~and an outrageously funny one...

I thought of Sir Reginald the Snotty, Myron the Merciless, and a few others. They seemed to be lacking something.

I seriously considered Ben Dover - but it's not original, there was a Bandit by that name in Railroad Tycoon II.

This is a char that will be played at Legendary level, full bore, and I'm going to have him rip into the town guards of every hold in Skyrim just to see if he can do it! It will be a special exploration of a completely BLACK char, that I may even turn into a Vampire eventually and try to tear apart the Dawnguard with.

Suggestions?

Don Quixote

Do it.

William Wharton from the Green Mile. Otherwise known as Wild Bill, Billy the Kid, and Will Bonney.

I might add some other names later.

An Imperial?

Hurtus Apatheaus

Cronabus Hunstly

-Lester the Molester Cockenschtuff

-dike Sledge

-Haywood Jablowme

-Jack Mehoff

I'm bad with lore.

Those all sound like porm names.

Nazeem the wretched.

Dagoth Ur. Is a total anti hero

Nevermind, what will be the race of your character?

If Dunmer, any dunmer name will fit, in UESP is a full list of names

Gerald Terrant, good anti-hero, not funny though

Were the character female, Dalhia Mordant

I'm not good at funny names. Google a name generator or just type in "name male evil" you'll come up with some.

Bob.

Brutus

Ben Dover hasn't been original for a good few hundred years now

Tordelbane is a good one I've literally just invented taken a shine to, it might be up your street.

Artyem

(Art Yam)

Marcus MacFallange.

Biggus dikeus!

biggus dikeus

I third this.