I was kidding myself when I decided that the hat blending into the background did not bother me. The story is a little sad and funny. This was shot in the theater during intermission during dress rehearsal. Being the last day of rehearsal before the show; I had all of two minutes to get four headshots and three scenes. I brought two lights, but got all confused when I couldn't bounce one off the ceiling. To further complicate maters I felt the need to make the light hot to compensate.
On the bright side; actors are easy to shoot. I will now separate the head from the background with a light.