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Chappell Roan (or Kayleigh Rose Amstutz), the singer-songwriter from Willard, Missouri, gained global attention last year with the release of her debut studio album, The Rise and Fall of a Midwest Princess. However, it wasn't Roan's entry into the music industry but her comeback in it.
The first time Chappell established herself as a singer was in 2015 when she was still a teenager. The 17-year-old was signed to Atlantic Records at the time. However, five years later in 2020, the record label dropped Roan from their roster. According to Vox, the reason behind the drop was explained by the label to be Chappell's "underperforming" music.
Following the drop, Chappell Roan remained without a music contract for three years while she uploaded her music independently, before getting signed by Island Records in 2023.
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Atlantic Records dropped Chappell Roan after five years of partnership
Chappell Roan's debut song, released on YouTube, made way for her partnership with Atlantic Records in 2015. Roan recorded and uploaded her first track - called Die Young - in November 2014, under her given name, Kayleigh Rose Amstutz.
The 16-year-old had written the song during her summer camp at the Interlochen Center for the Arts. When the song was discovered by Atlantic Records, the label approached Roan to sign a partnership, for which she traveled to New York.
After signing the deal, Roan moved a lot, between the label's LA and New York studios, from her parent's home in Missouri. Two years later, Chappell's first single with the label was released in August 2017, titled Good Hurt.
A month later, the track was followed by her debut EP, School Nights. The EP contained five songs - the previously released Good Hurt and Roan's first self-released Die Young, Meantime, Sugar High, and Bad For You.
It was around this time that Kayleigh gave up her given name and adopted Chappell Roan as her stage name. According to Vox:
“Don’t call me baby, and don’t call me Kayleigh,” she would say at the opening of her shows.
Three years later, Chappell released her sleeper hit track, Pink Pony Club, marking her first collaboration with music producer Dan Nigro. The song followed the journey of a small-town girl who becomes a stripper at the namesake club. Despite the song's genius, it didn't appeal to listeners amid the ongoing pandemic in March 2020, and neither did her next two - California and Love Me Anyway.
It was ten days after the release of California that Atlantic Records decided to drop Chappell Roan as they found her music to be "underperforming."
Roan's Naked in Manhattan marked her comeback in the industry
Vox reported that Chapell Roan's four-year relationship with a man ended the same week she was dropped by Atlantic Records, making it a difficult time in her life. Talking to People magazine about it in September 2023, the Casual singer reflected how she had to move back to Willard where she picked a barista job at a coffee kiosk.
“I lost all my money and had to move home,” she recalled.
It took Roan several months before returning to Los Angeles, where she continued to work on her music while taking on part-time jobs as a nanny and a production assistant to pay her bills. In her words, this was Chappell's final try at making music work.
By 2022, Roan landed a publishing deal with Sony to release Naked in Manhattan - another one of her tracks that was produced by Nigro. Soon after its release, the track became a queer crush anthem, paving the way for Chappell Roan's success.
Naked in Manhattan was followed by other hit tracks like Femininomenon, Casual, and My Kink is Karma. All these hits made way for Roan's second record label deal with Island Records in early 2023.
Later in the year, the singer-songwriter released her debut studio album The Rise and Fall of a Midwest Princess with Amusement Records, a sister concern of Island Records. Speaking to People about her album after its release in September 2023, Chappell said:
"I think people like to party and I think my project feels like a party."
Roan's album peaked in the top 10 of Billboard 200 album chart nine months after its release.
Chappell Roan is currently touring with The Midwest Princess Tour that started on September 25, 2023, and is scheduled to conclude on October 11, 2024, after 89 concerts in nine countries and three continents.
