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I've been going through an old AMA by Michael Kirkbride recently (which I assume was genuine) and I noticed in one of his posts that he was critical of how the Dark Brotherhood were depicted in Oblivion and Skyrim (he argues that they are "a boring kind of evil"). As I've only really paid any serious attention to them when they've been in these two games, it did get me wondering about what they were like before. So, my question to the lore buffs is: What are the differences between pre-Oblivion Dark Brotherhood and the Dark Brotherhood from Oblivion onwards?

No idea, to be honest. They weren't very well developed. In Daggerfall and Morrowind they seemed like a guild of contract killers, which is far more boring than the death cult vibe in my opinion. The Morag Tong does the professional stuff way better. I actually think the Brotherhood has been extremely well written since Oblivion, so if that's considered "a boring kind of evil" I'd like to see what isn't.

Well, that's all about it. DB is an assassin guild. Pre- and post-Oblivion. More developed in the latter case just. Morag Tong is an assassin guild as well, except that it is more traditional and 100% legal (I guess more costly for their services too), and in lore they branched from one organisation.

I guess what MK was referring to is that DB was made far less mysterious than in TES II and III. It was some secretive faceless assassin society back then, and in TES IV it suddenly gets not so faceless and far more 'earthly'.

An issue here is that the Dark Brotherhood is presented as a guild. Like the Fighter's Guild, the stated goal is to run it as a business venture. Instead of a necromantic daedric cult working as the instrument of a higher means to fulfill some mystic end, we get a bunch of assassins who don't care much for "the big picture".

Weirdly enough, the Morag Tong as it was written for Dram's backstory in Redguard worshiped Sithis, who apparently reincarnates his Champions multiple times. Dram was in his third life cycle or something when he confronted Cyrus. This may have been an early iteration of the Kalpic thing, and evidence that even MK's ideas about how these organizations relate hadn't solidified at the time, because during Morrowind's development the Morag Tong changed to be Mephala devotees, and the Sithis worship of the Dark Brotherhood is what caused the split/exile in the first place.

I believe he intended the murders they commit to serve some greater cosmic purpose. Something about balance. Rather than just being "We're eeeeeevil and we killlll people. Bwahahahaha", it was supposed to have some sort of effect on the Aurbis itself. This was all design stuff during the time of Morrowind that never actually made it into a game. It was going to be different from both Daggerfall's version and Oblivion's version. The one part of the Yin-Yang thing that got kept was the black and white stones that the Nightmother put into the eye sockets of her victims. This was part of the original "Light and Dark" cosmic mythos.