There are often very personal reasons for an actor to have new headshots taken. But as a general rule, the following situations would make it a priority:
People say you're better-looking in person. Example: You look like Brad Pitt but your headshot makes you look more like Screech from "Saved by the Bell." Or conversely, you resemble Ugly Betty but your headshot makes you look like Angelina Jolie. Embrace the true you!
You're stuck in a time warp and still using black-and-white when nowadays color is the way to go (don't tell me you still own a black-and-white television?). Your clothing and hair are out of style (that Britney Spears belly shirt seemed like a great idea in 2000). Your appearance has altered since your last headshot: You've got a new hair color; you wear your hair short when it used to be long; you've lost a lot of weight (good for you) or gained a lot of weight (not so good for you). You're now a 45-year-old balding father of two, but your headshot was taken when you were a freshman in college and sporting an Afro (act your age, grandpa!).
You have only one headshot that you use for everything but would benefit from having several different headshots that represent different sides of your personality. This allows you to market yourself, with the appropriate headshot, specifically for the role described in the character breakdown. Casting directors don't have time to have an imagination.
Los Angeles and New York
To me, it's a given that your shots are going to look like you, so any obvious change in physical appearance will require a new headshot. If you look different today than you did yesterday, time to get new headshots.
When you walk through the door at an audition, you must meet the expectation set by the headshot and vice versa. If you look like your shot but your personal energy doesn't match the shot, it's time to get new headshots.
Aside from the above, it is absolutely vital to consider brand management. If you think of yourself as a product—and you are—there is a high level of branding that has to be the foundation of your career. This is a first-impression business. If your headshot is not dynamic, if it doesn't stand out on a computer screen among hundreds of thumbnails, then you need to get new headshots. You have to be honest with yourself. Try to look at yourself objectively and say, "Is this an undeniable, dynamic headshot?" If the answer is no, then you need new headshots. Period.
Start researching and find the photographer whose shots stop you in your tracks. You have a single moment to stop someone from clicking by you or jumping to the next page. The industry moves quickly and the trends shift on a dime. It is important to stay on top of it. Make the investment, constantly reinvent, and continue to grow.
You need a new headshot when you no longer look like your current headshot. When the casting folks can't pick you out from your headshot, you know it's time! And when your agent or manager says you need a new headshot, pay attention. They have your career and marketing in mind.
In addition to these basic reasons, you may need or want a new headshot:
- Anytime your current headshot doesn't make you feel attractive and confident in your professional presentation. You won't mail it if you don't love it.
- When you add new skills—for instance, film or commercial credits to your mostly theater résumé. You'll need a different photo for Sunny D than for Lady Macbeth.
- When the technology changes. If you have only a black-and-white photo in 2010, you need color shots, including emailable JPEGs.
- When you're tired of looking at "the same photo." In this case, try another image from your most recent headshot session to keep yourself inspired. It's less expensive than a new photo shoot. If you had only one keeper from that session, be sure to plan for more variety in your next one.