Which daedric prince do you think sheogorath would have a hard time tricking/fooling? We know hircine lost to sheogorath in a duel from one of the books. The only prince that seems to ever beat sheogorath was azura(morrowind shrine quest).

Sanguine. But only by sinking to Sheogorathian methods.

There was no implication that the mission was success on Azura's side. Hell, one can mess up the mission just by walking in the house and later heard Azura rant on how she lost the bet to the Madgod.

I'd love to see Sheogorath and Clavicus Vile go at it in a battle of wits and subterfuge

Ditto.

Herma Mora maybe too.

Edit: Although I don't think Herma Mora would concern himself with such matters.

No one. "Out-thinking" someone requires that you force them to behave in a predictable pattern; Sheogorath is by nature unpredictable, he has no pattern, his very existence is a oddly shaped blemish in the universal scheme.

or date [censored].

That's Molag Bal.

This i think is the key. Sheogorath is by hus nature unthinking and unpredictable. Very rarely does he do anything that isn't on impulse of completely hokerrs. The only Daedra who has a possiblity of actually outwitting him, i think, would be Boethia, because thats pretty much what she does. Even then, i'd say it was 50/50 at best, because you can't always be sure Sheo won't go way off in left field. Like that thing with the flaming dogs...

I don't know, Sanguine's based off of Satyrs and Bacchus (who was attended by Satyrs), and they were pretty infamous for having six with anything that moved, willing or not. Molag Bal is all about "corrupt the pure, crush the righteous." His [censored]'s more about Christian notions of six and sixuality being tied with Original Sin and so forcibly corrupting you with Sin.

My submission (pun intended) to the pot would be Mephala, but their contests would never be declared. Mephala would just be spinning plots to trip him up for a centuries old insult.

Sheogorath would introduce Sanguine to Felldew then cut him off from it, showing the Prince of Hedonism the lingering madness that indulgence can bring.

Sheo by his very nature seems the least vulnerable to plots and suchlike of them all. I don't think it's necessarily that he couldn't be out-thought, but rather that out-thinking him wouldn't do any good.

I can only imagine an equivalent of the Azura and the Box experiment performed with Sheogorath. I don't think the Dwemer would've taken away anything valuable from the experience.

Hermaeus Mora is the only person I can imagine actually being able to predict Sheogorath's actions, other than Sheogorath himself (sometimes).

Honestly, I'd like a 16 Accords of Madness for every Daedric Prince. I imagine Hermaeus's one would end with Mora admitting that he knew that Sheogorath would end up on top somehow, but he simply wanted to see what he would do, ending with a moral that sometimes an extremely stupid and irrational action could accidentally lead to better consequences than a well-thought out one.

Me too,I really do, loved those tales.

You have to outmaneuver Sheogorath to help Azura win a bit in Morrowind.

Actually, we never find out who won the bet in the end. The player is only helping Azura because Sheogorath keeps cheating.

None of them, because The Mad God doesn't think. He acts, he is completely compulsive. Any 'plans' he cooks up aren't from careful consideration, they just come to him.

This topic really makes me want the rest of the 16 accords of madness,