Ok, so you send your awesome new headshot/resume to a handful of agents and you need a cover letter on top. I have opened many of these and I will tell you my experience. These envelopes are usually not opened by the person that you will end up interviewing with when you go to meet the agency. They are opened by actors that intern in said office. Maybe they are opened by assistants or people that may be paid for their jobs, but probably not. When I pulled your headshot out of the envelope, if a cover letter was not stapled to the back, it usually got separated and thrown away. I didn’t take the time to staple or tape your cover letter to your headshot if you hadn’t done that. Here’s the thing… DON’T staple it to the front of your photo. Staple it to the back. That way we see your awesome face first and can flip over and see your resume and cover letter next. Then a pile is made and that pile is set aside to be gone through later by the important people in the office that do that. I have never worked in any office that didn’t open something. Everything gets opened and looked at so I feel that envelopes with windows are a waste of money. Just don’t seal your envelope. It hurts fingers after a while to unclasp or open all those piles of submissions.
Now, to the content of your cover letter. You write “Dear… I am seeking representation” I say… REALLY??? OH, THAT’S why you are sending me your headshot. Duh…I know that. That’s sort of a given. Then you go on to tell me that you are an actor who absolutely LOVES acting and is passionate and that with the right representation blah blah. Thank you. Actor. Look, there is nothing wrong with that cover letter. It’s just the same cover letter that the every other generic actor sent in to the agency.
My feeling is that you need to say what makes you unique without being a smarty-pants, seeming angry or detrimental to yourself. It’s funny because the things that make us unique are usually the things we try to hide in our headshot. Be creative. It’s your job. You are expected to be a creative person in this industry, that’s why you will be hired. So, choose a creative way to introduce yourself with a couple sentences. No, it’s not easy, but this business is not easy. Use it as an exercise. You may just learn something about what makes you special in the process.