Role Model Is Setting Himself Up For Happiness

Where should we begin? Perhaps at an LA bungalow, where Tucker Pillsbury is in repose. Sprawled across his boho patterned couch, the singer more commonly known as Role Model has his head cradled on the armrest, his socked feet stretched across the cushions. A scattering of torso tattoos peek out from the unbuttoned top and bottom of a blue striped shirt he’s paired with black jeans. He’s wearing a Poconos hat from his own merch line and a gold necklace with the outline of his home state, Maine.

The casualness of his pose, which the 29-year-old eases into over the course of an hour-plus conversation in mid-July at his home, matches his unexpected vulnerability. In public, Pillsbury’s persona normally involves a certain kind of showmanship. He’s a podcast guest who is prone to banter and sarcastic quips. A man who kept up a yearlong gag imploring fans to stream his music and buy tickets to his tour so that he could afford a Birkin bag. An artist who became known for getting assorted celebrities — Hilary Duff, Olivia Rodrigo, Kate Hudson, Robert Irwin, and many more — to gleefully dance onstage during his peppy hit “Sally, When the Wine Runs Out.”

But reclining in the sunny living room of his Spanish-style house in the Los Feliz neighborhood of Los Angeles, Pillsbury seems eager to speak from the heart — perhaps because he just started seeing a therapist for the first time the week prior. “It’s going well. I don’t know if once a week is enough for me,” he says. “I feel like since I’ve got 30 years of sh*t I’ve got to start dealing with, I need more therapy.”

This interview isn’t not like a therapy session. I’m perched across from him in a green velvet chair, notepad in hand, separated by the zen tableau of a large wooden coffee table topped with dried billy button flowers, an unlit Le Labo Santal 26 candle, and Pillsbury’s half-drunk iced coffee. For the most part, music has been where Pillsbury has been able to freely express his feelings. Over the course of his career, he’s segued from rap to electro-pop to what people around him have described as “lake pop,” country-tinged songs whose upbeat summertime sounds mask the outpouring of emotions within. “I want it to sound fun and distract people from whatever I’m going to be saying,” he says. “I don’t want to drag people down with me.”

Now he’s about to unload a new batch of confessions on his third studio album, Chuck Timely & the Hourglass, out Aug. 7. “Making the album and writing all those songs — I think me going to therapy now is a result of that. There’s a lot of self-discovery through mindlessly dating or intentionally dating,” he says, referencing the subject matter of many of the tracks. “You start to question if maybe you’re the problem, and I think maybe there are things in myself that I need to change before I’m — I don’t know. The album did something very good for me in the way that it made me look at myself a little bit deeper and question how much I actually have it all figured out.”

One question he wasn’t asking: how to follow up the viral success of “Sally.” “I weirdly did not feel pressure,” he says, popping a Zyn. “I think it’s because I love ‘Sally,’ and I’ll be performing that till I’m in a wheelchair, but lyrically, that song could have been written by a 5-year-old, especially the bridge, which is the most famous part. Those are some of my worst lyrics. So I didn’t feel pressure because, to me, the bar was really low.”

He began working on Chuck Timely early last year, putting together a mood board of visual inspirations for the era and the album’s title avatar — including Paul Newman at his coolest and Charli xcx’s The Moment poster — but he says his label wasn’t totally sold on introducing another character just as mainstream audiences were wrapping their heads around the name Role Model. “Obviously there’s something about me and alter egos,” Pillsbury jokes. “I haven’t analyzed that yet.”

When he first started releasing music in 2016, he tried a few mononyms — Tucker, Dillis — before eventually settling on Role Model. “I think Role Model is the dumbest stage name, but I’m in too deep,” he says. Chuck Timely was actually another alias he originally considered — to the point that he snagged the Instagram handle years ago and held on to it, intending to secretly release music as Chuck on the side. But he eventually ditched that idea and decided to use the name for this album instead. “There was never a plan to go method” with Chuck for this era, he says. “It was literally just something to represent the themes in the album and how we went about producing the songs.”

He wanted Chuck Timely — introduced earlier this summer with lead singles “High Hopes 3000” and “Joy” — to feel like “a journey that someone goes on, like one of those dumbass Lord of the Rings movies or something,” he says. In this case, Pillsbury wrote about his quest for contentment and companionship after heartache. “Even if I go into a healthy relationship, there’s still something wrong that kind of eats me alive a little bit,” he says. “I am trying to figure out what that is, but I don’t think dating or finding love can fully heal that.”

