Combat on Atari 2600 has you and a friend flying two planes around two large circles. But that's pretty vague, right? Oh, and it was released with the 2600 on September 11, 1977.
In-Universe example from Chrono Trigger: As you head off to the Millenial Fair at the beginning, one NPC you can talk to says "You're going to have to wait a thousand years for another Millenial Fair!" Unknown to you, a thousand years from then, the world will have just been destroyed by Lavos.
Through controversial already since it was based on the film, Death Race 2000, Carmageddon had two drivers, one of them called Die Anna, played on to the name Diana. Keep in mind, the PC version, which came first, was released on June 30, 1997. It was altered to a zombie game in order to only a release in the United Kingdom. A month later, Diana, Princess of Wales, was killed in a car accident.
The game series Rampage, where the object of the game is to destroy skyscrapers as a Captain Ersatz of Godzilla or King Kong, among other monsters, in a city has become this since 9/11. It took them 7 years to produce a new game because of it. Worse still, you can actually target some real-world landmarks in a few of the games.
Metal Gear Solid 4 managed to turn much of Metal Gear Solid 3: Snake Eater into a "Funny Aneurysm" Moment: bad enough that Naked Snake ends up becoming Big Boss, the villain of the first two Metal Gear games, but MGS4 reveals that the rest of your team - Sigint, Para-Medic and the all-important Major Zero - went on with EVA and Ocelot to found the Patriots, the organization which eventually became the shadow government of the United States, and that Big Boss - originally one of the group - set off the Outer Heaven and Zanzibar Land incidents in order to throw off their control. Furthermore, it's revealed that both Sigint and Para-Medic, a.k.a. DARPA Chief Donald Anderson, who probably indirectly created the AIs, and Dr. Clark, the creator of the Les Enfants Terribles project and the person who turned Frank Jaeger into the Cyborg Ninja, were both killed; Dr. Clark shortly before the events of the first Metal Gear Solid, and Sigint/Ocelot were aware of their true allegiances when Ocelot killed Sigint; by the end of MGS4, none of the original members are left, though it's a surprise as to which one is really the last to die. It's actually Big Boss, who survived Metal Gear 2 and was in a coma until saved by Ocelot and EVA.
In the first Metal Gear Solid, there's a funny sequence where Naomi lectures Snake about what happens to the body when someone smokes, and informs him that if he carries on doing it he will get cancer and die. In Metal Gear Solid 4, Naomi dies, of cancer. Suddenly the conversation isn't funny.
Less unfunny, more squicky/Back to the Future: In Metal Gear Solid: Portable Ops Plus, Old Snake is a bonus playable character. As a bonus detail, all the girly magazines in Portable Ops use pictures of EVA. Being a man, Snake is not immune to the irresistible lure of pictures of his beloved naked, smoldering - mother. Lampshaded by CMP Studios, a Metal GearMachinima group, in a one-shot special - "I apologize for what I used your pictures for".
Similarly, there was a movie on Metal Gear Solid 3's Secret Theatre where Snake and Para-Medic argue about whether Snake should kill and eat The Boss's horse, with The Boss becoming incensed enough to storm away quickly and send GRU soldiers over to their location. It's not so funny in Peace Walker when Big Boss is forced to euthanize The Boss's horse with his gun in a manner similar to his killing The Boss, after the horse was critically and mortally wounded from falling off the Costa Rican/Nicaraguan border while in pursuit of Peace Walker.
In the same game, Otacon in an optional Codec call will reprimand Snake for throwing away a lit cigarette into the harbor from the George Washington Bridge. Shortly after the release of the game, it was shown that Otacon wasn't the only person upset with Snake's actions, as quite a few people were in an uproar over this fact, enough to have Kojima have Naked Snake actually stamp out his Cigar just before doing his HALO jump at Tselinoyarsk in the next game.
