If you go back in time to yesterday (just scroll down, no need to rush out and build a time machine) you'll notice that I had Maggie take my headshots! I mentioned how interesting and useful it was to be back in the hot seat, and I'm still thinking about the experience today. What's arguably harder than having your headshot taken, however, is making the right choice out of the (hopefully) 100-200 photos that the photographer sent your way.
Most people (especially at events) will notice the camera in my hand and say "please don't take my picture," "I hate having my picture taken," "I don't look good in pictures," or something along those lines. After having my picture taken professionally for the first time in a couple years (and armed with all of my knowledge of photography), I can understand why. Photographs, especially candid photos, often capture us simply being. We aren't used to seeing ourselves in that state of being, though- we see our own faces most often in mirrors, in our reflections as we walk by car windows, or in the front-facing cameras we use on our phones when taking selfies. Anytime we're ready to see our face, either in real-time or immediately after a photo is taken, we make sure and position ourselves, consciously or not, in poses and angles that flatter our features. For example (as I found in my headshots) I'm guilty of clenching my jaw to make my jawline look stronger, of narrowing my eyes, pursing my lips a little bit- I'm sure we all have weird little faces we make in the mirror to make ourselves look more attractive...to ourselves.
When you pay $200 for 200 printed copies of your headshot plus anywhere from $150-$1500 for the session itself, I hope that you do end up handing those directors a headshot that you love. Obviously you have to like the photo you hand out- you're ultimately in charge of that decision. But the reason why I so strongly advocate for showing a gallery of photos to your peers, mentors, family, loved ones, etc, is so that you can get feedback on your photos from people who see you all the time. If you live with someone; a parent or significant other or roommate, if you go to work and see the same co-workers every day, I guarantee that these people see you more than you see you. You (hopefully) spend way more time out in the world, living in full view of the same few people every singe day than you do gazing into a mirror or snapping photos of yourself with your phone. So it would follow, that though your own opinion of your "best" headshot matters, I would argue that the opinions of important people in your life carry more weight when it comes to picking your photo than yours does. The most valuable opinions of all come from people who work in the same industry as you and know you really well- think professors, directors, bosses, fellow actors, and anyone else who knows not just who you are but also what kind of photo is most useful in your field.
One other trend I've noticed with folks (including myself) picking out photographs, is that often we choose our favorite photo based on our aspirations. Like buying a pair of jeans that are just a little too tight (but we'll lose the weight in a month and then they'll fit, I promise!), I've seen a lot of my clients pick a photo that is a good picture, but it is really nothing like who they are right now- rather it is a photo that looks like who they want to be, or who they are working on being. Not that I profess that two hours with someone qualifies as "knowing them really well", but people's impressions of you are often formed in a five minute interview or audition, so my opinion as someone generating a first impression also carries a lot of weight!
The great thing about headshots is (if you can afford it) you can always get new ones. The people who are looking at your headshots want to see you, how you look, at your best, right now. They will be disappointed if you are twenty years older than you look in your shot. They'll be upset at you for wasting their time if you are, in reality, a slight, skinny dude, but you went to the gym right before your headshot, wore a tanktop, and used hard overhead lighting so you look way more muscular than you are. If you keep getting cast and called in for comedic roles because you're goofy, bright, and bubbly, don't pick the photo with the smoky-eyed scowl. The thing we forget as actors (and humans) is that there's some role, job, person, out there that is a perfect fit for us. Sure, there are more roles for certain stock "looks" and "types", but trends change, and you never know when you- the real authentic you version of you- is going to be exactly what someone is looking for. Of course, if you're that skinny guy, for example, and you put in the work and go to the gym and get totally ripped, get a new headshot! But don't use your headshot as some kind of aspirational goalpost.
I guess the final, simple sort of roundabout conclusion to this rambling is something that I read somewhere: "You are Cilantro." I think it applied to dating in the article, but it is a great point. I'm guessing, like me, you have very strong feelings about Cilantro. I happen to LOVE it- as do some people, but many other people find it disgusting. This isn't Cilantro's fault- it's just being Cilantro, adding its flavor to things, ruining dishes for some and making them sublime for others. But if Cilantro were to change- to become say, iceberg lettuce, be harmless, flavorless, but generally sort of "agreed-upon" by all, it wouldn't be Cilantro anymore. It wouldn't be hated, I guess, but it certainly wouldn't be loved, and those who want Cilantro would lose out on something magical. So: Be Cilantro- be yourself- pick a headshot that is you (and that is professional, beautiful, and unique) - and don't worry about what you think people want to see, what you think you are, or what you hope to be. Pick a photo that is who you are- and hopefully there are lots of people in your life who are happy to weigh in on exactly what that might be. Good luck!