October 3, 2021
Although it's my face in the picture, I don't consider this a self-portrait, because I'm playing a character. The idea is that the guy in the picture is sort of a dweeb who just got his first job on Wall Street and is really self-satisfied about it.
He's not supposed to look cool—he's supposed to look like he thinks he looks cool.
This picture was fun to work on because I tried a new technique. Instead of painting directly in color, I started by painting in black and white ("grisaille").
Once the grisaille layer dried, I went over it fairly opaquely with color.[Note 1] It was a bit easier this way, even though I basically had to paint the face and hands twice.
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You might think you could put the color on transparently, but it's not so easy. If you put a transparent skin color over the entire face, that changes the values.
For example, white and black in the underpainting are supposed to remain white and black in the final colored picture. But if you put transparent flesh color over black and white, they become lighter and darker, respectively.
So to do it right, you either have to paint the wrong values in the underpainting and then apply a uniform transparent glaze, or else paint the proper values in the underpainting and then apply the color more opaquely with matching values.