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Overall
Vision
Originality
Technique
Impact
I think the shading is very good, shows the distribution of light quite well, the creases in his clothing, his skin. Showing a lot of depth.
This has a very vice 1950s drama vibe, inspired by his appearance in Casablanca?
I think his ears look a tiny bit off, though Ears are tricky as heck to do. and the proportion of his eyes are a little big to me.
(There is an awesome tutorial by Mark Crilley of YouTube, who did some fantastic eye tutorial vids)
I like how you shaded the background to make the lighter tones pop more, I do it to. And I have an Issue I see here.
I think a smoother shading technique might make the background less scratchy. Sometimes I get tired when I get to that part, and my technique suffers for it.
All in all a really classy looking pic!