San Diego painter David Darrow paints Reader writer

"A portrait is a painting with something a little wrong with the mouth"

The first time I chat with painter David Darrow on the telephone, I ask him how I might pose. I tell him that I like the highly individual stagings of Annie Leibovitz's photographs. Darrow tells me that mine will only be a 16"x20" painting from the chest up, so we won't have to worry too much about my pose. And as for how I should appear — sidelong glance, coy grin, gazing into the distance, serious and stylish — he'll probably be able to figure that out just by meeting me for a cup of coffee. I've already seen Darrow's paintings online, and I can tell that he's good with paint. His representations are realistic, and he handles light and color elegantly. But I can also tell from his online blog that he's witty and good with words. One of Darrow's blog entries that involves painting in the rain begins, "Weather or not... That is not a typo, it's a pun." Darrow, 50, is solidly built and stands an even 6 feet tall. He sports a goatee ("the facial hair of the fat man," he calls it), and his hair spills halfway down the sides of his round head in elaborate wisps. When he shows up at Starbucks for that coffee, Darrow is wearing the same outfit in which I'll see him again and again over the course of the next week: old jeans, a black Hawaiian shirt, and a wide-brimmed hat. As he'll tell me later, this is his painting outfit. I start our first conversation by asking Darrow a pointed question, a test of sorts. In this day and age of cameras and computers, why would anyone want to get a portrait painted? "I guess it's for the same reason that people don't just listen to CDs," Darrow answers thoughtfully. "They still go to concerts. They still want something that can only be done one time and can never be duplicated." A few days later, Darrow will refine his answer and tell me that the reason to have an artist paint you is because you like the work of that particular artist. I like this answer better. I've always wondered how Picasso might have seen me. Or Paul Klee. But Darrow's expertise isn't abstract stylizations like Picasso's or Klee's. Darrow's specialty is dead-on painterly representations. "I've painted hundreds of heads," Darrow says. "Maybe thousands. I've never really thought about how many." Darrow, who lives and paints in Oceanside, used to make a living drawing preliminary art for Hollywood movie posters. "I made better money back then," he jokes, perfectly seriously. "But now I still haven't figured out what my day job is. I paint, I do video editing, photography, webpage design, graphic design... Oh, and I do rock balancing. I get paid for that. It's not lucrative, but..." Rock balancing?

Darrow laughs. "Yes," he says, drolly. "Believe it or not. I balance rocks one on top of the other, and it looks very strange to someone who's never seen it before, because they are actually balanced. I can make a tower of little eight-inch boulders that's four or five feet high."

Why? Why would Darrow do that?

"I got into it as a hobby and a thing to do at the beach," he says.

And why would anyone pay to see rocks balanced?

"Because it's odd," he says. "It's a freak show. I occasionally get hired to do demonstrations for conventions and stuff like that."

Turns out you can see Darrow's rock-balancing feats online -- www.rockbalancer.com -- and they do look interesting.

So I infer that Darrow must have very steady hands.

"Yes," he says with sly intelligence. "Before I have coffee, yes."

Darrow tells me he went to art school at Art Center College of Design in Pasadena. "I wanted to be an illustrator," he says. "And I did that for about 16 years, before the illustration market dried up for me."

He has an exacting sense of his tastes and a light sense of humor, no matter how serious the subject. "I don't like to paint landscapes," Darrow says. "I'd rather be broke, and so far, that's working out great." He laughs. "I've reached that goal. A broke artist! But it would make my day dreary to paint landscapes. It's more interesting to me to paint a head."

All three of Darrow's children are also artistic. His oldest son, Drew, 24, is a graphically oriented artist who works in "shapes, colors, and textures, on found materials." His second son, Greyson, 20, is a sculptor, drawer, and painter whose work won Best in Show at the San Diego County Fair when he was in high school. And his daughter, Danielle, who is 15, has "fantastic natural ability," although Darrow doesn't know whether she wants to be a painter. "They've got the genetics for art," Darrow says. "I believe in that. Artistic talent, for the most part, is genetic. You either get it or you don't. Although I could teach anyone to paint better. I don't know if I could turn a nonartist into an artist, but I could definitely teach them to paint better."

Darrow has taught art at the college level in the past, and he's currently trying to organize his own workshop. "I need to find a space for a workshop," he says. "I know how to paint, and I know how to teach others how to paint. I know how to do that because I had to learn it all myself, little by little. It didn't just come to me naturally."

