After 10 Skyrim Playthroughs, I Always Make These Quests My Top Priority

by

For almost 15 years and through many different releases, players have spent countless hours enjoying The Elder Scrolls 5: Skyrim, and I’m one of them. My first time playing Bethesda’s huge fantasy RPG back in 2011 was a defining moment and truly changed how I thought about games. The fact that I, along with so many others, keep coming back to Skyrim shows just how well-made it is and why it remains one of the most consistently popular, deeply engaging, and responsive open-world games ever made.

There are countless ways to start a new game of Skyrim, offering many different story paths, roleplaying options, and ways to play. However, after spending over 300 hours in the game, I consistently found myself drawn to one particularly famous, and in my view, the most rewarding questline: The Dark Brotherhood.

I played through the game using various versions, and sometimes with significant breaks in between. However, I wanted to create a Dragonborn character for each of Skyrim‘s playable races.

I Always Went Straight For The Dark Brotherhood Questline in All of My Skyrim Runs

Out of all the storylines in Skyrim, the Dark Brotherhood is definitely my favorite. I remember playing through its dark and winding plot years ago and immediately falling in love with it-it’s the one I’ve replayed the most. I also think it’s the most captivating of all the faction quests. That’s not to say other storylines, such as the Thieves’ Guild or the Stormcloaks, aren’t fun. It’s just that this one, with its constant mystery, well-developed characters, and many unforgettable scenes, has stayed with me the longest.

Because I already knew about the Dark Brotherhood from TES4: Oblivion, I probably did what many players did in Skyrim: I tried to trigger the questline by killing a random person, hoping a member would contact me the next night. When that didn’t work, I started asking around in taverns for rumors, which eventually led me to Aventus Aretino in Windhelm and started me on the Brotherhood’s secretive path. And every time I’ve replayed the game, that journey has always been a really exciting experience.

In My Opinion, Skyrim’s Dark Brotherhood Quests Are the Pinnacle of its Best Parts

It’s not simply that being an assassin for Sithis seems cool, but the way Skyrim portrays the guild and its members is, in my opinion, the most complex and believable of all the games in the TES series. By the time of Skyrim‘s story, the guild is falling apart and fighting to stay alive, and this sense of danger and desperation is clear in its members. Consider Babette, who is arguably one of Skyrim‘s most unsettling characters. She’s a vampire who’s lived for centuries, but looks like a harmless 10-year-old, and she uses this to her benefit when carrying out assignments. It’s darkly humorous, but it completely makes sense.

Personally, Cicero is my absolute favorite follower in the game. You can also spot him carrying his strange belongings just outside Whiterun, which is a great way to begin his questline. Despite his frequently unsettling quirks and behaviors, Cicero genuinely cares about the Brotherhood and wants to see it succeed. When you add his personal struggles to the shocking reveal of Astrid’s betrayal and her desperate request for forgiveness as she dies, the story becomes incredibly powerful and emotionally resonant, even if you’ve experienced it many times before.

Why I Love Skyrim’s Dark Brotherhood Questline So Much and Always Tackled It First

I was absolutely stunned when I first climbed the ranks of the Dark Brotherhood, eventually becoming the Listener and then daringly assassinating the emperor. What really sealed the deal for me was rebuilding the sanctuary in Dawnstar – it’s one of the best-looking places once you’ve fully renovated it. Every time I started a new character in Skyrim, no matter what else I had planned, I’d immediately begin the Dark Brotherhood questline again, eager to relive those moments and interact with those characters.

I always love telling the story of how I, like so many other players, was totally blindsided by the destruction of the Falkreath Sanctuary during my first Skyrim playthrough. It was such a visually impressive moment and a huge twist, but to make matters worse, I’d been using it as storage! When I realized everything I’d collected was gone, I’ll admit I reloaded an earlier save and moved all my best gear to one of my other houses. It really felt like a total bait-and-switch, both in terms of the story and the gameplay. But honestly, that’s just another reason why the Dark Brotherhood questline is so incredibly gripping. It just keeps you on your toes, you know? I wasn’t expecting that at all!

The quests are definitely memorable and worth doing each playthrough, but completing them early also offers some helpful advantages. You’ll get good equipment, which is particularly beneficial if you’re planning a Skyrim stealth archer or a similar character build. Plus, you can use the location as a safe base of operations-at least before it’s destroyed, of course.

I was also really pleased to unlock the ability to summon the ghost of Lucien Lachance, who used to be the leader of the Black Hand – a secret group within the Oblivion-based Brotherhood in Cyrodiil. Getting his horse, Shadowmere, as a ride was a great bonus, too. It all adds so much interesting and realistic detail to how the Brotherhood is portrayed in Skyrim. Because of all this, it’s the questline I always prioritize at the beginning of each new game, and I’m sure I’ll do it again when I start my next playthrough.

Read More

2025-10-05 19:50