Over the past few years, more and more video games are reveling in making players feel terrible. It seems like every other major title I dig into at this point goes out of its way to remind me that I am a bad person. And to be fair, this is on me for continuing to love these kinds of experiences. Despite no real-life stakes whatsover, great games will put weight behind the decisions they present you with. And, just like life, sometimes there are no perfect answers. Sometimes you just have to make a choice and live with the consequences. Unless, of course, you have a save point. Then you can make all the choices. You have become as unto a god.
There are plenty of games that offer you very clear branching paths between Good and Evil, and a lot of those heavy handed decisions come with false sets of ethical "scores" or devices that cancel each other out. In Bioshock you sure have to be History's Greatest Monster to want to murder those little girls for the sweet, sweet tapeworms inside of them, but taken the Clearly Good path yields almost the exact same rewards within a few minutes. This list is reserved for those moment in gaming that stick with you because there was a genuine unpleasantness that goes beyond in game rewards. This is the real Bad Stuff.
SPOILERS TO FOLLOW
This one is easy, and that's what makes it so hard. At the end of the very first episode of Telltale's first season of The Walking Dead, the game company famous for asking you to make difficult choices throws out a situation with a very short time limit: zombies break into your hiding place and you have to choose whether to save Doug or Carly. Again, this is at the start of the story, so you really have no buy-in to either character yet, making this choice shoot out of your body by instinct alone. You also don't know, going into the choice, that the other person is going to die.
Character deaths are a pretty easy way to add drama, but this pivotal decision dictates the entire rest of the game, and you have no context when making your decision. The longer the game goes, the more this comes back to haunt you with "what if" scenarios. A few years after my initial playthrough, I still question why I made the choice I did. Watching my wife play through the episode and make the same choice convinced me we were in love. (Okay, it didn't. That would be an insane thing to say. Still.)
If you still haven't played Ubisoft's 2008 African Blood Diamond Sim, you owe it to yourself to get mired in complicated regional strife and mowing down waves of militia fighters. It's a good time! You spend the entire game in pursuit of ending a power-player called The Jackal who has been providing both sides of a conflict with weapons. At the end, you wind up fighting alongside him, because Life Is Complicated. You wind up in a small hut with Mr. Jackal, shootin' the shit, when he reveals that there's a chance to save the lives of two million refugees -- and maybe redeem your soul in the process.
You have a choice on how to go about this, either suicide bombing their way to safety or bribing some guards with blood diamonds (but shooting yourself in the head) for reasons. Either way, you will not make it out alive. This one actually comes down to a choice between watching yourself die or going out in a blaze of glory that fades to black. This one is at least based in doing The Right Thing in the end, but as Shakespeare would say: "These violent delights have violent ends."
This indie relationship nightmare is a series of choices from start to finish, but the prologue proves it belongs it absolutely belongs on this list. Your choices during the text-heavy sequence establish your backstory and narrows down exactly what kind of ruined person you're going to be, before you even get into making the actual choices of the game's story. It's a Choose Your Own Adventure for emotional baggage and there are no right answers and no clear paths through.
You're damned from the start, but the game lets you decide how and where this will hurt you the most. As the architect of your own Feelings Demise, there's more than enough difficulty to carry with you post-game on this one.
The Oasis quest in Fallout 3 is the gold standard here. Like the best sidemissions, Oasis creates a series of branching compromises that leave no one happy but still teach you a little something about yourself on the way. The storyline opens when you find a community centered around a living tree named Harold. If the book The Giving Tree came to life, it would probably be something like this, especially because the tree is in terrible pain and just wants to die. Thing is, Harold at the center of Oasis, a lush green paradise that sprung up in the middle of Fallout's harsh nuclear wasteland. Harold wants nothing more than for you to dive into a cave full of monsters and destroy its heart, but that would put this natural utopia at risk.
Before you land on a solution, you can explore the town and get advice from everyone who lives in Oasis. Some want to let Harold pass, some want to rub a chemical on his heart that will cause him to expand across the Wasteland and live forever in torment. You can also just set him on fire with one of your weapons and kill him in a terrible way that turns the town against you. No matter what you go with, some feelings are going to be hurt and a nice tree man will meet one of a few different awful fates.
This one's complicated because... well it's Elder Scrolls and I'm not sure if I can even explain what happens here. I'm normally pretty lost in fantasy games and boy howdy is this series action packed with stuff I skipped through to get back to murdering orcs or whatever. But the gist here is that there's a world-conquering weapon in the form of an ancient golem (the Numidium) that you acquire the ability to control -- via a septem you steal from a king. Yeah, it's like that. Picture the end of Fallout 3 with the giant murder robot, except there's a lot of choices to make about how this ends, and who rules over what remains.
Basically, there's a half-dozen different factions that you can choose to hand this power over to, and what they do next shouldn't surprise you. They vanquish their enemies and either unite the kingdom or wind up creating one hell of an unpleasant world. There was even an unfinished ending that involved the player taking the power only to get destroyed by the Numidium, but it's just as unrewarding to let someone else win. No matter who you side with, the whole thing a culmination of a long game that basically tells the hero: "Guess what? It's not about you." A few sequels later, Bethesda would make everything about the player character in Skyrim, which went on to sells tens of millions of copies. Funny how that works.
Fable 2's ending throw a lot of spaghetti at the wall, by surprising you with the death of your dog and your family and a bunch of the employees from Fable's version of the Death Star. It offers you a chance to undo one of these terrible wrongs... or take a bunch of a cash, to use post-game? It's a really, really terrible way of trying to give weight to a choice by creating a pointless choice and foisting weights on it. Fable 3 does something far more clever: You're fighting back against an evil tyrant, who you overthrow to become king. And then you get to decide whether to execute him.
Only then do you discover that this guy was being a jerk for a reason: There's an unstoppable evil coming to murder the kingdom. So when any other game would end, your game is just beginning, as you must decide whether to undertake cruel actions for the greater good and become what you once fought against, or try to find a way forward without losing your humanity. There aren't many better versions of the "Surprise! You're The Villain!" trope in gaming, mostly thanks to how slowly you find yourself growing horns.