How to Win At the Headshot Game

Your headshot needs to capture you. Your unique personality and how you’re castable.

How to win at headshots

The title of this post, How To Win At The Headshot Game, could have easily been swapped for: What I Wish I Knew As An Actor When I Was Graduating From Rutgers MFA Program And Getting My First Set of Professional Headshots. But it was way too long. So I shortened it. Just like what you’re about to read below: The highlights of everything that I’ve learned as an actor and headshot photographer here in NYC over the last 11 years.

If I could go back in time and talk to Michael of the past knowing what I know now this is everything that I would tell myself. It would have helped me:

  1. Save money on headshots
  2. Book more work as an actor
  3. Accelerated the growth of my career

A bit about me before we dive in. Like you, I’m an actor. I hold a B.A. in Acting from DeSales University and an M.F.A in Acting from Rutgers University. I’ve spend lots of time both in front of and behind the camera. About 7 years ago, a camera found it’s way into my lap and my life took a new direction. Since then I’ve become a full-time headshot and branding photographer here in NYC and have had the privilege to have worked with hundreds of actors like you. My life is a magical adventure and I’ve never been happier. Why? Because I get to work every day with actors. And since us human beings are emotional creatures masquerading as logical ones, we never change or doing anything great because of what we know, only what we feel. That’s why I believe actors have one of the most important jobs in the world. No joke. Because one day someone is going to walk into a theater and see your performance. And as a result of what they felt, not what they thought, but felt, they’re going to make a change in their life. They’re going to make the call, they’re going to leave the relationship, they’re going to start the business or any number of things when us human beings are so deeply inspired by an actor’s performance that we decide to take action. Now I know what you might be thinking: “Isn’t this supposed to be a post about headshots?” It is, because wouldn’t it suck if you didn’t get to do your job as an actor because you have an ineffective headshot? Because you’re losing at the headshot game? It happens all the time. Actors not getting the auditions they deserve because they’re headshot isn’t what they need it to be. Let’s make sure that never happens to you.

In order to win at the headshot game we have to put ourselves in the shoes of the end users of your headshots. Who are the end users? Casting Directors, Producers, Directors – anyone that can hire you for a job. Let’s focus on Casting Directors – but first I want to share with you how to never worry about money again for the rest of your life.

It’s so simple. All you have to do to never worry about money again is to solve a problem. The bigger the problem you solve and the faster you solve it, the more money you’ll make. It’s how the world works. How does this apply to the headshot game? Every time a Casting Director get’s a new script they have a new set of problems: The roles they need to cast in a certain amount of time. This keeps them up at night. It’s their problem and if they don’t solve this problem by filling the roles with the best possible actors for each, they don’t get paid. You, the actor, are the solution to that problem. And it starts with your headshot.

For that reason your headshot needs to be three things:

  1. It needs to be a current and accurate representation of what you look like when you walk in the room.
  2. It has to capture you. Your unique personality and how you’re castable.
  3. We have to say ‘yes’ to the question do I want to meet this person.

If you can do those three things, you’re winning at the headshot game. And, believe it or not, most actors are losing at this game. You’re going to win, here’s how:

Your headshot needs to be a current and accurate representation of what you look like when you walk in the room.

What does this mean? It means that you have to keep your headshots up-to-date. If your look changes your shots need to reflect it. Longer hair, shorter hair, different colored hair, weight gain, weight loss, age/time and, often overlooked, you. While you might not look that different 2 years from now you’ll be quite a different human being because of life experience. And that shows up in your shots.

It also means that you don’t want highly stylized shot from a photographer who thinks it’s a good idea to use flashy studio lighting. Why? Because that flashy studio lighting won’t be there when you walk in the audition room. You’ll walk in and be a disappointment because you don’t look

like your shots. And because of that you’ll have wasted that Casting Director’s time AND have prevented another actor who may have been a better look for the part because you took that audition slot. What do you think the odds are this Casting Director is going to call you back again? It’s why we use natural light in our studio. It’s flattering and honest. And it’s what they’re shooting most major TV series with. Listen, I’m an actor, I get it. You want to look awesome. You will. You just need to make sure what show’s up in the photo and in person matches.

Your headshot needs to capture you. Your unique personality and how you’re castable.

This is 50% you and 50% your photographer. If you don’t know who you are and how you’re castable, the best photographer in the world can’t do anything but take a nice picture of you. This is not going to help you book work.

Some questions you need to ask yourself:

  • What roles am I most believable in? In the real world?
  • What is my core personality? Sure, you’re a dynamic human being that has lots to them. But we all have a kind of general energy we walk around with. What’s that for you?
  • Commercials. What kinds of products could you believably represent? The guy who we believe who is a Crossfit Trainer is a different looking guy that’s a Weekend Warrior. Who relates to you? Who is your demographic?

Once you get specific on what’s listed above, you have a blueprint. This is a MUST. Otherwise you’re just swinging around in the dark during your session.

Now for the photographer’s role… He or she has to be capable of helping you manage your psychology and give you the tools to bring out everything you need your shots to be. This is an art form unto itself. Your photographer’s job is to help you book work. If you’re not convinced they are committed to and qualified to do that, move on.

We have to say “Yes” to the question do I want to meet this person.

Certainty is attractive. Us human beings subconsciously gravitate towards it. You need to be absolutely certain in your headshot. It’s very rare that people are. Why? Because getting your headshot taken is something you probably only do every couple of years like the rest of us. It can be a nerve wracking situation. And unless this is something you can do on your own, you’re going to need help. From your photographer. Your photographer must possess the skillset to bring out the very best in you. They must be able to set you at ease and help you create the confidence you need to look certain in your shots. If you look certain – Casting Directors are going to naturally gravitate towards you.

This is why I always recommend meeting with your photographer before you book with them. It would have saved me a lot of money, time and loss of work when I was right out of acting school. If they won’t give you 15 minutes of their time for a free consult, I’d say move on.

In summary, if you do those three things and do them well – you’re winning at the headshot game and in the top 10% of anyone in the industry. At the end of the day to make sure those three things happen it has to be a collaboration between you and your photographer. It’s a team effort. Choosing the right one for you is essential and having a meeting with them before you book is the best way to make sure you’re making the right choice.

You can learn more about Michael Cinquino and what he does at:

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