The Undertaker's SmackDown! vs. Raw Curse qualifies. A storyline of the story mode in WWE Smackdown vs. Raw 2006 ends with Eddie Guerrero landing in a casket during a feud with The Undertaker; soon after the release of the game, Eddie Guerrero died. In the 2007 edition, a storyline has dialogue where The Undertaker tells Chris Benoit (who he's feuding with) that his grieving family will have no one to blame but himself; months later, the real Chris Benoit kills his wife, his son, and himself. In the 2008 edition, Undertaker has a feud with Jeff Hardy in the story mode; in 2008, Jeff Hardy suffered his second Wellness Policy strike, and during his Wellness Vacation, his house burnt down, destroying all of his possessions and killing his pet dog.
As a side note: in the 2009 edition, Undertaker feuds with Finlay and Santino Marella, and eventually you control one of them in an alternate "zombie" attire to aid him during the game's Road to WrestleMania story mode...
The WWF Raw video game for the SNES and SEGA Mega Drive (among others) allowed wrestlers to perform over-the-top "mega moves" in order to finish a match. The video game guide demonstrated Diesel's mega move, in which he tosses his opponent fifty feet in the air and lets them crash back down onto the mat, by having him do it to Owen Hart, who would wind up dying at the WWF's Over The Edge event five years later by falling fifty feet and crashing onto the mat due to a malfunctioned harness.
In WWE '13 if you are having a match with Eve Torres you'll occassionally hear Jerry Lawler make a comment about needing an EMT at ringside because his "heart skipped a beat." It's fairly cringeworthy when you remember that Lawler had a major heart attack on live TV in September 2012 that nearly killed him. In THQ's defense the audio commentary had been done for awhile at that point and Lawler himself has already made these kinds of jokes following his return.
In the 1992 arcade game Total Carnage, you control a one man army blowing his way through an insane landscape of chaos which is clearly inspired in several ways by the 1991 Iraq conflict (it's in a desert) mixed with a much higher dosage of constantly escalating madness (the mad general is called "General Ackboob", you battle hordes of mutant monsters). In 1992 the way your PC tears his way through all this chaos without any trouble save a quarter shortage is amusing in its insanity. Viewed in 2008 against the many complications of the second Iraq war...not as much.
The first time you play Halo, it seems like just a well-made, fun, alien shoot-'em-up. It's got little monkey enemies that like to panic at the first sign of you and marines shouting lots of funny things like, "Get up—SO I CAN KILL YOU AGAIN!" Then your AI guide sends you alone into an eerie containment facility where the mutated corpses of slain soldiers really do get up for you to kill again... and again....
Hilarious Outtakes feature Sgt. Johnson saying "Halo 4, I get a woman". Halo 4 was released... but Johnson got KIA at the tail end of Halo 3. The closest thing to Sgt. Johnson in Halo 4 is Commander Sarah Palmer.
It could also be interpreted now as Cortana, who was close to Johnson as well, Joining him since she sacraficed herself at the very end.
In the early 1990s, Doom enjoyed massive popularity which can be credited to a vast community of fans making Game Mods. One of which, "UAC Labs," featured modified enhanced gore, and levels where you are supposed to kill swarms of demons. The description of the WAD ends with "Good Luck Marine, and don't forget, KILL EEM AALLLL!" The copyright notice says "You may NOT change a damn thing with this WAD, if you do, i will blow you up." This mod was one of a handful made by Columbine shooter Eric Harris (one of which included an on-screen gametesting credit for accomplice Dylan Klebhold), and no, Eric did not make a Doom mod set in Columbine High School that allowed the player to shoot students.
In The Legend of Zelda: Ocarina of Time, at the entrance of Kakariko village, a solder introducing the village says that they're a small community and that he hopes they'll one day be as lively as the Castle Town market. Years later, when the market is overrun by ReDeads, the village ends up holding the escaped population of Hyrule's humans, making it the liveliest area in Hyrule.
Then there is the guard posted at the gate of Hyrule Castle Town, who complains about how boring things are, and that he wishes things would become more interesting. The player also learns about the guard's fascination with ghosts. Fast forward seven years, after Ganondorf had overtaken the castle, in the place where the guard was stationed sits a mysterious individual who buys and sells ghosts, who somehow earned Ganondorf's favor.
