very good portrait, the only drawback I see is the dull background, for this kind of portrait, a "real life" (even severely blurred) b/g would work a lot better, IMO.
Black and white - surely this cries out for a black and white treatment? You'd lose the rather toneless background colour (no loss), the bland colours of his clothes (no loss), and emphasise the the textures of his head, the white of his beard, and the highlight of that tear (all win).
Great detail, texture but kinda missing the story. I would suggest including something in the frame that would help to put the situation in context. For example, if this fellow is down on his luck and homeless, it might help tell the story if you could see a bit of worn/tattered clothing. This is a great shot, but it leaves you wondering why he is crying. I would also suggest cropping a bit of the dead space at the top.
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