The first time I taught portrait painting classes was back in 2007, and again in 2009, at DotArt in Dorchester, Massachusetts. I led a class of a dozen young adults, high school sophomores through beginning college-aged kids. The day-long classes met every day for six weeks in the summer inside a church at Ashmont Station.
It was part of an initiative to keep kids off the streets, but it was pure fun for me. I had one very capable young assistant, a talented painter himself.
I taught the students how to use acrylic paints to build vitality and structure, as well as graphic line definitions, relying heavily on cadmium red hues, burnt siennas, and ultramarine blues.
That final project included striking Shakespearean cutouts, as the director had enlisted the help of a Shakespeare in the Park actor. It's long ago, and I was too young to know I needed to keep tabs on everyone's names. So, if you recognize this young Hamlet by my assistant, let me know...
It wasn't until the pandemic that I again taught portrait painting online to individual students seeking relief from that experience.
I saw how developing artists can experiment and succeed with their portraits. I learned how to help my students create passable, even excellent, portraits from minimal experience with portrait painting. Often, people work too much on eyes and eyebrows to the detriment of the whole, and ended up with cadmium-red characters from Faust. I learned how to help artists avoid that.
So, here are some of my tricks:
1 – 4. DO NOT SPEND MORE TIME ON THE EYES THAN ON THE REST
5. Never (almost) paint the whites of the eyes as more than middle-toned tan or blue or whatever your palette is. The only time light glints that much in an eye is if someone is feverish and/or psychotic. If you saw that in real life, you'd run.
6. Consider the planes of the face as though you are welding it with sheet metal. Look at the work of Tamara de Lempicka for a sense of this – in general, the Futurists know how to do this.
7. Try to limit your palette to one warm light, one warm medium, one cool medium color, and one warm dark that is still only as dark as a 75% gray
Otherwise, just be patient. Absolute mess can still resolve into the right person.
Below are several time lapse videos of my portrait paintings, to give a sense of color and attention strategies: