This painting goes back a few years. OK, it goes back over 20 years. Way back, when I was an apprentice Matte Painter, my mentor Mike Lloyd gave me a training assignment to get me ready for all the cityscape paintings we were going to be doing on Dick Tracy. The assignment: find a bunch of photographs of New York and Chicago, and make painting copies...one a day (8 hours max.)...black and white only. Of course, as this was matte painting training, it went without saying that the paintings needed to look like photos.
Up until this point, I'd never really dealt with architectural rendering on this level, and was pretty lost as to how to include so much detail in such a relatively short period of time. As I progressed from painting to painting however, I discovered that the secret wasn't in the detail you included...but in the detail you left out. The trick was to edit and indicate. Keep it loose, but accurate. Big brushes. Big brush strokes. Practice, practice, practice.
This went on for about a month and culminated in the painting below.