“I am deserving of something real, something true, someday soon,” he sings on the album’s opener, “Chuck’s Mantra.” The line is, in fact, Pillsbury’s own mantra. The feelings he’s singing about, Pillsbury stresses, are explicitly his own — though the facade of Chuck, he admits, is nice cover for getting deep: “It kind of removes me from things a little bit.”

After a decade in the industry, Pillsbury is still navigating where to draw the line between his public and private personas. His previous long-term relationship with Emma Chamberlain wasn’t just public — it was intertwined with his career. She appeared in his 2022 music video for “neverletyougo,” from his debut album, Rx, and the pair hard-launched their relationship with a GQ cover story on Valentine’s Day 2023 before they reportedly split that fall. Pillsbury seemingly detailed the heartbreak that followed on 2024’s Kansas Anymore.

“Keeping things about music is what I’ve learned. Otherwise, the internet just has a field day,” he says. “Everyone’s a detective.”

Case in point: Since late 2025, Pillsbury has been linked — via TMZ and various paparazzi photos — to Dakota Johnson. (Johnson’s mother, Melanie Griffith, has also chimed in, saying she thinks Pillsbury is “fabulous.”) Pillsbury is trying to keep his relationship private, he says, but he does admit that they’re together. Johnson is also featured on Chuck Timely. The actor performs a spoken-word bridge on “Love I You,” a standout track that details Pillsbury’s loneliness during his single days of desperately seeking companionship and drinking his sorrows away. It culminates in a tipsy, flirtatious conversation between Pillsbury and Johnson.

“Hey, I think you’re perfect,” Pillsbury says on the bridge.

“You say that to everyone,” Johnson replies.

“K, well, is it working?” he says.

“Yeah, but don’t tell anyone,” she answers.

Pillsbury always planned to include a female voice on the song, though Johnson’s cameo happened somewhat by accident. “I had a lot of names to pick from for that, and then Dakota came to the studio one day, and Mason [Stoops, guitarist and producer] was like, ‘Why don’t you do it?’” Pillsbury recalls. “I was like, ‘Stop! We’re not mixing work and relationships. She was like, ‘I’ll do it,’ and stood right up and got in the booth and knocked it out better than we could have imagined. So I was like, OK, if she’s down — I mean, that’s an amazing cameo.”

Elsewhere, on a song called “Good Thing” — and then again on his couch — Pillsbury details his incredulity that a new romantic partner could actually be, well, a good thing: “I expect the worst-case scenario, always,” he tells me. “I wouldn’t change that about myself. I think it’s good to have those questions and not just be diving headfirst into things based on attraction or a first date going well.”

There’s also “Stain,” where he sings about an ex calling his house and making him feel like “a backup plan,” and “The Wedding,” which he wrote after attending his first nuptials as an adult last year and feeling “weirdly moved” by the experience. (For the record, he did not attend Taylor Swift and Travis Kelce’s wedding: “I couldn’t go,” he says. “I was busy in the middle of an album rollout, but it looked amazing.”)

“Marriage is not that romantic to me,” he says. “Being with someone for life is romantic to me. But the whole idea of going into a church and inviting all these people? … That was never attractive to me. Then I went to my first wedding, and I cried.”

The tears stemmed from a sense of his own stagnation and “watching people’s lives move on,” he says. Shortly after that wedding, his sister got married, resulting in “a double whammy” of self-reflection. “That one also kicked my ass.”

Pillsbury is close with his family. Despite having spent nearly a decade in Los Angeles, “home” for Pillsbury is still Cape Elizabeth, Maine, the small oceanside town just south of Portland, where he was born and raised. Living across the country from his parents, sister and brother, and baby niece has been hard. “This time every year, I have a bit of a crisis of like, ‘What am I doing?’ I miss home a lot as soon as summer starts creeping up, and it’s hard for me to focus on anything else other than I want to be home,” he says. “I was like, there’s obviously deeper things going on — book me a [therapy] appointment.”

These Pillsburys, to be clear, have no relation to the Doughboy-famous pastry dynasty — Tucker’s dad was a real-estate appraiser, and his mom was a special-ed teacher. (Not that that stopped classmates from poking his belly as a kid.) Still, he’s proud of his name and regrets not just using his birth name as his stage name. “I get made fun of for it,” he says, “but I’ve always loved my name.”

