Chappell Roan Came to Challenge Pop Music—and Win

Chappell Roan is a believer in the Enneagram test, which categorizes personality types. “I judge people based off their Enneagram,” she told me on a cold spring day in Manhattan. Roan was at the cover shoot for W, dressed in a heavily structured and generously padded Marc Jacobs look, her hair pouffed into a nimbus cloud of red frizz. “I’m an eight on the Enneagram scale,” she continued. “Eight is the Challenger.” She smiled. “It’s one of the most difficult numbers, because they challenge everything.”

In the past year, Roan, who is 27, has gone from being a virtual unknown to having worldwide fame. Her lyrics, which are a celebration of queer life and love, matched with her thrilling voice and eccentric stage presence, have catapulted her into superstar status. At the 2025 Grammy Awards, Roan was nominated for six awards; she won the hotly contested category of Best New Artist. Her newest release, “The Giver,” rose quickly to No. 1 on Billboard’s Hot Country Songs chart the same week it debuted at No. 5 on the Hot 100 list, a rare feat for a female vocalist, especially since the lyrics are about sex between women.

Roan makes these triumphs look easy, but she has had a bumpy road to success. She was born Kayleigh Rose Amstutz and grew up in Willard, Missouri, a small conservative town. Her mother is a veterinarian, and her father runs the family practice. She was raised in a strict Christian household—the family went to church three days a week, and Kayleigh attended Bible camp.

But Kayleigh always had a voice—she became known in her hometown as “the girl who could sing.” At 17, she signed a record deal and adopted Chappell Roan as her stage name, after her grandfather (Dennis Chappell) and his favorite song (Marty Robbins’s “The Strawberry Roan”). Unfortunately, Roan’s 2017 debut EP, School Nights, was not successful; neither was the 2020 release of “Pink Pony Club,” her anthem about the exhilaration of finding your tribe in a gay bar in West Hollywood. Roan was quickly dropped by her label.

In retrospect, this might have been a blessing in disguise: Roan needed to find her identity as a performer. She went home to Missouri, worked in various jobs, and saved money for her return to Los Angeles. Emboldened and inspired by drag queens, she started to develop the bedazzled, outrageous, passionately gay persona we now know. When Roan went back to L.A., she signed with the producer Dan Nigro, who had recently had huge success with Olivia Rodrigo. “Three or four days into meeting Chappell, I was convinced she was a superstar,” said Nigro, who won Producer of the Year (Nonclassical) at this year’s Grammy Awards.

Roan took her onstage character seriously, rejoicing in the idea that no outfit could be too extreme. In concert, she went from “Barbie Swan Lake” (a white feathered headdress) to the most dazzling prom date (a red strapless gown) to the Statue of Liberty (green body paint and a silver crown). In 2023, “Pink Pony Club” was rereleased as part of her debut album and went on to become a global hit. A year later, at Lollapalooza, Roan stole the show in a costume that was a mix of lucha libre wrestler and Wonder Woman. By then, her songs were inescapable: It’s impossible to hear “Hot to Go!” and not want to sing along.

When Roan walked into the W photo studio at 9:30 a.m., she was definitely Kayleigh rather than Chappell. She’s five feet two and rather delicate. Her perfect, pale skin was scrubbed clean, and her hair was tucked into a hoodie. She looked very young. Her makeup artist, Andrew Dahling, started to paint a rainbow on her forehead, and the transformation began. “If a 5-year-old could draw a pop star, it would be me,” Roan has said. But when you fuse the accessibility of a cartoonlike character with a fantastic vocal range and great songs that contain a message of liberation, you get more than a pop star—you get a challenger. Roan smiled. “The Challenger’s life purpose is to seek justice. And I feel like that’s for me.”

After your first record deal was canceled, you left L.A. and went back home. How did you keep hope alive?

Whenever I was working at my part-time jobs, like nannying or the drive-through or doughnut shop, I kept hope alive because I knew I was really good. I knew I had to just give it one more year. And I got that courage by, honestly, just being in hell for a very long time. I was like, this sucks so bad, but keep going. Every day I would think, Keep going, even if there was no sight of any light at the end of the tunnel. Zero! But I was like, what if it’s just around the corner? What if I stopped the day before that something is meant to happen? So I just kept going, and here we are!

Did you grow up listening to country music?

Yes. I love country music. I listened to a lot of George Strait, Dwight Yoakam, and Dolly Parton. And I love Shania Twain so much. I just love campy country songs. I heard them on the bus every morning or at football games: It was country being played over the big speakers. I think country is the campiest music! And so is metal.

Country music is known for narrative-based songwriting—it tells stories. I think that’s also true of your songs.

Country music taught me how to write narratively.

When was the first time you heard yourself on the radio?

I think it was in an Uber when I was on tour. I heard “Good Luck, Babe.” I grabbed my friend’s hand and I was like, “Oh my fucking.…” But I didn’t scream. I don’t sing along with myself. I never listen to my own music. If it’s out, I don’t want to hear it. I’ve heard it hundreds and hundreds of times.

What’s the first song you remember singing?

“Oops!…I Did It Again,” by Britney Spears. My mother took me out of gymnastics because I did the Britney dances instead of listening to the gymnastics teacher. I also sang, “Jesus loves me, this I know, for the Bible tells me so.”

