Sorry for the length of the post, but headshots are important and can make or break your career.

Before sending this CD, which may contain hundreds of shots, and be tossed in the round-file without even being looked at (along with your resume), you should narrow down the number of shots. Agents and Casting Directors are very busy people, and the more time you can save them the better. It doesn't matter if you are a great actor, if you can't get in for an audition and get representation, you'll likely get nowhere. There are a few easy ways to do this, and your headshot is the easiest and most visible means. Here are some ways to narrow the number of shots down that worked for me and a couple of my actor friends:

Mark out the ones that have flaws (this will likely be done as a part of the photo shoot with the photographer), then from those that are left, choose the five you like and you think shows the real you (really look at the eyes, and make sure they are alive and vibrant, that will sell you more than anything in your headshot). Print these five out on a single piece of paper, then choose your favorite, but don't write it on the paper.

Go through these five with your acting coach/mentor (if you have one), and get their choice of two of these top five (they may want to see all of them instead of just the five, and that is fine too, just make sure they only choose at most two shots to be considered).

Get a number of your actor friends to look through the five and tell you which two they like and think shows the "real" you.

Get one of those "brutally honest" friends to do the same (you know, the ones that will tell you the truth no matter what) you are more likely to get frank feedback from them.

More than likely there is going to be an overlap, and that will probably be your "best" shot (in the end though, it is totally your choice until you get an agent, and may still be your choice even after that). If it turns out there is no overlap, then you may have to choose on your own, but likely after taking you on as a client the agency will review your shots, and tell you if you should get new headshots (Be careful, there are some "agents" that want you to pay THEM for the new headshots and they have a specific photographer take them and this can be a scam and probably is.) The agency can sometimes be a good source for finding photographers that they have had good luck with in the past, but they should never demand or require you to get them from a certain person or pay the agency for them, you should always be able to get them anywhere you choose and from whomever you choose.

I can almost guarantee you that the agency or casting director will not have the time or inclination to pop a CD in to look at your headshot. You are expected to be a professional and have your "best" shot submitted. Sloppy "kitchen sink" submissions expecting them to wade through multiple shots will be thrown out. Being a working actor is a business, and you have to treat it that way, putting your best self forward is the first part of that, and respecting the time of others is a huge win for you and them. If you save time for those you are submitting yourself to, it is more likely they will look at you as a professional, and more likely you will get called for auditions. (If you use the Clear Headshot Envelopes Chad sells on the site here, that even saves them more time, and time is gold in the industry, so they could be more inclined to bring you in for an audition).

Best of Luck!
~Rob