Did a couple caricatures of Vladimir Nabokov and critic Lionel Trilling, recently featured in Uncle Eddie's Theory Corner.
Trilling's face (above) was drastically different depending on what angle he was facing the camera. His eyes were always kind of sunken and desperate, which I wish I had exaggerated a little more.
Nabokov's bean was round and squishy regardless of the angle, and his thick glasses often obscured his eyes from the camera, making him seem very withdrawn and mysterious. His manner of speech was also very reserved. I felt that there was a big sheet of glass preventing us from seeing Nabokov's entire personality too clearly, not just his eyes. If I were to draw him again I would choose a facial expression that better described that idea. It seems I figure out the best parts of a person after I've already finished my refined caricature of them.