Chappell Roan’s Reign Started in Small-Town Missouri

Missouri native turned international queer pop supernova, Kayleigh Rose Amstutz — better known as Chappell Roan — took the world by storm with her bold, sex-positive, in-your-face songs and flashy, drag-inspired appearance. 

Hailing from the small town of Willard, Missouri, Roan felt “disconnected and emotional” as she made her way through Willard High School. 

“I didn’t have a good time,” she tells the RFT on a phone call from Austin, Texas, where she’s on tour playing arenas as she opens for Olivia Rodrigo. “I was really struggling with bipolar and being a teenager was the hardest thing I’ve ever been through. I just felt really out of place and I couldn’t really understand myself. I always longed for an artist community like the one I have now.” 

Being gay in the Ozarks didn’t make things easier. Roan would later tell the Washington Post, in its words, that she was “caught between two selves” — going to church but “sneaking out frequently.” It took performing to reconcile who she really was. 

She signed with Atlantic Records and took the name Chappell Roan as a way to honor her late-grandfather, Dennis Chappell, and his favorite song, “The Strawberry Roan” by Marty Robbins. It’s a cowboy song about a horse breaker who more than meets his match in a “regular outlaw” of a strawberry roan, “the worst bucker I’ve seen on the range.” 

The name let Roan become a character — and “Chappell Roan,” she says, is “definitely a character.” 

“The character is like me, of course, but the dressing, the confidence, the makeup, like that is all kind of like a showgirl version of myself — or drag, if you will,” Roan says. “I dress pretty differently, more tomboy, I guess. I don’t wear bright colors anymore. I only wear black, white and gray. I like wearing crazy outfits, obviously but I like being alone and reading. I just love quiet because I feel like my life is so chaotic in every way, which I also love.”

In a profile of Roan that crowned her “pop’s next big thing,” the Guardian reported that Roan was initially terrified and thrilled in equal measure by Los Angeles (apparently “shaking in Trader Joe’s” when she saw women shopping for groceries in sports bras) but found freedom in the city’s gay bars. 

“I grew up thinking being gay was bad and a sin,” she told the Guardian. “I went to the gay club once and it was so impactful, like magic. It was the opposite of everything I was taught.’”

Shortly after visiting that first gay club, Roan wrote “Pink Pony Club” to showcase her newfound freedom, but the euphoria didn’t last. Atlantic Records dropped Roan and she moved back home, where she nannied and served coffee to get back to LA. 

“Money was like the biggest [obstacle],” Roan says. “I think it was like having no money to do this, and then like being bipolar, and the breakups and LA sucks sometimes, and missing my family, like all these like trillion obstacles.”

She adds, “Now I have a label, very grateful. But it’s really really difficult to get your feet off the ground whenever you are independent.”

Now signed with Island Records in Los Angeles, Roan continues to rise. Roan’s newest album, The Rise and Fall of a Midwest Princess, released September of 2023, speaks to her experiences with breakups, love and her embracing her queer identity. 

She also has songs: “California,” “Love Me Anyway,” “Naked in Manhattan,” “My Kink is Karma,” “Femininomenon,” “Casual,” “Kaleidoscope,” “Red Wine Supernova” and “Hot To Go.” The Guardian called the record “one of the most over-the-top, gloriously tasteless debuts in recent memory. It sounds, at turns, like Patsy Cline, 80s Madonna and RuPaul at his nastiest.” That’s some praise.

Roan, however, considers herself country — even if it’s like no country your mom (much less your grandpa) ever heard.

“I really started getting into music whenever I was, like, in high school,” she explains. “It was just based on like Christian rock and some country, but I just didn’t really identify with it at the time. Now I identify with country music in such a different way. I think it’s so camp and fun.”

Roan will be opening for Rodrigo on her “GUTS World Tour” in her native Missouri on March 12 at the Enterprise Center. Didn’t get tickets? She will be back Thursday, May 30 for her “The Midwest Princess Tour” at Saint Louis Music Park in Maryland Heights.

To learn more about Chappell Roan or to purchase tickets for her upcoming tour, visit her website.

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