Darrow tells me that it will take two or three sittings to paint my portrait. I'll have to stay still (and be more or less quiet) for four or five hours each day. "Most people don't have the time to pose for their portraits," he says. "So I usually paint from photographs."

It's not really the same, is it, painting from photographs?

"Some people think that painting from photographs is cheating," Darrow answers. "But I don't. Back when I did illustration, everything was from photographs. I didn't have time to be a purist about anything. But the bottom line is, I can paint. I can draw. I know what to do with the color and values in shadows to make the painting look like it was painted from life. But it's a lot easier to paint from photographs. Instead of my having to translate from three dimensions into two, it's already translated into 2-D."

According to the contemporary philosopher Giorgio Agamben, the truth of the face isn't what it looks like but rather the simultaneous manifestation of all of the face's possible appearances. This is a beautiful idea, and I'm reminded of it when I ask Darrow which mood of mine he's going to capture in his painting. I ask him this because I imagine that all of my thoughts and feelings are going to be passing through my face in some way as I sit there, day after day, posing for him. "I guess what I'll paint will end up being an average of all of your moods," Darrow says.

And it occurs to me that this is the reason why painting from life is more truthful, if not also more realistic, than painting from a photograph. (And perhaps this is why owning a painting of myself might be better than having dozens and dozens of snapshots.) The painting will be an interpretation by a human being, yes, but instead of a momentary rendering of a single mood, it will be the living average of many moods. Painting, in general, which happens over time, may be more truthful than photography, which extrapolates its truth from an instant. In painting, the whole gradual process is still visible even in the final result.

On the first day of painting, bright and early, Darrow shows up at my house with enough equipment to paint a chapel ceiling. Watching him set up is like seeing an army prepare to storm a fortified beach.

Lights, paints, an easel, rags, cameras, tripods, wires, even a microphone. "I'm going to film this," he says, sounding as though he's seizing an opportunity. "Since you're going to have me talking about my process, I figure I might want to use this session for an instructional video."

Darrow has even set things up in such a way -- with his video camera on a tripod -- that I can watch him drawing and painting me on my own television set. The act of watching myself being rendered falls somewhere between fascinating and distracting. Throughout the next few days, I try not to turn my head too much to watch Darrow's progress.

He's decided to start off with a quick "color-sketch," as he calls it. "I'm going to give myself 20 minutes," Darrow tells me, after his setup is complete. "A quick little study on a gessoed plywood panel. It's just so I can loosen up a little bit and feel like an artist. It's another place to go mentally. And it'll get me thinking abstractly about the shapes I'm seeing. It's not so much about capturing who you are or anything like that. It's just going to be real fast and furious, and ugly. But don't take that remark personally. I'm making comparisons and measurements, and later when I'm painting you for real I'll be able to use what I learn now. This is about going over the territory once, for future benefit."

Good, in theory. But I keep distracting him, so Darrow lets the timer run, and the sketch lasts for more like an hour. "You've got to stop moving your mouth," he tells me, more than once. Finally he jokes, "I bet you hear that a lot."

And so I do...

But I have tons of questions to ask, and instead of filing them away, I keep on asking them.

Who are Darrow's clients? Who pays upwards of $1000 to have their portraits painted nowadays?

"I don't even want to speculate on that," Darrow begins. "I mean, who are you? That's a whole funny thing by itself. I never ask why people want portraits. But I can tell you that I've never had a woman approach me about a portrait of herself. I think portraits of women are bought by husbands or commissioned by boards of directors to immortalize them and say that they're important and should be remembered."

I mention how I've seen advertisements littering the Internet saying that I could have my portrait painted for as little as $100. So why would I want a $1000 portrait? Or a $15,000 portrait, for that matter?

"Well," Darrow says, painting away. "You could have a nice copy of a photograph made in paint, but I wouldn't want one. There's generally no quality there."

I notice that Darrow has put on glasses to paint.

"Ten years ago," he says, "when I turned 40, I gradually began to realize that I needed glasses. So I had special bifocals made so that I can look up and over at my subject and see well and then look back down at my canvas and see well as well. The lower part -- the reading part -- is set to a focal distance that equals my extended arm plus the length of a brush handle. Regular reading distance is too close." Then he reflects, "It sucks to need glasses, especially because I use my eyes for my livelihood. But at least I got to design my bifocals the way I needed them."

