Chappell Roan’s journey from ‘trailer park’ to self-proclaimed ‘Midwest Princess’

Chappell Roan's "The Midwest Princess Tour" is coming to an end after the singer's rapid ascent to the height of pop superstardom over the past year. 

The 26-year-old's headlining performance on Oct. 13 during weekend two of the Austin City Limits Music Festival marks her final scheduled tour stop. 

In September 2023, Roan kicked off her 89-date tour in support of her debut album "The Rise and Fall of a Midwest Princess," which was released the same month. At the time, Roan had amassed a cult following and devoted online fandom but was far from a household name.

However, the first few months of 2024 proved to be a turning point in the recording artist's career. Roan's star began to rise when she performed as one of the opening acts on Olivia Rodrigo's Guts tour from February to April.

Chappell Roan is ending her "The Midwest Princess Tour" this weekend at the Austin City Lights Music Festival. (Getty/Chappell Roan Instagram)

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On April 5, Roan released her single "Good Luck, Babe!," which she described on Instagram as the "first song of the next chapter." "Good Luck, Babe!" which was not included on her debut album, went on to become her breakthrough hit and one of summer 2024's hottest songs. 

As "Good Luck, Babe!" was climbing the charts, Roan shot to mainstream fame after her viral performance at Coachella 2024 in April. In August, Roan's daytime performance at Lollapalooza in Chicago drew the biggest crowd in the festival's history, a Lollapalooza spokesperson told the Los Angeles Times.

"The Rise and Fall of a Midwest Princess," which didn't enter the Billboard Albums Chart for the first six months after its release, hit the No. 2 spot in August with six of Roan's songs appearing on the Billboard Hot 100 that month.

Roan had a meteoric rise to fame over the last year. (Getty Images)

Despite the appearance of almost overnight success, Roan's path to fame has been years in the making and paved with obstacles. Roan's journey to Hollywood began with her humble upbringing in the heart of the Midwest.

Born Kayleigh Rose Amstutz, Roan lived in a trailer park as a young child before her family moved to a house in Willard, Missouri, a small town with a population of approximately 6,000. 

Roan was raised in a conservative Christian household and previously said she attended church three times a week growing up. In a September 2023 interview with Polyester magazine, the singer, who later embraced her queer identity after moving to Los Angeles, explained that she often felt out of place in her hometown.

"But the Midwest remains a very big part of who I am. It's where I grew up, and I do love certain parts of it — the peace and growing up in a trailer park, four wheeling, the farm and bonfires."

— Chappell Roan

"I’m from the Bible Belt," she said. "There's a lot of churches and there's a lot of straight people with families, and it's just really encouraged to take on the role of a wife and mother. There’s this mentality that a woman should be treated like a princess, but also she should be a cook, a cleaner, a driver and so on."

Roan continued, "I never fit into that mold. I tried. I really, really tried. I thought I was going to get married right out of high school at 18 or 19, and I thought I was going to have a baby by 23. I tried to fit myself into that mold, and it didn't work. It left me with a really interesting relationship with the Midwest."

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"But the Midwest remains a very big part of who I am. It's where I grew up, and I do love certain parts of it — the peace and growing up in a trailer park, four wheeling, the farm and bonfires. I love it even more now because I can reflect on it all like, ‘Oh, my God, this is so camp.’"

"I'm very grateful now looking back that I am from such a conservative Christian background, because I understand the communities there, and I understand where they're coming from," she added. "It's very easy to label communities that you don't understand, and because I know the inner workings of it, I don't see it as anything it’s not."

The singer lived in a trailer park when she was a child before moving to a house in a small Missouri town. (Getty Images)

Roan began playing piano at a young age and started uploading videos of herself singing covers to YouTube. She caught the attention of music labels in 2014 when she uploaded a clip in which she sang her original song "Die Young." Roan signed with Atlantic Records in 2015 at age 17.

In 2016, the singer took on the stage name of Chappell Roan in honor of her late grandfather, Dennis K. Chappell, and his favorite song, Curley Fletcher's "The Strawberry Roan."

