Sheogorath once made a deal with Arch-Mage Shalidor; in exchange for the Folium Discognitum, Sheogorath would receive the Eyevea. Sometime after the exchange was made, Shalidor came to regret this deal and blamed the Mad God for tricking the Arch-Mage into it.
During the Mages Guild questline, Sheogorath agrees to let Shalidor reclaim four tomes needed to reclaim Eyevea, but the Vestige must perform several tasks in order to receive each tome. Due to an enchantment placed upon the tomes, Shalidor cannot read the tomes himself and must rely on his assistant, Valaste, to translate the books for him at a slower pace.
Unknown to the Vestige or Shalidor, Sheogorath had cursed the tomes to slowly drive Valaste insane. Sheogorath intends to offer a second deal - reminiscent of the first one he made with Shalidor - by taking Valaste back with him to the Shivering Isles in exchange for the Folium Discognitum, or cure Valaste of her madness and not give the Folium. The decision is up to the Vestige.
Sheogorath is a sadistic Daedric Prince who finds entertainment by inflicting madness on helpless individuals and driving people to commit murder. He has little remorse for mortals, whom he calls "playthings," and will freely renegade on a deal with them if he finds an alternative to be more beneficial to him. He will also discard a loyal follower should they fail to meet his expectations, usually by getting someone to kill them.
As with mortals, Sheogorath has little regard for his fellow Princes and will happily steal from them to "keep them on their feet." The death of his personal underlings, such as the Dark Seducers, is fair game if watching them fight someone is entertaining.
In the final test, Sheogorath wants the Vestige to take a vacation in his family's chateau. However, all the three guest rooms are occupied, and two guests are cannibals. The correct guest is the one that isn't playing his role right and wants to get out. Next, the Vestige must find their way through a dark maze. Finally, they must fight their way through Madmen and Madwomen to a boss fight with Uncle Leo, a flesh atronach.
The Vestige and Shalidor journey to Eyevea, but Sheogorath left portals to Oblivion open and the island is covered in daedra. The Vestige fights Haskill. Sheogorath, who has been making Valaste slowly insane with his cursed books, offers to take her to the Shivering Isles. They can decide whether or not to save her.
"Look Haskill! Forky's back! It's so nice to see him again! Oh. And good to see you too, mortal. I guess."
Yes, here they are."Wonderful! I'll just take ... forky! I've missed you so much, forky! Let's never be parted again. Gives me goosebumps to hold him in my hand again."
What about this staff?"Ahh, the Wabbajack. Maleel held it down in that dusty tomb for so long ... Say, why don't you clear its throat. Take it in hand and use it on some of these holier-than-thou temple types."
What am I signing up for?"No need to worry your pretty mortal head. The Wabbajack ... it unleashes the potential in everyone. The unrecognized essence of artistic beauty that swells and beats within the ... Look, you want the book? Whack some folks with the Wabbajack."
If you insist.
After using the Wabbajack:
"A bit rusty, but not bad! So funny, watching you mortals muck around with things you can't possibly understand. I'll be needing that back, now."
Here it is."And, as promised, the book. Go ahead. Take it!"
Thank you."Once it's yours, it'll send you straight back to Tamriel. Funny how books have a way of transporting you ... Simply hold your breath, close your eyes. And count to ... let's say a million?"
"Well, look who got their soul back from Molag Bal! And is that Meridia I smell? You've been a busy little vestige! Don't worry about these levelheaded losers. No one can see me but you. You possess a special untapped talent for unhinged insanity!"
What do you want?"What does Sheogorath always want? I am the Mad Star! The Mad God! Ironically, I'm actually quite happy. But I'm neither here nor anywhere. All that matters at the moment is infusing some entertainment into this dreadfully dull bloodshed."
War isn't supposed to be entertaining."Not with that attitude, it isn't. I can teach you a trick that will swing the war in your alliance's favor while bringing a smile to the ever-changing face of your favorite Daedric Prince. I'm talking about me, just in case that wasn't clear."
I'm listening."I don't mind you mortals constantly murdering each other, but would it kill you to crack more skulls? I think I have just the thing."
What do you have in mind?"That, my mortal friend, is a dangerous and delicious inquiry. I want to give you the power of Volendrung. Don't be fooled by the funny name. Malacath's giant hammer is no laughing matter. Unless you're like me and you enjoy watching skulls explode."
You stole Malacath's hammer?"Of course not. I simply borrowed it for an indeterminate amount of time. And now you can borrow it from me to shower the battlefield with the brains of your enemies! I don't recommend literally showering in anyone's brains, by the way. Too slippery."
Where is Volendrung now?"Back in Cheesemonger's Hollow, with the rest of my madness! Would you like to visit? I can open a portal, and take us there right now. I don't know how often you travel by portal, but it really is quite nice."
All right. I'll visit Chessemonger's Hollow.
"That was as brain-bashingly entertaining as I'd hoped! I've always said that everything is better with exploding heads. You have to use this hammer in the Three-Banners War. I might finally be able to watch an entire battle without falling asleep."