And what about that hat? Why is Darrow wearing a hat to paint?

"It's because I look dashing," he says, diverting into a characteristic joke. "The chicks dig it." And then he turns more serious. "Actually, I need to keep the glare of the overhead lights out of my eyes. I want light on my subject but not in my face."

Later on, Darrow mentions his jeans and his shirt. "I wear a black shirt when I paint because the paint's reflective, and I can't get the values right if there's light reflecting back at me." And "Every once in a while, by accident, I make myself a new pair of 'painting pants.' And these are my painting pants now because I accidentally got paint on them one time and I couldn't get it out, so they've just become that pair of pants I put on for painting because now I don't care what happens to them."

Darrow's favorite diversion while he paints is talk radio, but we're not listening to talk radio now. It's the weekend, and Darrow doesn't like the weekend radio talk shows. Besides, we're both chattering away and recording our painting conversation, and talk radio would get in the way.

I'm watching Darrow's demo painting come together on my television, and I wonder how he would describe his own style.

"Painterly," he says, with very little hesitation. "And by 'painterly' I mean, when you look at the painting, you know it's painted. You know that there was an artist involved with brushes. You're not thinking, 'Was this done on a computer?' Or, 'Is this a photograph?' You see the strokes -- the individual colors that make up the painting."

An hour's gone by, and it's not that the color sketch doesn't look anything like me. In fact, it looks a lot like me at 12 years old. Darrow agrees it's a poor likeness but declares it a successful study because he's gotten what he needed out of it. "At the very least, it's an interesting orchestration of brushstrokes," he says.

After making the demo painting, Darrow and I break for lunch. Over turkey sandwiches, we talk about his formative years as an artist.

"You know how some kids are just real disturbances in school, and you think it has something to do with their parenting?" Darrow asks me rhetorically. "Well, my parents were really good parents, but it's just true that I was a difficult student. I was a difficult kid. Once, for fun, because it was fun to watch, my friend and I threw a bunch of boulders in a neighbor's pool. We thought it was cool to watch these trailing clouds of dirt as all the boulders sunk to the bottom of the pool. We didn't do it to cause damage but because it looked cool. I was seven years old. I had no sense of the consequences."

Darrow takes a bite of his sandwich, chews, and thinks a moment. "So I was a lot of trouble in school, and I think it was just the 'shiny things syndrome.' You know, 'Ooh! There's something else that got my attention. Now I'm over there.' I was always distractible; I'd always get in trouble in school; every report card had 'visits with neighbors.' I was out of control. So finally, in fifth grade, we moved from Costa Mesa up to Playa del Rey, up near Los Angeles, and after a couple of weeks of my troublemaking, the teacher decided to put a chair outside the room and set me on it. And for the next three weeks, I was to check in and then walk out and sit in that chair, and that was where I'd sit for the remainder of the school day. So to entertain my active little mind, I would just draw. I had drawn before, here and there, when I was younger, but that was the first time where I drew for an extended period of time. And some of my fellow students thought it was cool that I could draw."

Then Darrow puts the moral on his story. He says, "In an environment, in a world, in an experience in which I felt no acceptance whatsoever, drawing brought me back into some kind of contact with others. My drawings were the only thing I had to fit back in."

After lunch, Darrow sits me back in my chair and dispenses a short lesson on posing.

"Okay, when I say, 'Move a little bit,' I mean like this," Darrow begins, and then he apparently -- to my eye, anyway -- doesn't move at all. It's funny, but I get the point. "And if I sound like I'm bawling you out, there's nothing you can do to anger me, so don't worry about it." He laughs. "I have to teach all my models these things."

Darrow wants me to move in "one-degree increments" because he's "looking for a good shadow shape" on me, and he wants to find an attitude that is definitely me.

I look straight at him, and he says, sagely, "I've come to know you as being slightly chin-down." And then, after a few slight shifts, apparently I've got it. "That's it, right there," Darrow says. "That's how you were sitting before when we were just talking. I think that's pretty much you. Is that comfortable?"

I'm sitting comfortably in my comfortable chair, with my hands in my lap and my shoulders relaxed. I'm looking straight ahead, across six or seven feet of space, to where Darrow is seated behind his easel, squinting back at me. My chin is slightly down. We're ready to begin.

