"This guy had an envelopes with each actors picture in it (from Drowsy)- it was like a professional headshot. He had multiples of some actors- some regular headshots, some just production photos from the show."
That sounds like a pair of men I kept running into on West 45th Street this time last year. They each had a folder full of headshot. One had a list of names with thumbnails of the headshots and names. They'd see someone, check their list of pictures to see if it was someone on it, then pounce with a headshot and Sharpie. One afternoon, I was standing near Garvey's waiting for a friend. They passed me, glanced at their picture list to see if I was on it (ha...I'm not) and moved on. They spotted Greg Jbara and made the proverbial bee-line across the street to catch him. He was on his phone and about to walk into the Imperial.
I saw them a few days later when I was talking with Hugh Panaro. Hugh was holding his dinner, his dry-cleaning. He didn't have his hands free and was in the middle of a conversation. And, sure enough, these two guys approached with barely a "pardon me" to ask him.
Now, if you're a real fan and you have a headshot for whatever reason...you came across it at the flea market or something...I don't really see too much of a problem asking to have it signed. It's not too different from some young fan who prints out her favorite picture from an actor's site and asks to have it autographed.
http://www.hugh-panaro.net