Related to this, many characters, including Maya Fey, Ema and Lana Skye and Detective Gumshoe have joked about Phoenix giving up or even losing his badge. It was funny during the first three games, since the players reaction was guaranteed to be "Yeah, like that'd ever happen!"... Then, Apollo Justice: Ace Attorney came along and the jokes turned into nightmarish Foreshadowing instead.
In Trials and Tribulations Case 2, Pearl jokes that Phoenix will one day grow famous enough to have imitators. In Case 3, Tigre gets Maggey thrown in jail by impersonating Phoenix and doing a deliberately awful defense at her trial.
And at the end of that case it's revealed that Godot cannot see red on white. The name of Mia Fey's murderer in the English version of the game? Redd White.
Mia's reaction to Phoenix eating the pendant bottle in Case 1 is mildly amusing at the time, but if you consider the events of Case 4 it's no longer funny: it was not her first time seeing her client swallow poison in court to cover for his lover.
Godot's line, "by the way, I've tried salt in my coffee. It tastes terrible," Take a look at the end of Flashback case 3-4, Mia is crying that Terry Fawles commits suicide, Dahlia got away with that murder and Diego says "relax, kitten, your tears are getting my coffee salty."
In Dual Destinies, watching the astronaut Solomon Starbuck act as if he's in a malfunctioning spacecraft madly pushing buttons in episode 4 whenever he's stressed, is hilarious. It can also come off as hilariously ironic that he has a fear of space. That is, until you find out that he's suffering from extreme post-traumatic stress disorder due to almost dying in the depths of space when a terrorist sabotaged his spacecraft. He very, very, VERY almost didn't make it back alive, and from that day foward he developed an intense fear of space and, presumably, a habit to flashback and act like he's in that situation. Although he still looks over the top while he thinks he's in space, it does make it less of a laughing moment and more of a "... you OK, dude?" moment.
The arcade game Michael Jackson's Moonwalker might be weird enough, but it just gets creepier (or sillier) each year: You touch kids (in the video game sense, and they're all girls, but still... the fact they are at the height of Michael's crotch does NOT help.) to gain points and powerups (and in home version, you cannot advance unless you get ALL the kids, which could be... hiding), or touch Bubbles the Chimp to get a super cyborg transformation. One of the attacks is Michael grabbing his crotch. And then there's the dance attack: MJ does his moonwalker gig, and it wipes out all the enemies on the screen. The Angry Video Game Nerd lampshaded it during in his review of the game.
Moe's constant sleeping in Da Capo when you get to the end of her route. Suddenly the Cloud Cuckoolander thing and all her sleeping are a bit less charming, aren't they? And the vitamins... She's trying to sleep as much as possible so she can see the childhood friend who died saving her. She stopped taking the vitamins - read: sleeping pills - when she started dating Junichi but started taking more and more after the cherry tree died and she couldn't dream anymore. Eventually, she tries to overdose on sleeping pills where she met her friend right as Junichi convinces her to move on with her life. She gets better but... For extra fun, remember that the tree dies in lots of routes and she doesn't have the hero around to help her.... Yay...
Subverted in Spider-Man: Web of Shadows. During the battle with Black Cat, Spidey takes a metareferencial jab at his movies when encountering a Kingpin Tech Flyer for the first time: "Green Goblin is so 7 years ago! The kids are into guys like Venom and Sandman now!" The kids probably aren't liking Venom some time later in the game after he resurfaced with his symbiote army that turned New York into a deserted city, almost devoid of human activity (which is far more than what he did in Spider-Man 3). The catch? The player was well aware of that, for this would have been a straight example if the game didn't start In Medias Res.
Plants vs. Zombies, which came out in May 2009, featured a zombie version of Michael Jackson, complete with "Thriller"-style backup dancers. Six weeks after the game's release, Michael Jackson died suddenly from cardiac arrest. Needless to say, the dancing zombie has been turned into a Disco Dan in a patch.
Making things even worse, if you look up that enemy type ("Dancing Zombie") in the in-game encyclopedia, the entry states "Any resemblance between Dancing Zombie and persons living or dead is purely coincidental" (again, a joke on the Thriller Credits Gag).