"The first thing I'm going to do is draw you," Darrow says, without further ado. He's taken the plywood panel down from his easel and replaced it with the prepared 16- by 20-inch canvas. He's got a piece of bare, vine charcoal in his hand. He begins to concentrate and move his arm and shoulder, and I can hear the scratch of charcoal on canvas.

Darrow starts out with the rough shape and size of my head and then draws a line, and he tells me, "Across where my tear ducts fall." I can see this when I glance over to my television set. "The eyes are generally halfway between the top of the head and the bottom of the chin," Darrow says. "Most people think the eyes are higher than that, but they're really not."

He's teaching me the general rules from which slight deviations will create individual features on a particular person's face. "There's usually room for a third eye between a person's real eyes," for instance. And, "How long to make a nose is a challenge. The actual features of the nose -- the nostrils or shadows underneath -- are so far from the eyes that you have to make this leap from the eyes down to here somewhere and just put them in. That's dangerous, so you have to find other features and value changes in between to measure correctly and get it right."

As he draws, he looks back and forth from the canvas to my face. Sometimes he holds the charcoal up to make a measurement, to get accurate proportion. Every few seconds he looks directly at me and scrunches up his face.

"I squint when I paint," Darrow says, seemingly anticipating what I'm about to ask him next. "I squint a lot."

Why squint? Bad habit?

"When I squint way down," Darrow explains, "it reduces what I'm seeing to one level of light and one level of dark. It helps me see the bigger shapes better. Squinting takes anything that's remotely in shadow and makes it all dark. And it becomes a general shape. It helps reduce a face to its basic elements."

Then Darrow introduces an intriguing concept. "When you look at pictures in a yearbook," he says, "and you look at a group picture of the guys on the football team, their heads are no bigger than a lentil in the picture, but you still know who's who. You can see absolutely no details about them except for the shape of the shadows in their eye sockets, under their nose, and maybe their cheekbones, and that's all you've got to go on. But you still know who it is. It strikes up some recognition in your mind. And so a portrait doesn't have to have all the details for it to look like the person. What's important is getting those major shapes as accurate as possible. Even color doesn't matter nearly as much as those shapes. So my goal in the charcoal drawing is to get those shapes down accurately on canvas. I start with big shapes and then zero in on the smaller shapes."

After an hour or so, we decide to break for the day. Darrow says, either jokingly or ominously, "Get a good night's sleep. Tomorrow the real work starts."

But on the second day, Darrow shows up in good spirits and announces that he's thought about it, and he doesn't like his preliminary drawing, done the day before. He then proceeds to erase it. "It's just not right," he says flatly. "You can't do a good painting on top of a bad drawing. I think drawing is the most important part of painting."

Darrow then tries to apologize for having to more or less start over, but I won't hear it. I know that art is often a case of two steps forward, one step back. In fact, I know well enough that art is often one step forward and then two steps back. No worries taking some extra time with the process if that's what the process demands.

In fact, Darrow tells me that, for him, editing is a big part of the creative process.

"I think of painting as putting something down to start with and then correcting it to get it more accurate, then painting some more and correcting that, and so on until it's done," he says. "I feel like that's all I'm doing the whole time is correcting. I kind of assume the whole thing is wrong but close enough that I know what to work with."

Darrow's second charcoal drawing takes the better part of my second day of sitting for him. He's taking his time, and we're talking all the while. I'm glancing over to watch him draw me on my television set. The details of my face seem to be coming together much better this time.

When he finally has me get up to have a close look at the finished drawing, Darrow asks me what I think of it. I decide to be forthcoming. I tell him that the accuracy of the right eye (actually my own left eye) makes the other eye look unfinished, and I tell him that I think the mouth looks sad. He addresses the eye comment by saying that it will be more in shadow and will look a lot better once it's painted. But as for the mouth, Darrow doesn't think it looks sad at all. "I even see the hint of a casual smile," he says. And then he tells me, "At some point you're just going to have to accept that this is the way I see you."

True enough. But surely the way Darrow has seen some of his subjects has gotten him into trouble in the past? Has he ever painted someone a little too realistically? I remember the stories of how Napoleon demanded to appear taller in his portraits or how certain queens and kings wanted to be better looking than they actually were.

