The Dark Brotherhood is a group shrouded in great mystery. To become a member is anything but simple, and to be one of its targets for assassination is sheer nightmare. In Skyrim, one of the last safe havens of these talented killers can be found and joined by the Dragonborn after killing Grelod the Kind.

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Under the guidance of its Mistress, Astrid, you'll train to become a feared assassin. However, be careful who you trust and remain cautious of your time in the Brotherhood, as the members are as ruthless as they come, and the tasks ahead must be performed in absolute cold blood. Here, we've compiled ten of the most insidious and cruel things the Dark Brotherhood has committed in Skyrim. Buckle up, and let's have a look.

10 Capturing Three Innocents

When you're first being considered as a candidate for the Dark Brotherhood, you'll wake up in this mysterious shack with Astrid, who instructs you to kill one or more of the three prisoners. According to her, one of them has a contract to their name, and it's your task to find out who it is.

Unfortunately, we never really find out, and we also realize that doesn't exactly matter in the Dark Brotherhood. If you can't kill, you can't be part of the team, and that's the only reason why Astrid puts us through this test and sacrifices three, most likely completely innocent civilians in the process.

9 Killing A Beggar

Once you do become a rookie member of the guild, the contracts start flooding in fast, along with the cash. One of your targets is Narfi, a beggar living in a destroyed house by Ivarstead. You might wonder why someone would want Narfi dead, given that he's just a harmless beggar, and you'd be right.

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There's no real, apparent reason to kill him. Sure, he might be a little bit soft in the head, but can you really blame the man? He's been waiting for his sister's return for a year now and is unable to accept the fact that she's long dead. A man struck hard by tragedy, it's senseless to kill him, and whoever ordered his death is definitely one with a cold heart.

8 Scaring A Paranoid Man

Ennodius Papius is another famous tragedy in Skyrim, one that most of us would be compelled to help. You see, there was once a time when he wasn't quite as jumpy and scared as he is now. He seems to believe someone is after him, and he'd be right about it, since the Brotherhood wants him dead.

However, back in the day, he was the owner of a mill, and he was fairly successful at his job. It's unclear what made him go insane. Perhaps someone threatened him enough to scare him away and turn him into a sad recluse. It definitely feels wrong to kill him, since he's of no harm to anyone and just wants to be left alone.

7 Punishing Someone For Lack Of Skill

Skyrim screenshot of Lurbuk with an argonian

Who doesn't love to hear a nice song after a long day of adventuring? In just about any inn, you'll be graced with the lovely tunes played by talented bards. That is, unless you come across Lurbuk. Apparently, he's the worst bard in the entirety of Skyrim. We learn from Nazir that a bunch of people wanted him dead, so much so that Astrid held a lottery to decide who would be the actual client.

All this, and for what? Lurbuk is just a passionate musician who wants to share his love for tunes with others. Surely his lack of skill doesn't merit death? It's a massive overkill to punish him for not being as good as the rest.

6 Assassinating An Innocent Merchant

Ma'randru-jo is one of the many Khajiit merchants you'll most likely come across while adventuring through Skyrim. Since the Khajiit aren't allowed to trade within city walls, you'll often spot him outside with his wares and some of his fellow Khajiit friends.

Again, we're not sure why Ma'randru-jo is on someone's death list. From listening to his conversations, it seems he's dreamed of traveling all his life and loves to see new places. Trading is then no doubt something he does in order to finance his trips, which he prioritizes even when dearly misses his home. He's an innocent Khajiit, and wouldn't harm a fly, but that's none of the Brotherhood's business.

5 Killing An Elderly Maid

The elderly are a special kind in Skyrim. Some might appear weaker than they actually are, while some are just, well, normal elderly people that don't deserve any harm coming their way.

Such is the case of Agnis, a woman who has worked as a maid in Fort Greymoor for forever it seems. All she cares about is the fort and its well-being, nothing more. Therefore, it's a bit strange that the Brotherhood sends us off to hunt her down and kill her. After all the hard work she's put into maintaining the fort, it's incredibly cruel and unfair to just take it all away from her.

4 Hunting Down A Beloved Son

One of the more interesting missions in the Brotherhood involve you hunting down Gaius Maro, the son of a leader of the Imperial guards. His job is to inspect safety in the various cities of Skyrim prior to the Emperor's visit.

However, when you reach him at Dragon's Bridge upon his departure, you'll witness his father, Commander Maro, bid his farewells to his son and worry about his safety. If this doesn't break your heart just a little bit, then you're definitely the definition of pure evil. Knowing that his son will pass no matter what is the worst feeling ever, and we dread attacking poor Maro as soon as he makes it out of his father's vicinity.

3 Ending The Career Of A Celebrity

Screenshot of NPC Balagog gro-Nolob

There are many famous people in Tamriel, but none quite like The Gourmet. Hailed for being the best chef out there, able to create a feast worthy of a king, he actually becomes one of the targets of the Brotherhood that seeks to infiltrate the Emperor's abode during his visit.

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In order to take The Gourmet's spot, we're forced to kill this highly talented and well-liked Orsimer man. Just think of all the amazing food he could have invented in the future, and all the light and celebration he could have brought into the world! It's such an unfortunate death, and so cruel from the Brotherhood to just destroy all of it.

2 Betraying Its Own

Unfortunately, the Brotherhood isn't just about ruining the lives of the innocents outside of its circle of trust. In fact, even its members are scheming individuals, always out to reap the benefits. Astrid is no different in this regard.

When the Dragonborn begins to show signs of being the next Listener, she feels threatened and is ready to cooperate even with the Imperials in order to kill the Dragonborn and maintain her position as the uncontested leader. Although things don't go as planned for her, it's truly evil how Astrid, after guiding and teaching us the ways of the Brotherhood, still doesn't care one bit about us. It goes to show there's no true loyalty in this faction.

1 Killing The Emperor

Perhaps the height of the Brotherhood quest line is when you're tasked to kill the Emperor himself. Whether you side yourself with the Imperial-hating Stormcloaks or the loyal Imperials, you have to agree Titus Mede II is, in some sense, the symbol of all species in Tamriel coming together into one.

He represents the entire continent, and what it seeks to be: a peaceful whole, where everyone can do as they please within the limits of its laws. When he's killed, the symbol of Tamriel dies with him, and society is left in disarray. People don't quite know how to feel or where to go, all because of the greed of the Brotherhood.

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