Why Chappell Roan's friends, fans keep rooting for hometown princess

On Broadway Boulevard in Kansas City, next to Hamburger Mary's — a bar and grill that hosts regular drag shows — is a mural. A pale white face with bright pink mascara, bold lips, and blue eye shadow is engulfed in vivid red, curly locks of hair. Beneath the face is golden ribbon with the moniker "MIDWEST PRINCESS."

It's the sort of portrait that suggests a dramatic transformation, a painted mask for a larger-than-life character on stage. For many who knew the princess before the crown, the paint and glitter simply reveal what they saw years before.

"One time she was doing something silly in class, and I said, 'I cannot wait till you're famous so I can get an interview and tell them how crazy you are …,'" said Kathy Tobin, a speech and debate teacher at Willard High. "She'd laugh."

"She" being Kayleigh Amstutz, or as most folks outside Willard city limits know her, Chappell Roan.

Described during her 2024 breakout as "Your favorite artist's favorite artist," a reference to drag queen Sasha Colby, Roan's ascent appeared to take place overnight. As soon as people learned her name, she was topping the charts for iTunes and Spotify streaming. Now, for many, Roan is simply "your favorite artist."

But before she was Chappell Roan — a name inspired by her late grandfather, Dennis K. Chappell, and his favorite song, "The Strawberry Roan," by Curley Fletcher — she was Kayleigh Rose Amstutz, born in Willard in 1998, the oldest of four. Her mother, a veterinarian, and father, retired from the Navy, were known to bring donuts to cross country practice.

Before her ascension to pop stardom, most of Willard High School's most notable alumni were athletes: Olympic volleyball player Lori Endicott-Vandersnick, professional football player Forrest Merrill, and Olympic track and field star Jason Pyrah.

Roan had a successful high school cross-country career, too, including a personal best time of 20:06 at a course in Ha Ha Tonka State Park in Camdenton. Her coach, Clark Giboney, believes Roan could have had a collegiate running career if she wanted, but something else was calling her.

"She knew she was going to make it [in show business] … She was just driven from the beginning," said Tobin.

Fellow students saw it, too. Kori Bujarski, who competed with Roan in speech and debate and cross country, recalled, "There's just something different about the people who just know that they're gonna be big. I feel like she just knew that this was destined for her. She would just be like, 'When I become a singer, I'm gonna remember Willard, Missouri ...' She was just talking like it already happened."

Her family was equally determined.

"I can very vividly recall her dad saying to me, in a very confident and sure tone, that she was going to make it," recalled Giboney, who would run with Roan's father. "He just said, 'Coach, she's going to make it big. She really is. She's going to make it big.' I mean, I can remember him saying that like it was yesterday."

More: Chappell Roan is a singer from Willard. She just made the big time.

Katelynn Wilson recalled meeting Roan in middle school.

"She was so weird" — in a good way, Wilson said. The first time they met, Roan was wearing a belt buckle the size of a mango in the middle of her waist, and blue mascara. "I just remember that she was always fun, genuine, and made me laugh."

The friends started a tradition in their speech and debate class, writing letters to each other at the end of the school year and hiding them in the ceiling tiles. Roan was a "very vivid artist," drawing "the weirdest looking creatures" and leaving them in the ceiling and in shared classroom drawers. She drew an outlandish mermaid in Wilson's yearbook and a sketch of Wilson kissing her boyfriend "with very, very, very long lips."

Roan was also something of a prankster.

"One time, it was like, 'Where are all my scissors going?' And then finally I realized she was hiding them all in a cabinet," Tobin said. "She was always being silly."

For speech and debate, Roan competed in the categories of humorous interpretation and storytelling, becoming district champion and nearly reaching the state finals in her freshman year.

The same year, she qualified for state in cross country, where her nickname was "Mad Dog." Giboney gave her the nickname as a joke because she was petite but had an aggressive and assertive style while running. He even tried to convince her to write a song called "Mad Dog." (He's still waiting.)

