The result of a doodle that went out of control, originally for giving Dravven a new hairstyle. For something I hadn't planned out, this worked out surprisingly well. He was going to be holding the Blade of Woe or something, but I already have a picture of him doing that so I ended up drawing a gash. Then I decided it wasn't enough blood, and realized that the gash could be quite easily converted to a Daedric S.
Anyway, warning for big wall of text full of headcanon things no one but me needs to care about.
I figure at some point after the whole Shivering Isles thing, Sithis realized he was short one Listener and the Dark Brotherhood is losing power, so he went to the Madgod to get Dravven back. After some pestering, Sheogorath agreed and separated the part of him that was mostly comprised of the Hero of Kvatch and tossed it back into Nirn, conveniently during the time period of Skyrim so I can have Garik and Dravven go on deranged Dark Brotherhood adventures together. What fun! As a result of the separation, Dravven is even more unstable and neurotic than he had been in life and his love for the Brotherhood borders on fanaticism, but Sithis is okay with that as long as he can still function well enough to murder people.
Sheogorath wants to make a note that Dravven is still a part of him and is only to be lent to Sithis, so he carved a Daedric Seht into him, apparently failing to notice that Sithis also starts with an S...
And no, Dravven is not allowed to be happy because I delight in making him miserable.