After moving to L.A. in 2018, Roan released her first EP, "School Nights," and joined the tours of Vance Joy and Declan McKenna as an opening act. 

"I'm very grateful now looking back that I am from such a conservative Christian background, because I understand the communities there, and I understand where they're coming from."

— Chappell Roan

However, Roan didn't feel that "School Nights" was representative of the artist that she wanted to become, telling Variety in 2023 that she "hated all that music" on the EP. 

In 2018, she teamed up with songwriter and producer Dan Nigro, who would later produce Rodrigo's hit album "Sour." In 2020, Roan released the single "Pink Pony Club." Roan has said the song, which marked a sharp departure from her earlier music, was inspired by a night out at the famed West Hollywood gay bar The Abbey.

However, "Pink Pony Club" was rejected by Atlantic Records.

"I literally delivered it to the label, and they were like, ‘No.’ They said no for a year, and I believed them. I felt so defeated," Roan told Variety.

Her two other 2020 releases, "Love Me Anyway" and "California," failed to gain enough traction, and she was dropped by Atlantic Records. That same week, Roan's boyfriend of four years ended his relationship with her.

Roan suffered a career setback when her label dropped her, and she had to move back in with her parents. (Getty Images)

Afterward, Roan left L.A. and moved back in with her parents in Willard, where she worked at a drive-through coffee shop. 

During that time period, Roan continued to work on her music and her family encouraged her to not give up on her dreams.

"Thank God I came from the Midwest because I understand the people," she told Variety. "I have family who have complete opposite views of my views and my values, and they still support my project. I have this perspective that I think people on the coasts don’t have of the people there. I know where they’re coming from. It’s just not that black-and-white."

The singer eventually decided to give her professional music career another try and moved back to L.A. in October 2020. For the next two years, Roan worked as a barista, a nanny, a movie set production assistant and a doughnut shop employee to support herself.

While living in L.A., Roan began developing her own unique sound and stage persona, which she has said was inspired by her love of drag queens. Roan has cited '80s icons Kate Bush, Stevie Nicks and Cyndi Lauper and 2000s pop stars Lana Del Rey, Ellie Goulding and Lorde among her musical influences.

After landing a publishing deal with Sony, Roan was able to quit her side gigs and focus on her music full time. She reconnected with Nigro in 2022 and the two started collaborating again on songs that she released independently. 

In 2023, Nigro founded Amusement Records, an independent record label and an imprint of Island Records. Roan became the first artist that Nigro signed to the label and the two worked together to produce "The Rise and Fall of a Midwest Princess." 

Along with new tracks, the album features "Pink Pony Club" and "California" and several of Roan's independently released singles, including "Hot to Go!" "My Kink Is Karma," "Red Wine Supernova," "Femininomenon," "Casual" and "Kaleidoscope."

"I love this music, and that’s a big difference between my EP and now," Roan told Variety. "I rose from the ashes of losing all my money and moving back in with my parents and working the drive-through — this beautiful project came to life from the deep pits of hell."

The pop star found whirlwind success with her hit song "Good Luck, Babe!" and her album "The Rise and Fall of a Midwest Princess." (Scott Kowalchyk/CBS via Getty Images)

After a seven-year struggle, Roan emerged triumphant with the explosive success of "The Rise and Fall of a Midwest Princess." Last week, the album reached No. 1 on Billboard's Top Album Sales for the first time and Roan also topped the Billboard Artist 100, another first for the singer.

However, the singer has faced signigicant difficulty coping with the pitfalls of fame. In August, Roan posted a series of TikTok videos in which she called out "entitled" fans for "stalking" and harassing her.

A few days later, Roan took to Instagram to accuse some fans of "predatory behavior," which she said is "disguised as ‘superfan’ behavior."

"For the past 10 years[.] l've been going nonstop to build my project and it's come to the point that I need to draw lines and set boundaries. I want to be an artist for a very very long time," she shared in a post.

Roan asked her fans to respect her privacy in her personal life and issued a warning, saying she does not "accept harassment."