In FEAR 2: Project Origin, Stokes asks Snake Fist who Alma is. Snake Fist replies "She's the mother of the apocalypse!" This amusingly unhelpful description becomes somewhat less amusing in light of the game's ending - Alma rapes the player character and becomes pregnant with his child who is, due to the nature ofher parents, possibly the Antichrist.
Yuuichi and Ayu's pinky swears in Kanon suddenly become a lot less childishly innocent at the end than they were to start. Or rather, they remain the same childish innocent gesture but...
Ever17: Tsugumi and Takeshi's scene in the flooding elevator while talking about the Archimedes Principle becomes a lot less amusing when the mini sub they're in starts to sink and they need to lose about 100lbs in order to start rising again. Takeshi distracts her with by asking her about it again the leaps into the airlock and moments later out into the ocean which is ice cold and in a setting that does not ignore the effects of water pressure or the human swimming ability.
Second example: At the beginning of Coco's route, there's a moment where Takeshi, You, and Coco are looking at a photo album of You's. When they see a picture of a baby Takeshi humorously asks You if it's her baby, which she reacts with a brief "no". Later in the route, we find out it actually IS her baby/clone, which she only had because she's dying of a lethal heart disease and made her to carry on her legacy. Ouch...
In the Tex Murphy game The Pandora Directive, set in the 2030s, Tex meets an NSA agent who reminds him of the Graham Act, a law that was passed "40 years ago" in response to increased terrorist threats to the US, giving the NSA carte blanche when dealing with internal security matters. The game was made a full 5 years before 9/11 and the resulting Patriot Act.
The antagonists of the first three games in the Mega Man Zero series all have the Greek letter Omega as their symbol. Sure most of them are Knight Templars, but they still mean well, fighting for the sake of humanity. But later we're introduced to an actual character named Omega, who is everything that the antagonists ever stood against.
Somewhat related: in Mega Man X2, Zero, freshly Back from the Dead, very easily destroys a weak clone of himself that the Big Bad made. Cue Zero 3, where Omega (the same one mentioned above) is the original body of Zero, while The Hero is the clone. But it was subverted, the clone Zero didn't mind the irony of the situation he was in, and goes on to defeat Omega Zero easily. Also, The Hero may be using a duplicate body, but the mind is real; he is still the real Zero. Omega Zero is now just a mindless puppet.
In Disgaea: Hour of Darkness, when Flonne is introduced she says she wants to be like the flowers. In most of the endings, Flonne is turned into a flower by Seraph Lamington as her punishment, before the final battle. In the Good ending, she is revived as a Fallen Angel, in the Neutral ending, Laharl sacrifices himself to resurrect her, and in one of the bad endings, he picks the flower and wanders the Netherworld for eternity.
In Dragon Age: Origins, if you choose the Human Noble origin, your young nephew asks his father (who is about to ship off for war) to bring him back a sword as a present. His father replies something along the lines of "Don't worry, you'll be able to see one up close soon". Your nephew and the rest of your family are brutally murdered shortly thereafter by the armies of a rival nobleman.
Similarly, if you play a City Elf, when you talk to your cousin Soris, he'll say that his bride-to-be sounds like a dying mouse, to which you can respond (paraphrased) 'maybe I should get you a cage for your wedding gift'. Considerably less funny later on when she and a few other female wedding guests are imprisoned in a human noble's mansion so that he can rape and kill them one at a time.
There's also a banter between Alistair and Oghren where Alistair asks how Oghren is so drunk all the time - "Do we even have that much alcohol with us? I wish I could be drunk all the time!" If you recruit Loghain into your party and you either don't make Alistair king or haven't hardened him, Alistair ends up becoming a drunken vagrant out of despair.
In Dragon Age II, one comes at the beginning of Act II. The Viscount of Kirkwall is becoming exasperated over the growing problems with the Qunari, and humorously grumbles, "I really should spend more time with my son. This life is just too short." They're both dead by the end of the Act. Too short indeed.
