In Planescape: Torment, quite a few of The Nameless One's previous incarnations were Crazy-Prepared — and for the most part, you benefit greatly from their contingencies, if you use them without being physically (or morally) offended.
At the last dungeon of every game, by default, Link is Crazy Prepared for any obstacle it may have due to having spent the journey of each of The Legend of Zelda games collecting various useful items and supplies.
Jagged Alliance 2's extensive panoply of weapons (specifically, in the fan-made v1.13) means you have the ability to outfit your mercs with the tools they need for any battlefield situation (multiple enemies at mid-range, close-range combat, enemies holed up in a building, tanks...). Limited carry weight of your mercs makes this a bit more difficult, but it's easy to compartmentalize.
In Resident Evil 4, Leon goes to the Spanish village only to investigate and ask questions, yet he brought along a pistol, knife, attache case, flashlight, radio, binoculars, a tracking device, and a grappling hook (And, if you played the game on Easy, a shotgun). Of course, he was investigating a group that had kidnapped the President's daughter, so he had pretty good reason to expect trouble.
When Travis Touchdown arrives at the Rank 25 fight in No More Heroes 2: Desperate Struggle, assassin Charlie MacDonald and his cheerleading squad transform into a Humongous Mecha. Travis responds: "I thought something like this might happen." He then summons his own Humongous Mecha and he and Charlie proceed to have a giant mecha fight in the middle of Santa Destroy.
Old Sierra adventure games required you to be insanely prepared for everything at all times, or render the game completely impossible to finish.
The only thing worse than how Crazy Prepared you have to be is how Crazy Prepared Sierra is about expecting you to be Crazy Prepared. In some games, you can take everything that's nailed down along with the nails, only for the nails to kill you of tetanus a few screens later. Just because Sierra knew you would pick them up.
Quite a bit of Nethack's gameplay consists of packratting items that can counter the game's many deathtraps: a lizard corpse to prevent being petrified, greased clothing in case a monster tries to grab you, boots of levitation to avoid pits, and an amulet of self-resurrection if everything else fails. Though the vast majority of them will, in fact, be used in a given successful run — certainly, you will have to fight Medusa with a mirror and deal with the cloak-grabbing enemies around her, find a castle which you need an instrument to enter, fly, resist fire, have an instant-kill available, dig out quick routes from one set of stairs to another for a fast escape, detect traps or have a stockpile of food (and detecting traps actually requires a detect gold scroll and something that conveys confusion), and I'm just listing things tied to fixed dungeon events, not individual monsters like the cockatrice or golems. A towel is also a very useful item to have.
The Crysis Nanosuit always seemed to be crazy prepared. It can breathe underwater, has thrusters to work in zero gravity, can survive being frozen to -200 degrees and also provides a decent amount of protection against rockets and artillery. Yet it can't seem to survive a single bite from a medium-sized shark...
Any experienced Armored Core players know well enough to venture into an unknown mission not carrying equipment for all kinds of situations. These include radar equipped with bio-sensors so one can target biological threats, weapons that can track even the fastest of opponents such as machineguns or missiles, and weapons that cause a lot of damage to armored enemies. Some very professional players deliberately use overweighted ACs loaded with every weapon for any situations in Arenas, and eject any unnecessary weapons when the fight begins, depending on the enemy.
Some weapons in Baldur's Gate II. Against mages, if they're not protected from magical weapons: Carsomyr (otherwise an unenchanted weapon). Against fire elementals or salamanders: The Wave. Against Air Elementals: Staff of Air. Against Undead: Runehammer. Against trolls or golems: Crom Faeyr. Against anyone that wouldn't die by loss of hitpoints: Chaos. For shopping (yes, for shopping): the Rose Blade. For Warrior/Cleric Multiclasses: Flail of Ages. For Backstabs: Black Blade of Disaster (or the Staff of the Ram). And then you move onto choosing spells for the wizards, clerics, and druids. Never leave home without: Insect Plague (for rendering casters unable to use their spells), Polymorph Self (flind form has a + 3 magic weapon, mustard jelly is 100% magic resistant), Spell Turning, multiple healing/resurrection spells, Polymorph Other (in case your allies are charmed), Glitterdust (for dealing with invisibles), Burning Hands/Acid Arrow (in case of trolls), Chaos (to leave your enemies fighting each other), Drain Resistance (to deal with magic resistant enemies), Fireball (because it's Fireball)...
