Shot with my new super-sharp Carl Zeiss 50/2.8 lens (cost £1.70) which seems even sharper than the Canon 50/1.8 ... and then run through a softening filter : )
Aiming for something similar to the Jim Morrison 'crucifiction' look but keeping it a lot darker.
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i don't know anything about portraiture, so i'm using your image as a guinnea pig as to what i think i would or wouldn't do in this situation, as well as what i notice and get out of your image.
if the purpose of portraiture is to capture the essence of the individual, i believe you have succeeded. the lighting, pose, and composition all come together here. this really is an amazing image. good luck!