Oblivion's Dark Brotherhood actually nailed what Skyrim's got wrong

[ScrollsOfTamriel]

The more I replay both games, the more I realize Oblivion's DB questline just hits different. Like, in Skyrim you get Astrid basically handing you contracts and suddenly you're the Listener. It's fine, the quests are solid, but there's no real sense of... infiltration? Earning your place?

Oblivion makes you work for it. You start as a random person who stumbles into the Sanctuary, and every early contract feels like you're proving yourself. The questline actually makes you feel like an outsider climbing ranks instead of just being the chosen one immediately. And the whole thing with the traitor and the Purification questline actually has stakes because you've been there long enough to care about these people.

Plus Oblivion's contracts are just more interesting mechanically. You're not just sneaking into a bandit cave - you're staging accidents, you're poisoning people, you're working around guards in ways that feel creative instead of "sneak archer go brrr."

I know Skyrim's DB has better individual quests (Bound Until Death is genuinely great), but the arc as a whole? Oblivion wins. The Skyrim version feels like you're doing favors for Astrid's weird family rather than joining an actual organization.

Does anyone else feel like Skyrim rushed the DB questline just to get you to the assassination contracts faster?

 

[EbonyWarrior]

You're hitting on something real here. Oblivion's DB definitely made you prove yourself - that slow burn of doing odd jobs and actually meeting people before you're trusted with the big contracts. Skyrim just... accelerates you into leadership almost immediately, which yeah, undercuts the whole "joining a secret society" fantasy.

That said, I think Skyrim's individual contract design is actually where it shines, even if the overall arc suffers. The Oblivion contracts were creative in concept (stage an accident, poison someone), but mechanically? A lot of them boiled down to finding the target and doing the thing. Skyrim's quests like Bound Until Death or the one with the Dark Brotherhood traitor - those had actual story beats and environmental variety that made them feel less like checklist jobs. Oblivion was more about the roleplay of it; Skyrim was more about the quest itself.

But you're right that Skyrim fumbles the "joining" part. Getting recruited by Astrid in that cave and then suddenly being Listener because Sithis says so? It feels unearned. Even the Thieves Guild questline in Skyrim does a better job of making you climb ranks - you actually have to do jobs for Delvin and Vex before you get trusted with the bigger stuff. The DB should've had that same structure instead of just handing you the top job after like three quests.

Honestly I wonder if Skyrim's writers were just trying to get you to the assassination contracts faster because that's what people wanted to do anyway. But that's a design problem, not a story problem.