There's probably some good literary theory out there somewhere that speaks to this better than I can, but I think that there are people who write plays to find the cutting edge of the medium, people who write to fill in the 'new normal' in the wake of successful cutting edge achievements in the medium, and people who write the equivalent of genre fiction - something expected that does not challenge or transform, but lightly entertains and feeds a general audience who wants to go the the 'theatre' without risking anything.
Most of the cutting edge is terrible and flawed and messy and a failure, but some of it pushes us forward into new and exciting territory. For some, it's worth it to see ten of these plays in the off chance that one will be that transformative experience.
In the wake of a popularized cutting edge success, other writers rush in to write more stuff like that, explore the ideas, and map out the new territory in all it's intricacies. Most of that is terrible, too, but some of it is amazing.
Eventually, some of these new territories become safe places for safe plays. You might think I wouldn't like any of these plays, but that's not true. I think some of these plays will be great as well, while most of them will be forgettable in every way.
One could argue that the great plays we associate with different eras of theatre history aren't very often the cutting edge pieces that forged new paths. More often, they fall into that second exploratory category, but many are in the safe space - these were plays that capitalized on what audiences were clamoring for and achieved a level of commercial success. There are certainly plays from these times that were more cutting edge or interesting or groundbreaking - but unless they achieved commercial success, they weren't widely produced or published.
I think there are times when audiences are more interested in being pushed into the unknown, and other times when they are more interested in exploring the new territory that everyone agrees is a great thing. I think the vast quantity of theatre audience members aren't that interested in being challenged or transformed - they want to be entertained, to have a night out, to have an experience. If they are challenged, they want it to be an expected challenge that they can safely put in a box and keep on a shelf and point to to prove that they are willing to explore new ideas.
I feel that I will have written a good play when the audience is transformed in a way that can't be undone by going home. I would most like it if audiences find themselves identifying with characters that seem to be good, solid, right-thinking people, but upon later reflection it becomes clear that they are actually terrible human beings.
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