Tarhiel, creator of the Scroll of Icarian Flight, from Morrowind.

He was so close to greatness. Instead he's the laughingstock of every to-be Nerevarine.

Janus Hassildor, Count of Skingrad, TES4: Oblivion.

I love his questline. He and his wife were turned into vampires. While he embraced his vampiric side, his wife saw it as a waking nightmare, and fell into a coma after refusing to feed on peoples blood. Janus then seeks a cure for vampirism, enter the player, who does the legwork.

After gaining the cure, he administers it to his wife, ending her vampirism-induced coma. Waking long enough to say goodbye to her husband, she thanks him for letting her die as a human before embracing her end.

My post TES4 head-canon is that he uses his vampire immortality to form a small coven based out of Skingrad, which has flourished under his rule.

I always thought Caius Cosades in Morrowind is a wild character. He's your primary contact for a big portion of the main quest and has a high rank in the snobby Blades. Also, he's old, a drug addict and chills half-naked in his tiny house all day long.

I've only played Skyrim, and I really like M'aiq. He's really silly.

Divayth Fyr

He could be the dictator of Morrowind, but chooses to live in seclusion, fuck his clones, and study ways to become immortal without using necromancy.

Morrowinds M'Aiq.