Observing Generated Faces and Real Portraits
Thinking about my struggles with portrait drawing and observing AI-generated portrait drawings
I’ve always been terrible at portrait drawing, and have really never enjoyed drawing humans in general. When you grow up in the cesspool of humanity that I did and have to work your way out of that, I think that’s just one of the long-standing remnants that scars your desire to create anything that remotely resembles the things that caused so much harm.
You’re thinking - but there are so many drawings of people on Moon Child!
Yes. This year, I wanted to try to improve not just the technical skill of anatomy or proportions of drawing human faces or figures, but also the emotion and unspoken words that we often convey. Portrait drawings are, in my opinion, one of the hardest things to do because the subject is something we look at every single day. We are intimately aware of and can read other human faces, and we know immediately when something is uncanny.
It’s probably some scientific biological thing long-seeded in our monkey brains, since we needed to know when another homo sapien wanted to murder us. Then, I read this quote:
“Every portrait that is painted with feeling is a portrait of the artist, not of the sitter.” ― Oscar Wilde, The Picture of Dorian Gray
This made me think: What is it about facial expressions that really say so much? What does it say about me as I learn to do portrait drawings less based on logical structure and anatomy and more on how I personally interpret the emotions people express? Can AI-generated faces tell us anything? What does it say about AI?

I prompted Dall-E to generate an image of a sad looking girl facing forward. Ignoring the fact that the shading doesn’t look realistic at all, I actually don’t feel much emotion from this. How does this image make you feel?
Thinking about all of these questions, I started today’s drawings with a simple sketch study from life of random people. I especially like how the girl with the coffee came out.
There’s a lot that can be conveyed based on sketch lines as well, not just realistic portraits and more finished pieces.


I still have a long way to go with portraits and human figures, but I appreciate all of you coming along this journey with me. Please share any feedback you have on how I might improve my portrait efforts - there’s a lot of learning I still have to do.
Let me know your thoughts on what you think differs between how generated images make you feel versus hand-drawn art!
It's a great reminder that art is about rendering what we see. DALL-e is not seeing emotion as we feel it - your sketches show a human observer at the core. And I love the fluidity of your sketches here.
I like your portraits, especially your minimalist sketches.