Made this pirate assassin guy. What do you guys think?
7/10
He needs more of a scowl. Show what a fearsome pirate-assassin you are!

9/10 I think some facial hair would set it off. :)
Splendid. A more complete background might be nice, since context always seems really helpful with these sorts of things, but then again I might only be saying that because there's a background at ALL. Would that be less of a distraction if there weren't anything around him? I don't know.