Dylan O’Brien knows he’s been on your mind lately. From starring as the heartbreaker lead in Taylor Swift’s “All Too Well” short film to going viral for his bleach-blond buzzcut, the former Teen Wolf star has been the main character on social media more than once this past year.
But now, he’s stepping into a role that is much less meta. With his new film The Outfit, a crime thriller that details one violent night in an English tailor’s shop, he portrays Richie, the gruff son of a local Chicago mob boss. The film, which feels less cinematic and more like a play, let O’Brien live out his theater dreams. “While this was still a film medium, at the end of the day, this could exist on Broadway,” he says over Zoom from his New York City apartment. “It’s five characters in a space and all dialogue.”
Ahead of its release, O’Brien discussed that viral photo, working with Taylor Swift and why he declined to do the forthcoming Teen Wolf movie.
GQ: The Outfit really feels like a stage production. Did you approach your role as Richie with that in the back of your head?
Yeah. It was not a lot of set pieces, not big action sequences—it’s five characters in a space and all dialogue. It was very important for this piece in particular to like, have rehearsal time, and we had a full week of rehearsals. It felt like we were doing a play. We were in the space on the set; we were staying a block down from [the stage]. We shot it sequentially, which is another complete rarity. But because we just had one space we were able to do that, which is really cool. In terms of how I prepped differently, I knew all my scenes like the back of my hand before I ever shot one of them. I could have performed the entire thing. I don’t wanna speak for Mark [Rylance, the film’s lead] who had 120 pages of [dialogue], but I think we all were dialed in on our scenes because of the amount of preparation time that we had before we even started.
You’ve never performed on Broadway. Did this film ignite the flame for it?
I always have had stage aspirations; I’ve always been curious about that. It’s not Broadway, but one of my first ever experiences was a small play in Los Angeles. I was 18, and I had very little acting experience. To this day, it’s one of the experiences that I cherish the most. They always say, “TV is for the writers, film is for the directors, the stage is for the actors,” and there’s something very true to that. There’s something very special about being able to breathe out a story all in one without any interruptions for an audience that is there to receive that story. While this was still a film medium, at the end of the day, this could exist on Broadway. I have to do Broadway before I call it a career, for sure.
What initially drew you to The Outfit?
It was an amazing script. In the industry nowadays, the script is the last thing to come together now. It’s very common that you receive scripts with a disclaimer that “it needs work” or “it’s not finished, but are you interested?” It’s hard to make those decisions. This [movie] was so old-school in the way of being so polished and dialed in. It was ready to be shot the second I read it; it was just fucking structurally sound and dripping with character. It was original, but it paid homage to a really cool period of film—this Chicago, noir, gangster thriller in a contained environment with a whodunit vibe. I literally stood up and clapped after I read the script like an audience member.
Did you take any inspiration from any other mob movies or characters in particular for your role?
I could lie and say that I wanted to be like The Maltese Falcon, but I didn’t, actually. I wanted it to feel like homage but not derivative. I didn’t want to mess with it, but I didn’t want to build my character from a place of copy. It’s one of those superstitions when you’re prepping something. So when I made this movie, I was going to bed every night watching Vanderpump Rules. Not even kidding. It soothes me; there’s something about the chaos that settles me.
Who’s your favorite cast member on Vanderpump Rules?
I’m a big Schwartzy guy. But I love all of them—for all of their qualities, both good and bad.
You went viral on social media when a photo of you with bleach blond hair and tattoos surfaced while shooting your next movie Not Okay. What was that experience like for you?
It’s so meta. I mean, that’s the entire point of the movie, too, so that was really funny. My whole idea of that character is this person that has sort of been birthed in this last decade. It’s like a Fortnite skin—bleached hair, full tats, like absolute appropriation. They’re usually from predominantly white, suburban neighborhoods, but they talk like they’re from the streets. We find that very appealing right now. And I say we, because I do, too. To say that I’m not a part of any of this is a complete lie. We, collectively as humanity, are on our phones, on TikTok. It’s such a piece of our culture that we all participate in, no matter how much you like to think that you rebel against it. The response to it was really interesting because I feel like we can use all those responses in the movie.
