The Elder Scrolls V: Skyrim lets the player embark on their own grand hero's journey, but there are some quests that can make the player feel bad for seeing them through. The Dragonborn is supposed to be Skyrim's greatest hero who wards off the biggest threats to the world. Even that lofty reputation can't prevent the player from doing some rather underhanded things, though.
One of Skyrim's biggest strengths is the incredible amount of quests that are available to the player. Even beyond the main story, civil war, and various factions, the player can find new tasks just by traveling from city to city. Skyrim rewards inquisitive players with a wealth of missions and storylines to discover and play through. Most of these quests involve the player either helping people in need, or fighting off some source of evil in the world. However, there are a few quests where Skyrim's Dragonborn can be the bad guy, and a rather scary one at that.
Being evil in Skyrim is one thing, but some quest options available to the player are just cruel, even beyond being selfish. A few in particular can make the player question whether they are actually the hero in the first place if they go through with them. Even if the player intends to make a fully evil character, some of these quests are liable to make them feel bad regardless.
A Dark Brotherhood Contract In Skyrim Can Destroy A Family
The Dark Brotherhood in Skyrim offers a lot of the game's darkest quests, as one would expect from its name and nature. As a guild of assassins, the player will receive several tasks from them to kill various people, so players who join Skyrim's Dark Brotherhood probably know what they're getting into. One of these contracts, from a girl named Muiri, requires them to kill a bandit named Alain Dufont. While Alain deserves no sympathy, an addition to Muiri's request requires the player to leave their morality behind.
Muiri was good friends with the Shatter-Shield family, but Alain stole a family heirloom from them and blamed it on Muiri, causing them to shun her. Out of fury and heartbreak, Muiri adds the Shatter-Shields' only surviving daughter to the assassination contract out of revenge. The Shatter-Shields had lost their previous daughter to Riften's serial killer, and the death of Nilsine would only make things worse. The despairing mother Tova ends up dying of suicide, and the father Torbjorn is left in a depressive state, having lost his entire family. Even though the player has to kill to join Skyrim's Dark Brotherhood, they likely hadn't steeled themselves to see a family fall apart by their hand.
While one can feel sorry for Muiri due to how rough her life has been, her attempt to take revenge on the Shatter-Shields is over the line. While players can kill off Alain without much care, putting Nilsine to the sword requires a much colder heart. Thankfully, Nilsine's death isn't required, but taking that option anyway would be liable to leave the player with a heavy conscience afterwards.
Namira's Quest Makes The Dragonborn A Cannibal
Namira's Daedric quest in Skyrim is in contention for one of the series' most disturbing. Considering that Namira is the Daedric Prince of all things disgusting and repugnant, this should not be much of a surprise. Namira's quest, "The Taste of Death," not only allows the Dragonborn to do something truly heinous, but it also reveals a disturbing secret about Skyrim's most interesting city, Markarth, that the player wouldn't have known about otherwise.
In Markarth, the player meets a priest named Verulus who wants to investigate signs of cannibalism in the Hall of the Dead. It turns out that his suspicions are right, as the player meets a member of Namira's cannibal cult, Eola, who invites them to a feast with Verulus as the main course. Not only that, but a handful of NPCs from Markarth, some of whom the player had likely spoken with before, are revealed to be cannibalistic followers of Namira. In order to complete the quest and earn Namira's favor as well as her artifact, Namira's Ring, the Dragonborn must kill Verulus and be the first to feast on him.
Killing and eating Verulus is obviously abhorrent, especially since he was only trying to do the right thing. Even if Namira's Ring was one of Skyrim's best Daedric artifacts, what has to be done for it is a tall order. Thankfully, the player also has the option to save Verulus and take out the cultists earning his gratitude. However, if the player really wants Namira's Ring, then they have to take the cruelest path.
Boethiah's Quest Requires The Player To Sacrifice A Follower
Followers in Skyrim are some of the game's most important NPCs. For most of them, the player had to do a quest or help them out in order to earn their favor. Even in other circumstances, whether they had to win a brawl or pay them, the player is likely to get attached to their followers, especially if they travel with them for a long time. This can make Skyrim's "Boethiah's Calling" Daedric quest a serious shock, since the player must sacrifice a follower in order to complete it.
There are admittedly a few ways for the player to get around this requirement without giving up a beloved follower. They could freshly recruit a follower that they don't like or care for, or pay one of the mercenary followers to join them for the quest's goal. Even so, the quest still carries a strong edge of betrayal even if the player brings a follower that they have only known for only a few minutes. Very few RPGs ask the player to kill off their own party members, but Boethiah's quest makes that exact demand.
There are a lot of followers in Skyrim, so one can assume that they can replace whoever they give up to Boethiah easily, especially if they choose one of Skyrim's worst recruitable followers. However, the idea of losing a character for the rest of the save can weigh heavily on the minds of a lot of players. Out of every quest in Skyrim, sacrificing a follower to Boethiah is the most personal betrayal that the player can commit.
In Skyrim, most players will want to be the hero of the realm, and the game is set up perfectly for them to do that. At the same time, Skyrim can also let players enter some seriously dark territory when it comes to the deeds that the Dragonborn can commit. However, even someone trying to play the most evil Dragonborn in Skyrim may be taken aback by a few of their potential misdeeds.