It starts with a murder. Not a heroic duel or a scripted cutscene where a villain twirls their mustache, but a cold, calculated choice made by you, the player. You kill an innocent NPC—maybe a beggar in the Imperial City or a shopkeeper in Cheydinhal—and then you sleep. When you wake up, Lucien Lachance is standing over you in the dark. He’s wearing those iconic black robes, his voice is a sandpaper rasp, and honestly, the vibe is immediately different from anything else in The Elder Scrolls IV: Oblivion.
The Dark Brotherhood Oblivion questline isn't just a series of "go here, kill that" missions. It’s a descent into a cult that feels like a family, right before it tears itself apart in the most gut-wrenching way possible. Most modern RPGs try to replicate this feeling of belonging and betrayal, but they almost always fail because they’re too afraid to make the player feel like a genuine villain. In Cyrodiil, you aren't a misunderstood anti-hero. You're a professional killer.
The genius of the contract design
Early on, the game teaches you that how you kill matters just as much as who you kill. Take the quest "Accidents Happen." You’re sent to Bruma to kill a man named Baenlin. The catch? You have to make it look like an accident by loosening the fastenings on a stuffed head of a Great Hunt over his chair. If you pull it off while he's relaxing, his manservant discovers the body and the sheer grief in the room is palpable. It’s dark. It’s uncomfortable. It’s brilliant.
Compare this to the Dark Brotherhood in Skyrim. In the later game, the missions feel a bit more like errands. In Oblivion, the bonus objectives—the "Dead Drops"—actually forced you to engage with the world’s mechanics. If you followed the rules, you got unique items like the Sufferthorn dagger or the Black Band. If you messed up, you just got gold. It rewarded creativity and patience over brute force.
"Whodunit?" is arguably the greatest quest Bethesda has ever designed. You’re locked in a house in Skingrad with five guests who think there’s a chest of gold hidden somewhere. Your job is to kill them all without anyone seeing you do it. You can talk to them, build rapport, and even convince them to turn on each other. Watching Neville get paranoid or telling Matilde Septim that you’re the killer right before you strike is peak roleplaying. It’s a social deduction game inside an action RPG, and it works because the AI (for all its "Radiant" flaws) reacts to the dwindling numbers in the house.
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A family built on blood
What makes the betrayal later in the Dark Brotherhood Oblivion questline hurt so much is the Sanctuary in Cheydinhal. You spend hours there. You talk to Teinaava about his Shadowscale heritage. You listen to M'raaj-Dar insult your boots. You get advice from Vicente Valtieri, a vampire who has been around for centuries.
The Sanctuary feels safe. It’s the only place in the game where you aren't the Hero of Kvatch. You’re just a Brother or Sister. When Lucien Lachance eventually gives you the order for "The Purification," it isn't just a quest marker. It’s a genuine "wait, what?" moment. You have to execute everyone you’ve spent the last ten hours befriending because a traitor has supposedly infiltrated the cell.
Bethesda didn't give you a way out. You couldn't "Paragon" your way through it. You had to kill the Ocheeva, the calm leader. You had to kill the Orc who finally started to respect you. That’s the nuance people miss: the game forces you to be a tool of the Night Mother, proving that your loyalty is actually just blind obedience.
The Lucien Lachance tragedy
Lucien is the face of the faction, and his arc is a masterclass in tragic irony. He’s the one who recruits you, mentors you, and trusts you with the Dead Drops. When the questline shifts and you start picking up orders from hidden containers in the wilderness, the game subtly begins to gaslight you. You think you’re killing enemies of the Brotherhood, but you’re actually picking off the members of the Black Hand—the leadership itself.
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The realization hits when you find yourself standing over the body of a target, only for Lucien to scream at you that you’ve been deceived. The traitor was swapping the orders. Seeing Lucien—this cold, untouchable assassin—reduced to a panicked, hunted man is jarring.
Then comes the "Next of Kin" quest aftermath. The remaining Black Hand members believe Lucien is the traitor. When you arrive at Applewatch, you find what’s left of him hanging from the ceiling. It’s one of the most gruesome visuals in a T-rated game. The irony? The real traitor, Mathieu Bellamont, is standing right there with the rest of the hooded figures, pretending to be outraged.
Why the ending feels different
Most players remember the ending for the trip to the Night Mother’s crypt under the statue of the Lucky Old Lady in Bravil. It’s a spooky, atmospheric finale. But the real weight is the mechanical shift. Once you become the Listener, the questline "ends," but it doesn't stop. You have to maintain the faction.
You visit the Night Mother once a week, hear the names, and pass them to your subordinate. It’s a job. It cements the idea that the Dark Brotherhood isn't just a story you finished; it’s an institution that outlasts its members.
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Common misconceptions about the questline
- You have to be a stealth build: Nope. While the bonuses are easier to get with high Sneak and Illusion, you can brute force almost every kill. It just feels "wrong" narratively.
- The traitor is obvious: On a second playthrough, yeah, Mathieu Bellamont’s diary (which you can find in his mother’s house) spells it all out. But in 2006? Most people were genuinely shocked.
- The rewards are just gold: The real rewards are the unique items. Shadowmere, the invincible horse, is arguably the best "utility" reward in the entire game.
Tactical takeaways for a modern playthrough
If you’re heading back to Cyrodiil to relive this, don't just rush the kills. The writing is in the margins.
- Read the journals: Every target in the "Dead Drop" phase has a life. Reading their letters before you kill them adds a layer of guilt that makes the eventual revelation of the traitor hit harder.
- Use the environment: In the quest "The Locked Box," you can kill a target with a poisoned apple. It’s a mechanic most players ignore, but it’s incredibly satisfying to watch.
- Don't skip the dialogue: Talk to the Sanctuary members after every single rank up. Their dialogue changes based on your progress, and it’s the only way to actually feel the "family" dynamic before you’re forced to destroy it.
The Dark Brotherhood Oblivion questline remains a benchmark for how to handle player agency and narrative stakes. It doesn't treat you like a hero, and it doesn't give you a happy ending. It gives you a dark, complicated, and ultimately lonely seat at the top of a mountain of corpses. It’s exactly what a guild of assassins should be.
To truly master this questline today, focus on the "Whodunit?" quest as a sandbox for the game's Disposition system. Try to finish that specific mission by convincing the guests to kill each other without you ever drawing a blade. It requires high Speechcraft and a bit of luck, but it represents the absolute peak of what this 20-year-old engine can do when pushed to its limits. Once you finish the Bravil crypt sequence, your next step should be heading to the Deepscorn Hollow DLC (if you have it), which provides the perfect thematic home for a newly minted Listener of the Dread Father.