"I did a commissioned charcoal of a guy once," Darrow says. "He was a nice-looking guy, good facial structure, and he had these sunshine-induced crow's-feet around his eyes. He wasn't the same guy without the crow's-feet. They defined his smile. But he was very sensitive about them, so he ended up being unhappy with the portrait." Darrow had already sprayed the drawing with a fixative, so he couldn't have changed it even if he wanted to.

Darrow is usually paid for his portraits "half up front and the balance when you're satisfied." On his website, he states that it can be alarming to look at your portrait for the first time. Part of this, according to Darrow, is because we learn our own faces backwards. That is, we learn what we look like by looking at ourselves in mirrors. As a result, Darrow requires that his subjects live with their portraits for two weeks and have other people look at and comment on the portrait as well before he will agree to any changes. And in all his years as a portraitist, he's never had a painting returned for rework.

On this front, Darrow relates a quote he's read from John Singer Sargent: "He said, 'A portrait is a painting with something a little wrong with the mouth.' Because that's what happens. Someone sees their portrait, and it's startling, and they have a tendency to want to find something wrong with it."

I mention how I've noticed that I never like the sound of my own voice on a tape recorder.

"There's an unknown quantity in all art," Darrow begins, by way of answering me, "and that's people's perception. People just see things differently. I met somebody once who doesn't like oranges. Who doesn't like a slice of orange? So it's got to be just different tastes. And if it affects your tongue, it's got to affect your mind and your eyes. You know, we tend to agree on what 'blue' is, but who's to say that we all see blue the same way?" He pauses and looks up from his work. "That's why they call it 'color theory.' "

But in this case, Darrow's perception is very important. He is, after all, the creator of the work of art. I mention a famous quote of Oscar Wilde's: "Every portrait that is painted with feeling is a portrait of the artist, not of the sitter."

Darrow thinks a moment. "I've never heard that quote," he says. "But I've heard many people say over the years that they think an artist paints eyes like his own. Like, the only eyes I really know are mine, and no matter whose eyes I paint, they're going to come out looking like mine. But a skilled artist isn't going to do that. He's going to paint your eyes. I think it's inescapable for an artist to keep his personality out of the work. But I wouldn't say that I'm injecting anything physical into a portrait, as far as, 'Well, I think the face should look more like mine.' But I might agree that I make decisions about the shapes of my brushstrokes based on how I think they should look. And that is totally me going into the painting."

The shapes of his brushstrokes?

"I wouldn't claim that a good brushstroke makes a painting for a nonartist." Darrow searches for his words carefully. "But when I'm painting, I'm painting for other artists more than anything else. 'Girls dress for other girls,' they say. Well, I paint for other artists. I do care if people like my work, but I've got to like it, and what I really want is for another painter to look at my work and go, 'Hey, nice portrait.' And that usually comes down to brushstrokes."

So how does an artist consciously make brushstrokes?

"When I'm abstracting the shape of something," Darrow begins, "say, the shape of the highlight on your forehead, then I get a sense of how I'm going to make that with my brush. And then I load the brush with paint and think about how I want to drag it across the canvas. For instance, do I want to point the brush downward and drag it? Or do I want to lay it down and butter it on?"

Do brushstrokes have names?

"Not really," Darrow says. And then he makes another reference to one of the great portrait painters of all time, John Singer Sargent. "Brushstrokes don't really have names until they become associated with the artists who made them. Like, 'Oh, those look like Sargent brushstrokes.' But some artists do refer to their brushwork as calligraphy. It's like your own handwriting style. The way I do a brushstroke is going to be uniquely mine because of my own nervous system blended with my sensibilities and my energy behind it."

On the third day, it's finally time to paint.

Darrow starts out by arraying bright oily blobs of 13 different colors across his wooden palette. They go from white through yellows into reds and browns and blues. The colors bear names like alizarin, ochre, and sienna.

Oil paints themselves can be quite beautiful and interesting, regardless of what any artist does with them. Most pigments come from the earth, somehow: some are from plants, some are from chemical salts, some are oxidized materials. And some pigments are the result of burning, like carbon black, which is burnt bone, harkening back to the most ancient of art materials. And these natural pigments float around in the viscosity of all-natural linseed oil.

"When I start painting," Darrow says, "I'll begin with your eyes, and most probably with your right eye, because that's the eye I'm looking at when I look at you."