The "glistening elves" potential Party Banter between Isabela and Fenris. The former, true to her typical sense of humor, asks the latter what sort of bent his slavery had, and Fenris responds with flat audible exasperation that he was a bodyguard. It seems innocuous enough with the exasperation pinned to Fenris's usual attitude as The Comically Serious. And then you meet Fenris's former master, and hear a few comments that Word of God has since confirmed the implications of.
In the theater level of Psychonauts, it's a bit hard to find the over-the-top, sickly-sweet "happy" play put on by kids in flower costumes to be amusing once they start talking about Gloria's mom, if you've played before and already know what happened to her...
Similarly, Milla's Dance Party is pretty much impossible to look at the same way once you find out her backstory. She wasn't kidding when she called it a "party killer".
In 1998, the makers of Doonesbury released Doonesbury Flashbacks: 25 Years of Serious Fun, which contained an archive of every strip published up until that point, as well as numerous extras. Each menu on the disc featured "fun" little animations. The menu for the archive itself was an exterior shot of the White House. One of the many "wacky" things that goes on if the viewer leaves the menu on long enough: an airplane crashing on the White House lawn.
Note that a small plane crashed on the South Lawn of the White House in 1994, and that's probably what the menu animation is referring to.
After the death of Heihachi's voice actor, the end of the arcade intro for Tekken 5 that proclaims "Heihachi Mishima is dead." definitely qualifies.
In-universe example: Tidus in Final Fantasy X keeps telling Yuna about how much he's looking forward to going back to Zanarkand with her, and about how great things will be once they get there and all the stuff he'd like to do with her once the pilgrimage is over. He says this a lot. Much later in the game, he finds out that Zanarkand is the ultimate destination of the pilgrimage, where Yuna will acquire the Final Aeon, but in defeating Sin will die. Upon realizing how boneheaded this makes him seem and how much pain it must have caused Yuna to hear him talk about it all so cheerfully, Tidus experiences a brief Heroic BSOD before freaking out over why nobody told him this. Some players felt this way too.
It gets worse if you play through the whole game again. Some of the seemingly-innocuous lines become really dark.
In BlazBlue: Calamity Trigger, Taokaka's joke ending involves having been trained with Bang until an unknown enemy attacks, forcing Bang to make a Heroic Sacrifice, while Tao is left to fend off against the antagonist: Jin and Litchi, played out like an upcoming movie, which turns out to be Taokaka's lies. Cue the sequel, Litchi herself ends up reluctantly making a Face-Heel Turn, going from neutral to antagonist because her beloved's life is in danger and she has no choice if she wants to save him. Way to go in your imagination, Tao... Let's hope that Bang doesn't end up biting it in Continuum Shift's sequel.
And then there is a case of Hey, It's That Voice!, Bang's Japanese VA Tsuyoshi Koyama is known in Japan for voicing Old King, Odin and Phil Ackman, three rather antagonistic characters. Two of which are bloody killers the other works for Gym Ghinningham. The Hero of Justice's previous roles are not so heroic in a nutshell
In Anachronox, there is a segment where you have to vote on a battery of silly Propositions affecting a planet's society. Even though you just arrived on the planet 10 minutes prior. Your goal is to vote in the same way the ruling High Council does in order to gain their trust. One measure attempts to legalize marriage between the Planet-dwellers and Ring-dwellers (lower and upper caste), which the Council has voted against. The measure? Proposition 8.
Mass Effect - "This is all Joker's fault! What a tool he was! I have all spend all day computing pi because he plugged in the Overlord!" Cue the Overlord DLC where David, who's been forcibly plugged into a VI and kept alive with machines, spends all day computing Pi as part of an experiment conducted by his own brother. And to just add cruelty, he's autistic and has to communicate with hundreds of geths at the same time, which is torture to him. Untill Shepard rolled along, he had no way of freeing himself and the "MAKE IT STOP!" screams were both Tear Jerker and terrifying at the same time.
Also, in Mass Effect 2, if you bring up his past hobby as an actor, Mordin will sing a modified version of the Major General Song to the amusement of both the players and Shepard. The moment becomes really depressing in Mass Effect 3, if Mordin sacrifices his life in order to cure the Genophage, as he quietly sings it (if he sang it in the second game) as the building collapses and explodes around him in one of the biggest tear jerkers in whole game serie.
