The Dark Brotherhood remains one of the most popular guilds in Oblivion. Its questline, characters, rewards, twists, and turns have made it timeless, with those who played it years ago remembering it fondly while new players are discovering it with Oblivion Remastered.

As with other quests in Oblivion Remastered, it can be difficult to know when to do questlines, or what order to complete the factions. The Dark Brotherhood can be especially tricky, as it increases Infamy points, which interferes with the Knights of the Nine DLC, but it also requires the player to kill an innocent victim, which can be difficult to roleplay if the player character isn't one to kill everything in sight.

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Joining the Dark Brotherhood Early

There are several approaches to when to start the Dark Brotherhood, and all depend on whether the player prioritizes roleplaying or access to better gear and resources. Players who begin the Dark Brotherhood quest between levels 1 and 15 will get access to the Blade of Woe, some good armor, and Shadowmere early in their playthrough. The Blade of Woe is incredibly powerful when enchanted, and Shadowmere is a fast, immortal horse that can transform traveling in Cyrodiil. Missing out on Shadowmere, the Blade of Woe, and the armor the Dark Brotherhood provides early game can be detrimental to a playthrough.

A player who uses this approach can roleplay their Hero of Kvatch as a redeemed villain story, beginning Oblivion as a member of the Dark Brotherhood before committing to Oblivion's main questline. This works especially well as the player character has just escaped from prison for an unknown crime. Another advantage is that the Dark Brotherhood pays for contracts, giving the player a good source of income.

Joining the Dark Brotherhood Later in Oblivion

A major downside to playing the Dark Brotherhood early is that the Blade of Woe is leveled when the player has it enchanted after completing the quest Honor Thy Mother. The strength of the Blade of Woe and its enchantment depends on the level of the player, with Level 30 being its strongest. As the Dark Brotherhood is an evil guild that requires killing innocent NPCs, it can be difficult to justify joining the organization when playing a morally good, kind character. The Dark Brotherhood also grants Infamy points, which can make it impossible to wear the relics of the Crusader until they revisit the Wayshrines of every member of the Nine.

However, roleplaying can overcome these barriers. The Dark Brotherhood serves as the perfect path for a Hero who has fallen from grace and embraced the darkness. As the Hero of Kvatch experiences loss and traverses hell itself in Oblivion's main questline, they may take a turn for the worse and join the Dark Brotherhood in response. In this scenario, it's likely they would turn away from the Nine to embrace Sithis, and so wouldn't wear the relics of the Crusader. This also has the perfect lead-in to beginning Shivering Isles, as a character who has lost themselves and wants to succumb to madness.

This approach has some advantages, as quests will become easier as the Hero is more skilled and has better gear. The Dark Brotherhood doesn't need to be started once every questline and all side content has been completed, which gives the player the chance to use the skills and gear that the faction rewards.

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The Elder Scrolls IV: Oblivion Remastered
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Action
RPG
Open-World
Adventure
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Systems
Xbox-1 PlayStation-1 PC-1
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Top Critic Avg: 82 /100 Critics Rec: 87%
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Released
April 22, 2025
ESRB
Mature 17+ // Blood and Gore, Sexual Themes, Violence
Developer(s)
Virtuos, Bethesda
Publisher(s)
Bethesda
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WHERE TO PLAY

SUBSCRIPTION
DIGITAL
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The Elder Scrolls IV: Oblivion™ Remastered modernizes the 2006 Game of the Year with all new stunning visuals and refined gameplay. Explore the vast landscape of Cyrodiil like never before and stop the forces of Oblivion from overtaking the land in one of the greatest RPGs ever from the award-winning Bethesda Game Studios.

Rediscover Cyrodiil
Journey through the rich world of Tamriel and battle across the planes of Oblivion where handcrafted details have been meticulously recreated to ensure each moment of exploration is awe-inspiring.   

Navigate Your Own Story
From the noble warrior to the sinister assassin, wizened sorcerer, or scrappy blacksmith, forge your path and play the way you want.     

Experience an Epic Adventure
Step inside a universe bursting with captivating stories and encounter an unforgettable cast of characters. Master swordcraft and wield powerful magic as you fight to save Tamriel from the Daedric invasion.  

The Complete Story  
Experience everything Oblivion has to offer with previously released story expansions Shivering Isles, Knights of the Nine, and additional downloadable content included in The Elder Scrolls IV: Oblivion Remastered.

Engine
Unreal Engine 5