Which quests or quest choices (not questlines) are profoundly wicked in your opinion? Rank them in a top and know that you can list more than 5 if you want to.

Most of the Daedric quests. Particularly Molag Bal's and Boethiah's. Vaermina offers a pretty despicable choice at the end of her quest. "In My Time of Need" can have some pretty selfish and devious conclusions, if the player wants.

Unfortunately, there doesn't seem to be all that many that offer choices like that.

This is pretty funny considering the why is Skyrim so dark thread. Different strokes for different folks

Boethiah, Molag Bal, the first dark brotherhood contracts, Vittoria Vici, Siding with Eola.

Holy crap, I can't believe I forgot about the Dark Brotherhood completely. XD They're about as evil as you can get. Especially killing a woman at her own wedding ceremony.

1. Boethiah's calling

I picked Faendal the first time (for practical purposes). He was my first TES follower and I felt terribly all the way. It was a good quest since it played so well with emotion.
2. Killing Paarthurnax
Another masterpiece build on emtion. Even my worst character regrets killing her mentor.

To this I might add Vittoria Vici, Eola's request, Muiri's request regarding Nilsine Shatter-Shield, Molag Bal's quest and Vaermina who managed to trick me on my first playthrough into distrusting my follower.

Any of the Daedric quests are fairly evil really.

Too lazy to look it up, but powering up that Daedric Blade by killing your friends is pretty cold.

Ooh yes, Mephala is not someone to be dealing with unless you are emotionally disturbed really =D.

Killing Narfi just as low as one can get. Who is the sicko that orders his killing ='(.

Maybe in our society. In The Elder Scrolls world it's just business with no evil intent intended, unless maybe your character leans in that direction. http://www.gamesas.com/index.php?s=a0ff6d8ee3431f9905b3e7f80549d8be&&app=forums&module=extras§ion=legends#

Killing Paarthurnax is the only "evil" quest that comes to mind that does not seem like a "2edgy4me" like the rest of the so called evil quest.

Mind you I never do it, not going to kill Grandpa Paarthy.

You forgot the worst of all. Eating a corpse

The most evil thing I do in the game is blackmail for Frost, simply because I want a better horse. I feel sorry for the guy, but damgummit, I need a better horse!

I dunno, that's bad, but I feel like bludgeoning a defenseless old man to death with a rusty mace -- repeatedly -- is pretty damn bad lol. Honestly, the only two Daedric quests that don't have some form of sadism are Azura's and Meridia's. Well, maybe Sanguine. Not really evil, just general debauchery.

I wouldn't call Sheogorath's quest particularly evil either. In fact Malacath isn't really an evil quest either, nor are Peryite, Vaermina och Mehrunes Dagon. Like with Namira you can choose to side with evil or be tricked by the Daedra lord in some of them but you don't have to. Hmm, Clavicus Vile and Hircine isn't forcing you to commit evil really are they?

Molag Bal, Mephala, Boethiah is a whole other issue.

Yes I think that one ranks #1 for me. Boethiahs and Molag Bals also involve deceit lying and turning your back on someone that trusts you, but the Ebony Blade quest requires you to betray 10 of your friends and followers, again people that trust you. That's pretty messed up.

It really doesn't get more evil than that.

True, forgot about Sheogorath's. I dunno about Peryite, though, he basically had you murder a crapload of sick people purely because they didn't want to follow him anymore. Maybe not as bad as others, since they're automatically hostile, but they never struck me as really bad people. Most of them just offer evil choices toward the end of their quests. Clavicus Vile is always an [censored], though lol.

Dagon, obviously. Has you reforge an evil dagger and asks you to kill your partner with it. My female Altmer refused to have anything to do with the Mythic Dawn, remembering what it was like during the Oblivion Crisis 200 years prior.

Yeah, Peryite, I looked upon them as Deadra worshippers and therefore people who have crossed the line to the "evil" side. But maybe I'm to hard on them and I should figure them just unfortunate and desperate to get a cure from the source of their disease? I have tried to reason with the afflicted but as yet no such luck .

Yes, but you can refuse to do his bidding, kill his dremora, ransack his temple and piss on his altar if you prefer =).

Technically, Peryite only asks you to kill their leader, who was disobedient, or something. I've forgotten the actual dialog. It doesn't seem like the majority of Afflicted have decided to stop worshiping.

Dark Brotherhood, Thieves Guild depending on how evil you consider Daedra and the acts of the this incarnation's Guild, Boethiah, Molag Bal, Mephala, Companions depending on how evil you consider werewolves are, choosing the vampiric side in Dawnguard, Dragonborn has its contenders, Mehrunes Dagon...there's a lot.

I dunno, murdering Grelod in front of the kids is pretty bad. Ok, she's awful, but shouldn't she loose her job and get prosecuted for child neglect/abuse by the civil authorities instead of being murdered? I know, that's now how Skyrim works but that was one of the first quests I stumbled into when I started playing and it set a pretty nasty tone.

While the player doesn't really do anything evil, besides funding a murderer a couple thousand septims, Unearthed is pretty evil.