I heard that as long as you send the theatre stage door a self-addressed/stamped envelope for the Playbill, they usually send one back. I am not sure about it being signed though.
I've only requested from "The Best Man," and got one in about a week (signed by everyone except Angela Lansbury and James Earl Jones, as far as I can tell).
Loliveve, James Earl Jones's assistant is very nice. You may try and get him to take your playbill backstage. When I stagedoored, there was a guy who had some Star Wars posters he wanted signed. The assistant took them and the cynic in me wondered if he would indeed be the one signing them. Well he also took my camera and took a picture of Mr.Jones in his dressing room for me. Can't speak for the signature, but the picture was definately him. Also same day got a really good picture of Angela, who posed for me(no smile though and glasses), but I never thought I would ever get one.
Within the past week I have received playbills from:
Peter and the Starcatcher Stephanie J Block - Anything Goes Angela Lansbury - The Best Man Million Dollar Quartet Jeremy Jordan - Newsies
These all took about 7-9 days
Most shows respond anywhere from a week to a couple of months. I sent to How to Succeed last August, and saw that the chance of getting a response was very slim, but in November I looked in the mail and I got a playbill signed by Daniel Radcliffe. So there is always hope.
joined:11/1/11
Posted: 7/1/12 at 01:39am