This is a portrait of Reddit user petitoctopus, drawn for /r/DrawMeNSFW.
I put some limitations on myself doing this one. I watched a maddeningly talented artist on YouTube do a portrait of Gandalf and it got in my head. He threw down a gauntlet, challenging people to paint using a single, basic brush. He doesn’t even blend! Watching him, it was clear he wasn’t painting objects, like I tend to do, but painting shapes with light and shadow.
The reference picture is monochrome, which filled me with dread. I hadn’t made a decent monochrome painting before this. I failed a few times! Terrible, embarrassing things! But I tried a technique that worked for me. I made a palette on screen with 10 value steps, ranging from 5% to 95% gray, and then sampled from those color patches to build the figure.
I can’t take credit for the composition. The original photo is wonderful. But I do think there’s some good to the painted version. The crease on his thigh, the shadow cast from his penis, and the pointed finger on his left hand are all solid.