Hmm...I agree that the principal's behavior is cause for concern, particularly with something like "It didn't wow me," which sure sounds like an artistic evaluation (by someone who is likely not qualified to give one).

The guy is your boss, so it's a fine line, but it appears that there are two areas to discuss:
1.  The difference between doing preemptive damage control vs. his trying to do your job.
2.  The timely review of materials.

I think the trick is finding a way to broach these subjects in an "I need your help" sort of way rather than attacking him, even though he's out of line.  Can you ask, for example, if he requires approval, that you establish some sort of procedure and timeline in writing for script submission and approval?

Also, is there a way to ask, respectfully, that he focus on community standards issues and allow you to apply your expertise to choosing plays that you feel will be a good fit for you and your students?  You can tell him that you understand he may not always agree with your taste or choices, but hope that as long as he finds the play suitable for the school community, that he'll respect them.

Good luck!

p.s. Love (Awkwardly) is a solid play.

Thanks for the feedback. I'm going to have to find my manliness and stand up to him. I'm doing my fourth show at this school and have been extremely successful with raising the bar with quality and expectations.

I ended up selecting The Somewhat True Tale of Robin Hood for the spring play. We're excited, and the kids are really stepping up.

I've decided on my fall play for next school year, but I'm still looking for the spring show