Why is it so important that you have a great headshot? Because it is your key to the world.
Remember that casting directors don't use their imagination. They want to limit the chance of making a bad choice and so are much more likely to throw someone's headshot out than to call them in. The headshot and resume is the only thing they have to help them make that choice.
Your headshot is really the only thing besides a resume that will give the casting director a sense of your acting. Therefore they are expecting that what you will send them is going to look just like what they have imagined in their mind. If you send them something else, they will get rid of it.
One of my best suggestions is to get different looks. When people say different looks, this doesn't just mean different outfits or different expressions. It actually means different characters. Imagine: a guy playing the role of a rich businessman would look different in that role than when he is playing a gang member, right? Right.
So wouldn't that mean that he would use different headshots to get the different roles? He would submit a headshot of himself in a business suit for the first role, and maybe wearing a leather jacket and looking mean in the second role. These are important things to keep in mind.
When you are thinking about what to bring to your headshot session, think about what roles you want, and the roles you can play well.
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