Chappell Roan’s Unconventional Journey: From Midwest Princess to Pop Sensation

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Chappell Roan, the pop sensation poised to be L.A.’s next superstar, has unveiled her long-awaited debut album, “The Rise and Fall of a Midwest Princess.” Her journey to stardom has been an unconventional one, filled with highs, lows, and unexpected turns that have shaped the artist we know today.

Formerly known as Kayleigh Rose Amstutz, Roan’s foray into the music scene began at the tender age of 17, with the upload of her original tracks to YouTube. In a touching tribute to her late grandfather, Dennis K. Chappell, and his beloved song “The Strawberry Roan,” she adopted the moniker Chappell Roan. Little did she know, her path would lead her from small-town dreams to the bright lights of Los Angeles and beyond.

Roan’s musical odyssey kicked off when she ventured to New York City, captivating audiences with her soulful performances at a series of musical showcases. It wasn’t long before Atlantic Records recognized her undeniable talent and signed her on. Yet, as fate would have it, her partnership with the label was short-lived. Despite the success of her 2020 hit single, “Pink Pony Club,” Atlantic Records chose to part ways with her. This setback prompted Roan to return to her roots in her Missouri hometown during the pandemic, navigating the economic challenges that many artists faced.

But true artists persist, and Roan clawed her way back into the spotlight as an independent recording artist. Two years later, in 2023, her tenacity paid off when she signed with Island Records. These twists and turns, along with her unwavering determination, are beautifully reflected in her debut album.

Leading up to the album’s release, Roan treated fans to a mesmerizing two-part docuseries, “Chappell Roan—The Rise and Fall of a Midwest Princess.” The series chronicles her return to her Willard, Missouri hometown, offering a poignant glimpse into the profound influence of her conservative Midwestern upbringing on her musical journey.

Chappell Roan's Unconventional Journey: From Midwest Princess to Pop Sensation
Photo: Ryan Clemens

“I’ve always wanted to tie my project back here,” Roan shared. “I have to honor this place that raised me, no matter how I feel about it. Like, it’s just always going to be a part of me.”

“The Rise and Fall of a Midwest Princess” explores Roan’s complex relationship with her roots, a theme echoed throughout her album.

The inspiration behind the album’s title, however, is a bit less complex; “The Rise and Fall of a Midwest Princess,” stems from a personal touch—Roan’s very own tramp stamp.

“I have a tramp stamp that says princess and ‘Midwest princess,’ me being from the Midwest, it just made sense,” Roan shared in a recent interview.

Many of the album’s tracks delve into the realm of dreams and fantasies, inviting listeners into Roan’s world of uninhibited self-expression. Take “Pink Pony Club,” for instance, a therapeutic anthem that solidified her status as a queer icon. The song recounts the story of a girl leaving her small-town Tennessee life behind to pursue her dreams in the dazzling lights of West Hollywood.

“All of a sudden, I realized I could truly be any way I wanted to be, and no one would bat an eye,” Roan confessed.

“The Rise and Fall of a Midwest Princess” achieves a delicate balance between pop perfection and heartfelt ballads. Tracks like “Super Graphic Ultra Modern Girl” and “HOT TO GO!” deliver pure, unadulterated fun, channeling Y2K vibes that will have you singing and dancing in no time. Accompanied by vibrant music videos, these songs represent a bold shift in Roan’s career, one she once questioned but now wholeheartedly embraces.

“I thought it made me ‘less of a writer’ to write a song that really had nothing to do with anything other than having fun and being hot,” Roan admitted. “I was wrong…”

As Roan embarks on her tour, fans eagerly anticipate her performance at the College Street Music Hall in New Haven in April. Tickets are available on Eventbrite and her website. Additionally, she will be the opening act for the first leg of Olivia Rodrigo’s GUTS tour, promising an unforgettable musical experience.

In “The Rise and Fall of a Midwest Princess,” released on September 22 via Amusement/Island Records, Roan artfully navigates the journey of a “small-town girl [who] goes to a big city,” grappling with the reality that the spotlight isn’t quite as alluring as she once envisioned. Born Kayleigh Amstutz, this singer-songwriter’s path has been a remarkable one, and her debut album is a testament to her evolution as an artist. From humble beginnings to dazzling heights, Chappell Roan is a name to watch in the world of entertainment.

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