So I've been going through Joseph Todorovitch's portrait class on new masters academy and this is what I've made so far.
This one is a quick exercise for limiting tones to only 4 - 5 values.
This was the first time I did an ambient occlusion pass on a digital painting, so I wanted to see how it would turn out.
This second one I actually like a lot. Instead of line, I just used shapes instead
This third one I did get kind of impatient with it when I started drawing it. I probably started this over like four times. So I just took a hard edged brush and just did a quick drawing of it. I ended up with this stylized look.
This forth one was pretty difficult because the ref had flash on it so there isn't really clear shadow shapes. I made the silhouette with a hard edge brush and then I actually painted the whole thing with the soft edged brush on one layer to build it up slowly. I like the end result but not sure how I feel about that process just yet. It was difficult to wrangle in the facial features.