When is the best time to get headshots?

In my opinion I think the worst time to get headshots done is the first two weeks of June or the last two weeks of December. The business stop in June and agents are cleaning house. Wait and let that happen and then put together a headshot session. The weather is usually great on  both coasts and chances are you've had some sun and some outdoor time if you are an actor living in NYC. Early December is OK, but the last two weeks forget it. Everyone is beat and you have probably been eating everything in sight since Thanksgiving. The rest of the year is wide open.