The Noodle Incident involving farming equipment is much less funny when you realized He was forced to savagely kill a Krogan sentry in cold blood, not only brutally injuring himself but also that all of the defenders at the camp were female Krogan makes the incident less funny.
In the original game, a Tali/Liara elevator conversation has Tali mentioning that most of the technology she wanted to send back to the flotilla tried to kill her. In the second game, she is accused of sending active geth parts back to the flotilla, which proceeded to kill everyone aboard the Alarei, but it was actually her father who was responsible.
In Mass Effect 3, Diana Allers says "Have you ever seen how fast an e-democracy can turn on its allies?". After the game came out, everyone saw...
In an elevator conversation, Wrex can ask Kaidan whether he would win if he fought Shepard, and Kaidan replies that as Shepard is his superior officer, he can't imagine them fighting; this also implies that Wrex believes that Shepard would win against him. In the third game, Shepard can (and potentially must, depending on how many mistakes you've made) kill Kaidan during the standoff with Udina. To make this a two-fer, Shepard can also be forced to kill Wrex at one of two points in the game- if you fail to talk him down on Virmire or if you sabotage the genophage cure.
Remember Ereba, the asari who whined about having to be married to a krogan for a lifetime while with a human she'd only have to wait a century before they died? Well Charr, her (possible) husband is a krogan that dies in the six months between the second and third game. She got what she wanted.
If you take Ashley Williams with you on the final mission and she gets heavily injured and airlifted. She insists that she can still fight and when you tell her she needs to go, she'll respond by saying "With all due respect, sir...". This is a callback to a humorous and often quoted line of hers in the first game ("why is it that when people say "with all due respect", they really mean KISS MY ASS?!")
Do a playthrough with the Citadel DLC where you save Miranda from Kai Leng, and Jack will make fun of her for having trouble with a "guy with a sword". Then do a playthrough where you fail to warn Miranda about Kai Leng, leading to her death. That particular bit of banter suddenly stops being funny.
Umineko no Naku Koro ni: Maria constantly adds the words 'uu uu' to her sentences, infuriating her mother, Rosa, who scolds her for her childishness. Taking this to be a comment on cute characters and their catchphrases, the reader finds this therapeutic. Then Episode 4 rolls by. Rosa is shown to be both severely abusive and neglectful of her child in private. It also turns out that the catchphrase is a spell Maria invented which she believes will make her mother happy. This is based on a moment in the past where Maria forgot the words to a song she was singing and merely went 'uu uu', which made her mother smile. It now has the opposite effect, but that only makes Maria think that she has to say it more, which causes her to suffer further abuse.
Space Channel 5 has Space Michael, who was voiced by the King of Pop himself. Due to his death, it's hard to talk about him without feeling upset, even in the fanbase. It becomes a "Funny Aneurysm" Moment when you realize that some of the fanbase wished for him to be dead....
X-Men Legends featured a trivia game that would ask questions about the X-Men in exchange for experience. One of them gave you a list of 5 characters and asked which one of them was not a mutant. The correct answer to the question is Juggernaut, although Jubilee is one of the choices. Jubilee lost her powers as of M-Day.
Tales of the Abyss, has a particularly nasty example, Guy's fear of women. Most of the fellow characters, and even the players snicker at seeing him freak out whenever women get too close to him. Some characters even make fun of it, and the female members may occasionally touch him deliberately in spite of that (like when Tear grabs his hand after he jokes about her having Luke "whipped"). Then you find out his fear stems from being hidden under the dead bodies of his sister and the maids who sacrificed themselves to save him when Kimlascan soldiers massacred his family. When he was around FIVE. Cue the three female party members feeling like jerkasses.
Motor Storm Apocalypse is a racing game involving a group of adrenaline junkies that hold a racing festival in a ruined city during an earthquake (and other disasters). The early videos featured buildings collapsing around your ears during aftershocks, explosions and tsunamis. During release week... uh... the game was pulled from shelves in New Zealand and Japan.
