This post covers everything relevant to Chester as far as the localization is concerned. It is based on a reddit post from January 2018. Quotes include the official English script, my translation, and the official Japanese script in that order.
Not So Marvelous
Yes, of course. Exactly what happened to me. We are both strangers in this strange land. But, at least now there are two of us.
I see, as I thought… We are both strange ones. It’s an unfamiliar age, and there will be inconveniences. Let’s help each other out, shall we?
Chester starts out friendly enough. He recognizes that we are both out of place in this time period and proposes we team up. If we keep that info to ourselves, he still thinks that we should cooperate as fellow travelers. But then…
So, what did that giant mushroom make you do? Not that I care. It’s none of my business. Heh heh heh…
Oh, heard out the request of that mushroom, did you? My goodness… quite the fanciful one. Keh heh heh.
When we actually tell him about our mission to save Dusk, he has apparently heard it too, and thinks our attempted heroics are unrealistic whimsy. He doesn’t seem to be the heroic type…
Did you happen across Knight Artorias? The legendary Abysswalker, from the old tales…Well, if you haven’t, it’s just as well… He’s a colourless sort, if you ask me. Mwah hah hah!
Have you met Knight Artorias? The Abyss-hunting hero who was in a legend of the future age… Well, if you haven’t met him, it’s fine. It is ultimately a boring story… Keh heh heh.
Chester isn’t talking about Artorias being dull, but the story. “Boring”, or tsumaran, can also mean to be silly, absurd, worthless, or disappointing. In essence, he is insinuating that the reality doesn’t live up to the legend and thinks that is hilarious! No heroes for this dandy!
Did you really slay Knight Artorias? I’ve heard the Abyss found him first, but even still… That’s absolutely treacherous. Yes, magnificently so! Mwah hah hah!
Oh, you really felled Knight Artorias? Although he was consumed by the Abyss, you slew that hero… No, that is magnificent. Very magnificent… Keh heh heh.
He actually cuts short of saying a verb, but it is obvious that he is talking about us defeating the knight.
Chester didn’t necessarily “hear” this from anyone. After giving the vaguest of warnings implying that he saw what became of Artorias, he is surprised that we actually made it out alive. Almost as if he deliberately wanted us to die against him…
But then a new idea springs into his head. He is “Magnificent Chester” after all. He can just invade us in town while we are exhausted! He has got to keep that abnormally huge number of humanity in-stock somehow!
But that isn’t the end of him criticizing our fancifulness:
Believe it or not… Oolacile has brought the Abyss upon itself. Fooled by that toothy serpent, they upturned the grave of primeval man, and incited his ornery wrath. What could they have been thinking? But to you and I, it’s all ancient history. You have to ask yourself. Does it really matter? Heh heh heh…
Nevertheless, you really are a fanciful one. The Abyss and the like is definitely something Oolacile brought upon itself. They were deceived by a great, toothy serpent, dug up a grave, and disgraced the corpse of an ancient man and all that. Surely shameless fools, no? Besides, it is ultimately a story of long ago to us. You probably won’t even be known about. Keh heh heh.
According to Chester, they were misled into their acts, though Gough has a bone to pick with that. Regardless, it is clear that Oolacile is to blame for their current fate, so us trying to save them is absurd to him. Moreover, the events are already set in stone! If our heroics weren’t recognized before, we either failed to accomplish it or failed to be recognized for it! There is nothing to gain by helping! Give up already!
Oh, for Juniper’s sake. Put some spring into your step! Mwah hah hah!
Oh, you, what is it? Strangely dispirited, aren’t you? Keh heh heh.
Chester simply takes joy in our setbacks, pocking fun at our fortitude and expecting that we will die or give up soon enough. Either way, he will reap the rewards from our corpse.
Not long ago, I had another visitor. A human like thineself, from a far-away time. Only, he was dreadfully odious… And I am afraid that he is still amongst us. He wore a hat and a long black coat…
Which reminds me, there was another visitor a little while ago. Very much the smell of man, a human of the far future, like you. But… unlike you… it was very bad… He is likely still in this time. He was a man with a black coat and a hat. Please be careful…
If the black attire, dark, demeaning humor, or attempt on our life wasn’t enough, Elizabeth can smell he is a shady fella. She is kind enough to warn us in the Japanese script but the English threw it out for whatever reason. Her suspicion is apparent in cut dialogue from our first mention of Elizabeth to him:
But I do wonder about those sorceries of hers…
But, I see, so it knows sorcery, huh…
Again, he actually cuts short of the verb here, but it is obvious where his train of thought is headed. Elizabeth didn’t tell him about her being one with Oolacile’s sorcery, some of which would be very useful for someone of his… profession. Unlike us, he was clearly the type to misuse them.
I assume this was cut because it is a plot thread that goes nowhere. It feels extraneous to bring it up when Chester’s limited to being Patches 2.0. His only other plot-involvement was also cut:
…That ring… It was purloined by a man in a long coat… I know not how you came upon it, but its owner met his death here. He was a dear companion, and I wish to return the ring to his grave. Would you be willing to part with it?
… You, that ring was… something stolen by a man in a coat… I don’t know why you have it, but it is an important memento of a man who was felled here. I was that man’s friend. That’s why I want to offer that memento at his funeral. How about it? You wouldn’t give it away, would you?
I assume this was cut to avoid any time paradox scenarios where we could already have the ring while Chester has it. But it well established Chester as a seedy fella. So let us do the sensible thing and kill him!
What now? You think this is my fault? How very, very petty of you! Very petty indeed!
What are you doing? Unjustified resentment, is it? Not good, not good! That’s not good at all!
Sakaurami is being (often) unduly resented for something. He says this even before he has invaded us, so the double meaning is likely in play.
What? Now you’re feeling the heat? You should have thought long and hard… Before you sided with a bloody mushroom! Nyah hah hah hah hah!
What’s wrong? Seem you going to die? Fools are ultimately like that, aren’t they! Enemies for something like that, don’t make me laugh! Nyah hah hah hah hah hah.
The last line was ultimately cut, presumably because it was getting pretty long for a half-health commentary. It was clearly designed to cover a variety of scenarios, not just “siding” with the mushroom.
Hrrg… You win…please… Oh, please…have mercy…
Ugh… I give up, help me, please… I beg you… gods have mercy…
He’s not asking for our mercy, he’s crying out for gods to have mercy on him. But, alas, we don’t.
Black top hat worn by Marvellous Chester, a man of mystery lost in the past.
The wearer of this top hat cracks a dubious, permanent grin. The Curse of Chester!
Black long hat of Magnificent Chester, an enigmatic man met in Oolacile’s past.
Perhaps it is due to Chester’s grudge? The face of the person wearing this is said to always have a strange smile plastered across their whole face.
I have seen it suggested that Chester’s mask is cursed so that he doesn’t have a face or something. It may be cursed, but by him. “Grudge” or onnen is also the name of the exploding heads found in the Catacombs and spawning from New Londo’s “mountain of corpses” (死体の山) enemy. And feelings have power in Dark Souls.
In short, Chester’s resentment over being killed was so great, it translated into us always smiling while wearing the cheerful mask and top hat we looted from his corpse. Very petty indeed!