When you take a headshot for film/tv/theatre: Should the headshot represent my personality how I am as a person or it should represent what type of characters I would like to play?
A headshot should show both your "type" and your personality. When a casting director looks at your picture, they should know what to cast you as (ie. young dad, best friend, character actor, etc.). That is your type (not necessarily the characters you want to play but those you are most likely to be auditioning for at first). Your type is easily suggested in your headshot by what you wear and hair/makeup. They should also get a sense of who you are - your unique personality. That's the harder part of a headshot shoot. You need to be relaxed enough to get across who you are and what makes you unique. Ideally, a casting director should look at your headshot and think, "I want to meet this person".