I sit back in my comfortable and, by now, all-too-familiar position. Every few moments, I glance over to my television set to catch the progress of my face coming into painterly focus.

For most of this third session, Darrow concentrates and paints in silence. Every so often, he notices something he wants to talk about, and he provides a running commentary.

"Edges are a very important part of painting," he says, at one point. "An edge is what you do where one value meets another value. And by 'value' I mean light versus dark. So there are four kinds of edges in art: hard, firm, soft, and lost. A hard edge is where one value butts up against another, like a dark hat brim against a white background. A firm edge is a highlight or shadow that is easy to see, like value changes of bony areas around the bridge of the nose or cheekbones: fairly abrupt but with a softening. Soft edges are more like transitions, like those across a forehead or down a round cheek or a stomach. And then you work all the way to lost edges, where no matter how long you look at them, you can't tell exactly where the edge is. Lost edges can make a painting a lot more interesting, because it leaves more to the imagination."

I do my best to keep quiet and pose and listen, but sometimes Darrow moves me to ask a question, based on either something he says or something he does.

When he mentions leaving things to the imagination, I ask him what he thinks about abstract art, which leaves so much to the imagination, versus realistic art, which does a lot of the work for the viewer.

"I don't relate to abstract art, in general," Darrow says. "I'm being abstract when I paint. I'm seeing abstract shapes, and I'm reproducing them. But for me the final result needs to be realistic. I can appreciate some abstract art because I can tell the difference between when somebody puts something into it, and when they're seeing what they can get away with, or when they're just pretending to be an artist, or they're just having a moment that involves some paint."

So that explains why Darrow paints realistically. But then, how does he choose his subject matter?

"I feel compelled to paint beauty," he says, succinctly. "I don't want to depict ugliness or death or scary stuff. And it's not because I think it would be necessarily wrong. It's just that I've been given a talent: I can paint beautiful things. And I think the world needs more beauty."

But isn't beauty inherent everywhere, seen differently by different beholders?

"Yes," Darrow answers. "I see where you're going with that. I paint everyday objects as well, and I see the beauty in those mundane things as well. But what I mean is more, well, for example, when I've taught some young artists before, most of what they draw on their own looks like demons and big, evil-looking things with scary eyes and blood and guts and devil horns. It's all distortions of what's beautiful. And I was talking to one of my classes one time about it, and I told them that they could never improve upon what God came up with. You can't improve on the human. You'll never draw anything that's more beautiful than the most beautiful humans. But it's really easy to draw something that's much uglier. So that's what I'm talking about. I don't want to draw distortions or depict sadness or fear. I don't want my work to bring out the evil in the imagination or the evil in the world. There are plenty of people doing that. But there are better uses for God-given talent."

We're both deeply interested in the conversation, but we have to remain slightly disinterested at the same time. Darrow has to be slightly disinterested in our conversation because he's trying to paint and I'm distracting him. And I have to be slightly disinterested because Darrow is trying to paint and I'm distracting him.

At the end of the third day, there I am, almost. You can tell the painting is me and no one else. The shapes are all there, and the basic outlay of color is already in place. "I'll be able to finish the coloring from here using the photographs we took," Darrow says.

And so my time of posing is over. Darrow packs up his army's worth of stuff and leaves. My house is back to normal. And my head is filled with thoughts of art.

I wait a few days, and Darrow calls to tell me that the portrait is nearly finished. We arrange to meet over coffee the following afternoon so I can have a look. He reminds me that I'll probably find the image a little disturbing at first and that I should live with it for a while and get as many opinions as possible before I form my own final opinion about it.

By now, I think I'm looking forward to owning the portrait. I'm not sure that I'll be comfortable living with it just yet, but maybe I'll keep it in my closet for a few years and drag it out now and again to see how I may have changed my estimation of it. Who knows? Maybe this portrait will be like the one in the Oscar Wilde novel The Picture of Dorian Gray. The one that was "more a portrait of the painter than of the subject." Maybe my portrait will get old for me, and I'll stay the same age.

But while I still have Darrow on the phone, before I've seen the painting, I ask him what he's had to do with it to finish it.

"Since I saw you last," he begins, "I've done something that I think is often done, except by the painters who have people sit for them. I've taken the portrait and compared it to a printed-out photograph, and I made adjustments where I'd gotten shapes or proportions wrong, and basically I adjusted it and refined it."

