This is a hard one. There are a lot of questions that you guys (actors) keep asking me, but I'll try my best here.
Some of the best things to do if you want to find free headshots are to visit different websites that host contests or places like craigslist where people are offering free sessions in exchange for being able to use your image in their portfolio.
The problem with getting free headshots from people building portfolios of course is the fact that they don't have very much experience and you're likely not going to get very good images. At least it's free though, right?
I would highly recommend entering contests though. For instance, I give out a free headshot session once per month to people who refer three other subscribers to my newsletter. If you stay on my newsletter, eventually you may win a one-hour session, which you can redeem at any point.
Search in Google for free headshots and contests and you should find some different deals. The best way to get a free session though is to apply into as many contests as you can because eventually you'll start winning. And the more you enter to the higher your chances.
Additionally, I'll give a free session to the first person who comments on this post. We'll see how many people read this far (remember, it pays to read my posts, because you never know when I'll offer something for free!). I also do things like this on my newsletter, so sign up and you can get lots of free things.
So yeah, first person who comments gets a free one hour photo session. Everyone after gets a free copy of my eBook for actor self promotion tips (valued at $20).
Headshots NYC - Cheap, Professional Headshots in New York City