Every ten years or so, I get this obsessive need to paint oil portraits.Most of them are not very good, since I have no technique whatsoever, but each of them fulfills a need to capture the essence of a friend or loved one on canvas.There’s no telling what will set me off.The last time, I was challenged to enter an art contest. I didn’t win, but a couple of people told me they liked my work. Praise whore that I am, I did at least five more canvasses in the next few months, only stopping after I painted a highly inaccurate portrait of my beautiful niece and nephew. She is too gorgeous for anyone of my limited ability to grasp properly, and he was at a highly unfortunate stage of adolescent development, which I managed to capture with unkind precision. Had I known he would become so bloody good looking in the next few years, I might have waited to paint him.Either way, my niece and nephew were highly offended, which deflated my sails and got me to put down the brushes.Until now.During that paint-a-thon, I did a portrait of myself and my husband with which I was never quite happy. It looked too painted; the colors weren’t blended well, and my lips looked really fake… too big, and frightfully purple. He looked good… sweet and soulful, with beautiful bright eyes… but I looked like a very aggressive clown.A few months ago, I happened to read somewhere that Rembrandt achieved the luminosity in his portraits by painting his skin tones with layer after layer of very thin paint. I wondered whether this would help my little painting… kind of like adding foundation to flawed skin, you know what I mean? So I grabbed the poor thing, and started giving it a weekly coat of glaze.In time, it grew to look more blended… but the lights and shadows started to disappear, and it became hard to distinguish any features if you stood more than a few feet away.I decided to get forceful and fix it.First, I went to YouTube and started watching portrait-painting tutorials.None of the featured painters do the same thing, and all of them do stuff I’d never heard of.A couple of them started their portraits doing something called “grisaille,” which is basically painting the entire picture in grayscale, and then putting color on top of that. This seemed to me like a colossal waste of time, until I realized it gave you the impetus to really concentrate on the placement of your darks and lights, and the relationship between the various shadows.Is that what people mean by “tone values?” For once, I wasn’t as interested in the vocabulary as in the substance of the message.One guy then covered his darkest shadows in a color that looked like Army Jeep green; since he was painting a young lady, I was afraid he would make her look like ten miles of bad road. Somehow, he covered this in some mixture of burnt umber, alizarin crimson, lead white and unicorn urine, and managed to create astonishingly lovely skin tones, which he blended with paper towels, q-tips, and his fingers, so they didn’t look “brushed on.”Then there was the woman who didn’t’ use “grisaille” (I like that word!), but who started out by painting the model’s hair blue and burgundy, with green highlights. She then painted all the flesh-colored parts of the face, leaving the eyes and mouth for last. “How can she do that?” I wondered. To me, the eyes and the mouth are the soul of the painting; I want to look at them first, and connect with the person who’s eventually going to emerge from the canvas.Whatever she did, it worked; the young lady she painted was stunning, and the picture that emerged was astonishingly realistic and beautiful.However, one thing she did was familiar… every now and then, when the painting looked fine and very close to finished, she would add a stroke of color, or try to correct a line, and totally muck up huge sections of the picture, if not the whole thing. Then she had to go back and correct her what she’d done; I was very glad to see that other people also screwed up their work, and had to go back and fix the result of their fussing.Eventually, I was so overwhelmed watching other people paint that I said, “F’ it. I need to get started.”I grabbed my painting, my little box of beginner’s oil paints, a bottle of turpentine, some linseed oil, brushes and paper towels, and the one tool that’s new to my repertoire: my cell phone.I needed that so I could dig deep deep deep inside my Facebook photo albums, where I found the original picture that I had tried to copy.Was Jeff’s face ever so full? Was my hair really that dark?And look! I had already started growing my second chin, but the turkey wattle hadn’t appeared yet. Very nice.One thing struck me immediately: the picture had some very prominent areas of extreme dark and extreme light; I really hadn’t done them justice.So, I went to town. I made the dark areas very dark, and the light areas very light.To blend the colors with everything around them, I took a big, soft, dry brush and swished across the picture with a very light touch; I believe Bob Ross used to call this “a hair and some air.”Then I attacked my mouth.I tried outlining it. That only made it look bigger.I looked at the original picture, and really stared at the shape of my lips.Damn! I always thought I had bow lips. Turns out they’re not that well defined.I rounded out the top lip, highlighted its outline, and rounded it out again. After three or four tries, I just grabbed the blender brush and rubbed off the definition of the shape.Ha!Blurry, it looked better.Then I went back to the original picture, and noticed something surprising.My tongue was visible under the top teeth.How could I have missed this the first time I painted the picture?I had to completely refashion my lips and my teeth, which led to a complete rerendering of my chin.I wondered whether I shouldn’t just chuck the entire damned picture.But I continued. I made sure to put lighter shadows on the lower lip than on the upper one, just like the people on television, and to tone down the teeth by making them duller than the brightest highlights. They’re a tad pink right now, but they don’t look bad. Let people think I never wiped off a lipstick smudge; it will add to the realism.When I was finished with myself, I looked over at Jeff, and noticed that one of the shadows under his eyes had disappeared. I put it back, and made a few other “corrections.” It wasn’t until I photographed the picture (and published it on Facebook, moron that I am) that I realized I’d made one half of his face too pink.I fixed that this morning.And now, I think I’m done.Except I’m not sure the skin tones shouldn’t be better blended.But I’m done.Really, I am. I am done.I even started a new portrait… my son and his boo are my next victims.Subjects.I have to decide whether to do a grisaille first, or just dive into color the way I usually do.I wish I weren’t so obsessed with portraits.I wish I could follow in the footsteps of Bob Ross, and paint happy little trees without eyes, or noses, or tongues, or teeth, or ears, or facial hair, or multiple chins… happy little trees who wouldn’t say, “Hey,.that doesn’t look like me!”But that would be too easy.