As Roan continued to pursue music, speech and debate and cross country became less of a focus. Then, she was gone — missing her senior year at Willard to chase her dreams. Wilson, who now teaches speech and debate in the Kansas City area, remembers her high school friend fondly. She enjoys telling her students that she was friends with Roan in high school and showing them pictures when they don't believe her.

Wilson remembers the last thing Roan wrote to her. "She wrote one final letter, wishing me like, 'I hope you enjoy your senior year. Really live it up, because I won't be here. I'm gonna do what I'm meant to do. I'm gonna go off, and I'm gonna be Chappell Roan.'"

Show Me State Roots

Much of Roan's time is now spent outside of Missouri, performing across the globe — in Australia and New Zealand in February, then Brazil and Chile in March. But wherever she finds herself in the world, she's still a Missourian. After performing a pop-up concert in Kansas City in October, she wrote this on her Instagram: "KC I've never had a city show up for me the way you have. I felt so special and so emotional the whole time. I really feel so supported by my home state and had such an incredible time performing for you. I love you so much."

"Missourians love people from Missouri, that's true. I think anytime there's someone from our state that's being celebrated on a national scale, we take pride in that," said Jared Horman, the designer of Roan's mural in Kansas City. "And I think her sort of like, 'doing it my-own-way' attitude, even if it doesn't necessarily align with a lot of Missourians' politics, is very Show Me State."

Horman, who is gay, thinks it's important that someone like Roan hails from the Show Me State and views the Kansas City mural as a "gift to all of the queer folks, the outsiders, the up-and-coming artists that are in the Midwest."

The moniker "Midwest Princess" was important for Horman to incorporate into the mural because of the singer's embrace of "Midwestern and Missouri-hood." Roan named her 2023 album The Rise and Fall of a Midwest Princess . Horman views her rising star as one that "is shining a light on a state that many folks on the coasts ... don't think of as like, 'Oh, there's something incredible coming out of here.'"

Horman admires Roan for several reasons: her support of local LGBT organizations, her efforts to support drag artists and trans creators, and her willingness to say no . He views Roan as a cross between Lady Gaga and Dolly Parton and compares her ability to bring people together to the Queen of Country. At a Roan concert he attended, Horman said he was struck by a wide array of people in attendance — those wearing pink cowboy hats or sequins, drag queens, Roan impersonators, and more "regular dudes."

"We all just wanted to dance," he said.

Christine Riutzel is a muralist who assisted Horman with the Kansas City artwork and who painted a separate mural of Roan next to drag queen Sasha Colby inside the French restaurant LaRue on Commercial Street in Springfield, depicting Roan in her "Saturday Night Live" dragonfly outfit.

"It's really cool to have a worldwide celebrity like her come from such a small town," says Riutzel, who appreciates Roan's use of local hairstylists, makeup artists, and young costume designers, along with her decision to use Springfield as the setting of her "HOT TO GO!" music video. In the video, Roan displays staples of the area: Andy's Frozen Custard, the World's Largest Fork in Chesterfield Village, the Wild Horses mural on South Campbell Avenue, Fun Acre Miniature Golf Course, and The Gillioz Theatre.

More: Chappell Roan's 'HOT TO GO!' music video features these Springfield locations

"When I saw the 'HOT TO GO!' music video, I was like, 'This is so cool.' She would do something that I would do, which is, make it big, go to Hollywood, but then come back and show appreciation to her hometown, and film a music video all around Springfield, like all the places that we recognize," Riutzel says. "That's really neat that, as much as you can sing about growing up in high school and struggling and not being understood or being different, that you can still love and appreciate the good aspect of growing up in the Midwest."

Roan has said she feels most grounded at home. The slower pace creates an "extreme nostalgia," making her feel like "time hasn't passed" and that she is "in high school again."

"She's uniquely Chappell Roan, and I think that's what people are drawn to. She has causes that she supports, and she's very, you know, outspoken, and she's just authentically herself in that venue, and I think that draws people in, and the music is a bonus," said Jerry Scott, a former music teacher at Willard High who had Roan in a history of rock and roll class, though she wasn't involved in high school choir.

