Your Headshot: The Shoot, The Prints
Your headshot should look identical to you. Memorize that. Sadly, too many actors get called in based on their headshot and come in looking totally different. These are casting directors and producers calling you in, folks! Don't bait and switch on them! A common complaint is that actors waste their time by sending in photos that make them seem right for a part that clearly they're not right for when they show up in person. This wastes your time, too, and could even harm your chances at future meetings with that person. So get a shot that's an accurate, current representation of you. How do you look when you have half an hour to get to an audition? That's how you should look in your picture, 'cause that's what they're going to get when you show up.
Make sure you get enough sleep the night before you shoot your headshots, and don't make any major plans before your appointment. This day should be all about having a great shoot. When considering what shots you need, you'll have chosen a variety of outfits to bring to your shoot, so that you can emphasize certain aspects of you, such as the work-a-day you and the casual, kicky you. Keep it simple. Your photographer can help you choose the right clothes.
You'll also determine how many shots of each look you want, including tight headshots, and possibly ¾ shots. Headshots are great because they give the viewer of your photo a good, close look at your face and eyes, but the ¾ shot helps determine your overall look. At the time of your shoot, the photographer will help you determine which type of shot is currently being used the most. When in doubt, get some of each. You can always decide which to blow up later. You should focus on having at least one solid theatrical headshot for more dramatic roles, and a good smiley shot for lighter stuff, such as comedies and commercials. Casting directors want to know if your teeth are suitable for a television audience, and a smile is essential in conveying the warmth and humor that make this shot work. This is probably going to be the hardest shot to get with a photographer, as you have to be very comfortable and able to capture a natural, spontaneous moment. Additionally, you will have probably also discussed where you're shooting with your photographer. I recommend shooting outside for better results.
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