The Dark Brotherhood questline gets genuinely better the second time around

[RiftenWanderer]

I'm on my 4th playthrough and just finished the Dark Brotherhood stuff again, and I think I've been sleeping on how well it's structured. First time through I was just doing quests for the gold and the Daedric artifact, but this run I actually paid attention to the story beats and wow, it's way more cohesive than I remembered.

Like, the whole thing builds to something. You go from random contract kills to realizing there's actual politics happening with Astrid and Sithis, and by the time you get to the end you understand why everything had to happen that way. The contracts in the middle aren't just filler - they're character work. You're learning what the Brotherhood actually is while you're doing them.

Also Cicero is legitimately unsettling when you're not just skipping dialogue. The guy is weird on purpose and it pays off.

 

[ScrollsOfTamriel]

Yeah, I get that. The DB questline has this weird thing where it's easy to miss on a speed-run because you're just grabbing contracts and moving on, but the moment you actually listen to what people are saying it clicks. Astrid's whole arc is the linchpin - she's not just an obstacle, she's someone who fundamentally misunderstands what the Brotherhood is supposed to be, and that tension runs through everything.

The contract work actually does matter too. You're not just racking up kills, you're proving yourself to a faction that's supposed to be built on secrecy and devotion to Sithis. Each one is testing whether you understand that this isn't mercenary work - it's something else entirely. And then the game shows you what happens when someone (Astrid) tries to turn it into mercenary work anyway.

Cicero's great because he's the only one who actually gets it. He's annoying and creepy and obsessed with the Night Mother, but he's the only person in that sanctuary who hasn't compromised. Everyone else has been running a contract business. He's been doing the actual religion. Makes the ending hit different when you realize that.

What got you to pay attention this time around? Just naturally or did you find yourself wanting to engage with the story more on a later playthrough?