It started with helping an acting friend out, Kevin Viol, because he'd gotten some crappy shots from some guy who bought a decent digital camera but was still using brown cloth backdrops from the 90s. (This was back when the people who used digital were somehow more legit or unique). Since then I've shot numerous other people's headshots and been a casting director for my own productions (normally fashion and lifestyle/commercial stills productions). I've also spoken with a few people who are also casting directors for respectable theatre organizations or cast for on camera projects.
The one thing that connects what everyone needs is the shot that really shows who you are and especially what they can do with your look/presence. That means probably not too far in one direction and not forgetting your important features. For example, one of my friends is a female actor but she's tall and strong. That matters on stage especially as it makes her more commanding. So her shot shows her whole body in proportion to her surroundings to give the viewer a sense of what she has to offer physically. Another friend is pretty much a blonde bombshell so she has a nice warm and slighly sultry picture. But both of these opposite type actors lean to the middle and play it slightly safe stylistically in the pictures. Subtlety is key here.
Recently Rj Dugan, a designer and art director for new media projects in Chicago wanted to do a professional portrait/headshot session that showed him as approachable, slightly edgy, current, and commanding. Things that showed good leadership qualities but still made him seem like a nice guy and someone you want to like. Professional yet creative.
When I shoot models for agencies, normally two routes are taken and done in varying degrees of intensity. If they are more commercial minded and do mostly catalog work, a nice warm and happy shoot is needed. A beauty shot may come but the makeup is never too strong to let the model's natural features shine. If the model does more runway and editorial work or needs to fill out that part of their book then that's the other direction. The makeup tends to get stronger and stronger as the shoot progresses as its easier to add than to take off.
Here's a bunch of images that I would consider successful heashots and or portraits that I've done over the years. That are everything for actors to musicians to personal art projects to my friends.
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