Tucker Pillsbury was a college freshman when some rapper friends of his left their recording equipment in his dorm room.

Pillsbury was majoring in film and had never sung or played an instrument while growing up in Cape Elizabeth. But he loved to write and create stories, so he decided to put the equipment to use. He went online and found YouTube tutorials about how to rap and record.

His rapping soon turned to singing and songwriting. Today, about five years after his accidental introduction to music, Pillsbury, 23, is a pop recording artist. Performing under the name Role Model, he has a recording deal with Interscope Records, whose roster of talent includes Ellie Goulding, Lana Del Rey and Lady Gaga, among many others. He released the six-song EP “Oh, How Perfect” in November and followed it with a headlining tour across the U.S. He’s currently living in Los Angeles and working on an album to be released later this year. When he came home to Maine for Christmas, fans seeking photos followed him and family members on shopping and skiing excursions.

“Writing was the only thing in school I really loved, but I had never thought about writing songs or putting my writing to music,” Pillsbury said.”You could just write stories, make up fantasies. The best thing a teacher could do for me is to have free-writing day.”

Tucker Pillsbury is a Cape Elizabeth native who performs and records pop songs using the name Role Model. Photo by Clare Gillen

Several of Pillsbury’s songs are ballads that deal with the insecurities and angst of people his age, a general theme he began writing about a couple of years ago after a skiing accident at Sugarloaf left him with a broken wrist. A few months later, a skateboard accident led to another broken wrist. The injuries sent him into a depression, but also led him to explore somber themes, which he likes to set to pretty, relatively upbeat melodies. His song “Hello!” is a good example, with lyrics about keeping feelings bottled up inside, but a slightly ’60s pop sound that includes horns, piano and strings. Pillsbury sings in a slightly breathy way, with just a hint of gravel in his voice. “To find someone who cares is getting hard to find/We should be dancing in the sun/It’s hard when everything is numb/I’d like to try and feel okay/So if I call what would you say?”

An earlier song, “Minimal,” includes the lines: “There’s too much going on/I wish the world would end/But it keeps on going/I think we should keep it … minimal, minimal.”



Pillsbury grew up in Cape Elizabeth, the youngest of three children. His mother, Susan Pillsbury, is a special education teacher in Cape Elizabeth schools, and his father, Rusty, is a real estate appraiser. Though he didn’t sing in chorus or play music growing up, Pillsbury says he was influenced by the music he heard playing in his house, including ’70s singer-songwriter Jackson Browne and ’60s jam band pioneers The Grateful Dead. He also had what he calls “a weird fascination” with Elvis Presley, the signing icon who died two decades before Pillsbury was born. He had an Elvis lunchbox and a giant cardboard cutout of the singer.

In school, he loved to write poetry and wild stories. He also drew and painted from a young age.  As he got older, his interests turned to film. He’d make videos of friends skateboarding, or skiing, something his family did often.

“He was a creative early on, and he was always a writer. I remember reading his writing in high school and thinking how easy it seemed to be for him, how different his writing was,” his mother said. “In college he’d come home and have me buy some canvases and just start painting. He’d have these images in his mind and was ready to paint.”

After graduating from Cape Elizabeth High School in 2014, Pillsbury decided to go to Point Park University in Pittsburgh, Pennsylvania, to study film. But early on, he started toying around with that recording equipment left in his room and hanging around with other students who rapped. Like all the creative ventures he had tried before, he seemed adept and comfortable at it. He soon thought about dropping out of college to pursue music full time, but his parents convinced him to stay. So he started performing rap at Pittsburgh clubs and making music that he’d put online.

Using the name Dillis, he performed at a show at the Maine State Pier in June 2016 that featured Post Malone and Fat Joe. But while listening to music for his raps, he began humming a melody and found that he wanted to sing. He decided to make music as a pop singer-songwriter and, by early 2017, was performing and recording music under the name Role Model. He picked the name because he loved Paul Rudd in the 2008 comedy film “Role Models,” as an energy drink salesman who is ordered by the court to mentor kids after being charged with assault and disorderly conduct.


“When he started making music, it wasn’t a surprise. The surprise was seeing him get up on stage,” his mother said.

Tucker Pillsbury at home this past Christmas, with his grandmother and cousins. Photo courtesy of Susan Pillsbury

In 2016 and 2017, as Role Model, Pillsbury recorded some songs and began selling them online. He also put out an EP called “Arizona in Summer.” His songs released in that period, including “Girl in New York,” gained a wide internet following and attracted national attention.

They also got the attention of Pillsbury’s current manager, Cole Silberman, who was then a business and communications student at Ohio State University. Silberman said, as soon as he heard Pillsbury’s songs, he knew “what was going on with him as a person and a musician,” and he wanted to be involved. He called Pillsbury and talked to him for hours. He’s been working with him on his music ever since. Pillsbury devoted so much time to music that his studies suffered and he ended up leaving school.

Rapper Mac Miller, who was from Pittsburgh and died in 2018, heard Pillsbury and invited him to Los Angeles, where Pillsbury met other musicians and producers and started making connections. By 2018, Silberman was fielding offers from recording companies, and Pillsbury eventually signed with Interscope. Pillsbury wrote the lyrics on the album, with various producers in Los Angeles helping with the music.

He currently has about a million monthly listeners on Spotify, including for the songs on “Oh, How Perfect.” When the EP was released in November, it garnered attention from music writers and bloggers around the country. On online music magazine DJBooth, managing editor Donna-Claire Chesman wrote that Pillsbury “commands our attention off the sheer strength of his potential.”

Pillsbury began his first headlining tour in November in Portland, Oregon, and continued onto Seattle, Denver, Chicago, Cleveland, Toronto, Boston, Brooklyn, Washington, D.C., and several cities in the south before finishing up in San Francisco in December. He played clubs that hold 500 or 600 people and nearly sold them out. He has not played Portland, Maine, yet, something he says his family “yells” at him about. But he said his goal is to be big enough to play Portland’s State Theatre on Congress Street, which holds more than 1,900.


Pillsbury got a tattoo of the “P” from the Press Herald logo to remind him of home. Photo courtesy of Tucker Pillsbury

Though he lives in Los Angeles, Pillsbury stays connected to Maine through family and friends. He also has a tattoo on his right hand of the “P” from the logo for the Portland Press Herald. He said he wanted a tattoo to remind him of home, but not something as obvious as a lighthouse or map of Maine.

On his headlining tour this past fall, he took a band with him, plus several longtime friends from Maine, on the road. Devon Forde, who met Pillsbury in grammar school, was the tour manager, dealing with hotels and venues. Forde said he was impressed with how comfortable Pillsbury is on stage, and how he can get “a crowd moving.” His mother, Susan Pillsbury, has seen her son perform several times and has a similar opinion.

She said their family is very proud and “blown away” by what’s he’s done in music so far, especially since he did it all on his own. And that his old friends are still friends.

“It is comforting for us to know his best friends are still with him,” she said.

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