Now Darrow tells me something that just about blows me away.

"At one point," he says, "I felt like something was way, way off. And I used a fairly standard trick to be able to see things more abstractly so I could get the proportions back correctly. And I discovered that I'd made your head too wide at the top, and one of your ears was too big. And these are decisions that I was only able to see once I could stop seeing your face. So what I did was, I flipped the photograph upside down, and I flipped the painting upside down, and that's when all the errors became apparent. Because I was no longer painting a face. I was looking at shapes. And so I painted out the mistakes with them both upside down, and I actually worked that way for about four hours. And when I flipped the painting back over, it looked much more like you."

But that can work only when Darrow is painting from a photograph. What will he do in a live sitting situation? He can't flip his subject upside down.

"No," Darrow answers. "Of course not. The closest you could come to that is, a lot of artists in live sittings have a full-sized mirror behind them at an angle, so all they have to do is glance to the side, and then they can see their subject in reverse, which has a similar effect."

So Darrow painted me upside down for a while. Then what did he do next?

"Next," he says, "I just filled in the background. I've tried to keep the background fairly abstract, but I'm representing the chair and your jacket and the bookcase behind you. But I'm not doing them in very much detail. It helps the whole painting look like it was done very fast while still looking competent."

And why does Darrow want a painting that looks as if it was painted quickly?

"This may be too much of a secret," he says. "But I do sometimes work over areas to make them look like they were done with a couple of really good, really fast brushstrokes. A little more devil-may-care, when in fact it was a lot more planned."

Then he concludes, "You don't want to take away the illusion that this stuff just falls off your brush onto the canvas and looks great. I think that's what people pay for. A little bit of a magician's secret. But I can say in some areas of this painting, I've spent 15 or 20 minutes trying to make it look like it was three brushstrokes that solved that edge."

The next day, it turns out that I don't have time for coffee, so Darrow and I meet in a parking lot in La Jolla so that he can give me the painting. In some way, it seems fitting that we meet in a parking lot behind a building, because what we're doing does feel a little illicit. It's kind of embarrassing. I'm the only person I know who has a portrait. Before I even look at it, I don't want anyone to see it.

But then I look at it, and my heart jumps. Immediately, I find a dozen things that I don't like: I seem heavy, the brushstrokes are too visible in some spots, why does my eye look like that?, etc., etc. Darrow reiterates to me that I have to live with it for a while. "Also, it wasn't meant to be looked at in full afternoon sunlight," he says. "Take it indoors. Get some other opinions."

And so I do.

Most of my friends make fun of it, as I expected they would. My boss says he likes the painting better than he likes me because the painting keeps its mouth shut. Someone else tells me it makes me look like Richard Gere. Another friend tells me it makes me look more gentle than I am. But in the end, everyone seems to like it. They all think it's beautifully done and more or less completely accurate.

But I don't. In a word, the painting makes me uncomfortable.

I try to articulate my discomfort in an e-mail to my parents. I write, "So I keep looking at the painting, and every time, I think something different. Like, the eyes aren't right, or, the nose is just wrong, or something else, or something else. In a certain light, and at a certain distance, it does look perfect. But if I look too long, or too close, or if the light's too bright, then I notice things and notice things. It's a lot like when I look at myself in a mirror for more than a moment. I start to fixate on blemishes and whatnot and I begin to lose sight of the whole."

But then I wake up the next day, and I have new opinions. And the next day, I have new opinions still. It becomes evident to me that I'm overthinking it. I put the painting in my closet and busy myself with other matters.

Ten days have passed, and I have my portrait propped on top of one of my bookcases in my living room, in full view. I haven't hung it permanently yet, and I haven't framed it, but I have to say that I wouldn't change a single thing about it. I've come to the conclusion that I wouldn't change anything, because I can't come to any conclusions. I still think something different every time I look at it. I have no internal critical consensus whatsoever. Sometimes the eyes look wrong, and sometimes they look just right. Sometimes the lighting bothers me, and sometimes it seems sublime. Therefore, in the end, I must decide that the painting is good.

My mother sums it up in two beautiful, simple sentences in one of her e-mails. She writes, "So, the artist captured your elusiveness. It must be a terrific portrait."

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