The Space MMORPG EVE Online features a form of this, with players not only having to haul around different types of ammunition, missiles and drones for engaging targets at different ranges or fighting different types of enemies strong against particular types of damage and capacitor batteries for sustaining fire or damage, but also spare modules, since some may mean the difference between winning a fight and being made utterly useless, which often leads to utterly dead. What's more, in many situations, whether you are flying a large or a small ship, it doesn't matter how high your skills are or expensive your ship and gear; you have to change to different ship. Naturally, in the economy of EvE, with experienced players often having whole stacks of ships in hangars strewn about and the ability to travel light years in an instant, this isn't such a big deal.
Princess Liesel from visual novelPrincess Waltz is physically weak, but a great blacksmith. As such she is defined by her Hope Spot killing, pulling out device after device to counter any attack her opponent makes. Being a bit of a Chessmaster she normally makes sure her opponents are where, when and how she wants them too.
Neverwinter Nights 2 combines a crafting system with various types of damage resistance. If you're smart, you'll be carrying at least one self-made and -enchanted Silver, Cold Iron and Adamantine version of your favored weapon, if neccessary an additional bludgeoning weapon, and remember to add an alignment-enchanted weapon as well, so that you have the means to effectively hurt all the Werecreatures, devils and demons, Golems, Skeletons, Liches and what have you with the proper weapon of choice. Or just play a monk, where your hands end up being all those things anyway.
Setsumi in Narcissu has prepared several things in case she escapes, which she never does. This becomes handy after she did escape with the protagonist.
The RTS Total Annihilation has an expansion pack called The Core Contingency, where its about the Core Empire's plan to fucking IMPLODE the galaxy in on itself in case they lost, which they did.
Dr. Light from the Mega Man X series. Before his death, he had set up approximately 53 (or more) capsules containing upgrades all over the world for the main characters, even Zero, which is odd, seeing as Zero isn't even a creation of Light at all. And the hologram that shows up with each capsule falls into the Energy BeingObi Wan category, allowing himself to talk with both of them.
In the case of Zero, the only capsules that he uses (outside of the Xtreme duo on the Game Boy Color) are for semi-game-breaking 'ultimate armors,' the functions of which go unexplained, so the canonicity of Zero's capsules is suspect. Specifically in X5, (the only game where you can use Zero's alternate armor without unlocking it via a button code or other means, like in X8) X's and Zero's Ultimate Armors are found from the same capsule in one of the game's final levels, so you can only get both if you grab it with one character, die, and then come back with the other.
Every MMO encourages this by virtue of having so many scenarios possible. The old EverQuest has a decade of content available for picking up neat toys.
Dr. Bian Zoldark from Super Robot Wars does a good job of being this trope. In the Original Generation series, his plan to unite the world against the alien threat could've suceeded, even if the heroes failed, and in Super Robot Wars Alpha, he's managed to get bloody near every superweapon (such as Mazinger, Getter, Daitarn 3, etc.) maker or user in on his plans and drew up plans to keep Earth from being blown up, and went as far as to leave backup plans (the Earth and Moon Cradle in both continuities), just in case.
In Dwarf Fortress, one of the more extreme "facilities" developed by players is called the "Fuck The World" device, which will lock your fortress up tight and flood the surrounding area with magma. Some fortresses also allow different areas of the fortress to be locked off and flooded. Or set up the main dining hall's roof to collapse, dropping hundreds of tons of rock on everyone inside. Or drop everyone in the trading depot into a room where dragons breath fire on them through a grate. There's even a concept for a Fortress that monitors foot traffic inside the fortress: If there's abnormal activity indicating a catastrophic population loss or an extended "Tantrum Spiral", the fortress will lock itself and activate the Fuck The World device, taking the world down with it.
