So why do I love this picture?
Perfect Exposure
Nothing is blown out. From foreground to background, the image contains all the detail the photographer intended to show. Look at the detail and contrast on those bricks, just lovely. While the subject is somewhat silhouetted, the exposure is just right so that the man in the hat isn't completely dark. On somewhat of a tangent note, I don't understand so-called photography purists, who rail against post-processing. Post-processing took place even in the film days. It just took much longer and happened in the darkroom. Photoshop actions are generally derived from old film developing processes. While I tend to generally agree with photography right-wingers on most issues, on this point, I must respectfully disagree.
Great Use of Natural Light
Through his genius choice of location in an open alley, the photographer introduces light from the back, sides, and even ever so gently from the front. Though the man is wearing a hat, there is even a little bit of hairlight coming from the sky. The subject is sitting in the perfect spot to be hit by all that muted light. I would guess that this photo was taken on a cloudy day, which essentially provided a huge softbox in the sky. A softbox that was channeled perfectly onto the subject to create a semi-silhouette.
Great Lines/Composition
While there is a lot going on in this photo, the lines in the image all bring the focus back to the subject. Strong powerful lines bring your eyes right back to the mysterious man in the hat (more on him later). I particularly love the line that perfectly intersects the bottom left corner. Did that happen by accident? I think not, artfully, thoughtfully, and masterfully executed. Since I've been going on tangents, I will veer off on another one. Art certainly does have a spontaneous element to it. However, photography definitely requires technical competence. Even beginners might stumble their way to a decent image once in a while, but knowing what you are doing will increase the percentage of keepers and good images. And I don't think "great" images happen purely by accident, though certain elements are definitely out of our control.
Mystery
This is always the X-factor for all great images. Where to begin? So who is the guy in the hat? Why does he have that particular hat on? His body language also seems to be saying something. And what is the deal with the cat? There is a story here, and much of it is left to the imagination. And why is it all taking place in a random alley in New York City? The great thing about this photograph is that it spurs many questions. And there are no real answers to those questions. And that, I believe is the diving board into a sea called art.
As my photography improves, I like to take an occasional look back at my old photographs. After my first burst of improvement, I couldn't stand looking at the products of my initial foray into photography. It all just looked like crap. I literally had to turn my eyes away, because it was so painful to look at images that I had once thought were good. I was ashamed. Now, I take a little more time to look at my old photos, because I think it is helpful to break down exactly why they suck. Yet, it does tickle me that I would still consider a few of my old photographs to be decent. The difference is that now I can actually tell you why I think they are alright, even though I was pretty much stumbling around in the dark.
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