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 called 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 recently via Zoom on an afternoon in November. “It has now become a kind of drag name, which does not minimize the meaning, but only expands it.”
Now 25 years old, the singer-songwriter has gone from buzzy TikTok sensation to 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 industry like Elton John. Her music is a flashy, flashy and daring mosaic of pop, with a range that fluctuates between the low, melancholic tones of Karen Carpenter or Lana Del Rey to the in-your-face messiness and humor of a 2010 Kesha hit. like the outfits she wears, Roan is largely self-made, helping her grow an audience before gaining the backing of a major label by writing unabashedly honest songs that appealed to the queer Gen Z experience. In September, she released her debut album, “The Rise and Fall of a Midwest Princess,” which received rave reviews from critics.
It’s fitting that Roan has adopted something of a drag name for himself. On stage, the singer is often dripping with rhinestones, wearing glittering corsets, and wearing hats and gloves dripping with tassels or fringe. Her wild mane of curly red hair feels like a striking reference to “The Strawberry Roan,” the classic country song about an unruly horse from which she took her last name. She never jumps from one side of the stage to the other for long during her often sold-out shows, belting out a chorus or pumping 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 truly find her voice as an artist. “There wasn’t a big creative community in Willard, let alone a gay community,” she says during our video call from her LA apartment
So she turned to music, uploading original songs and covers to YouTube, which landed her a contract with Atlantic Records at the age of 17. Not long after, she packed her bags for Hollywood. It was a night and day difference from the life she had known in Missouri. For the first time, she was surrounded by a community of people who were exuberant 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”, in collaboration with Dan Nigro, Rodrigo’s producer and main collaborator. The perfect marriage between Roan’s roots in the Midwest and her pop ambitions. The song tells the story of a girl who leaves Tennessee to become a stripper in LA. In the wrong hands it could be the setup for a tragic country song, but in Roan’s it’s a serious, sparkling pop song about becoming the person you were always meant to be.
Although the song gained traction on TikTok and eventually became the singer’s breakthrough hit, it did not perform well enough for Atlantic, and the label dropped her. She moved back home in the middle of the pandemic. But by the end of the year, she was ready to return to LA – this time as an independent artist. She sewed her own costumes, recruited her friends to shoot her music videos, and posted the process to a growing audience on social media. ‘Pink Pony Club’ may have told a fictional story, but it sparked something in Roan that she finally wanted to embrace.
“Growing up, I didn’t feel tactful or stylish,” she says, in which she explained that she was ashamed of the kitschy Midwestern aesthetic she had grown up with. Now thrifty pastel prom dresses and glamorous Western are central to her image as a ‘do-it-yourself pop star’. “I rejected that version of myself because I didn’t think it was smart,” Roan recalls. “But I realized that maybe I’m not tactful or classy, but I am am smart. I leaned into that and started to love who I was as an artist. The numbers started clicking and the whole brand started working.
Roan wanted to continue working for Nigro, but when ‘Driver’s License’ became an overnight sensation in 2021, he ended production of Pickles became his top priority. In early 2022, he and Roan started writing again, revisiting old songs and giving new workshops. The singer soon made waves with “Naked in Manhattan,” an ’80s synth song that captures the rush and seduction of a crush as it becomes something more. (“Touch me, baby, put your lips on mine,” she sings. “It might go to hell, but it’ll probably be okay.”)
Subsequent releases, ‘My Kink is Karma’ and ‘Femininomenon’, capitalized 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 she eventually signed with Island Records. “Being an independent artist has shown me that I don’t need a label,” she says. “Of course it helps. But I took the time to choose one because I had influence. I had created a brand with my friends that was self-sustaining. I wasn’t scared, like, ‘Oh my God, what if I never get another contract?’ Because I did all this without it.”
It took almost four years to create, but with her debut album finally released in September, Roan has felt some peace. (“All those years were worth it,” she says. “Thank God I kept pushing.”) Just a few days after the album’s release, the singer began her headlining tour of North America. When she performs live, the songs become something completely new, transformed by an audience that sees itself in Roan’s own journey, connecting with lyrics about ‘forbidden’ slumber parties, self-discovery, strange chaos – and strange joy.
Each night of Roan’s tour is built around a different theme, such as “Slumber Party Kissin'” or “Pink Cowgirl,” all of which are followed by an audience following the singer’s DIY aesthetic. And instead of going the route of a traditional opener, Roan has always opted to solicit applications from local drag queens, who warm up the room before taking the stage. “No one can get the crowd going more than a damn drag queen,” she says.
With the rise of drag bans and laws targeting members of the LGBTQ+ community, it was important for Roan to redouble her efforts to highlight local drag artists; she donated a portion of the proceeds from her shows to LGBTQ+ organizations such as For the Gworls and The Glo Center. “There’s so much homophobia and transphobia in the US 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 just give them some comfort for two hours, then that’s what I’m going to do.”