Jeremy O. Harris’s Writer’s Residency Under the Tuscan Sun

CASTIGLIONCELLO DEL TRINORO, Italy — Just two weeks ago, the lives of four promising playwrights were upended: Not only did they receive an email announcing that their work had been shortlisted for the 2023 Yale Drama Series Prize, but they were also invited to participate in a monthlong residency in Tuscany, led by the American playwright Jeremy O. Harris.

Which is how those playwrights found themselves eating gourmet meals this week in a medieval village turned boutique hotel with breathtaking views of the postcard-perfect Val d’Orcia countryside. With access to a sauna and spa, as well as pasta-making classes and truffle-hunting, they are very much in a pinch-me-I-can’t-believe-it’s-true state.

“The first two or three days I was like, ‘How am I here, this is insane,’” Rianna Simons, 21, said of working alongside “very lovely, very talented people in a crazy, beautiful environment.” Simons, a Bermudian-British writer who lives in London, almost didn’t come, she said, laughing, because she initially thought the email about her play “White Girls Gang” was a scam.

There are no hard and fast rules for the fellows in the program, called Substratum, which was conceived by Harris (“Slave Play,” “Daddy”), a graduate of the Yale School of Drama, who judged the competition. “I just want people to write,” he said in an interview this week. The finalists, who were among those who submitted about 1,700 works, are “writers doing something a little different,” he said. “A little off the beaten path.”

The prize went to Jesús Valles for his play “Bathhouse.pptx,” an exploration of queer history. But because Valles was unable to leave his studies at Brown University, where he is pursuing an M.F.A. in playwriting, his slot went to Raffaella Donatich, Harris’s former assistant and an “exciting emerging writer,” Harris said.

The other fellows, all at various stages of their careers, agreed that having the time to write without distractions — and not having to sweat the small stuff — was the real reward.

“There’s something about having everything taken care of,” said Chloë Myerson, a 32-year-old writer from London whose play “Class” was shortlisted. Being outside of her normal life felt almost like a “weird punishment,” she said, “because as a writer, I’m always trying to carve out space” from the demands of work, relationships and life.

For Donatich, 26, who lives in New York, having “so much unstructured time” was forcing her “to define the reasons why I like the thing I claim to like to do.”

And Asa Haynes, 27, an actor turned playwright from London who was recognized for his work “RACISM: an unfocused theater essay,” said the experience was giving his imagination free rein. “Writing isn’t necessarily sitting down at a table with a glass of water or a cup of tea listening to some music. It’s also taking in the sun, the views, going to the spa and having a very hot sauna,” he said. “Writing is actually a lot more thinking and ruminating.”

This sort of pampering is exactly what Harris envisioned for the fellows participating in the residency — the first, he hopes, of many.

The residency is sponsored by the luxury brand Gucci, which Harris has worked for. “I always remind them that the only reason they know who I am is because of the theater, and so it feels disingenuous of me to accept a paycheck without figuring out a way to bring it back to the theater somehow,” he said.

Having spent time in Italy during pandemic lockdown, he decided it was the perfect place for writers to immerse themselves in an unfamiliar culture and “get the type of inspiration that can really shift an artist’s brain from the consciousness of society that you’re a part of to some new amalgamation of the expat brain,” he said.

He was introduced to Michael L. Cioffi, the owner of Monteverdi Tuscany, the boutique property where fellows are staying. (Monteverdi is underwriting many of the on-property expenses and experiences, like the pasta-making classes.) Cioffi, a Cincinnati-based lawyer, came to Tuscany about two decades ago, and later encountered the decaying hilltop hamlet of Castiglioncello del Trinoro, about halfway between Florence and Rome.

An initial purchase became a passion project, and eventually Cioffi bought many of the hamlet’s houses, transforming abandoned stables and dilapidated farmhouses into guest rooms, a restaurant and a wellness center and spa. Only a few original residents remain.

From the start, Cioffi said in a Zoom interview, he conceived of the Monteverdi as a “place to share with people, but also create a platform where people could really experience the arts in a meaningful way.” He established an artist-in-residence program and a concert series; the property had already attracted the likes of Wes Anderson, who, according to hotel lore, wrote “Moonrise Kingdom” there.

“I was like, well, it already has been like the muse has already wandered the halls there, and I want to meet her and see what she has to offer us,” Harris said of the space.

The group is sharing a six-bedroom house called Muri Antichi (Ancient Walls), with en-suite bathrooms, and spacious common rooms where they’ve been gathering after dinner to watch movies.

Days are mostly self-structured for the fellows. Mentoring has been informal as well. Harris said he was as eager to learn “from everyone here” as he was to mentor the playwrights.

For DJ Hills, 27, whose play “Trunk Brief Jock Thong” was shortlisted, the pampering is giving him a “because you’re worth it” moment. “There is so much flagellation as an artist; I need to be constantly throwing myself onto the ground for my work,” Hills said, adding that time in the spa has been a gift. “I, as an artist, am worth the 30 minutes to be here.”

As for Harris, he is keen to work on projects that had been put on the back burner while he basked in the success of his Tony-nominated “Slave Play” and sundry other projects which, besides modeling for Gucci, include releasing a capsule collection, producing plays, writing for television and cinema and performing in the Netflix series “Emily in Paris.”

“I need to get back to my actual writing,” he said, “because while it’s been really exciting to support other people, I am still an artist, you know, so I need to create my art.”

In the coming weeks, the fellows will encounter a range of artists (and possibly producers), including the filmmakers Pete Ohs (“Jethica”) and Eliza Hittman (“Never Rarely Sometimes Always,” “Beach Rats”), the playwrights Jordan Tannahill and Jasmine Lee-Jones and the author Erika J. Simpson.

Harris’s experience in 2015 at MacDowell, a prestigious artists’ residency program in New Hampshire, also inspired this new program. He called that residency a confidence-boosting experience that “restructured my sense of self,” adding that he hoped the Tuscan experience would do the same for the fellows.

MacDowell also showed him the importance of sharing meals. “That’s the only rule,” he added, “dinners where you can catch up on your day, see how things have gone,” and just talk.

Two recent meals were an indication of the sort of banter that takes place, with topics ranging from — and this is just a small sampling — playwrights contemporary and not (from Aristotle to David Ireland and plenty in between); Pier Paolo Pasolini (whose film “Theorem” they had watched the night before); K-dramas and their Shakespearean influences; British actors doing American accents (not so great, some said); Fassbinder films; the biblical king David; olive oil; Shonda Rhimes (and how she’s not given enough credit for her innovations); a new stage adaptation of “Brokeback Mountain”; Michelin-starred restaurants; elaborate European film titles; and, because Monday was game night, good games to play (Spades, Exploding Kittens, Salad Bowl).

Before dinner, the fellows learned to make ravioli and picci, a local pasta. “Also theater, you know,” said Harris, who had earlier described meals he’d eaten in terms of the pleasure he’d gotten from the chef’s storytelling, even more than the food.

The group kneaded and rolled out the dough and joked happily.

“Jeremy’s like the most wonderful fairy godmother,” Hills said. “We’re very fortunate to have him.”