Shao Khan in the third Mortal Kombat game; despite all his blabber about You Have Failed Me to his minions, he knew he might end up failing to win Earthrealm through legal means, so arranged to have his dead wife revived and Brainwashed and Crazy on Earthrealm, allowing him to step through the dimensional borders to claim her, and thus force a merger between Earth and Outworld. First three things he does upon doing so? Lock down his wife with bodyguards, steal the souls of everyone on Earth that isn't The Chosen One, and send a vast army of bloodthirsty, nigh-invulnerable beasts after said Chosen Ones to prevent them from ruining his plans. It didn't work out quite as planned, but you've got to give him credit for trying. He also shows this off in later games; anticipating that his "loyal" minions might one day attempt to overthrow him, he places a decoy in his place during the events of Deadly Alliance, thus surviving his infamous assassination attempt. Then, in Armageddon, he revives Shang Tsung (who had been vaporized by Raiden's attempt to destroy the Dragon King in Deception) and forces fealty on him, revealing that all minions swearing loyalty to him get hit with a spell that, if Khan dies at any time, causes them to die too, as well as giving him the ability to revive them at will.
Mortal Kombat 9 reveals he had his victory speech planned waaaaaaay in advance as well.
Manfred von Karma is one example of this from Ace Attorney — he retrains the parrot to get a guilty verdict! The other Crazy-Prepared person is Phoenix Wright aka the player. You may not know why you have to "pick up" random pieces of "evidence", but they will come in handy, because you're ready with them.
The OTHER other person is Lana Skye. Maybe not as crazy as von Karma or Phoenix, but she does have people doing work for her while she's in containment. One case is when she kept very conclusive evidence in the back of an Evidence Law book.
And for bonus points, the Evidence Law book itself was the final piece of evidence needed to convict the killer.
A large part of the PokémonMeta Game in competitive battles involves preparing for possible counterattacks and compensating for specific weaknesses in your party that an opponent might take advantage of.
Practically any opponent in the PWT in Black 2 and White 2 qualifies (of course, it's not supposed to be easy). Using type advantage rarely works here, because they usually have a precaution against that. For instance, Sabrina uses Psychics, and the most common strategy against such Pokemon is to use Dark Pokemon; however, she almost always opens with an Alakazam that is incredibly fast which knows Focus Blast, a powerful Fighting attack that can flatten most Dark-types before any of them can hurt it. On top of that, it has a Colbur Berry, which means that it can resist most damage from the first Dark attack that hits it.
Let's hope your Kingdom of Loathing character remembered to bring a spider web, a barbed-wire fence, a baseball, a firecracker, a blowgun, and a can of hairspray (among others) to the Naughty Sorceress' tower, or you're not getting through. The game involves farming and combining ridiculous items to pass the challenges. Softcore speed runners have to be be Crazy-Prepared too. If you want to finish that fast run, you had better have your Ancestral Storage well stocked with everything from ghost pickles to drum machines to hockey sticks of furious angry rage.
In Alpha Protocol, when requesting backup from superspy extrodinaire Steven Heck, during your infiltration into a subway in Taipei, Steven tells you not to worry about the details, he's got you covered. When heavily under fire, you make the call and Steven's backup involves him hurtling by the platform in a stolen subway car and strafing the platform with a minigun he's bolted to the back of it, cackling maniacally all the while. He'd prepared that years ago, just in case.
Mike: [before the mission] Why do I get the feeling you've already planned for this?
Steven: Because I have, Mike!
A mandatory trait for a successful game in S.T.A.L.K.E.R.. Going for a routine artifact hunting trip? Don't forget your hunting shotgun, Warsaw Pact-based assault rifle, NATO-based assault rifle, at least one scope and suppressor for both rifles, and a sniper rifle specifically for long range engagements. Along with all of this you'll likely need at least a couple hundred rounds of each type of ammunition for each gun, as many of the three different kinds of medkits you can find, and a veritable pharmacy of drugs in order to help you combat the massive variety of anomalies you can encounter. After all, you never know when your fight with mutated wildlife in the middle of an electrical anomaly field will be interrupted by heavily armed Western Bloc mercenaries and a ghost possessing the power of pyrokinesis...
