Dark Souls doesn't scare me. I consider it to be marginally difficult (I'm just awful at it). Few experiences shake me.
Why?
I've been playing roguelikes for over a decade. Closer to two decades now. Some of my first games were roguelikes.
To paraphrase a line from everyone's second-favorite Batman villain:
"You merely adopted the difficulty. I was born in it, molded by it. I didn't survive a level until I was nearly a man, by then it was nothing to me but surprising!"
In one of my earliest gaming memories (barring Yoda Stories, which I remember fondly, and The Neverhood, which gave me a phobia of certain sorts of claymation) I distinctly recall carefully practicing in the "newbie dungeons" of Tales of Middle Earth, then immediately getting stomped by a seven-headed hydra (the number of heads may be inflated for the purpose of my ego) when I made the mistake of leaving town by the south exit instead of any of the other, marginally safer, exits.
Even Demon Souls, which includes a scripted loss as part of its introduction scenes, is more forgiving, especially when you consider that in most roguelikes a dead character is gone forever (unless you savescum, but I never resorted to that).
Particularly onerous was ADOM, a game I remember fondly as one of the most persistent and popular roguelikes, and yet never beat or even came close to beating. I often cheat (in the "like a politician filing taxes" sense) when I play single-player games, and I attribute this to paranoia about sudden difficulty spikes. Sometimes you beat a dungeon, sometimes a dungeon beats you.
Technically, back in my day ADOM didn't feature command hints. Also, this character has somehow not died yet, or even taken damage. Orc Chaos Knights are apparently the build I've always been looking for. Even the hardest game of my youth has softened for modern audiences. Soon I'll have to politely ask you all to get off my lawn.
Ach, my spleen!
"They wrote in the old days that it is sweet and fitting to die on a hard level. But in roguelikes there is nothing sweet nor fitting in your dying. You will die like a dog for no good reason."
ā Ernest Hemingway (not really)
Roguelikes have no qualms with killing you in a single turn. This is probably something that's shaped me a lot as I became a roleplayer, where I'm a little notorious for putting my characters way in harm's way and being totally fine with going through multiple characters in the time it takes the other players to make a character.
Part of the mystique for me with roguelikes is the brutality and realism they offer. I've been playing a lot of Cataclysm recently, where a large number of my deaths have been self-inflicted after mishaps due to emergent systems. Sadly, I seem to have lost some of the saves I had in a botched update, but the most recent "embarrassing" death came when I threw an incendiary grenade and died of smoke inhalation (well, technically, passed out from smoke inhalation: it was the burning that got me in the end).
I kind of like this complexity, however. I remember playing Dwarf Fortress and trying to keep dwarves alive as they kept losing important body parts. Roguelikes offer a unique experience in terms of difficulty that other games don't offer. I remember one, Iter Vehemens ad Necem, which was particularly refined at offering the "how long can you stay alive now that you only have one hand" experience.
Many games are perfectly happy to have you lose, but refuse to give you a death spiral or penalties.
Roguelikes will kick you while you're down. Stunlock? Try being knocked unconscious, losing limbs, and then having such a level of pain that the shock kills you, rather than the trauma.
Not all roguelikes were as brutal, GearHead comes to mind, though its creator also made Dead Cold, one of the best hard sci-fi survival roguelikes. Both will happily kill you in one bad term, but at least GearHead doesn't have permadeath (and has scaling difficulty, so if you get too beat up it starts going easy on you).
Gimme Shelter
One of the things that I find interesting about roguelikes is that as much as I try my best to go to pains to avoid difficulties in other genres, I tend to be fine with getting kicked around in roguelikes. Some of this might come from the fact that I've had enough time with them that I've developed Stockholm Syndrome, but I think it might go deeper.
The challenge presented by roguelikes demands a high degree of personal skill, especially if you're playing in the old ASCII style (which I generally prefer, with the exception of a couple games like Tales of Maj'Eyal and Cataclysm, though I mostly use graphics with Cataclysm because I occasionally record it).
It's also very much oriented around the notion that surviving is an accomplishment. With other games, they're very goal-driven. I hate dying in Skyrim or Fallout, for instance, because I feel like it keeps me from accomplishing my goals of checking out what's around the corner.
In roguelikes, the survival is the achievement, and everything else is just to give you a clue of where to go. When I went back and played Fallout 4 in a "horror" setup (using the Pilgrim ENB setup, Atrium Carceri and Sabled Sun in the background, cranked up difficulty), I found that I was much more prone to accepting the difficulty.
So that's why I'll send an orc chaos knight down into the dungeon, heedless of their safety, and keep on going back for more.
When dying's normal, it's not frustrating.
I've seen things you players wouldn't believe. Loot chests plundered off the seventh level of Angband. I watched grid bugs glitter off the treasures of Moria. All those moments will be lost, like saves in Yendor. Time to die.
This post was written for @archdruid's Challenging Gaming Moments contest. Go check them out for more great content! The contest remains open for about another day and a half (if my math is right), if anyone's interested in writing their own entry.