How many headshots do I need?
Minimally you need two headshots. You need a commercial headshot and a theatrical headshot. Please check out the page Commercial vs. Theatrical to get a full concept between those two. But having more headshots is a great thing to do. It adds diversity and allows you to have more specific headshots for electronic submittal. When you or your agent send a submittal through LA Casting or another service like LA Casting, you can pick from the images that you have uploaded to show up as your primary headshot when the casting director takes a look. In this way you can isolate what types of headshots will work better for certain types of movies, plays and TV shows.
Before getting your headshots you should really think about what your casting is and what you are aiming for. This way you can have a ton of images that communicate what you are going for. Please read the section on casting if you are uncertain on casting in any way. Once you know what your casting is you shape your photo shoot around it. Focus on what you are aiming to communicate in your primary headshots and your casting specific headshots. Then survey which shots are best before printing your two needed headshots. Then take a look at the other shots. See which ones are really specific headshots that would be great for isolated submittals or show depth of range when put next to other shots.
Marketing is a very important step for any performer. I highly recommend services like myactingsite.com and registering on Actors Access and LA Casting. When you have your own website or service site like the two listed above you can really shape your marketing. You can submit specific headshots electronically that seem to fit better for a certain role or director that you are targeting. If you have your own website, which is what myactingsite.com will provide you, then you can put up a ton of images that really reflect what you are going for.
I have a very good friend here in LA who is a character actor. He plays the bad guy, the thug, the circus freak. He was a pirate in "Pirates of the Caribbean." He has 12 headshots that communicate a good deal of his characters. Only three are printed. The rest are on his website. On his headshots he is not extreme on any of these shots. In other words he is not dressed as a pirate. He did not make himself strung out looking to play a junkie. But he did do simple things that slightly change the shots to communicate these various characters. On his website he has a variety of shots of him as a pirate on set, as a clown in a horror film, as a junkie in an indie short did. He has shots as a mobster in a film that he did. His website is where he puts those various images. But he will not submit those for roles. He knows better. Put a taste in of a character and make it a shot that can stand on its own. When you line them up they communicate those characters and his range without looking cheesy.
The cheesy way, which I have seen at least a hundred times, is when an actor makes up each character and stands in front of a brightly colored or white background and gets pictures in each character. What I have seen over and over, which is the real problem with this concept is that you end up with a person in different poses and looks but none of them actually communicate anything other than someone playing dress up.
When I was at a local duplication spot where actors get 8x10s made I was talking to the owner and he showed me a set of photographs that a girl brought in for printing. She was printing up about 6 different pictures. Only one of her headshots was able to stand alone as a headshot. It would have worked as a commercial shot. That was her girl next door shot. But the others could not really stand alone. I could tell that she was aiming for shots of specific characters. But she approached it like an extra approaches their extras submittal page. One was a drug addict. She was all strung out looking and it sort of looked like a mug shot. Her makeup was done to make her pale and sickly. She looked like she had been on a week long drug binge. Another shot was as if she walked off the set of "Revenge of the Nerds" completely over done with pocket protector, taped up glasses, hair in uneven pigtails and makeup added freckles.
So what you think a casting director would get from those shots? How many roles do you think she can submit those pictures to in a week? I can say that if I was casting for "Train Spotting" and got the one looking like she was on a drug binge I would be hoping that it was just a character shot, but I still would not call her in. It was too extreme. Same with the geek picture. It looked like a Halloween costume! Not like an actress with range.
You can pick as many shots as you seem fit to demonstrate your casting and your career goals. But do not be cheesy about it. You do not need to be in scrubs to get a role as a doctor or nurse. Just choose certain colors and poses that can communicate that. Take a look at the page on casting. I have a few samples up that show range within a persons casting. The main thing to remember on that is any headshot, even casting specific shots, should be able to stand on their own as a headshot.