You auditioned for The Voice and America’s Got Talent. What did you sing?

When I auditioned for The Voice, I was 15 and I sang “Stay,” by Rihanna. That was when the Bruno Mars song “When I Was Your Man” was really big, and I thought I was so unique in switching it around and singing “When you were my man” and making it about gender. But every girl was like, “I’m switching it around.” By the way, when I did the Voice audition, the producer or whoever the fuck was watching did not even look up from his phone. He was like, “Okay, next.” And I went up there and sang a cappella, the scariest thing ever. He never really looked at me. With America’s Got Talent, I was 13, and we flew to Austin, Texas, and waited in line with thousands of people at 4 a.m. I sang “True Colors,” by Cyndi Lauper. Did not make it either.

What was your favorite Halloween costume?

I am not a Halloween girl. My favorite Halloween costumes I admire from afar, because I’m always the bitch who has the cat ears on and that’s it. My work outfit is like Halloween! But when I was a child, I was a red M&M for three years in a row.

Why red?

Girl, that’s what was at Goodwill!

Have you seen versions of yourself at Halloween?

Yes! I’ve seen so many baby Chappell Roans. There’s so many different outfits to choose from! That is something new in the past six months—the audience is growing to include children, and it’s so cute. “Hot to Go!” taught them how to spell and dance.

You just went to Fashion Week in Paris. What was your impression?

I don’t know why I expected every show to be two hours long, but they are literally nine minutes, 12 minutes. It was kind of refreshing. I was in the makeup chair for the entirety of Paris Fashion Week—it was so crazy: changing looks, changing wigs, go, go, go. I didn’t realize that this was a dream I always had. But it was very interesting for my psyche, because when I walked into a fashion show, it had nothing to do with a performance I was about to give, or a speech, or writing a song. It was truly just about how I looked. I don’t know if I want to feel that way all the time, but I thought it was incredible to wear these outfits. The Valentino, in particular, was so gorgeous. It was amazing.

Do you get starstruck?

I get starstruck by drag queens! There’s this queen here in New York named Janelle No. 5, and I saw her on Sunday, and I was the bitch who was like, “I’m sorry—I don’t mean to bother you!” In my head, I was thinking, What are you doing? But, for me, she’s like royalty!

What song or film or TV show makes you cry?

“I Can’t Make You Love Me,” by Bonnie Raitt, makes me cry every time. And I sobbed so hard watching the film Roma; it’s so beautiful. And I just watched a documentary about Linda Ronstadt. I cried at the end because she has Parkinson’s disease and she lost her voice. It just put so much in perspective, like: fuck everything; I have the ability to use my voice! She’s one of the greatest vocalists of all time, and to see her struggle was gut-wrenching.

What is your pet peeve?

When people name-drop. I immediately don’t trust them. I’m not the girl to care about that stuff. It is an immediate turnoff in a romantic or a friendship way. I’m like, if you name-drop, I’m probably not going to be your friend.

Where was your first kiss?

In my parents’ driveway. I was 15. I made the move. I usually make the first move! We had been seeing each other, going on dates every weekend for a month, and I was like, it’s time to kiss. It was fun. But I would say that kissing girls is funner.

At the Grammys, when you accepted your award for Best New Artist, you seemed to be reading from a diary. Is that your actual diary?

Yes. I’ve been keeping a diary for—oh my god—like, 15 years. I started in middle school. I love looking back at what I had to say as a 12-year-old. I wrote that every day was “horrible.” It’s amazing to see what would ruin my day back then. It felt as dramatic as my life feels now. Throughout my life, I had a fear of losing my memory, so I kept a journal to log all these important events. As I’ve gotten older, it’s been harder and harder to keep a diary. Sometimes, when I’m having a bad day, I won’t journal, because I won’t want to remember.

Have you been asked to be in films?

I met John Waters last night, which was insane. One of my idols! And I was talking about how there are only so many “firsts” you can have with your career. And he said, “No, no, no—there are all the firsts to go through when you become an actress!” And I said, “I’m not an actress—what are you talking about?” He said, “Every singer is an actress!” And I was like, okay, maybe I am! Damn! If John Waters says I’m an actress, maybe I am!

Hair by Mustafa Yanaz for Bumble and Bumble at Art + Commerce; makeup by Andrew Dahling for MAC at the Only Agency; manicure by Dawn Sterling for Dior Beauty at E.D.M.A. World. Set design by Nicholas Des Jardins at Streeters. Prop fairies by Rhea Thierstein and Sophie Lincoln.

Produced by Hudson Hill Production; executive producer: Wei-Li Wang; producer: Arbelis Santana; first photo assistant: Antonio Perricone; lighting director: Dean Dodos; photo assistant: Tom Maltbie; digital technician: Charley Parden; retouching: Touch Digital; styling assistants: Liv Vitalie, Cash Weaver, Dylan Gue, Tyler VanVranken, Lila Hathaway; production assistants: Jarrett Funderburk, Linette Estrella; hair assistants: Rachel Hopkins, Sinaia Campora; makeup assistant: Tommy Tafoya; art assistants: Jeankarlos Cruz, Kirk Palsma, Andrew Riley, Bella Anselmi, Alexa Harrington; tailor: Todd Thomas.