The Dark Brotherhood is one of the most iconic factions inThe Elder Scrollsseries. Known for its connections to Sithis and his bride, the organization is a cult of assassins who’ve sworn to kill in the name of the Night Mother. In-game, the Dark Brotherhood has some of the most enjoyable quests in the game as it challenges the player to take out targets in specific ways.
This is certainly the case inOblivionandSkyrim— the most recent single-playerElder Scrollsgames. However, there’s been plenty of debate in the community as to which title did it better. Admittedly, it isn’t easy to come up with a categorical answer as both questlines have their fair share of pros on cons, but it’s worth comparing and contrasting the Dark Brotherhood quests ofOblivionandSkyrim.

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The Dark Brotherhood of The Elder Scrolls 4: Oblivion
TheDark Brotherhood questline inOblivionofficially begins when the player kills any “innocent” NPC. This can be anyone from a town guard to the Adoring Fan. Doing so will prompt an ominous system message that reads, “Your killing has been observed by forces unknown…” Should the player then sleep in a safe location, a man named Lucien Lachance will wake them and send them on an initiation quest, “A Knife in the Dark.” Upon completion, Lachance will show up again and welcome the player to the Dark Brotherhood.
Following their recruitment, the player will need to accomplish multiple assassinations. Though these are essentially “filler” quests that lead up to the main conflict withinOblivion’sDark Brotherhood, they’re still very enjoyable. This is primarily because the assassination quests offer bonuses should the player execute the target in a specific way. The “Whodunit?” quest, for example, is one of themost memorable inOblivion. Here, the player must enter a mansion along with five other guests and kill them off. Accomplishing this without being caught as the murderer grants the player a bonus.

Once the player climbs enough ranks within the Dark Brotherhood, they’ll be called on again byLucien Lachance ofOblivion, who reveals that there is a traitor among the Dark Brotherhood. This is where the questline delves into the organization’s internal conflicts. Though the ensuing quests arguably aren’t as fun as the initial ones, they’re more emotionally charged as the player not only purges the Dark Brotherhood Sanctuary but must also see Lachance killed. Even though the player beats the traitor in the end, it’s still a bittersweet victory.
The Dark Brotherhood of The Elder Scrolls 5: Skyrim
The Dark Brotherhood questline inSkyrimbegins when the player “steals” a kill from the organization. This is done by killing Grelod the Kind for young Aventus Aretino. After doing this, the next time the player sleeps in a safe location, they’ll wake up in the Abandoned Shack, where Astrid will try to recruit them into theDark Brotherhood ofSkyrim.
Theassassination quests inSkyrimaren’t as challenging as those inOblivionas the former doesn’t offer bonus rewards for killing the target in a specific way (save for a few exceptions). Still, the overall questline forSkyrim’s Dark Brotherhood is far grander in scheme, compared toOblivion’s. Rather than just focusing on the organization’s internal conflicts,Skyrim’s Dark Brotherhood introduced a lofty goal: to kill an Emperor.

Thus, the “filler” quests are simply interspersed between the player’s main tasks, which set up the plan for theEmperor’s assassination inSkyrim. The way Cicero and Astrid butted heads also added to the overall story as the insane jester represented the organization’s old ways, while Astrid stood for more modern principles and independence from the Night Mother’s grasp. In the end, the Night Mother’s influence wins over Astrid’s beliefs, but not without help from the player.
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Comparing Questlines
ObliviontrumpsSkyrimin quest qualityand replayability. This is because so many of the quests can be completed in different ways, and there are more assassination contracts inOblivion, in general. Thus, players often feel more like an assassin there than in theSkyrimquestline. The fact that completing these quests also increased the player’s rank within the organization also gave a better sense of progression and pacing.
That said, theSkyrimDark Brotherhood had far more memorable characters — most notably,Cicero ofSkyrim. Though both theOblivionandSkyrimassassins are interesting in their own right, Cicero blows everyone out of the water with his excellent voice acting and genuinely unhinged behavior. Astrid, though not as compelling, is also a serviceable minor antagonist in the narrative.Skyrimalso has a somewhat better endgame thanOblivion’sDark Brotherhood since the player unlocks a new Sanctuary and can outfit it with new furnishings.
Another thing worth noting abouttheSkyrimDark Brotherhood questlineis that the player can choose to go against the organization. Though the “Destroy the Dark Brotherhood!” route isn’t nearly as complex as the faction’s main questline, the option is still there, givingSkyrima bit of a leg up onOblivion.
To sum it all up,Oblivion’sDark Brotherhood arc is better for its quests, whileSkyrim’sis better for its characters, plus its endgame options. The narrative for both questlines is good, but they would have benefited from a little more attention to detail. For instance,Oblivion’s twist would have been better if the traitor was hinted at more, whileSkyrim’s would have improved from a more pronounced conflict between Astrid and Cicero.
All this should be taken into account forThe Elder Scrolls 6, asa Dark Brotherhood questline with quests likeOblivion’sand characters likeSkyrim’s would be top-notch. Wrap those together in a compelling narrative, and it’s bound to be an enjoyable questline. It’s also worth crafting an alternative route for players who want to defeat theDark Brotherhood as this adds toThe Elder Scrolls 6’sreplayabilitywhile also improving its roleplaying potential.
The Elder Scrolls 5: Skyrimis available now on PC, PS4, PS5, Switch, Xbox One, and Xbox Series X|S.