Dylan O’Brien Joins the Grown-Up Gang with The Outfit

The former teen heartthrob and Tumblr fanfic muse is getting into decidedly more mature territory, but he’s still in on all of the jokes.

by Iana Murray

Dylan O'Brien
Courtesy of Vincent Perella.

Dylan O’Brien can recall the precise moment he broke the internet. It was during the summer of 2021, when he was filming TikTok videos sporting a Balenciaga shirt, a platinum blond buzzcut, and a temporary snake tattoo slithering up his forearm. The actor’s fans went rabid, fawning over his new look. But the thing is, that wasn’t him—the Dylan O’Brien who prefers to keep his appearance, as he puts it, “plain” and “accessory-less”—that was a character for the upcoming social media satire, Not Okay.

He looks back on that transformation like a scientist examining an otherworldly specimen under Twitter’s global microscope. “I was still exactly who I was,” the actor says. “And then I just put on this video game skin, and people were like, ‘That’s what we want you to look like.’” But before that can be interpreted as a gloomy statement on how the world would perhaps prefer O’Brien emulate Pete Davidson, he breaks out into a wholesome smile. “I thought I looked awesome! I’ve never looked so cool.”

It’s somewhat understandable why O’Brien’s fans were so pleasantly surprised. The actor rose to fame as a dorky sidekick in cult smash series Teen Wolf, then ascended even higher as a straight-laced, affable leading man in The Maze Runner franchise and Love & Monsters. He’s equally as down-to-earth when he joins our Zoom call from his home in Los Angeles. Dressed in a white t-shirt (sans accessories), he’s quick to lighten the mood even when the topic of conversation threatens to turn serious.

O’Brien’s latest film, the ’50s gangster whodunnit The Outfit, sees him explore the murkier depths of morality, a side of him rarely exhibited since Stiles Stilinkski was possessed by an ancient spirit at Teen Wolf’s peak. (Unless you count his turn as the scarf-stealing boyfriend in Taylor Swift’s All Too Well short film.) “There was something really special about this script,” he says, remembering that when he read it for the first time on a plane he “stood up and clapped.” Soon after landing, he emailed an audition tape straight to director Graham Moore, a method he admits to having a very low success rate. (So far, it’s worked only once.) “I've definitely done that before when I feel particularly passionate about something,” he explains. “But it's a line you don't want to [cross]. I don't want to beg for things. You want to be wanted. It's weird how this business works, it's like dating,” he jokes, bursting into laughter. “You have to play hard to get.”

Still, his enthusiasm ended up working in his favor. Both Moore and The Outfit co-star Mark Rylance have praised O’Brien’s tape as the best audition they’ve ever seen, a fact that makes the actor grimace in disbelief. “I don't think it was that good!” he says, completely incredulous. “I even remember being somewhat upset with it.” Despite how well it went down, that tape stays with him like those mortifying memories that resurge every once in a while. Like the porous sponge for feedback he is, he went so far as to preface his audition with a disclaimer that if his performance hit a wrong note, he’d love to discuss it further.

His character, Richie, is the head mobster’s son whose naivety and arrogance belies his intimidating status. As filming began on a soundstage in London, O’Brien says he came to realize that Richie is just a “kid [in] way over his head.” “When I first read [the script], I was like, ‘Oh, what a cocky shit,’” he says. “Everyone’s operating in this gangster world, and it’s all about survival. I ultimately came away [with the understanding] that he’s the least equipped to survive this game, meaning that he might actually have the most good in him.”

To a certain extent, The Outfit, which is set entirely in a tailor’s workshop, is also a tribute to the craft behind a well-made suit. A self-proclaimed “sweatpants wearing motherfucker,” O’Brien does not feel remotely at home in luxury clothing, but exquisite tailoring has that singular power to change you from the inside out. “There's such a flashy thing about [Richie] that you need to feel a little bit,” he says.

On set, O’Brien would quickly discover how fun it is to perform opposite Rylance, despite his reputation as a classically trained, Academy Award-winning actor. (“He does have a very childlike spirit that he's still in tune with,” he says of his co-star.) He recalls Rylance showing up to the first day of rehearsals with a ball in his bag so the cast could play four square. And O’Brien puts on a gravelly British accent to demonstrate how, during the film’s gruesome sequence in which Rylance’s character stitches up Ritchie’s gunshot wound with a sewing needle, Rylance would tickle him while asking the director for notes.

What O’Brien admires most about Rylance, he says, was the way he “stood up for the actors’ process,” forcing him to reflect on how he wasn’t afforded the same level of respect in his own career. “I grew up in a medium that didn't necessarily prioritize [actors],” he confesses. “If anything, I would get gaslit in a way. If I ever wanted to stand up for my process, it would be like, ‘Shut the fuck up. Are you getting big headed now?’ As a younger actor, I was made to feel like I was being difficult if I had an idea or I wasn't feeling right about something, which are all things that an actor should bring to the table.” When asked for a specific instance, he’s reticent to share the finer details, but he acknowledges that he fell victim to ego-driven bosses eager to squash the inexperienced kid. “I think certain people would try to use [my age] to get control. [But] an actor should absolutely have autonomy over their performance. A director said to Tom Hanks that an actor needs to know the text, show up with a head full of ideas, and be on time, and that’s always stuck with me.”

It’s perhaps in this search for autonomy over his work that he chose against reprising Stiles in the recently announced Teen Wolf movie. The thought process behind that decision was both “complicated and not,” he says, but he doesn’t hesitate to elaborate on why he’s not returning to Beacon Hills.

“Ultimately, it didn’t feel like it was going to hold the same spirit,” he explains, adding that the people he met through the show are still dear to him and were “instrumental” to his career. “I loved the way we had closed the book on it, so unearthing that again is a big deal. It was all happening very fast. Tyler [Posey] and I were in communication on a daily basis throughout the entire thing.” With a sigh, he adds: “They also blindsided us with it a little bit. Nobody really knew that was going to happen. It just didn't work out, and I'm really comfortable leaving it where we left it.”

Seemingly everything O’Brien does makes headlines: turning down Teen Wolf, dyeing his hair blond, and everything in between. In the middle of lockdown, he delighted millions once again with his rendition of the infamous “fuck you flip flops” scene from The Social Network, a show-stopping monologue he had committed to memory ever since he saw David Fincher’s modern classic at 19. On a trip to Vegas with a group of friends (including the Mark Zuckerberg to his Eduardo Saverin, Sarah Ramos), he noticed that it had circulated all the way back to Andrew Garfield himself. “He was a really good sport about that,” O’Brien says with a sheepish chuckle. “It's just super cool that a video we screwed around with two years ago is relevant enough to still be addressed by the guy who did the scene,” he adds with the humility of someone still not wholly aware of the hold he has on the online zeitgeist.