A good headshot is one that gets you auditions. A great headshot gets you the right auditions: auditions where the casting directors are looking for an actor just like you.
Rule #1: A Great Headshot Looks Like You
Your headshot should look like you on your very best of days, one of those days when you look in the mirror and say “oh, yeahhh.”
If the headshot lands you an audition but you don’t look like the person in the picture when you walk through the door, then forget about it. In person, if you’re younger, older, thinner, heavier, etc. you’re not going to get the part.
Or even worse: they might want someone who looks just like you, but you won’t get the audition if the headshot leads them astray because it doesn’t look like you.
Rule #2: A Great Headshot Shows Your “Type”
Your headshot, particularly a legit/theatrical headshot, should reveal a type. You want the casting director to look at your photo and know right away if you’re the best friend, the professional, the con man, the leading lady, the comic sidekick, the mom, etc. If you don’t know your type, talk to casting directors, agents, acting instructors, or friends in the business. Then talk to your photographer beforehand. If you know what you’re looking for and can convey that to your photographer, your final shot will be much better. Trying to be the jack-of-all-trades who can play anything rarely works. If you’re seeking auditions for distinctly different types, take multiple headshots that reveal those types and send them out accordingly.
Rule #3: A Great Headshot Shows Your Personality
Your headshot should express something unique about you. It should be engaging and interesting. Maybe it’s a special twinkle you have in your eyes; a bemused smile that’s just your own; a big/roaring personality. Whatever it is, show off what makes you special and sets you apart from the hundreds of other actors whose headshots casting directors look at every day.
Rule #4: A Great Headshot Is About You, Not Your Photographer
This isn’t to say that you don’t need a great photographer. But regardless of the photographer, the picture should show off your style, not the photographer’s. Some photographers have a very distinct look, and that look is their personal “brand.” It doesn’t matter who you are, they are going to make your headshot fit their brand. When looking for a photographer, be sure your photographer will take a photograph that emphasizes your brand, not his or hers.