“Day By Day” — Nat Wolff on Chekhov, Self-Discovery, and Dressing Room Debauchery

At The Pershing Square Signature Center..., just past 9th Avenue, there’s a bit of debauchery going on. It may or may not be onstage, but it is definitely occurring in the All Gender dressing room for The Seagull/Woodstock NY.

“I don’t think there's ever been so much fun and raucous wild energy as in that dressing room, in the history of theatre. I think we could take down Peter O’Toole, we could take down any of these motherfuckers. Laurence Olivier? We could take them down in terms of just pure debauchery in the dressing room. I’d like to go on record with that.”

Nat Wolff and I are wrapping up our conversation at Chez Josephine, a French restaurant tucked just a few doors down from the theatre where Wolff stars in The New Group’s production. We’ve covered the ups and downs of this experience and when I ask if there’s anything else he’d like to add, anything I’ve overlooked at our corner table, Wolff starts to tell me about his dressing room. The “we” he uses refers to costars Hari Nef, Aleyse Shannon, Patrick Foley, and David Cale (“David is now my best friend”). It’s unclear exactly what level of debauchery is taking place, but don’t worry, there’s still plenty of wholesome activity. Like painting nails.

“Hari hooked me up. She paints it on me. Aleyse has done it for me a couple of times, too, because I’d never done my nails. But yeah, it just felt right.”

In the show, Wolff appears with black painted nails, completing the look for his emotional, and at times volatile, artist character Kevin.

“It’s been a good ritual, but it just felt right for my character, who is doing everything he can on the outside to feel like an artist because on the inside he feels like a fraud.”

Wolff’s character Kevin is a take on Chekhov’s Konstantin in parallel with The Seagull/Woodstock NY as a take on The Seagull. He’s an artist trying to make something important, occasionally shrouded by a star actress (also Kevin’s mother) and an ensemble of moody, explosive individuals. Written by Thomas Bradshaw, this new play follows the well-known plot and dynamics, but brings plenty in the way of its contemporary update. Case(s) in point: Irene (Parker Posey) is tangled up in Goop, Sasha (Hari Nef) is wearing Crocs, and Kevin is vaping.

While there are plenty of laughs for those well-versed in 2023 culture, the play doesn’t lean into this comedy. It just sort of…happens. It’s a comedy and a tragedy of happenstance, neither of punchlines or sob stories. So your girlfriend is having an affair with your mom’s boyfriend? You can either cry or laugh.

“My character gets a lot of laughs, but in the moment I’m not really sure why people are laughing,” Wolff explains, describing the dynamics between the text and its reception. “I’m just taking it as seriously as can be. And sometimes it’s perplexing to be laughed at while you're crying every night.”

This show, and this role, has pushed Wolff to extremes. The play addresses a number of mental health topics, including self-harm, suicide, and psychiatric medication. At times, that depth of content can be taxing, but Wolff is looking at this from multiple sides.

“By the end of the play [the audience] starts to empathize and you start to feel the pain… I think weirdly, as soon as people start laughing at or with Kevin, that’s usually the people that are really moved by him by the end, because it means that they’re with him, they’re feeling him and, you know, it’s a magical thing to be part of.”

Looking at Wolff’s previous works—TV, movies, and theatre—everything has led to this role. Prior to The Seagull…, he appeared in The New Group’s 2016 production of Buried Child (“This is just a hell of a lot harder,” he laughs). Seeing Wolff’s Kevin onstage was not a shock; in fact, the dark and troubled young person persona is where I’ve seen Wolff the most. In the early and mid-2010’s, he starred in a string of indie films riddled with talking points on troubled American teens. In 2012’s Stuck in Love, Wolff plays a depressed young writer in love with an addict ingenue. 2013’s Palo Alto spotlights Wolff as a semi-delinquent (“I really felt for that character, even though he was, in a lot of ways, an asshole,”) amid writer James Franco and director Gia Coppola’s watercolor pastel storytelling. These are, of course, in addition to teen sensations The Fault in Our Stars (2014) and Paper Towns (2015). Taking a step back from any specific project, I ask Wolff how he’s constantly in such dark, challenging, roles. Is he looking to play characters tasked with challenges and rough relationships?

“When I’ve played characters that aren’t, I actually find it harder to relate to them. I think each time I play a character, the closer and closer I get to understanding myself, so it’s a real journey of self-discovery.” That’s what drew him to Kevin specifically. “With any part, it’s about bringing yourself to it as fully and creatively and sensitively as possible. And I really related to some of [Kevin’s] mental health struggles.”

Outside of these acting self-discoveries, Wolff is exploring these themes in his music as well.

Those who are familiar with Wolff from his earliest days in the Nickelodeon franchise, The Naked Brothers Band, may know that the duo (Nat and his brother Alex) are still creating music together. Their latest single, “Head’s On Loose,” brings back the parallels between Wolff and Kevin. He describes the creation of the song stemming from his “grappling with some mental health stuff,” similar to his onstage character. The timing of its release, due to busy schedules, was more of a coincidence, but he feels the overlap in themes is appropriate.

Working—and living—with these ideas all the time is not easy; in fact, it’s proving to be quite the long haul for Wolff. Some nights he’ll find himself awake until 5 AM, “wired like a kid who ate too much candy.” But, just like The Seagull, for every event of darkness, there is levity. To counteract the grim action that ends the show, Wolff’s been rewatching Friends each night. And writing his own plays (which he jokingly described as other Chehov adaptations). And thinking about getting a dog.

“That feels like a huge step for me, because it’s a lot of responsibility to have a dog. And it feels like the first steps towards adulthood. I tried to get a dog last year, but Christoph [Waltz, who Wolff worked with on the Amazon series The Consultant] wouldn’t let me get a dog because he was like, [in a Waltz-esque accent] ‘You are not ready for a dog. If you get a puppy, you’re going to be up on stage and the puppy is going to be saying, ‘Where’s Nat, where’s Nat…,’ [regular voice again] but that would be a huge step.”

Because that would involve slowing down…and maybe that’s exactly what Wolff is looking for. Our conversation has turned reminiscent, quoting his old movies and describing scenes that are still a bit haunting. Wolff’s previous work shaped a generation of teens as intensely as they shaped him, the effects still prominent a decade later. He’s bringing all of those experiences and stories to the stage for The Seagull/Woodstock NY, yet he remains completely open-minded about what may be in store next.

“I think things for me tend to go better if I just follow my nose and play it by ear…I think I just need to take it day by day.”

Day by day, one role, and one episode of Friends at a time.

‍The Seagull/Woodstock, NY is now playing through April 9 at The Pershing Square Signature Center in New York, NY. Tickets are available here.

Credits
‍Photo: Michaelah Reynolds
Grooming: Chelsea Gehr for Exclusive Artists using Kevin Murphy
Styling: Chloe Hartstein
Location: Chez Josephine