The cityscape painter needs a thicker skin than other kinds of painters. It's very rare, for example, for someone who is sensitively painting a delicately composed still life to be sideswiped by a truck. Likewise, it's an unusually difficult portrait session that ends in a fistfight. But violence of this type can often befall even the most peace-loving of cityscape painters. The city, after all, is an abrasive sort of place, and a cityscape painter needs nerves of steel, sharp reflexes, diehard determination, and the consistent ability to find, no matter how complex and difficult the urban terrain, a bathroom.

Physical injury and bathroom inaccessibility, though, aren't the only threats to successful cityscape painting. There's one other hazard out there that can be far more disruptive, something that can sabotage even the most promising start—we're talking about every cityscape painter's worst fear—the talker. People love to talk to a painter. Scientists don't yet know why, but no matter how little you want interaction, if you're standing, brush in hand, in front of an easel, the message received is "Let's chat." Other city dwellers who work in the streets don't stir up this conversational yearning—bricklayers, street sweep-ers, drug dealers—are all able to ply their trade in peace and quiet, but start putting paint on a canvas, and you might as well drag out a couple of arm chairs and a coffee table. Popular topics include, "My uncle used to paint," "I can't draw a straight line," and, always least appealing, "What's that a picture of?"

Over the years, I've heard a lot of theories about how best to stop this chattering. Many like the "I no speak English" approach; the large, ear engulfing walk-man has its fans; but in my opinion there's no more effective chat eradication device than the prominent placement of tin cup with some change in it. I have found that the Donations Accepted receptacle will almost always disperse with the crowds.

If you've tried these approaches, though, and still find someone attached to your painting process like a dog to a mail-man, then there is another tactic, one that I first learned from the legendary cityscape painter Anthony Springer. It's what we might call the absorb-the-blow approach. I should say, first of all, that if there were a cityscape painter Hall of Fame, Tony Springer would have his own wing. This was a man who lived to paint cityscapes. Almost everyday of the year would find him out on the street somewhere in lower Manhattan, painting away. Weather had no effect on him. I remember once struggling through a blizzard in Greenwich Village, leaning almost horizontally into the freezing wind, rounding a corner and coming upon Tony peacefully dabbing at his canvas. His secret was a Zen-like approach to problems. He didn't fight them; he didn't wish them away. He absorbed them. And that was how he handled unsolicited conversation. He just joined in. If the scene got chatty, he chatted. And he didn't stop there. This was a man so relaxed about ego that he would absorb criticism just as casually as praise. He was so easygoing that he once told me, "If someone says that the tree in my painting should be bigger...I just make it bigger." That's a more advanced form of Zen than I, at least, can even aspire to (Zen monks have been known to damage themselves trying to get to this level), but I do think the best way to enjoy the cityscape scene is to yield to what's happening.

Before worrying too much about how to handle your public, of course, you have to figure out what it is you're going to paint. Hours can go by while you hunt for the perfect site. What's difficult is that you're really needing to find two sites: a. what you're going to paint, and b. where you're going to stand while painting it. A. is hard enough—you want something with interesting lighting, good color, human interest—but b. can be almost impossible. To stand a little out of the way of the milling throngs, to keep direct sun off your canvas, to have a unimpeded view of the subject—all these can make you throw up your hands and head back to the still lifes. After an hour of lugging around your French easel, you may start settling for subjects that might be better left unpainted. Your standards may start to drop. Thoughts like "That parking garage doesn't look so bad" are warning signs.

And this brings us to an issue that's a thorny one for every cityscape painter— modern architecture. As we all know, shortly after the end of World War II, one influential architect said to another influential architect: "I'll bet I can design an uglier building than you can." Ever since, members of this profession have been trying to outdo each other in the ugly building department. Early on, it was clear that the stark box was the area of heaviest com-petition and a lot of energy went into making the stark box starker. Soon the land was filled with domino-like structures that generated all sorts of aesthetic theories and theoretical justifications, but, despite the rhetoric, when they were depicted in oil painting, they tended to look, unfortunately, awful. The sensitive cityscape painter, if that's not an oxy-moron, will avoid them like last week's lasagna.

What's wanted is buildings with personality. Buildings with humanity. Buildings with cornices. That's what an artist wants to paint. Weathered paint, softened edges, broken pediments, structural elements that tell the story of usage. Buildings that have been through some stuff. The fact that many of these structures are decaying and in danger of falling down only makes the artist's job more enjoyable, unless, of course, they actually fall down on the artist. Character is the key. Whether in architecture, pots, or faces, how much character the subject has determines how much will show up in the painting.

If your picture is a transcendent masterpiece, being out in public is no problem. We tend not to mind showing off glorious skills in front of an admiring throng. But, unfortunately, not all city-scapes turn out to be masterpieces. Tragically, every now and then, a picture nosedives. Then the artist has to come to grips with that recurring companion to every cityscape painter, that unsought but frequent tag along to the urban artist: public humiliation. There's no question about it; it's embarrassing to be standing in front of a horrible looking picture when it's clear that you're the unfortunate person who painted it. We generally want to avoid failure, but the cityscape painter has to be brave enough to risk irredeemable failure right in the middle of a teeming city. You have to be willing to disgrace yourself in front of a whole horde of passersby. Passersby who don't know or care that you can usually do better. Passersby who are indifferent to earlier successes. When you're standing in front of your horrible failure, as far as they're concerned, that's what you do. Fail. Horribly. Somehow the cityscape painter has to learn not to shun but to embrace this occasional problem. The artist needs to be willing to proclaim to the world: "This picture stinks and I painted it" (inwardly that is, we don't want you to be carted off), and, with this kind of clear, focused shamelessness, he or she may be able to shed a lot of public opinion anxieties.

What are the rewards of cityscape painting? What lessons can be learned from this gritty, rigorous activity? In a word, lots. For instance, pictorial thinking: Cityscape painting heightens one's sense of what makes a picture and what doesn't. What are the rewards of cityscape painting? What lessons can be learned from this gritty, rigorous activity? In a word, lots. For instance, pictorial thinking: Cityscape painting heightens one's sense of what makes a picture and what doesn't. Since there are so many details out there in the urban landscape—cars, streetlights, windows, etc.—you're forced to figure out what's relevant for your painting. You get good at prioritizing reality and reducing complexity to simple design ideas. Speed: The pace of the city doesn't allow for a lot of aesthetic agonizing. No time for extended pondering or sullen pacing. Schedule those for when you get home. Out on the street you learn to put it down and move on. Flexibility: Cityscape painting teaches you to roll with the punches (sometimes literally). A weather shift may force you to turn that gloomy overcast scene you started into a celebration of dappled light. Or a picture that you were going to call The Store across the Street may eventually have to be reconceived as The Delivery Truck That Wouldn't Move.

These pitfalls and hazards and rewards we've been describing constitute some of the complexities of cityscape painting. It's not an activity to be pursued indifferently; it's not an endeavor for the faint of heart, but I firmly believe that if you grit your teeth, and make the effort, and don't yield to doubt, and keep your eye on the ball, you just might end up with something that will make people look up and say: "What's that a picture of?"