Simple, clean lines and basic, well-defined shapes go together in black and white. They are in the basic nature of being a cartoonist. You translate what you see into line drawings where a few simple lines become a complex and meaningful image.
My one-legged Batman is an exercise in foreshortening and trying to burst through the two-dimensional confines of the page to grab the viewer. I learned this trick from comic book artist Jim Lee.
His sidekick is rendered as a static portrait where the computer monitor in front of him lights up Robin’s intense and thoughtful face.
She was an excellent teacher and former nun… she was a mentor to me, taught me a lot about life and love and great beauty. How do you adequately portray the wisdom and the patience in those highly magnified eyes? I drew from memory only. She never considered herself beautiful. But she was. And it hurts not to be able to capture it correctly.
Not every portrait is literal. Sometimes you exaggerate facial characteristics and behavioral quirks are emphasized to create humor in the portrait.
When I was first married I did a double portrait of us as a knight and his lady fair. I know, I know… it is so sickeningly sweet that it punches me right in the diabetes. But, hey, it doesn’t really look like me anyway. It is more of a portrait of Porky Pig in glasses and hair.
There is an art to pen and ink that cuts right to the heart of who you are and who you want to be. Simple lines in black and white… there is no more incisive tool for putting my goofy old mind down on paper.
Catch a Falling Star 
Your illustration of your teacher from memory reminds me of how some of our most important and cherished people, fur babies, places, and events were not photographed enough or never at all. The recalls over the years become more hazy, and we try our best to manifest something concrete. And even though I love photography, there’s something extra in a portrait. Quote from Monster’s Ball: “I’ve always believed that a portrait captures a person far better than a photograph. It truly takes a human being to really see a human being.”
Thank you for that insight. She was a very important person.