I'll be honest up front: I'm not a head shot photographer by trade.
I've been learning more about what makes a good head shot ever since I started shooting them a few years ago. Every time I shoot a head shot session I learn new tricks to getting a fantastic image. I spent a few weeks casting for America's Got Talent back in 2007, and I watched Casting Directors toss away so many head shots for the silliest reasons. I'm not a Casting Director, but I've worked with actors in the past, and I've seen my fair share of head shots, good and bad. That being said, art is about breaking the rules sometimes....