It doesn't help that one of Tenshi's victory quotes against her in the fighting games is, "Say, you're not related to the earthquake on the surface, right? Right?" For that matter, Tenshi herself has come under fire for this, as she had stated she wanted to set off a massive earthquake on the surface world...
Utsuho's power is nuclear FUSION, a.k.a the one going on inside stars, which combine atoms. Our reactors are FISSION, which splits said atoms, and is much more dangerous and unstable.
A milder version kind of occurs in fandom. Let's just say that Running Gag about Youmu Konpaku idolizing Sakuya Izayoi as her Onee-sama to ridiculous proportions gets less meaning or could be unfunny as Youmu gets included in Touhou 13 without Sakuya, who's more probably jealous like hell.
Then again, Sakuya did say that she was just a maid and that the role was for... something. It was in the dialogue for one of the games.
In Police Quest 2 when you hit pause you get a screen saying that every cop needs a break now and then. The unpause option on the screen? The words: "Let's roll!" It doesn't seem like much until you happen to pause the game as you try to defeat the terrorists on the airplane.
Many lines in Dragon Age: Origins – Awakening became Funny Aneurysm Moments due to the plot twists involving Anders in Dragon Age II. Among these are Justice's discussions with Anders and Nathaniel about possession, Anders accusing Velanna having a "chip on her shoulder that replaced her head" and Anders joking that he's fond of "iconoclasm" since in Dragon Age II he blows up the Chantry in Kirkwall to incite a war.
There was a Super Nintendo game call Air Strike Patrol that was unashamedly centered on the Gulf War, despite changing the name to Zarak. It is possible to beat the game, but no matter what you do you get one of the bad endings because of casualties, money or politics, despite being told you were doing well. Compared to the current Iraq war, this is rather uncomfortable.
In World of Warcraft up to the end of Wrath of the Lich King, Horde players were given quests during the holiday of Hallow's End (the equivalent of Hallowe'en) to bomb the little town of Southshore with stinkbombs. Then the Cataclysm expansion came out... and the Forsaken have since bombed the town with something far less harmless, the Blight, killing everyone who lived there and polluting the earth itself. The place is now inhabited only by sentient slimes.
On the way to meet with Page to sneak into Reaver's masquerade in Fable III, at the entrance of her base, you pass by Captain Swift, who's off to stir up further support for the uprising among the soldiers at Castle Bowerstone - before leaving, when Page refuses to let him come with the two of you, Ben half-jokingly whines that he should've just gone with Swift (who is for the record essentially the Walter to Ben's "you"). The next and last time he sees him is at his public execution. It's also a little of a downer on a replay that one of the promises you make to your supporters for when you're on the throne is to put Swift in charge of your army.
Not only that, but the reason he was executed was because he was trying to recruit soldiers for the cause.
Meta-example relating to Katawa Shoujo: the Act 1 preview prominently featured deaf-mute Shizune and her sign language interpreter/Voice for the Voiceless Misha as close friends. Naturally, they were a popular pairing in discussion and fanart. Come the full release, Shizune's route reveals Misha is in love with Shizune, and confessed before the start of the game. Shizune rejected her, but offered continued friendship anyway. The ongoing consequences of this form much of the tension within the route's plot. Many shippers shat bricks.
Also on that subject, Emi asks in Act 3 of her route why Misha would hang around with someone as bossy as Shizune, in a somewhat lighthearted moment. If you've played Shizune's route, you know why.
Late in Act 1, one of the scenes leading up to Lilly's route has her joking with Akira about how bad Akira is at cooking. Later on, it's revealed that Akira was essentially forced to raise Lilly by herself when they were 19 and 12, respectively, after their parents left for Scotland. Akira believes that she was a failure as a substitute parent, and couldn't do as much for Lilly as she should have.
Guild Wars: Eye of the North introduces Gadd, a vitriolic and insufferable genius who is unrelentingly hard on his son, Vekk. Vekk declares he'd sooner push Gadd off a bridge if they didn't need Gadd's help. Not long after, Gadd is killed during battle and a grieving Vekk scatters his ashes from a bridge.