"Please stop touching me. Please stop being weird to my family and friends. Please stop assuming things about me," she pleaded.

"There is always more to the story & I am scared and tired. And please don't call me Kayleigh," she added, referring to her legal first name. "I feel more love than I ever have in my life. I feel the most unsafe I have ever felt in my life."

She ended her statement with, "There is a part of myself that I save just for my project and all of you. There is a part of myself that is just for me, and I don't want that taken away from me."

Roan has publicly addressed the downsides of fame. (Getty Images)

In September, Roan clashed with a photographer on the red carpet at the 2024 MTV Video Music Awards. 

While posing for photos, the pop star had a heated exchange with a photographer who yelled, "Shut the f--- up."

She immediately turned, pointed her finger at the photographer after the crass comment was made and replied, "You shut the f--- up."

"Don’t! Not me, b----!" Roan added. A voice in the background was heard cheering her on, saying, "Tell ‘em, girl!"

Later in the night, Roan gave a fiery and acclaimed performance of "Good Luck, Babe!" and won the best new artist award. 

"I dedicate this to queer and trans people that fuel pop," Roan, who came out as a lesbian this year, said in her acceptance speech, via People magazine. "To the gays who dedicate my songs to someone they love — or hate.

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"And thank you to the people who are fans, who listen to me, who hear me when I share my joy and my fears," she added. "Thank you. For all the queer kids in the Midwest watching right now: I see you. I understand you because I'm one of you, and don't ever let anyone tell you that you can't be exactly who you want to be."

The singer gave a fiery performance of "Good Luck, Babe!" at the MTV VMAs. (Noam Galai/Getty Images for MTV)

Despite the high points, Roan has continued to publicly struggle with her sudden fame. Days after the VMAs, Roan told The Face that she "might quit" the music industry if it becomes "dangerous."

In September, Roan faced backlash from some fans online after she refused to endorse Democrat presidential nominee Kamala Harris in the upcoming election. 

"I have so many issues with our government in every way," she told The Guardian. There are so many things that I would want to change. So I don’t feel pressured to endorse someone. There’s problems on both sides. I encourage people to use your critical thinking skills, use your vote – vote small, vote for what’s going on in your city."

Roan later posted two TikTok videos in response to the controversy. She clarified that she would be voting for Harris but said that she had issues with both parties and could not support either.

The hitmaker later dropped out of the All Things Go festival, where she was scheduled to give performances in New York City on Sept. 28 and Washington, D.C., on Sept. 29.

She dropped out of the All Things Go festival at the end of last month. (Marleen Moise/Getty Images)

One day before her first performance, Roan shared a statement on her Instagram Story, writing, "I apologize to people who have been waiting to see me in NYC & DC this weekend at All Things Go, but I am unable to perform."

"Things have gotten overwhelming over the past few weeks and I am really feeling it," she continued. "I feel pressures to prioritize a lot of things right now and I need a few days to prioritize my health. I want to be present when I perform and give the best shows possible."

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"Thank you for understanding," she added. "Be back soon xox."

Roan has been open about her struggles with her mental health. She previously revealed that she was diagnosed with bipolar II disorder in 2022. During her September interview with The Guardian, Roan said she sees a therapist twice a week and that a psychiatrist recently diagnosed her with severe depression, which the singer attributed to the ways in which her life changed due to fame.

Roan performed during the first weekend of ACL Fest and drew a massive crowd. (Erika Goldring/WireImage)

However, Roan returned to the stage last weekend for her first performance at ACL Fest, which drew a massive crowd.

Though this upcoming weekend's performance may mark Roan's last show for a while, fans can look forward to new music from the singer in the future. 

While speaking to BBC Radio, Roan was asked if "Good Luck, Babe!" was part of an album release.

"It's not," she said. "It's the first chapter of the new book I'm writing. And I just am going to follow what I did for the last record, which is just to write music that I love and put it out and with no other agenda than to have a great time onstage and like make something that I'm proud of."

"As I write songs, I'll just put them out, and eventually I'll get a collection and release an album."

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