I think that the second picture of the saxophone player has that "sense" of who he is that you're describing. I don't know why. Maybe it's the open suitcase where there is almost no money, the empty sidewalk, the way he is standing. I don't have the photographic language to describe it, but I think that you're harder on yourself than you need to be a lot of the time. You have an eye for pictures, and I think that you just need to up the consistency (consistancy?) when you're photographing strangers. But the second picture definitely has it, and you can fill in the blank for whatever "it" actually is.
The closer definitely has more of an impact on me - if it's a stranger and you're trying to show me how he's different, what makes him who he is, I want to be able to get tight right in there and really see what there is to see. And I think the beginning of the emotion connection is there in the first picture - but it feels more like I learned what he's about, not who he really is, if that makes any sense.
I like the first one. In the second he seems to be slightly off balance, or in motion, but it doesn't really seem to fit the scene. Also, in the first, there is a sign thats barely readable, though you can make out "caution" adding a sort of eerieness to it. Also in the first one you can see his face a bit better, and see that his eyes are closed, and depending on how you look at it he either looks sad or sorta mad. The depth of field of the second one also serves to distract from the subject, as the eye is drawn to the corner of the building and the architecture rather than the performer. This may be a good thing, depending on how you want to portay him, a man lost in a big city, a relic of older times etc.
The Millennium park shot is great. so is the first one because it defines the subject but also gives some atmosphere - the sign and the view down the street. the second picture has a subject but no definition, but then again, I know nothing about this.
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Anyway, well done.
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Also in the first one you can see his face a bit better, and see that his eyes are closed, and depending on how you look at it he either looks sad or sorta mad.
The depth of field of the second one also serves to distract from the subject, as the eye is drawn to the corner of the building and the architecture rather than the performer. This may be a good thing, depending on how you want to portay him, a man lost in a big city, a relic of older times etc.
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