For Playwrights, Making It to Midcareer Is a Cliffhanger

New York Times

19-02-2025

'Absolutely not,' Branden Jacobs-Jenkins declared.
Leslye Headland chuckled. 'Oh never, no.'
'I don't know anyone who could!' was Samuel D. Hunter's astonished response.
'Not really,' hedged Bess Wohl. 'Until maybe last year.'
The question that brought such universal denials from four frequently produced, much-awarded American playwrights was: 'Have you ever made enough to live on from your plays?'
To win audiences and awards for your efforts is undoubtedly affirming, but the financial returns for dramatists are slim. Even after the premiere of 'An Octoroon,' which would later win an Obie Award for best new American play, Jacobs-Jenkins was living in a 'horrible sublet on an air shaft,' with a possible case of whooping cough and a definite lack of health insurance. Headland considered herself a success not when her play 'Bachelorette' made a splash Off Broadway in 2010, but when she no longer had to work at Rocket Video to make ends meet. And Hunter told me that the most he'd earned in any one year from his plays — including 'The Whale' and 'A Case for the Existence of God' — was 'less than $30,000.'
Playwriting has never been a golden ticket, or even, for most, a subway pass. It's hard enough to get a first play written and produced; getting a second and third off the ground, let alone a 10th, has in recent decades seemed just about impossible. Who knows how many rich voices we never got to hear in maturity?
Especially since the Covid pandemic wiped out a host of emerging artist programs and career development grants, the problem has reached existential proportions. Theater, after all, depends on good plays, and good plays depend on authors with long professional horizons. Many of the greatest works of dramatic literature are neither early nor late but in between. ('Hamlet,' 'Twelfth Night' and 'Othello' are dead center in Shakespeare's professional timeline.) But how can playwrights have a midcareer if they can't survive the start?
Or so I have often worried.
Yet as I previewed the 2025 schedules of leading American theaters, I was delighted to find new work from more than a dozen writers I'd been following with great interest for years. Not just Jacobs-Jenkins, Headland, Hunter and Wohl, but also Joshua Harmon, Chisa Hutchinson, Tarell Alvin McCraney and Jordan Harrison are premiering new plays this season. All are well established in the field, with six or more major stage works on their résumés — in Hunter's case, 19. And all are in their 40s, though if I'd extended the range by just a year or two, I could have netted at least another four.
Together they constitute an unusual cohort, bucking the bad news of the American theater by having made it past emerging to emerged. Granted, pretty much all of them did so with the help of other industries. Jacobs-Jenkins and Hunter have both taught extensively, Hunter at one point covering Theater 101 for a football team. Headland has worked steadily in movies and television, including as a creator of the series 'Russian Doll.' In 2015, Wohl had to rush from rehearsals of her breakthrough play 'Small Mouth Sounds' to shoot a pilot she'd written for a series about 'lady cops.'
These nontheater jobs are, even now, how playwrights make real money and get health insurance. Still, Jacobs-Jenkins, 40, calls his cohort a 'weird bumper crop' of success and a 'guinea-pig generation.' He and the others were beneficiaries, he says, of a network of programs that arose in the late aughts specifically to make such careers less impossible. Bouncing from Soho Rep's Writer Director Lab to the Public Theater's Emerging Writers Group to the Ars Nova Play Group to the Lark Playwrights Workshop, they could keep turning out pages, if not yet afford their rent, thanks to the availability of stipends, grants, the occasional place to live and regular helpings of pizza.
JACOBS-JENKINS MAY WELL be the poster child for that guinea-pig generation, having recently achieved several midcareer highs. One, impossible without having a body of work to retrospect, is retrospective: His scathing comic drama 'Appropriate,' first produced Off Broadway in 2014, won the 2024 Tony Award for best revival of a play. Another is prospective; he says he could not have written 'Purpose,' a play about a large, blended political family that begins previews on Broadway this month, until he became a parent in 2021: 'I didn't have the authority.'