But won't it eat my soul?"Souls are overrated. Just ask Cadwell. He doesn't have a soul, and he's happy as a decapitated clam. We both know you want the power. Sometimes getting what you want means giving up a little bit of your eternal soul. What do you say?"
Can I get rid of Volendrung after I pick it up?"You can't leave Malacath's enchanted murder hammer lying around for just anyone to pick up. You can always bring it back here to play with. Uncle Sheo's house, Uncle Sheo's rules. But if you pick up a greater artifact in Cyrodiil, you're committed."
I don't want to trade my soul for power."Ah! Confusion and guilt are my bread and butter! Madness is my cheese! Moral fortitude is my melon-chevre salad! If I wasn't immortal, I would be starving right now! We're done here! Get out! Happy head exploding!"
"Well, if it isn't my old friend Hunts-For-Books! Now don't look so glum, or the skeevers'll notice. Then they hit you up for some spare gold, a few shin bones, your best pair of cheese-filled slippers. Insufferable beasts! They can't hold a conversation."
What do you want?"Mayor Aulus is a curd in the soup. A real fly in the whey, don't you say? Made a mess of me gift, the kind from the wrong end of a dog. I tried to encourage him. Even brought him a hero to destroy! But he couldn't go through with it. Can you imagine?"
You're talking about me."I led you right here to make it all boring again. And what did he do to stop you? Nothing! There I stood in my best old-lady suit, and he said it was all my fault! Ah, he just needs motivation. What better than an escaped prisoner seeking vengeance?"
You want me to kill him?"Could you kill someone you love? I can't! Well, I have. But not Mayor Aulus, it would be too pedestrian. No, I want you to try killing him."
Why should I try to kill him?"I want him to reach deep down, below all the marmalade and crushing failures defining his life, to find a seed of confidence, and grow it into a tree of gumption he'll use to beat your brains to paste. But if not, any brain paste'll do. Even his."
I'll do this if you swear to leave Southpoint forever."Deal! Oh, and one more thing. Daraneth stays behind. If you bore me too much, I'll turn her into a goose, roast her, and feed her to you covered in fine Eidar glaze. The goose, I mean. It's a might bit chilly for my Eidar-pants."
Whatever you say.
"Oh, you can't seem to catch a break, can you? Chin up, just like the bridge! Adversity is the brother-in-law of propensity! As they say."
Why are you doing this?"Eh, a proper hero needs obstacle. Struggle. Repeated attempts at bodily harm! You're going to play the proper hero so Autie can shine! Or our deal is off. And if it's off, so is Daraneth's head. To Skyrim! In a field! With berries growing from her eyes!"
"I can never decide between Choice and Free Will. Which will triumph in the end? But why not settle the matter for me? Or you could yank a lever, but that's hardly fun for either of us."
You asked me to kill the mayor. Why are you playing these games?"I just told you! Choice and Free Will are subjects I hold quite dear. So, you could fight a very good friend of mine. Or you could pull another lever. You're[sic] [Do not change this to Your. This misspelled word is how it appears in-game.] Choice!"
I'll fight your friend."Wonderful! Just say the word and I'll bring him here."
Inside the Cathedral of the Golden Path, after defeating Mayor Aulus:
"And that's why you're my new favorite mortal. When you kill something wonderful, you keep it interesting. Fresh! Dare I say, jovial? Makes me wonder if I should stick around, see what wonderful things you'll kill next."
We had a deal."Think I don't remember, you daft little sprig? Call me a debt-hedger, will you? A deal-fondler? Ah, but you're forgiven. I've always said grudges are like a good cheese. Hold them inside for too long, and you're the one to suffer."
"It was me the whole time! Are you surprised? I was surprised."
I already knew you were the Skooma Cat. I thought you said you'd let Sizenza go if I took her place."Oh, right. So I did! But then I thought it'd be more fun to just keep you both. I was half right. You're a little too good as a plaything. Not fair if you're always winning!"
What's not fair is you cheating."That's the best part of playing games with lunatics, they're always changing the rules! You'd get it, if you just let me whack you on the noggin a few hundred times. No? Well, game's over. Off with you now!"
Don't be a sore loser."Look at you. Making demands. In my games. In my realm. All right, one last impossible challenge for you then. How's that for sporting? Say my name three times backwards."
My name three times backwards."You took the words right out of me mouth! Next you’ll be plucking my teeth for a new princely smile. Well, you can’t have them! I need them to bite Haskill. Take a bite out of my anchor instead, would ya?"
<Turn your back.> Sheogorath, Sheogorath, Sheogorath."Bah! Knew I should have gone with frontwards! They never expect that. Anyone who'd turn their back to a Daedric Prince is a wedge short of a wheel. Go on and take that one. You earned it. Looney."
Htarogoehs, Htarogoehs, Htarogoehs!"Now how'd you--that can't be--I don't ... normally that'd twist your tongue around to taste the inside of your ears! Or was it my tongue? All right, you win again. Go on and take your prize. Oh! Ear cheese."
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