Shot with diffuser on 580 EXII flash. Tried a bunch of different shots, but it was this one that I shot while doing some testing and fooling with lighting and setup earlier in the day. Wanted to go for edgy high ISO, but couldn't quite get it how I wanted it.
Opened JPG
Adjusted Curves
Converted to greyscale
USM
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I like the tones but I wonder if could have cropped it tighter to the face to increase the impact. Because he has dark hair and you've got a dark background you've ended up with a large area of empty darkness at the top. I also wonder if his mouth could do with a bit more expression - more of a snarl perhaps.