I also feel like that photo came at an interesting time because you starred in the “All Too Well” short film not long after. What was your experience like working with Taylor?
First of all, it was surreal. She’s genuinely such an incredible person that it felt like friends making something. By the time we did it, it was just really fun, really cozy and a really comfortable environment. I trusted her implicitly and not surprisingly at all, she had a fucking plan and knew exactly what she wanted to do. From the second that we first talked, she sent me over her entire lookbook for the film. She had the DP that she wanted to reach out to, she had the aesthetic, she wanted to shoot on film, and she had it all locked in. I thought that it was an incredibly important thing that she was trying to say with the video, too, which I felt like I got and wanted to really take part in executing.
It’s so hard to execute relational dynamics, the complexities of a relationship, power dynamics and age dynamics. I think it is the hardest thing to achieve in a cinematic format, and she is somebody who I think is so brilliant, and so emotionally intelligent on that level of relationships. There are people on this earth who fundamentally understand how people work and how dynamics work more than others, and I think that’s what makes her such a brilliant writer. She’s such a fucking god-given poet. It was automatic that I was gonna say “yes” to it. I feel like she hit it out of the park more than I could have ever imagined.
Were you already a fan of “All Too Well” and Red before you were approached for the short film?
Stanship of Taylor has really heightened in the last four or five years. Obviously, I’ve always known who she is, but I think it was one of my good friends who really got me into her in-depth. I totally knew what “All Too Well” was; I knew what it meant to the fan base. The Red re-record, I’ve been all about it. She played [“All Too Well”] for me at her place, and she sang along for us—live. It was mind-blowing. I was like, “I can’t believe the person’s asking me to be a part of something that I know is so monumental for her.”
Did you model your character on anyone specific or pull inspiration from anybody?
No, I felt like I understood the assignment. From our first conversation I was just like, “I got it.” I got what she was trying to say, so I felt confident in my role in helping her execute. I’m really fascinated with relationships, too. In terms of executing that in a cinematic light is really hard to do, so I felt like I totally got the whole thing from the get-go and wanted to be a part of it.
I’d be remiss not to mention your cameo on Curb Your Enthusiasm last year. How did you end up on Larry David’s radar?
Curb was great. I love the “alter ego version of yourself” type of humor, so that was really fun. It was an audition, a Zoom improv with Larry. I actually tried to screen record it too (to have for my mom), but I had headphones on, so my recording doesn’t have sound. I just have this 10 minute silent improv with Larry on my iPad. Working with Larry was just such an all time moment. He wasn’t an asshole. You never really know until you get there, right? But he was so great. We talked about the Jets. And he’s quick to laugh at other people being funny in his space, which I think is a really important quality. Sometimes comedic icons like that can be sort of selfish and not want anyone else to be funny; I think it’s wonderful when someone who’s that successful and that respected is still just having fun and laughing with you. At the end of the day, that’s what we do it for, right? To have fun.
It was announced that the Teen Wolf film was happening but you wouldn’t be joining. Is that still the case?
Yeah. It was a tough decision because I love Teen Wolf, [my character] Stiles, and so many of the people that I worked with. It was my first job ever, so that show will always tug at my heartstrings. A lot of things went into the decision. It was really hard to wrangle this. First of all, I think it all happened really fast. It came as a surprise—we did not know that this was happening, so to announce and then try to wrangle everybody for a deal and be on set all within six months is a really hard thing to do.
I think everyone was trying to figure it out, and I was, too. I was talking to Tyler [Posey, his Teen Wolf co-star] every day all throughout it, but ultimately, I felt settled and at peace with where I left that. I felt like we all came back for the series finale and that was sort of that moment. It just felt nice where it was, and I didn’t want to fuck with that. I also never want to come to something if my full heart’s not in it, especially something as precious to me as Teen Wolf. But I love all those guys and I always will, and I hope it fucking rocks.