* Learn to draw the head before you worry about portraits. Get a skull — a plastic one from a medical supply house — and study the bones. Find a good anatomy reference. Also, get a copy of one Bridgman books.

* When you’re drawing the head, worry about getting the shape of the head right. Concentrate on big shapes — the cheek bone, the front and side planes of the forehead, and the eye socket. Make sure you make the cranial cavity big enough, and, if you have a 3/4 or profile view, make sure you don’t cut off the back of the head. If you get all that right, the features will usually take care of themselves.

* Don’t obsess over features. The eyes and mouth and such are psychologically important and people will often try to paint them first, without any regard for anything else about how they relate to the head. Instead, worry about features last.

* Draw/paint from life every chance you get. Even if you produce your final work from a photograph in the studio, you should do your initial studies from life. The eye can see so much more than the camera can see.

On to some of Robert’s excellent questions:

* For proportion, I make sure that the eye is about at the midpoint of the face. Other than that, I just pay close attention to what I see; other rules my jump into my head from time to time. There’s a good book, Drawing the Human Head by Burne Hogarth. It’s full of all sorts of tips on proportion and such. The drawings in the book aren’t especially to my liking, but the information is extremely useful.

* For flesh tones, any combination of red, yellow, and blue (or sometimes green) mixed to create a dull orange will work. Some combinations, though, are easier than others. Most of the time I use a lot of W/N Yellow Ochre or Raw Sienna, M. Graham Cadmium Red Light, and cobalt or cerulean blue. For yellows, I have used everything from W/N Cad. Yellow Pale to a raw umber. I haven’t had much luck with burnt umber. For reds, I have used a wide range — from quinacridone rose to winsor red to a cadmium scarlet. I could go on about this for a long time … let me know if you want more details.

Basically, I will mix a very pale wash with my red and yellow on the palette, which I use for the initial wash. Then, I charge in pure color — red, yellow, blue — onto the wet paper.

* Which pose works best for me? I don’t have any particular preference. Each type of pose has its pitfalls. With frontal views, there’s a tendency for everything to flatten out, so you will want to make sure the lighting is good. With a 3/4 view, you want to make sure that you don’t include too much of the side of the face that’s turned away from you. It’s very tempting to want to show all the features even when you can’t see them — e.g. — “I know that person has two eyes, so I’m going to draw both of them even if only one is visible.” With a profile view, there is a tendency to cut off the back of the head.

* How to handle hair? It’s important to think of it as a solid mass, even though that’s not how you would paint it. Keep the same, big concept of light and dark that you use for the rest of the head. After that, I usually get a little wild with the hair. I tend to do hair wet-in-wet.

* What size brush? I use the biggest brush I can handle without having to choke up on the ferrule. When I start choking up on the ferrule, I move to a smaller brush. Big sable rounds are my friends. I haven’t had much luck with flats when painting heads.

* Shadows? I’m still playing around a lot with shadows. A lot depends on the type of lighting. I usually take a heavier concentration the same pigment that I use for the light area and then dull it down some — and I don’t really have a formula for how I dull it down. I almost certainly use some of whatever my cool pigment is. Sometimes I am very fond of ultramarine violet — is darkens/dulls while still maintaining some warmth in the shadow; it also handles well in washes. Sometimes I like perylene maroon — oops, I think there was a discussion of that in another thread.

* Background color? Once again, I don’t have a set formula. It kind of depends on what I want to pull forward or force to recede. Also, I use the background to balance off other parts of the composition. Usually I try to merge part of the head with the background. Usually, my background is less saturated that the foreground. Sometimes I will put in a cool background, especially when the face wash is a little blotchy. Recently, I have started doing the background before I do the rest of the head, and that works well.

* Do I strive for extreme contrast or middle value? It really depends on the pose. I generally try to err on the side of extreme contrast. I like to leave some of the face as white paper, if I can. It tends to make things more dramatic. Also, sometimes I have trouble articulating narrow ranges of middle values.