Only this plethora of stuff will likely put you over the weight limit, meaning you can't run from the pack of mutant dogs, and worse, chasing you down. Not only do you need to know what you may need but how much of it you can afford to carry.
It is entirely possible to beat every main quest in the game with an inventory of one rifle, 500 rounds of ammo, and a few baguettes - provided you use artifacts and their associated benefits/disadvantages judiciously. This requires an inordinate amount of face-shooting & bolt throwing, though.
Cynthia Weaver in Alan Wake, with a little more emphasis on the "crazy" part. The enemies in the game are made of darkness, so she always carries around a light of some sort, even in the middle of the day. She left behind supply caches of ammo and light-emitting objects like flares just in case an author got pulled into Cauldron Lake and the Dark Presence forced them to write it free; the caches are even marked with special light-sensitive ink that can only be seen by someone who was touched by the Dark Presence. None of this, however, compares to the Well-Lit Room. The name is actually a bit of an understatement; there are lightbulbs everywhere and absolutely no shadows inside. The room is connected to a decommissioned power plant, so there's no need to find a power source. Cynthia even knows what bulbs need to be changed when, right down their manufacturer and serial number.
In the fighting gameMarvel vs. Capcom 3, at least one of Doctor Doom's basic attacks and one of his hyper combos involve attacking the opponent with machinery he previously hid on the battle site. As fights in this game can take place anywhere from an ordinary city street to the X-Men's private training room to the extradimensional home of the Norse Gods, this demonstrates an impressive degree of preparedness on his part.
Rocket Raccoon gives one huge "Bitch, please" to Doom in Ultimate Marvel vs. Capcom 3. Hidden gigantic bear traps, remote-activated sinkholes, swinging log traps, and an air-strike just waiting for him to give the order while a helicopter assures he remains at a safe distance.
Hazama / Terumi Yuuki has proved to us that hundreds and hundreds of time loops, and an Evil Genius without like in its own universe, combined with an undying desire to throw the world into an abyss of despair, simply for the fact that "misery is interesting", can lead up to you taking a lot of precautions just to face him. And it may still not work 100% anyway. Oh Crap.
Terumi winds up deconstructing this, as he was only Crazy-Preparedbecause he had witnessed hundreds and hundreds of time loops. Without such preparation (as Slight Hope demonstrates and Chronophantasma ultimately confirms), his victories are due to overwhelming power and blind luck, and neither can last forever on their own. Makoto Nanaya intervening on the behalf of Tsubaki Yayoi led to his downfall in both instances - and in the latter, his death by Hakumen. Then again, considering what Makoto is, antagonizing herwas a very bad idea.
Mr. House, from Fallout: New Vegas, was not only aware that nuclear Armageddon was on the way but also made extensive preparation for his own and Vegas' survival during and after the fact. Though his projection of the date the war would break out was off - by less than a day - he saved a sizable chunk of Las Vegas from becoming blasted and irradiated wreckage (unlike, for example, Washington DC or Pittsburg in the same setting), and emerged two hundred years later to wall it off and claim it as his own territory from the tribes that had overtaken it in his absence. Without that one setback, it's very likely he would have ruled completely unchallenged for a long, long time. As they say, the House always wins.
Your character in Morrowind and Oblivion can be an example of this, if done right. While nearly all of these examples can be replicated with spells, hoarding potions is a great way to survive. Low on health or magicka? Chug some potions. Diseased? Chug potions. Water breathing? There's a potion for that. Need to be more liked by people? Potion for that. Need help in a fight? Slight twist here: there's a scroll for that. Need someone to start the fight instead of you? Again, scroll. Need to carry more loot? Potions and scrolls can help. And this isn't even bringing enchantments into play...
