For Playwrights, Making It to Midcareer Is a Cliffhanger

That these characters are, as Hunter puts it, “versions of me had I not found offramps” does not make them less dramatically valid. In a way, as he has been discovering ever since, it makes them more so. If “A Case for the Existence of God,” from 2022, is about the struggle to have children, his latest play, “Grangeville,” which opens this month at the Signature Theater, is about the struggle to care for parents. “I’m now in the sandwich generation,” he says.

Like Wohl and Jacobs-Jenkins, Hunter feels he could not have written his newer plays, with their newer concerns, sooner — nor, for that matter, his earlier plays now. One of the benefits of reaching midcareer is that a new life stage offers new stories to tell and a larger reserve of craft with which to tell them. Another benefit is that midcareers are obviously a prerequisite to late careers, with their witchy, molten qualities. You don’t get to write “The Tempest” unless you’ve already written “Hamlet.”

The question of what comes next for these playwrights is in any case no longer an anxious one, as it was in their youth. For Headland, 44, it seems to be pleasantly unanswerable. A cycle she calls the Seven Deadly Plays, which began with “Cinephilia” in 2008 and continued with “Bachelorette” in 2010, came to a close this season with “Cult of Love,” the first to make it to Broadway.

The sins were “such a good container,” Headland says, like breadcrumbs leading forward instead of backward. But despite having run through them all (“Bachelorette” was gluttony; “Cult of Love” was pride), she in no way feels at loose ends.

A highly praised TV series like “Russian Doll” and a “Star Wars” spinoff (“The Acolyte”) will do that. And perhaps it helps too that, atypically among the midcareer cohort, Headland’s dramatic interests have been “the same from day one”: addiction, God, the female experience “and some version of how those things conflate to make you grow or die.”