in fact a girl robot.
ThisAchewood strip starts off with Ray reading that scientists discovered Pluto was just a big piece of snow. "Ain't no planet at all!" Fast forward two years to when Pluto's status as a planet gets revoked for real...
Political cartoonist Matt Bors made a strip in 2013 against America's use of drones, with Malala Yousafzai telling President Obama that they fuel terrorism; a fake pundit responds she's wrong, as "one of them won a Nobel Prize, and one didn't." Guess who won the Nobel Prize the following year.
Shortpacked! had a 2006 plotline where Galasso tries to convince his employees to sire a child with his daughter, so that he can have a heir to his "empire" of toy stores. At one point, he goes to Robin- a woman, mind you. After hearing Galasso's request to notify him "the instant you have achieved impregnation", Robin responds by saying she's "fairly confident that's impossible." Seven years later, thanks to Rosenthal's tech skills, Leslie impregnated Robin.
Sandra and Woo: Landon's mom, Harriet, believed Larisa to actually be "a succubus that'll give birth to the antichrist". Fastforward to the Divine Comedy: Larisa makes a deal with the devil to save Sandra, and will become a succubus if she succeeds because it'll be a waste of her talents to be anything lesser than that.
This animated comic of a Kirby parody comic series shows Kirby eating a Nintendo Switch, and loving it (Though he still thinks it's not as good as the Nintendo GameCube). Shortly before the Switch's release, people actually started tasting Switch cartridges and they always say how terrible they tasted.
Unsounded: An Inept Mage tries to attack Duane with a pymaric that summons a huge spectral tentacle monster — which turns out to be completely benign. Four chapters later, it's revealed to have been a Gentle Giant pymaric, on clearance from the Happy Tentacle Love Hotel. Duane, fortunately, never learns that he was assaulted with a sex toy.