Darkrai from the second Pokémon Mystery Dungeon game. He had a total of five backup plans to try and kill the heroes. First, he tried to convince the heroes to "disappear". When that didn't work, he tricked a Physical God into trying to kill them. When that failed, he lured them to his lair to finish them. When they arrived, he trapped the hero in a nightmare where their partner joined Darkrai due to crossing the Despair Event Horizon. When they freed themselves, he summons an army of Mooks to help him kill them. When he and his minions are beaten, he reveals he'd already prepared a dimensional portal to escape through! The only thing he wasn't prepared for was the previously mentioned Physical God showing up and blasting the portal as he tried to escape.
Whoever was responsible for the packing list for the expedition in Shin Megami Tensei: Strange Journey was clearly a master of this mindset. There are several cases where the crew encounter something completely unexpected, only for the ship's AI Arthur to say that they've got tech for that. Perhaps most notably, the mental parasites in Sector Delphinus are countered by repurposing a mind control device. Most of the crew consider the fact that they even had this to be Paranoia Fuel.
At the beginning of Sonic Chronicles, Eggman was so prepared for the epic battle that he even anticipated his own defeat. According to what he says, this was the only reason he survived.
The final boss of Portal 2 is a colossal idiot who ends up almost causing the lab to self-destruct through neglect and incompetence. So after the fight, the player probably wouldn't have expected him to rig the stalemate button, which the player would certainly go for next, with explosives in case he lost the fight. Not only that, but he specifically leaves it out of his "Four Part Plan" speech detailing everything he's done to fix every flaw evident in GLaDOS' fight from the first game.
Additionally, Aperture Science has automated testing facility announcements in case GLaDOS is incapacitated. As such, they have prepared such announcements for any possibility. ANY possibility.
Merveille from Solatorobo. She "let" the intentionally "defective" Red escape with the Dahak - which she created specifically to protect him - seemingly as a backup plan or some form of insurance against Baion.
Daniel Clarke from Call of Duty: Black Ops. He set up THREE well-stocked armories, a fully mapped-out rooftop escape route (complete with mattresses stacked in a balcony in the event one would need to jump down), as well as having enough explosives rigged into his laboratory to take out an armoured helicopter in mid-flight that he detonates when Spetsnaz forces attempt to retrieve his research.
Among the functions of the MARS script for X3: Terran Conflict is automatically switching guns in and out of your ship's batteries based on what that battery is targeting as well as the target's distance, deflection, and speed. Naturally this only works if you have said weapons in your cargo bay, which means you're likely to be carrying two or three entire loadouts (anti-fighter, anti-capital, and maybe anti-corvette).
In the Mass Effect series, the Graal Spike Thrower is a shotgun specifically designed by the Krogan for hunting Thresher Maws. With that in mind, it features special built in blades, so that in the event that a Krogan gets swallowed by a Maw, they can either cut themselves out or cause severe internal bleeding to take it down with them. Overall, it says something about the Krogan that they designed a shotgun believing that it was a very real possibility that they might be eaten at some point.
During the Citadel DLC, during a quiet party, Garrus and Zaeed will decide to booby trap Shepard's apartment just in case another Shepard clone shows up. They rig up the glass by the entry door, the coffeemaker, and the refrigerator. Zaeed almost turns the hottub into a plasma bath up until Shepard points out that the DNA trigger won't work because his/her clone would have the same DNA.
In the Star Fox series, Andross had multiple contingency plans in case his life was threatened. Robot fake, resurrection-by-cloning, resurrection by stolen magic, and a Virtual Ghost. He also had his nephew trained in the ways of war in order to have an interim commander.
In Emerald City Confidential, one of the achievements you can get is defeating the wizard arena's resident champion on the first try. However, the only way you can do this is by collecting specific items which are seemingly random, such as s Heavy Cake, a Magic Rope and a Copper Rod.
In Meet the Spy from Team Fortress 2, the Scout jokingly asks the BLU Spy if he's the president of the RED Spy's fanclub. The Spy's retort? "No, that would be your mother!" after which he manages to show Scout pictures of the Spy having sex with his mother.