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I have a few questions about requesting playbills:

1. What size of SASE would be best for a playbill?

2. When should I send my request? Is it safe to send it out before the play starts or should I wait until it has started?

3. Is it best so send my request to the Stage Manager or to the cast member whose autograph I want to get?

Thanks

1. What size of SASE would be best for a playbill?

A C5 envelope is perfect!

2. When should I send my request? Is it safe to send it out before the play starts or should I wait until it has started?

Wait until atleast the preview starts.

3. Is it best so send my request to the Stage Manager or to the cast member whose autograph I want to get?

If it is a cast signed playbill you want, send to the stage manager. If it's only one specific actor you want, send it to them.

That's great thanks