Good lord, this seemed to take me forever, but I finally managed to draw Mairon (pre-LoTR Sauron for those who don't share my particular character fixations) and have it turn out somewhat like I picture him.
The smirk. I am so happy I got the smirk out of my head and onto paper.
I'm not sure why he wanted to sport vampire wings for this one. Actually, that's not true, he likes people to note that he's a skilled shapeshifter. He's dismissed every single other drawing I've done of him so far, so I'm exceedingly happy that this one worked like I wanted it to, except that I made his face too craggy.