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Before winning a Grammy and captivating audiences with her bold performances, Chappell Roan — born Kayleigh Rose Amstutz — was just a small-town girl chasing big dreams, navigating the harsh world of reality TV talent shows. Long before her breakout album The Rise and Fall of a Midwest Princess, Roan took a shot at stardom via America’s Got Talent at 13 and The Voice at 15 — only to be met with closed doors and crushing rejection.
In a candid interview with W Magazine, the now-celebrated pop artist opened up about her emotionally difficult Voice audition, revealing how a dismissive producer left her feeling humiliated. “The producer or whoever the f*ck was watching did not even look up from his phone,” she recalled. “He was like, ‘OK, next.’ And I went up there and sang a cappella, the scariest thing ever. He never really looked at me.” Her audition piece? Rihanna’s emotionally charged ballad, Stay.
Roan also shared memories of her earlier attempt at America’s Got Talent, when she traveled with her family to Austin, Texas, at just 13 years old. After waiting in line for hours, she sang Cyndi Lauper’s True Colors, only to be sent home without advancing to the next round.
Despite those early setbacks, Roan’s passion for music never wavered. Raised in a conservative Christian household in Willard, Missouri — her father a Naval Reservist, her mother a nurse — she began playing piano at 10 and performed publicly for the first time at 13. At 14, she started uploading videos on YouTube, slowly catching the attention of music labels.
In 2017, she signed with Atlantic Records and released her debut EP. While that project failed to make a major splash, Roan remained persistent. Her debut album, The Rise and Fall of a Midwest Princess, released years later, earned her a cult following and ultimately became the catalyst for her breakthrough.
In 2025, her perseverance was rewarded when she took home the Grammy for Best New Artist. During her acceptance speech, Roan used the moment to spotlight artist welfare in the music industry, saying, “Labels, we got you, but do you got us?” She advocated for record labels to provide artists with living wages and access to healthcare — a powerful message that underscored her journey from overlooked teen talent to industry trailblazer.
Now 27, Chappell Roan is known not only for her vocal prowess but for her unapologetically bold drag-inspired fashion and theatrical performances. Her path may have started with rejection, but her rise proves that resilience, authenticity, and talent can’t be ignored forever.