Most performers I know have at least a vague idea of what they want in their next headshot, but they don’t always know how to go about getting what they imagine. There are a lot of GREAT photographers out there, across every price range. How do you find somebody who’s going to get the best shots for your market and needs?
1. Do you like their work?
Sounds obvious, but there are a lot of different styles and aesthetics out there – do you LOVE the pictures you’re seeing the photographer showing off on their website?
Corollary: Variety is good. The best headshot photographers have a gift for making every subject and every photograph look and feel unique.
2. Does the photographer you’re considering “get” performer headshots?
Is it their main market or, if not, do they still understand what you need? Headshots for performers are a specialty market, and you want a photographer who doesn’t treat them like an “easy extra”, but really knows what performers AND those who do the casting need and want to see.
3. Do those great portfolio shots you like give you a sense of what the photographer could do for YOU?
Are there people you identify with in that portfolio (age, ethnicity, styling ie wardrobe and makeup, weight etc)? If the photographer is only showing slim 20-something models and hot magazine-styled Hollywood actors, a 40-something with curves or a comic actor playing up his quirks may not get the shot he or she needs and wants. This is even more true if you’re over-50, both male and female.
Corollary: Be realistic – look past the obvious physical attributes of the person to the SHOT and see if it speaks to you. If the expression is alive. If it’s about more than what that person “looks like”. If the photographer is consistently extracting personality, vibrancy, and energy in every single shot, it’s worth exploring further, even if their portfolio doesn’t offer samples of your age/type/genre.
4. Is the photographer familiar with your specific market?
Do they understand genres, roles, types, and trends? Different branches of the performing arts want to see different things in a photograph, and what is expected in each as far as styling (wardrobe/make-up etc) and photographic style can be quite different. Know what you need. If YOU don’t know, ask the photographer… and if they don’t know, consider finding a photographer who does.
Corollary: Regional differences pile on more “shoulds”; even different agencies/casting directors may want different specific things. The more your photographer knows about the market you are trying to reach, the more effectively the shots can promote you.
5. Do the photos look like the real people in them?
It’s great if you have a friend who has used a photographer, so you can get a firsthand feel for this). The person who walks into the audition MUST look like the photo they submitted to get invited to the audition. The rule of thumb: “A headshot should look like you on a really good day”.
Corollary: if anybody says their headshot had “no retouching at all”, they are probably fibbing, or the photographer just didn’t tell them what they did before showing it to them (exception: under-18s with perfect skin. And even then, I’m willing to bet a few stray hairs and minor shadows got digitally removed). See #5 – it MUST look like the person in real life. But stray hairs, blemishes, minor creases in clothing, minor undereye shadows and other minor adjustments to non-permanent features which make the shot look more polished but DON’T significantly alter the person’s “real” appearance are likely to have been taken care of in Photoshop. Really. Ask your photographer about retouching, how much they actually do, if that adds costs, and whether they do it themselves or send it out. I prefer to do my own – I saw the person in real life, and want my retouching to reflect exactly what I saw, not some 3rd-party’s “vision”.
6. Does the photographer make it feel like it’s all about you, rather than “their” look, and “their” portfolio?
As an actor/performer, your headshot is your single most important marketing tool. It needs to be YOUR personality which shines in the photograph, not the photographer’s or make-up artist’s. (This can be different from publicity/website images, of course, where you may WANT a particular photographic artistic sensibility. But an audition submission headshot is different, and should be ALL.ABOUT.YOU.)
7. Does the photographer make you feel comfortable?
Many performers (particularly those without film experience) are quite nervous in front of the camera; it’s different from being live onstage. Does the photographer seem to expect you to know how to pose and look your best, or is it clear they’ll be helping you out so you can relax and shine? Talk to them before your shoot, and try to get a feel for how they work – you want it to feel like something to look forward to, not a chore to dread. Speaking for myself, I want us both to have fun, and will do everything I can to make sure it is!
8. Does the photographer include full reproduction rights?
Full reproduction rights should be included in what you pay for the session (and any additional edits) so you can get them printed anywhere you like. Actors often need to mass reproduce their images, and cheap lithos/prints are the way to go, not the expensive archival prints you might buy directly through wedding or family portrait photographer.
Corrollary: you want a lot of proofs to choose from; the exact number will depend on the length of the shoot, but your photographer should for sure be offering you plenty of images from which to pick. Unlike a family or portrait shoot, the proofs won’t be fully edited/retouched until you have made your selections, but you want enough shots to choose from that you will to be able to pick from a good number of different expressions.
Headshots are definitely a niche market: a headshot isn’t only a “great picture” to show what you look like (although it should certainly be that!), but also needs to provide a lot of information about your personality, what you might deliver in a performance, and what a director might be able to turn you into if he chooses to invite you to audition based on what he sees in that photograph. Tall order… but it can be done!
divatography 
I think having a recent and professional headshot on hand in case you need to submit one for a job is important. I really like how you mention that you should pick a photographer whose work you really like. There are a bunch of different styles out there and that’s not bad. But you should choose the one with the style you like so you are happy with the headshots you get.
Yes indeed – it’s so easy now to get something that really appeals to your personal aesthetic. Just like picking a wardrobe, everybody’s taste is a little different, and it’s wonderful that we have so many choices now! Digital has really opened up options (as well as made them more affordable for everybody). Thanks for the comment!