[Having seen over several hundred headshots myself, as a director looking for actors, I agree with the below.—Dankwa Brooks]
Make sure that character comes alive in the elements of your headshot. A great photographer acts as a translator, giving visibility to information. Every element of the photo should combine to create the impact and statement of the shot. Let’s start with wardrobe. Use what you wear to help define your type. Your headshot wardrobe shouldn’t feel like a costume, it should be what you normally wear, but tailored to the way it frames your face, works with the palette of the shot, and represents your type. Romantic leads should wear clothes that are attractive, like you might wear out on a date. Bad guys wear dark, that’s just the way it is. Working class characters wear denim or flannel. It’s a language and your photographer should be able to make suggestions and help you prepare.
Once you have the wardrobe, work on expression. As dumb as it sounds, stand in front of a mirror and try some different expressions. Find what looks good on your face, practice, watch the evolution of an expression, find at what point of energy it looks best. Models do this all of the time. Your face is an instrument, learn to play it. Again, your photographer should be able to recognize the expressions that make you look your best and make your character come alive and help capture them at their peak. Big tip – you know the look that you give yourself in the mirror before you go out on the town and you are kind of flirting with yourself? Definitely try to reproduce that look in your session. Years of looking at your face has taught you the combination of minute muscle contractions that create your most attractive face. If you don’t know what I’m talking about, spend more time in front of the mirror. And watch the James Franco section of this amazing New York Times video called 14 Actors Acting. He and it are awesome!
Another element to play with in your session is body language. The physical attitude you present yourself in helps tell the viewer how to perceive you. Again, to the mirror, try looking powerful; what does your body want to do? Try nonchalance; how would you pose? These are all building blocks, and great photographers use them like brush strokes.
Joe Henson is a headshot photographer located in New York City. He also shoots frequently in Boston, Washington DC, various colleges and universities, and at large. You can see his work at http://www.joehenson.com.