"There are a lot of artists that come and go pretty quickly," Scott said. "I don't think Kayleigh will be one of those artists."

Giboney, the Willard cross-country coach, is also proud that Roan embraces her Show Me State upbringing.

"You're kind of incorporating people that wouldn't normally identify with you, and suddenly they are, because you're authentic and you're basically acknowledging your roots from the Midwest," he said. "So now all of a sudden, you got math teachers from Willard High School driving to Kansas City to see this person because they're from Willard, but also because she didn't become this LA princess. She's still talking about being a Midwest princess."

Giboney said he sometimes plays Roan's music when his students are working in class, and they have taught him the dance moves to "HOT TO GO!" He'll even jokingly evoke Roan by telling his students, "Hey, I talked to Chappell Roan, and she wants to make sure you're gonna do really well on your homeostasis quiz this week."

"A lot of those kids, man, they really look up to her, and they admire her, and they're pretty proud of the fact that they have a former Willard alum who's a superstar," he said. "I think for the students, it's a point of reference. They look at her and admire her, and can see that accomplishment, and it probably inspires them and gives them the idea that there's a world of possibility out there, even for someone from a small town like Willard."

Lily Brewer, a senior at Willard High, says it is "really awesome to see that she was able to leave a mark just outside of Willard and actually make a name for herself."

Brewer sees similarities between Roan's life and her own. Roan's song "California" holds a special place because its story "very much resembles my sister's story of leaving a small Midwestern town and moving to California." Brewer's older sister, Madelyne, moved to Los Angeles after graduating from high school to study fashion at The Fashion Institute of Design & Merchandising.

Brewer first learned about Roan through her best friend, who saw Roan open for Olivia Rodrigo in the fall of 2023. When Brewer heard the Willard alumni's music, she was hooked.

"Chappell helped push the idea that no one has to conform," Brewer said. "You can be your own person, and seeing people just fall in love with her art and show that she's queer and she's here." 

Roan came out as a lesbian at a 2024 concert in Ohio. Brewer, who identifies as queer and is of Filipino heritage, feels Roan's ascension has made it easier for students to be queer or even just different in communities like Willard. Brewer recalls being barked at, being called "gay" in a derogatory manner, and even having her hair pulled in the past. However, that treatment has dissipated, and while Brewer thinks it has something to do with her peers maturing, she also believes Roan's unapologetic embrace of herself has "really helped bring together a community at the school."

"I think she's just like a star, like she glows, and she kind of brings in this new revamping of our small town."

Brewer also appreciates the attention Roan brings to Missouri as a whole.

"I feel like we're a forgotten state," she said, but "we're people, and we have creativity and culture and queerness, and we can embrace that as a state." 

Tobin, the speech and debate teacher, said she is proud of what her former student has achieved and hopes she is recognized for more than pop stardom.

"I just think that she's relatable, and she found a group of people that needed someone to speak for them and to acknowledge them, and she validated them," said Tobin, who also praises Roan for her determination. "I think that people felt like she was an overnight sensation. But she's worked. She worked so hard to get there."

More: Springfield bookstore will donate part of Chappell Roan book sales to GLO Center

Giboney agreed, attributing Roan's success to personal grit and the support of those around her.

"She's had this resilience, and, I mean, some of that's just innate toughness ... But some of it's also when you have people in your camp, family members that love you — I mean, love every fiber of your being and believe in you to your core. Man, that's powerful," he said.

"I think that's a lesson ... she pursued something that she was passionate about, and is highly successful at it. That's that old adage that, basically, if you do what you enjoy, you won't work a day in your life, kind of thing. That's a good life lesson for kids, and they're seeing it with Kayleigh."

"I'm just really proud of her," Giboney said. "We're all really proud."

This article originally appeared on Springfield News-Leader: Chappell Roan's hometown friends, fans praise her authenticity