Picking Your First Kill in Oblivion’s Dark Brotherhood in 2025, Welcome to the Shadows

Let me tell you something that might sound a bit twisted – one of the most memorable moments in The Elder Scrolls IV: Oblivion isn’t saving the world or closing Oblivion gates. It’s committing your first cold-blooded murder to join the Dark Brotherhood. Yeah, I know how that sounds, but stick with me here.

After years of playing this game and discussing it with fellow fans, I’ve learned that choosing your first victim for the Dark Brotherhood is almost a rite of passage. It’s weird, it’s dark, and honestly, it’s one of the most morally questionable things you’ll do in a fantasy game – which is exactly why it’s so compelling.

Your First Kill in Oblivion: Choosing a Victim to Join the Dark Brotherhood

First of all, why join the Dark Brotherhood?

Let’s first discuss why you would want to join these terrible people before getting into the graphic specifics. One of Oblivion’s best-written questlines is undoubtedly the Dark Brotherhood one. Intriguing people, treachery, and some truly unexpected story twists are all here. Additionally, the rewards—unique spells, equipment, and abilities that you can’t obtain anyplace else—aren’t bad either.
The catch is that you must first kill an innocent person. Not kill a bandit in self-defense, not accidentally hit a guard during a fight – actual, premeditated murder. The game is pretty specific about this requirement, and it’s what makes many players pause and think, “Am I really about to do this?”

The Most Popular First Victims

Umbra – The Warrior’s Choice

If you’re looking for a challenge and don’t mind getting your hands dirty, Umbra is probably your best bet. She’s tucked away in the ruins of Vindasel, southwest of the Imperial City. Here’s the thing about Umbra – she’s tough as nails and wearing full Ebony armor, but she’s also completely isolated.

The beauty of choosing Umbra is that there are no moral qualms here. She’s aggressive, she attacks on sight, and you’re basically doing Cyrodiil a favor by taking her out. Plus, you get that sweet Ebony armor as a bonus. Just be careful when Lucien Lachance shows up afterward – apparently, he has a habit of walking into floor traps if you’re not quick about leaving the dungeon.

The Adoring Fan – The Meme Choice

Okay, let’s address the elephant in the room. Yes, many players choose to murder the Adoring Fan, and yes, it’s become something of a meme in the Oblivion community. “By Azura, by Azura, by Azura!” might be burned into your brain after completing the Arena questline, making this little guy’s death feel almost… justified?

But here’s the thing – he’s completely innocent. Annoying? Absolutely. Deserving of death? That’s between you and your conscience, friend.

Targets That Won’t Make You Feel Like a Monster

Alval Uvani – The Traveling Target

This is actually one of the smartest choices you can make. Alval Uvani travels between cities on a predictable schedule, which gives you plenty of opportunities to take him out without witnesses. He’s usually found in different cities throughout the week and catching him on the road between destinations is your best bet for avoiding any bounty.

Wilhelm the Worm – The Easy Target

Located in Anvil, Wilhelm is a low-level character who’s easy to dispatch quickly. He hangs around the docks and sleeps in the Harborside Warehouse. The guy’s basically a petty criminal anyway, so you won’t lose too much sleep over this one.

Beggars and Outlaws – The Morally Gray Choice

Throughout Cyrodiil, you’ll find various beggars and outlaws who, while not actively evil, aren’t exactly pillars of the community either. The waterfront areas are particularly good hunting grounds for these types. Just make sure you’re not seen – the last thing you want is a bounty on your head before you’ve even started your assassin career.

Methods That Won’t Land You in Prison

The Stealth Approach

Break into someone’s house at night while they’re sleeping. A quick dagger to the throat, and you’re done. The fine for breaking and entering is usually minimal compared to the murder bounty, assuming you don’t get caught in the act.

The Wilderness Ambush

Follow your target out of town and strike when there are no witnesses. This is particularly effective with traveling NPCs like Alval Uvani.

The Summoned Creature Method

Here’s a clever trick some players use: summon a creature and use it to do your dirty work. While you’ll still get credit for the murder (since you’re responsible for the summon), you might avoid some of the immediate consequences.

What NOT to Do

Don’t Kill Quest NPCs

This should be obvious, but I’ve seen too many players accidentally ruin their playthrough by killing someone important. Stick to generic NPCs or characters you know aren’t involved in major questlines.

Avoid the Gray Prince Method in Remastered

In the original Oblivion, killing the Gray Prince after learning about his backstory would count as murder without giving you a bounty. However, in the remastered version, this method reportedly doesn’t work anymore. Quest-initiated kills no longer count as murder, so you’ll need to find another victim.

Don’t Kill Guards Unless You’re Desperate

While killing a guard will definitely get the Dark Brotherhood’s attention, it’ll also get you a massive bounty and potentially ruin your standing with various factions. Save this as a last resort.

The Psychological Impact

Here’s something that doesn’t get talked about enough – murdering your first innocent NPC in Oblivion can actually be pretty unsettling. These aren’t just pixels and code; they’re characters with schedules, relationships, and dialogue. The game does a good job of making them feel like real people, which makes taking their lives feel genuinely wrong.

I remember my first time playing through this questline. I spent probably an hour just following around potential victims, trying to work up the nerve to go through with it. It’s a testament to the game’s design that even veteran players often struggle with this moral choice.

After the Deed is Done

Once you’ve committed your first murder and received that ominous “Your killing has been observed by forces unknown” message, all you have to do is wait. Sleep in a bed somewhere safe, and Lucien Lachance will visit you with your first contract. From there, the Dark Brotherhood questline opens up, and you’re in for one hell of a ride.

Final Thoughts

Joining the Dark Brotherhood in Oblivion is one of those gaming experiences that sticks with you. It forces you to make a choice that goes against every heroic instinct the game has been building up to that point. But it’s also the gateway to some of the most memorable content in the entire Elder Scrolls series.

Whether you choose Umbra for the challenge, a random beggar for convenience, or even the Adoring Fan for the memes, just remember – there’s no going back once you take that first life. The Dark Brotherhood doesn’t exactly have a resignation policy.

So, choose your victim wisely, steel yourself for what you’re about to do, and prepare for one of the darkest and most compelling questlines in RPG history. Welcome to the family.

For more gaming related articles visit Home – Total Apex Gaming

For more Oblivion Remastered related articles visit Total Apex Gaming – Oblivion Remastered