Chappell Roan: The Rise of Our Midwest Princess

Currently on her Midwest Princess Tour, Chappell Roan rises to new career heights and gives pink ponies a sense of belonging.

by Liz Maupin - Jul 20 2024
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Chappell Roan’s beginnings have certainly contributed to her quite literally breaking out. In her hit song “Pink Pony Club”, she sings the following:

" I know you wanted me to stay | But I can't ignore the crazy visions of me in LA | And I heard that there's a special place | Where boys and girls can all be queens every single day | I'm having wicked dreams of leaving Tennessee | Hear Santa Monica, I swear it's calling me | Won't make my mama proud, it's gonna cause a sceneShe sees her baby girl, I know she's gonna scream," she the budding artist. "God, what have you done? | You're a pink pony girl |And you dance at the club | Oh mama, I'm just having fun | On the stage in my heels | It's where I belong down at the Pink Pony Club." 

Hailing from (obviously) the Midwest, Roan sings in “Pink Pony Club” about having visions of leaving Tennessee and heading to Los Angeles, upsetting her presumably Christian mother who pleads to God, asking what he’s done, as her daughter is “regrettably” a pink pony girl.

Much of these lyrics seem to ring true to Roan’s own genesis. Born and raised in Missouri, the vocalist (whose birth name is Kayleigh Rose Amstutz) has described her upbringing as conservative and Christian. She attended church as a child and attended some summer Christian camps. In a previous interview with Variety she said, “I just wanted to feel like a good person, but I had this part of me that wanted to escape so bad. I just wanted to scream." 

And escape she did. In late 2014, she uploaded an original song titled “Die Young” to YouTube, which eventually led to her being signed to Atlantic Records in early 2015. This is when she adopted her stage name Chappell Roan. The persona was named after her late grandfather whose last name was Chappell and whose favorite song was “The Strawberry Roan” by Curley Fletcher.

In 2017, she released her EP through Atlantic Records titled, School Nights. However, it wasn't until 2018 when she moved to Los Angeles. Upon arrival, she sat down with Rolling Stone and came out for the first time as a queer woman.

“I feel allowed to be who I want to be here," said the chart-topping artist. "That changed everything."

From Jan. to March 2018, she toured domestically with Declan McKenna. In April 2020, Roan released “Pink Pony Club” and in May released two more singles, “Love Me Anyway” and “California”. Atlantic Records deemed these releases as not profitable and dropped her from the label. That very same week, her long-time boyfriend of four years ended their relationship. She then briefly moved back to Missouri to work on her music independently while supporting herself by working at a drive-thru.

Roan was able to move back to Los Angeles in Oct. 2020 to continue pursuing her music career and worked a series of odd-jobs to make ends meet, such as in a donut shop and as a production assistant. She then earned a publishing deal with Sony and by March 2022, found her way back to working with her preferred producer Dan Nigro. They created and released the song “Naked in Manhattan." Shortly after, Olivia Rodrigo chose her as her opening act on Rodrigo’s  Sour tour. 

By Feb. 2023, Roan began her own debut headlining tour titled Naked In North America. Each tour stop had a theme and she booked drag queens as her openers on the tour. On Sept. 22, 2023, she released her debut full-length album The Rise and Fall of a Midwest Princess. Roan then kicked off her second headlining tour titled the Midwest Princess Tour, including stops all throughout the country – including her now-infamous appearance at The Governors Ball in early June. She even headlined the Kentuckiana Pride Festival.

For the first time in the festival’s 24 year history, it sold out and around 45,000 people attended. On the Big Four Lawn at Waterfront Park in Louisville, Kentucky, Roan performed as fans danced and sang along, even from atop bridges overlooking the lawn. 

Fan Of View: Seeing TikToks of this from afar in Los Angeles as someone who was born and raised in Kentucky, watching so many people be able to openly come together, celebrate and be joyous in the place I lived for the first 26 years of my life brought tears to my eyes. I [Liz Maupin] was so happy for those attending. So happy that Chappell Roan allows and creates this space. So grateful that Kentuckiana Pride exists. So thankful for any loving space that allows one to be themselves and feel loved and understood and supported while doing so.

Growing up in Kentucky, I, like Roan, came from a conservative family and even from a young age began to internally question their values. I was fortunate enough to have a few friends in high school who were able to challenge what my parents taught me and attempted to instill in me, which ultimately allowed me to begin to feel less alone in my own beliefs.

Trying to function as myself within a conservative family and an overall conservative environment though was very challenging and led to feelings of alienation and loneliness, feelings which cemented and I still carry with me to this day. I was, without a doubt, the black sheep in my entire family, extended and otherwise. Eventually, I moved to Chicago for a few years and then lived in Los Angeles for nearly seven years, which helped me find friends who accepted, celebrated, and loved me for who I am, and who I am still becoming.

Rather than viewing myself as the black sheep, I can begin seeing myself as a pink pony – And that’s thanks to Chappell Roan.

 Photo Credit: @chappellroan on Instagram.

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