When he visits Cape Elizabeth, he stays in his childhood bedroom where the walls are still covered with a forest motif of animals that his mother painted when he was a kid. (“I go home a lot because I like the normalcy,” he says.) Eventually, he’d like to buy a home in Maine and split his time between coasts. “I need another ‘Sally’ in the books and I’ll do it,” he deadpans.

This go-round, he’ll spend his album release day playing his first-ever concert in his home state, something he’s “always wanted,” he says. “I love Maine so much, and I think I’m just now beginning to feel loved by it.”

When I point out that his passion for his home state resembles fellow New Englander Noah Kahan’s connection with Vermont, Pillsbury notes that Kahan’s 2020 EP, Cape Elizabeth, is named after Pillsbury’s hometown. “It’s a small world. We have some mutuals and some mutual favorite spots in Maine,” Pillsbury says. “Maybe we’ll throw a festival someday. That’d be awesome.”

When Pillsbury first thought about leaving Maine, he’d hoped to go to the Savannah College of Art and Design or a school in New York or Los Angeles. But he ultimately chose Point Park University in Pittsburgh because it was “the only one that gave me money,” he says with a laugh. He attended on a film scholarship but found college isolating; while struggling with depression, he began making rap mixtapes using his friends’ music equipment and uploading his creations to Soundcloud.

One such track caught the attention of Pittsburgh native Mac Miller, and Miller’s team flew Pillsbury to Los Angeles. After a quick trip home to grab his things, Pillsbury spent the next six months couch-surfing with friends and staying in Airbnbs while he networked and found his footing in the city. “I think everyone should go through that, but that was rough,” he says. “I remember texting my sister for $5 so that I could get a McDonald’s breakfast for the day, saving half of it for dinner.”

In the years that followed, Pillsbury’s status has, obviously, skyrocketed. He performed on Saturday Night Live, sold out Radio City, and was hand-selected by Lena Dunham to costar — under his own name, not Role Model — in her upcoming Netflix rom-com Good Sex, opposite Natalie Portman. “I had to do a chemistry read with her, and I was f*cking terrified,” he says. “But as soon as I got there, somehow the nerves went away, and I did a good enough job to get the part.”

The lifestyle shift that comes with fame has “been difficult,” he says. “There are amazing parts of it, and there are benefits that you can’t deny are great, but the part that I struggle with is you sometimes are in environments or around people of this certain level of status that make me feel very separate from the rest of the people in my life and where I’m from.” In particular, he takes issue with the “luxury of it. I don’t like that stuff. I joke a lot on the internet about wanting a G-Wagon, and the Birkin thing that went on for like two years, and it’s not real, obviously. That is not me.”

He struggles with the expectation that he’s in line to be “the next big male pop star,” as he puts it. “I’ve never said that I want to be that. Maybe because I’m not wearing a bunch of glittery leather jackets and nice clothes onstage or to events, people are like, ‘Oh yeah, no, this isn’t it. We want something shinier,’ but I’ve never said that that’s going to happen. Like, I’m going to continue to get a shirt that has stains on it and wear it for the next two months because I love that shirt.”

He continues: “I don’t ever want to set the bar for people. If I got a stylist and was like, ‘Put me in the nicest sh*t every time I’m onstage,’ then, if you step out onstage in a little T-shirt and jeans, people are like, ‘Oh, this is the downfall. This is the flop era.’ I don’t want to set people up for that.”

He doesn’t want to set himself up for disappointment, either, which is why he avoids specific career goals or aspirations. “I don’t want to get let down, so I think it makes the highs feel a little bit more high. It makes the lows feel a little bit less low,” he says. “I don’t have any goals. I’m going with the flow.”

Pillsbury will spend the fall away on tour — he’s retiring the “Sally” cameos, though he’s not ruling out the possibility of a new bit bubbling up — but he’s also, finally, found a way to make Los Angeles feel like home when he’s here. The artwork on the walls around us are all reminders of Maine: a painting of an ocean wave; an embroidery that reads “To a friend’s house the road is never long.” “When I don’t have success or when my career isn’t doing well,” he says, staring up at the ceiling as our session comes to a close, “I’m trying to set myself up to be happy.”

Top image credit: Versace clothing; Repetto shoes.