Tucker Pillsbury, who performs under the moniker Role Model, has reached pop's upper echelons through a string of career-defining moments. The 28-year-old artist points to supporting Gracie Abrams on tour, headlining storied venues such as Los Angeles' Greek Theatre and New York's Madison Square Garden, and generating viral buzz by performing his hit "Sally, When the Wine Runs Out" with surprise guests like Charli XCX and Natalie Portman