I have been working on this for a while now. I would love some feedback!
http://linus108nicole.deviantart.com/art/Captain-Kirk-175905803?q=&qo
http://linus108nicole.deviantart.com/art/Captain-Kirk-175905803?q=&qo
It looks almost like a photo I've seen of him
Truly beautiful work, Nicole. Your understanding of shading values here is perfect. In other words, the darks are exactly where you want darks to be, the parts that draw your attention first. Although the hair is dark, it's textured (beautifully!) rather than a giant patch of territory like on a map. So the viewer's eyes are drawn to the same part of the face as if the subject were a photograph: the eyes.
That's something a number of artists don't understand: You don't have to be a realist to adhere by the rule that you direct your viewer's attention the same way the real subject would. You want a portrait to draw attention realistically, even if it's stylized (and in this case, you're much more realistic than stylized anyway).
Suggestions for those future portraits you say are coming down the road: True, you're drawing exactly what you see, which is exactly what you should do. But good drawing (especially monochrome) is like good sculpting, which means you should try to see the face in 3D even when your subject is 2D. As an exercise: Hold your own thumb in front of your face, so that it blocks the lower right quadrant of your drawing (Shatner's left jaw). Let your mind fill in the rest of his face from the three-quarters that remain visible. Hold that image in your mind, then after a few minutes, remove your thumb. You'll see that his jaw appears to slip down and in from where the mind says it should be. That's not a problem of actual positioning, but rather of shading. His cheek runs smack into the white nothingness of the background, so the mind doesn't place it quite right on the Z-axis, if you will. There should be some backlighting that's not showing up here, which gives that portion of the cheek a 2D look.
This will get to be a challenge when you're drawing McCoy. De Kelley's face is distinguished not by the eyes or the nose or any one particular feature, but by its shape. If you get his shape right, you'll have his face; if you see it in 2D, it'll come out flat and pudgy.
Two more suggestions: 1) Let yourself do something with the background, even if it's just ethereal shading or fuzz. That will let the bright spots on the face (like the bridge of the nose) pop further forward, and that will help you properly shade those quirky cheek areas. 2) Don't worry about the detail in places that don't need the viewer's attention, like the folds of the shirt in the lower right corner. All you need is something that suggests the proper shape of shoulders -- too much detail, and your subject could end up looking like Vina's "true appearance," if you'll recall the reference.
Once you're done with Nimoy and Kelley, if you want a real challenge of a face, try Scott Bakula. I was absolutely shocked by how tricky he was to capture; it took me six or seven tries to come even close.
-DF "Men of a Certain Age" Scott
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