Yeah, he doesn't quite have a distinguishing feature to caricature so there's no wiggle room where you can get away with overemphasizing a certain feature while missing some other detail. He's too symmetrical and "average" so I think my brain reverts to those generic how-to-draw-a-face proportions which seem like they should be right for him, but then I end up with a generic face and not *him*.
Ackles