tough ass pic! i guess for the weary aspect it's all about body posture, i mean u got the facial expression down. the whole background has a mid-west cowboy outlaw thingy theme going on.

He's supposed to look weary here, but I see how that can translate into old.

it's good but he looks kinda... old.

Oh, that trademark cigarette! It looks great (the drawing, not the cigarette XD)!