When I send for Playbills, I always tell the Stage manager a bit about myself, then thank them for putting on a great production and mention what I like about a couple of the main cast and at the end ask politely if I can request a signed playbill. {up}

RYAN J. 8)

I don't think there is a right way of going about it, to be honest. A lot of it is down to luck. I think you might get a better chance if you wrote 'I am a fan of such and such and would love a playbill' but remember they are really busy. You might even be better off writing to one of the individual actors (like Dan), though I've yet to see any successes come from 'How to Succeed...'. Early days though. :)

I would like to write to "How to Succeed in Business Without Really Trying", and get a cast-signed Playbill, but although I've done the VV Broadway thing, I've never requested a Playbill before. I'm good to go with envelopes and stamps and things, but I have a question with regard to writing a letter to the stage manager. Do you have to explain yourself as you do with a celebrity? Like, "I love this show/actor and it would make my life to get an autographed Playbill"? Or more of a, "Please send me an autographed playbill using this self-addressed and stamped envelope," business letter type-thing? I was thinking more the latter, but figured it'd be best to ask. :)