Each spring, in the months leading up to the Tony Awards, Wesley Morris tries to see as many Broadway shows as he can. And this season’s spree (including “Ragtime,” “Cats: The Jellicle Ball,” “Proof,” “Dog Day Afternoon” and “Giant") left him with the question: Where are the challenging shows?

There were some great performances, but the productions seemed designed to reflect his values and make him feel good. Doesn’t the best theater raise uncomfortable questions, and not give clear answers? Shouldn’t the shows vying for Broadway’s top awards be a bit more difficult?

To work through these feelings, and to help wrap his head around this season, Wesley invites Helen Shaw, The Times’s chief theater critic, to compare notes.

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