After nearly 15 years and across multiple versions, gamers have continued to pour hours upon hours into The Elder Scrolls 5: Skyrim, and I am no exception. Experiencing Bethesda’s epic fantasy RPG for the first time in 2011 was formative and literally game-changing for me personally. And the fact I, like so many others, have returned to Skyrim numerous times is a testament to its staying power and appeal as one of the most perpetually popular, immersive, and reactive open-world games ever created.
There are a myriad of ways to approach each new run in Skyrim, with various story and roleplaying choices to make throughout, accompanied by a variety of playstyles to try. But after upwards of 300 hours in it, I pretty much always went for one of its most well-known, and in my opinion, the single most satisfying questline: The Dark Brotherhood.
My playthroughs were split between different editions and in some cases separated by long time gaps. But my goal was to play a Dragonborn as each of Skyrim‘s available races.
I Always Went Straight For The Dark Brotherhood Questline in All of My Skyrim Runs
Of all the questlines in Skyrim, the Dark Brotherhood is my personal favorite. The first time I found and followed through on its twisted tale all those years ago, I instantly loved it, and it’s become the one I’ve enjoyed doing the most in the whole game. I would addtionally argue that it’s the most compelling of the faction quests. This isn’t to say that some of the others, like the Thieves’ Guild or Stormcloaks, aren’t interesting. It’s simply that, as this one is so full of intrigue, complex characters, and many memorable moments, it’s stuck with me the most ever since.
Having been familiar with the nature and lore of the Dark Brotherhood from TES4: Oblivion, it’s likely the first thing I tried to contact the Brotherhood in Skyrim was something others did too: kill a random citizen and see if a member shows up the next night. When this didn’t work, I ended up asking around at inns for rumors, which pointed me toward Aventus Aretino in Windhelm and down the Brotherhood’s shadowy path. And upon repeat playthroughs, the journey never failed to deliver a thrilling sense of adventure for me.
In My Opinion, Skyrim's Dark Brotherhood Quests Are the Pinnacle of its Best Parts
It’s not just that becoming an assassin in the service of Sithis is intrinsically cool, but Skyrim‘s rendition of the guild and its members are, in my eyes, the most nuanced and well-realized within all of TES. By the time of Skyrim‘s events, the guild as a whole is fracturing and struggling to survive, and this dangerous desperation is often reflected in those who are part of it. Take Babette, for example, who is perhaps one of Skyrim‘s most sinister figures. As a centuries-old vampire who, to outside appearances, is an unassuming 10-year-old child, she uses this situation to her advantage to fulfill contracts. It’s morbidly funny but perfectly fitting.
Meanwhile, Cicero is hands down my favorite NPC follower. Of course, you can also find him hauling his unusual cargo near the outskirts of Whiterun as another fun way to start the questline. For all his often unnerving eccentricities and mannerisms, Cicero has the Brotherhood’s best interests and heart and truly does want it to thrive. Combined with his own internal conflicts and the reveal of Astrid’s betrayal and plea for redemption during her final moments, the storyline is incredibly impactful and really hits home, even after having seen it multiple times.
Why I Love Skyrim's Dark Brotherhood Questline So Much and Always Tackled It First
Rising up the ranks of the Dark Brotherhood to eventually become the Listener and later enacting a brazen assassination of the emperor himself really blew my mind the first time I initially did it all those years ago. The icing on the cake is then rebuilding the den in Dawnstar, which I think is one of the coolest looking locations once fully renovated. Each time I created a new character in Skyrim, regardless of any other choices I planned to make, I would pretty much immediately head out to begin the Brotherhood quest anew and revisit all those moments and characters.
One humorous anecdote I like to tell is that I (like a lot of others I assume) didn’t see the destruction of the Falkreath Sanctuary coming on my first run. Not only is it a striking setpiece and shocking turn, but I happened to have a lot of valuable items stored there. When I discovered that they were all gone in the aftermath, I admittedly reloaded a save and moved all my treasures to one of my other houses. It was both a narrative and mechanical rugpull. But I’d say that’s just more evidence as to why the Dark Brotherhood’s questline is so gripping in Skyrim.
And while the quests themselves are certainly standout and worth experiencing every time, there’s also a bunch of great gameplay benefits that come with seeking them out early. You’ll receive some solid gear which is especially useful if going for Skyrim‘s famous stealth archer or similar builds, as well as being able to use the sanctuary as a base (before it’s burned down, obviously.)
One other pleasant surprise for me came after being rewarded the ability to summon the spectre of Lucien Lachance himself, former Speaker of the Black Hand for the sect of the Brotherhood based in Oblivion‘s Cyrodiil, as well as being given his trusty steed Shadowmere as a mount. It all adds a lot of wonderful and believable flavor to Skyrim‘s depiction of the Brotherhood within the setting. And for all these reasons, that’s why it’s the questline I made sure to do as early as possible in every playthrough, and will undoubtedly do so again when I get around to my next one.