A possible In-Universe moment can happen in Fallout: New Vegas. In Old World Blues, the toaster says that "Soon the world will burn in nuclear fire, again!" You can't help but laugh as the Toaster is Ax-Crazy yet harmless (because he is a toaster). Then, Lonesome Road comes along, and the Big Bad try to launch nuclear missiles at the NCR/Legion/Mojave depending on your relations with all the factions in the Mojave. Whether the nukes hit the Legion/NCR/Both or aren't launched depends on your choices.
It was already forshadowed by the NCR soldiers who wished for a Nuclear Winter rather than patrolling in the Mojave in a fruitless march.
Record Of Agarest War 2 has it, of all the events that you can find in the game, in the third generation Hot Springs Episode. Normally a Hot Springs Episode is pretty funny in this series until Jude just had to say (in a joking manner at that point) that his father Jainus who's in heaven be at peace while Jainus tells him that he heard that and point out that he's not dead. This is just before Jainus' Heroic Sacrifice when they get surrounded by monsters who were attracted to Chaos' power leaking out from Grey. You can even watch it again at the Event Gallery and it just feels uncomfortable watching that entire scene again and knowing what's about to happen.
One of the editions of Microsoft Flight Simulator released in the late 1990s had an announcer in one mission suggest it would be cool if you flew into the World Trade Center. Needless to say, that dialoge got stripped out in a later version.
The original box-art (on a flap) for Command & Conquer: Red Alert 2 (released 2000) featured a plane headed for the World Trade Center. As of September 11, RA2 is only available in a boxed set with twoother games (including expansion sets), as Feelies for Red Alert III, and as part of The First Decade compilation CD, without the original box.
On top of that, the game featured a mission in New York where the twin towers could be destroyed (They weren't part of an objective, and you were probably better off garrisoning them). The patch changed the name of the towers to the generic "Civilian building". On top of that, the first USSR mission is to burn down the Pentagon, which suffered attack scant days after the WTC bombing. EA never addressed this one.
The majority of the first level of Duke Nukem 3D ("Hollywood Holocaust") takes place in a movie theater. After the Aurora theater tragedy, a shootout in a movie theater isn't as entertaining.
An in-universe example could be at the end of Duke Nukem 3D. The end text crawl says look for a Duke Nukem 3D sequel soon. That sequel was released over 15 years later, to mixed critical reviews.
An in-universe example in Hyperdimension Neptunia V. Plutia mistaking a CPU Memory for candy? Amusing. Blanc, Peashy, and Rei all making similar mistakes? One tragedy after the next. The world sucking outside of Lowee until Planeptune and Lastation came along? Interesting take on how things played out in real life. That's not the only thing taken from real life.
Some of the switches in Panic detonate bombs randomly placed in famous locations around the world. This was played for laughs back in 1993, especially considering that some of the "landmarks" include an igloo and a dog house. After certain events eight years later, the idea of blowing up monuments became less humorous. While there is no World Trade Center, some of the monuments include downtown Manhattan and the Statue of Liberty. In the Playstation 2 port, the explosions were changed to diarrhea.
Whenever he is in Space Paranoids, Sora will wear armor with Tron Lines that'll change color depending on what Drive Form he enters. Seeing him in Master Form in that world, which results in the lines turning yellow, looked cool until late 2010, when Tron: Legacy was released, in which it's Big Bad, Clu, also has yellow lines. Considering how cruel he is, especially what he did to the ISOs, Tron and to his own creator, this really brings a bitter aftertaste to players. What tops this off is that Sora gets Master Form DURING the first trip to Space Paranoids; not only that, using the form consumes both party members (temporary, fortunately), and Tron is a party member in Space Paranoids...
In Persona 3, many characters will talk about future plans they want the main character to be a part of, and how their lives have changed for the better ...and then the main character dies at the end of the game.
In a parody/homage to King Kong, Fur Fighters had a plane crash into the radio antenna of the New Quack World Trade Center. Funny in 2000 when the game was released, not so much a year later.
In Postal 2, you have the option to kill Gary Coleman (canonically, he dies whether or not you kill him), which, if you killed him, has the Postal Dude ask his wife how much an autographed book can sell for. Remember, this game did star Gary himself, and was made before his death...