Chappell Roan Redefines the “DIY Pop Star”

When she was just 17 years old, Kayleigh Rose Amstutz was reborn. She borrowed her late grandfather’s name, along with a reference to his favorite song, and rechristened herself Chappell Roan. Part stage name, part armor, the new moniker was just the beginning of her musical career. “My name means a lot to me,” she tells me over Zoom on a recent afternoon in November. “It’s become like a drag name now, which doesn’t minimize the meaning—it just expands it.”

Now 25 years old, the singer-songwriter has gone from a buzzy TikTok sensation to a rising queer pop star. Roan has toured with Olivia Rodrigo (she’ll join the singer again in February on the North American leg of her debut arena “Guts” tour), packed concert halls across the country, and even earned the approval of industry veterans like Elton John. Her music is a flashy, gaudy, and bold mosaic of pop—showcasing a range that swings between the low, melancholy tones of Karen Carpenter or Lana Del Rey to the in-your-face messiness and humor of a 2010s Kesha hit. Like the outfits she sports, Roan is largely self-made, growing an audience before she had the support of a major label by writing unabashedly honest songs that spoke to the queer, Gen Z experience. In September, she released her debut album, “The Rise and Fall of a Midwest Princess,” to rave reviews from critics.

It’s fitting that Roan took on a kind of drag name for herself. On stage, the singer is often dripping in rhinestones, sporting bedazzled corsets and hats and gloves dripping in tassels or fringe. Her wild mane of curly red hair feels like an apt reference to “The Strawberry Roan,” the classic country song about an unruly horse from which she took her last name. Never still for long, she bounds from one side of the stage to the other at her frequently sold-out shows, belting out a chorus or hyping up the crowd—a blur of glitter and chaos.

Born and raised in Willard, Missouri—a small, conservative town just outside of Springfield—it took Roan several years (and two moves to California) to really find her voice as an artist. “There wasn’t a big creative community in Willard, let alone a queer community,” she says during our video call from her apartment in L.A.

So she turned to music, uploading original songs and covers to YouTube that got her signed to Atlantic Records at 17 years old. Not long after, she packed her bags for Hollywood. It was a night-and-day difference from the life she’d known in Missouri. For the first time, she was surrounded by a community of people who were out and proud, giving her the space to fall for girls, get her heart broken, and write it all down.

In 2020, the singer released “Pink Pony Club,” working with Dan Nigro, Rodrigo’s producer and main collaborator. The perfect marriage of Roan’s Midwestern roots and her pop ambitions, the song tells the story of a girl who leaves Tennessee to become a stripper in L.A. In the wrong hands, it could be the setup to a tragic country song, but in Roan’s, it’s an earnest, glimmering pop anthem about becoming the person you were always meant to be.

Although the song gained traction on TikTok, and eventually became the singer’s breakout hit, it didn’t perform well enough for Atlantic, and the label dropped her. In the midst of the pandemic, she moved back home. But by the end of the year, she was ready to head back to L.A.—this time, as an independent artist. She sewed her own costumes, recruited her friends to shoot her music videos, and posted the process for a growing audience on social media. “Pink Pony Club,” might’ve told a fictional story, but it sparked something in Roan that she finally wanted to embrace.

“Growing up, I didn’t feel tactful or classy,” she says, explaining that she used to be embarrassed by the kitschy Midwestern aesthetic around which she’d grown up. Now, thrifted pastel prom dresses and glammed-out Western have become central to her image as a “DIY pop star.” “I rejected that version of myself because I thought it wasn’t smart,” Roan recalls. “But I realized, I might not be tactful or classy—but I am smart. I leaned into that and I started to love who I was as an artist. The songs started clicking, and the whole brand started working.”

Roan was eager to keep working with Nigro, but when “Driver’s License” became an overnight sensation in 2021, finishing up production on Sour became his top priority. In early 2022, he and Roan began writing again, revisiting old songs, and workshopping new ones. Soon, the singer made a splash with “Naked in Manhattan,” an ’80s synth track that captures the rush and temptation of a crush as it becomes something more. (“Touch me, baby, put your lips on mine,” she sings. “Could go to hell, but we’ll probably be fine.”)

The following releases, “My Kink is Karma,” and “Femininomenon,” cashed in on Roan’s irreverent humor, with the former celebrating an ex’s life going up in flames, and the latter lamenting men’s inability to satisfy women. Other labels started paying attention, and eventually, she signed to Island Records. “Being an independent artist showed me that I don’t need a label,” she says. “Obviously, it helps. But I took my time choosing one because I had leverage. I’d created a brand with my friends that was self-sufficient. I wasn’t scared, like, ‘Oh my god, what if I never get signed again?’ Because I did all of this without one.”

It took nearly four years to create, but with her debut album finally out in September, Roan has felt some peace. (“All these years were worth it,” she says. “Thank god I kept pushing.”) Just a few days after the album’s release, the singer embarked on her headlining North American tour. When she performs live, the songs become something completely new, transformed by an audience which sees itself in Roan’s own journey, connecting with lyrics about “forbidden” slumber party crushes, self-discovery, queer chaos—and queer joy.

Photograph by Cat Cardenas

Each night on Roan’s tour is built around a different theme, like “Slumber Party Kissin’” or “Pink Cowgirl,” all of which are followed by a crowd that takes after the singer’s own DIY aesthetic. And rather than go the route of a traditional opener, Roan’s always opted to solicit applications from local drag queens, who warm up the room before she takes the stage. “No one’s going to rally the crowd more than a fucking drag queen,” she says.

With the rise in drag bans and laws targeting members of the LGBTQ+ community, it was important for Roan to double down on her efforts to highlight local drag artists; she donated a portion of the proceeds from her shows to LGBTQ+ organizations like For the Gworls and The Glo Center. “There’s so much homophobia and transphobia in the U.S. that I think it’s hard for a lot of people in my generation to have a good time right now,” she says. “If I can give them some type of solace for just two hours, then that’s what I’m going to do.”

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