I spent a couple of hours today reviewing the properties of various erodible tip brushes in Photoshop. While I may never use them as a substitute to actual dry media such as charcoal and graphite, it's good to know that I can approximate something very similar if I tweak the settings just right.
I started with loose, broad strokes with one of my favorite "out of the box" bristle brushes while sticking to a grayscale palette. Eventually, a face started to emerge from the the blocks of value.
Next, I continued with a variation of small and large versions of the same brush, changing the opacity and the size along the way. For the more detailed areas around the mouth and eyes, i went with smaller strokes. I used large strokes to further model the larger areas and to differentiate the planes closest to and furthest from the imagined light source.
The phrase "My boots had no straps" came to mind in response to today being Independence Day and the popular idea that anyone with enough gumption can succeed through sheer will power and persistence. We're told of those who have "pulled themselves up by their own bootstraps" as a way of inspiring some and shaming other who fail due to a lack of hard work.
The prison number and stripes were added in this version on a separate layer as were the stars in an earlier iteration. The stripes and number suggested a hunched, figure in prison garb.
With a little more time, I think I might be able to take this into color and render it to a higher level of finish.