Though moving toward the center of the culture can feel peculiar when you have defined yourself as a useful outsider, Jacobs-Jenkins is learning to accept what it means to be midcareer — though he prefers to think of himself as a 'journeyman' on a journey of unknown duration. When he won the Tony, he says, 'there were a lot of us first-time nominees, realizing that we're not the brat pack anymore, that there's this vacuum pulling us forward. And it would be irresponsible to resist it because of all those institutions that helped us get there.'
Wohl, 49, is also ambivalent about the idea of a midcareer. 'I embrace the optimism of that term, but I don't take anything for granted,' she says. 'We all have encountered people who got successful early and became complacent.'
Wohl's work strikes me as the opposite of complacent, as each new piece explores new ways to 'break the box' of formal expectation. 'Small Mouth Sounds' took place at a silent retreat, of the kind she had been attending at the time. In the harrowing 'Make Believe,' which debuted in 2019, she challenged herself, in defiance of ancient theatrical wisdom, to put children onstage and expect them to carry the drama.
But with her latest play, 'Liberation,' which opens this month at the Roundabout Theater Company, the box she's breaking is not just formal (though blended timelines are involved). She is also trying to break the box of her own reserve — a reserve common among early-career playwrights. 'Liberation,' about mothers and daughters, tests that reserve with its autobiographical aspects.
Feeling exposed, Wohl threw several early drafts away, even some that were offered production. 'I only cracked it,' she says, 'by putting myself into the work in a more direct and legible way, which is something I couldn't have done when I was younger. I wouldn't have had the bravery. Now it's 'welcome to my journal!''
All the midcareer playwrights I spoke to mentioned a newfound confidence: not just in the value of their lives as worthy subjects for drama but also in their ability to make them into good theater. That they could write with at least a reasonable expectation of being produced was part of that confidence, but so was a deeper faith in their vocation. When you've won a bunch of playwriting awards, no one can say you're not a playwright.
'The biggest fear as a younger person is: What if the artistic impulse goes out?' Wohl says. 'And now I know that it won't.'
Or at any rate, can't. Somewhere between early and midcareer, not just Jacobs-Jenkins but also Wohl and Headland and Hunter became parents. The costs and the constant emergency of caring for a child that drives some people out of the arts drove them deeper in.
FOR HUNTER, IT WAS a relief. 'In your 20s, you write from such a place of anxiety,' he says. 'At 43, I'm a dad, we got a puppy, and we're finally in an apartment we really love. Once you have those middle-class things you never thought you were going to have, your shoulders drop a little bit.'
Neither he nor the others feel that the hunched shoulders and housing insecurity of their youth were good for their art. The 'La Bohème' portrait of impoverished painters and poets was after all a description, not a prescription. 'And at least they could afford the garret,' Jacobs-Jenkins says. 'In New York, forget it.'
Yet for Hunter especially, the arc of the concerns of his plays closely traces the arc of the concerns of his life, starting with 'a solidarity with people who are suffering' that stems from his upbringing in Idaho. When I ask about the obese protagonist of 'The Whale,' he says, 'At one point I weighed 375 pounds and was self-medicating with food.' And being outed at a fundamentalist Christian high school like the main character in 'The Harvest'?
'I was that guy!'
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.'
'Cult of Love' is about all three, like tornadoes inside tornadoes. That it was also a critical success is of course a nice capper, but Headland is less concerned about the fate of any one play than with overall output. Some will hit, some will flop, she says, but always 'more will be revealed.'
Which seems to be the greatest gift of the guinea-pig experiment. Those emerging playwright programs not only opened doors for their beneficiaries but helped them develop the stamina and wherewithal to trust that they can keep the doors open. Members of early Ars Nova Play Group cohorts, including Jacobs-Jenkins and Hunter, still meet 15 years later.
That they thus write with less anxiety (and more health insurance) is a boon for us too, allowing them to bring us newer, weirder ideas as they plow through their midcareers. It is entirely a good thing, despite 'La Bohème,' that the panic (as Headland puts it) is not there anymore — 'but the curiosity still is.'