When Tucker Pillsbury arrives on set, he carries himself with a cool nonchalance. Once he’s under the studio lights—a toothpick dangling from his lips, grime caking his face, and Calvin Klein denim draped over his shoulder—the shoot chips away at the affable Pillsbury to reveal Role Model, the rockstar.

The throngs of eager fans who have come to obsess over the Maine-born singer-songwriter know him for the twang of his voice and wry smile peeking out from under a trademark cowboy hat. From “Sally, When the Wine Runs Out” to “Some Protector”, his brand of heartsick, catchy rock has found itself nestled into the ears of countless devotees, obsessively bumping the recently released deluxe version of his 2024 album: Kansas Anymore. It’s a busy time for the rocker—about to release a reissue of his track “The Longest Goodbye” on July 9th, with a new feature from Laufey. Aside from his music, there’s another role on the horizon. Recently announced as the newest addition to Lena Dunham’s latest movie Good Sex, and currently playing sold-out arenas alongside Gracie Abrams (with a soon to come European tour of his own ), Role Model’s next venture is an evolution—and an apt one for someone whose initial love of music was rooted in making movies.

Inspired by an adolescent love of filmmaking, Pillsbury eventually went to film school in Pittsburgh, where another student showed him the possibilities of music production within the confines of a dormitory. “There were kids on my floor who were handing out CDs and had made mixtapes. And I was just curious, how are you doing this?” They revealed the impromptu recording studio, which spurred Pillsbury’s interest in the burgeoning hip-hop scene in Pittsburgh. “I hadn’t seen that before in Maine. At the time, that was pretty foreign. We did not have the music scene, and there definitely wasn’t a DIY sort of music scene like that, so that was new. And they were just like, ‘Do you want to try it?’ And I did, and I fell in love with it. They loaned me their gear. And for a month, I was just completely obsessed with it, and started pivoting towards that. I still love film, but my brain became fully obsessed with music.”

Infatuated with the music scene already establishing itself in Pittsburgh, Pillsbury began his career making hip hop. “Everyone was friends and were collaborating and doing shows together, making songs together. It was this cool local legends type of scene. And I just wanted to be a part of it,” he says, going on to explain how his music style evolved: “Later, as I was putting stuff out on the internet, I realized how big the world is, and the power of that. You don’t need to be what is happening in the city that you’re in, there’s a whole community and cool sub-genres all around the world. So I kind of departed and started experimenting with singing and writing songs that felt more personal and genuine.” This transition spurred Pillsbury’s early success, partially owed to the acclaim of his self-released EP Arizona in the Summer in 2017.

After he put out his EP, Mac Miller’s manager DMed Pillsbury, leading to a career-altering meet-up. Pillsbury is quick to admit that he didn’t necessarily grow up a diehard Mac Miller fan, but the Pittsburgh music scene quickly enveloped him. “His face is everywhere around the city, you kind of have to get to know it. And I fell in love with his music.” On this encounter with the beloved late rapper, he says: “I was blown away. Long story short, they flew me out to meet and hang, and make music. That was just the coolest moment of my life. And kind of the start of everything, because then labels started hearing about it, and my name started getting tossed around within the industry for the first time. I owe a lot to that moment and to him.”

When we ask Tucker about his alias and any association with the movie Role Models, he cheekily sighs: “The movie thing needs to die. The problem is, in my first ever interview, way back, I made a joke.” The sarcastic comment about an obsession with a 2009 Paul Rudd movie has since become an entry on his Wikipedia page and more or less the official story on the origins of his stage name. “I get TikToks that are like, ‘How Role Model Got His Name. Paul Rudd. Role Models.’ I didn’t know it wouldn’t translate over text,” he laughs before setting the record straight: “I was just young, and I thought it was funny and ironic, at a time when I was drinking and smoking a lot of weed. And then it sticks, and you forget that—if things work out—that is your name forever.”

Pillsbury has been on tour, on and off, with Gracie Abrams for the past year. A longtime friend, he now has the opportunity to close her tour in Mexico City together. “She was one of the first people I met and hung around with when I first moved to LA, and was just very welcoming. She was about to put out her first EP Minor. I feel like I’ve had the privilege of watching her from that very beginning moment to now doing massive arena shows around the world and exploding, rightfully so. It’s cool now, I get to watch it side stage. It’s a very full circle moment for me personally. And it’s the best—she’s just the nicest person I could ever meet.” 

“I came from the skate culture of: I’m the kid with the camera, and I just filmed my friends skating all day. And then that extends into other things. I got very much into filmmaking in that way, and music was a big part of that.“

—Role Model

In a melange of exciting things on the horizon, Pillsbury is about to embark on a new chapter in his career path. He was recently announced—alongside Mark Ruffalo—as the latest addition to Lena Dunham’s next Netflix romcom starring Natalie Portman. While it’s a newer discipline for Pillsbury, it doesn’t come entirely out of left field. “I always had a camera in my hand. I was the kid in the friend group who filmed everything,” Pilsbury explains when describing how his initial musical exploits evolved from filmmaking. “I came from the skate culture of: I’m the kid with the camera, and I just filmed my friends skating all day. And then that extends into other things. I got very much into filmmaking in that way, and music was a big part of that. I think there’s a lot of correlation there. I ended up going to film school, but I think just doing that and making stupid videos with my friends—the music in all these little videos and stuff mattered a lot to me. It was a chance for me to score these moments. And I think that was the first time I really started caring about music on a deeper level, and pairing it with visuals and everything.”

Despite his early interest in filmmaking, a movie star turn wasn’t the plan for Pillsbury. “I liked being behind the camera,” he explains, “but I think becoming an artist, doing shows, and learning how to perform in front of people probably brings out a new side—you start to like whatever it is you get. And there’s a piece of you that likes being on camera and being in front of people and performing for them.”

When I ask him about Lena Dunham, he lights up: “She’s insane. She’s become an actual friend, and she texts me pictures of her pigs every day.” He says he only recently watched Girls, “because everyone was like, ‘You haven’t seen Girls?’ I was getting cooked for it forever. And then finally I watched the first three episodes, and was like, I get it now. I get her brain.”

With a new version of his track “The Longest Goodbye” releasing July 9th, Pillsbury is excited for the world to hear Icelandic singer-songwriter Laufey’s take on the track: “I asked her to come sing it on stage during my LA show, and as soon as I heard her sing the first line of the second verse I was like, ‘Oh, we need to record this’. I couldn’t think of a better voice to sing that song. Her voice is timeless, and that was kind of the word of the day when I was originally writing that song last year. I wanted to end the album with a very sonically timeless and classic song, and her voice brought it there for me.”

And of course, “I’m excited for the movie,” he says. “That’s a brand new thing. I’m so curious to see if I love that.” Whether he’s the rockstar belting to a humming sold-out arena crowd or collaborating with one of contemporary television’s most enigmatic minds, Tucker Pillsbury is ready for his next role. 

Photography Richie Talboy 

Fashion Alexander Roth 

Creative Director / Editor-in-Chief Stephen Gan

Hair Luca Tullio

Makeup Mitch Yoshida (Streeters) using Clé de Peau Beauté

Casting Greg Krelenstein (GK-LD)

Set Design Lauren Bahr (Walter Schupfer Management)

Video David J Barron

Digital Technician Mitchell Mylius

Lighting Technician Pablo Espinoza

Location untitled nyc

Photo Assistant Clay Campbell

Fashion Assistants Arut Arustamyan, Carter Bright

Production Assistant Ha Chu

All clothing, shoes, and accessories Calvin Klein