No question: Flashman, from the Flashman series by G.M. Frasier.
Mavra Chang or Nathan Brazil.
Vanth Dreadstar.
Josey Wales.
Porter
Henry Hill
Would The Dude count?
The Gypsy in Snatch (actually, all of Snatch. 
)
Lobo (the DC character, not the guy who sang “Me and You and a Dog Named Boo”)
Lestat
Xanatos from gargoyles
Ender from ender’s game… well sorta.
Dorian gray from what I rememebr. I never finished the book.
Gotta second this one. Elric of Melnibone it is.
Tho Marc “Blackie” DuQuesne also qualifies in my book.
Thomas Covenant is too angsty.
Corwin ain’t angsty enough.
Nathan Brazil was sorta whiney, and creeped me out in his native form.
Dammit, that was my pick. If Henry Hill counts, Michael Corleone has to as well.
Hey, you recover from leprosy and have the first feeling in your skin for the first time in years, and then rape some woman, all within a couple of hours, and see how angsty you are. Heh.
Thomas Covenent? Bah. Lightweight.
Angus Thermopyle. Now that’s an anti-hero.
The guy from AC-DC?
Moving this to Cafe Society.
Heh. He was too angsty even before the rape.
Miller, Angus Thermopyle is a good choice too!
Let us not forget Roger Manning, space cadets!
William Munny, outta Missouri.
“That’s right, I’ve killed women and children. I’ve killed everything that walks or crawls at one time or another…and I’m here to kill you, Little Bill, for what you done to Ned.”
The Man With no Name
the brothers from Boondock Saints
Solid snake
Tommy Vercetti
Freddy Krueger
Jason Voorhees
Scorpius (and Harvey 
)
Ash (Evil Dead trilogy)
The Saint.
And I mean the real Simon Templar, not the wishy washy Roger Moore character, or the appalling Val Kilmer interpretation. I’m talking about the Saint in the original books, the one that would murder the criminals he faced, but not until he had stolen their loot. Mack Bolan: he’s a wannabe. Frank Castle: he’s Johnny come lately. The Saint is the real king of the vigilantes.
Wolverine
Punisher
Sabretooth (Age of Apocolypse)
Preacher
Made me laugh!
I nominate those damned movie hobbits.
King Kong.
