Chappell Roan spent 7 years becoming an overnight success

It’s undeniable: the era of Chappell Roan is upon us. At music festivals and on the lists forecasting pop’s next big thing, there she is: big red hair and big powerhouse voice, unapologetically queer lyrics and exuberant drag queen aesthetic. This is the summer Chappell Roan became impossible to ignore. 

Roan has been a working pop artist for years. Now 26, she signed her first record deal with Atlantic Records at 17 and has been putting out songs ever since — but for a long time, none of them seemed to quite hit. Last September, though, Roan released her first full album, The Rise and Fall of a Midwest Princess, and set off on tour as Olivia Rodrigo’s opener. In March, her appearance on NPR’s Tiny Desk Concert series went surprisingly viral (3.4 million views and counting), sending her Spotify monthly listeners count rocketing up by 500 percent. In April, she became one of the biggest stories out of Coachella. In June, she was the story of the Governor’s Ball. She’s been on Jimmy Fallon. She’s performed on The Late Show with Stephen Colbert. She is currently in the process of crossing the border that separates “working pop artist” and “pop star.”

One of the things that makes Roan’s story so compelling is how long it took her to get here and what a strikingly different artist and performer she was at the beginning of the journey. Today, a Chappell Roan show plays like a joyous drag ball. A few years ago, Roan was making broody Lorde-meets-Florence Welch power ballads about suffering deliciously for the love of a boy. She pitched her voice deep and sang her lyrics in smooth, diphthonged cursive. In her videos, she wore her hair dark and straight.

Roan’s trajectory from there to here reveals a lot about why, exactly, she’s taking off so precipitously right now. It’s the story of coming of age, both artistically and personally, at exactly the right time and place. 

How Kayleigh became Chappell

Roan grew up with the name Kayleigh Amstutz. She lived in what she sometimes describes as a trailer park in Willard, Missouri, population 6,000. Her childhood was deeply conservative. She went to church three times a week, she said in an interview with the Guardian, and was taught that “being gay was bad and a sin.” 

“I wish it was better. I wish I had better things to say,” she told Rolling Stone in 2022. “But mentally, I had a really tough time.” 

Her family and peers found out she could sing when they heard her in a middle school talent show, and she signed to Atlantic Records after she was scouted posting songs to YouTube. Flying back and forth between her parents’ home in Missouri and studios in LA and New York, she got to work. She released her first single, “Good Hurt,” in August 2017, and her first EP School Nights a month later.

Already, she had decided that she would not be performing as Kayleigh Amstutz. Instead, she created a stage name in honor of her grandfather, Dennis Chappell, and his favorite song, “The Strawberry Roan.” 

“The picking of the name was the hardest part of this entire thing,” Roan confided in her hometown newspaper, The Springfield News-Leader, in the lead-up to releasing School Nights in 2017. “It was the most stressful part.” 

A few years later, Roan had a different perspective on this part of her life. All of it seemed strange to her, stressful in its own way. “I felt very unprepared,” she told Rolling Stone. “I didn’t know the consequences of how much I had to sacrifice. I didn’t do my senior year. I didn’t go to prom. I didn’t go to graduation. I missed a lot of what would have been the end of my childhood to do this job.”

At the time, the job was to sing dark, moody songs about the sadomasochistic thrill of being in love with a bad boy. “No one else compares to who I had first,” Roan sings in “Good Hurt” as she submerges herself somberly in a lake of black water in the accompanying video. “All I really want is a good hurt.”

Roan of this era was a markedly different performer from the Roan we know now. There was no hint of queerness in her presentation yet, with her songs addressed mainly to an unnamed “beautiful boy.” With her long hair worn dark and straight, she gave off a witchy aura, an impression she magnified by gliding around in long white gowns — a far cry from the gleefully tacky drag get-ups she wears now. 

Perhaps most striking of all, the aesthetic Roan used in the 2010s doesn’t feel like one particular to her. She was doing a variation of the melancholy indie pop sound and look that was then in vogue. 

Roan now describes her sound of this era as “really dark, angsty pop that was pretty boring.” Her magnetic presence and vocal chops were enough to garner her a small and fervent fanbase, but it wasn’t yet a group large enough to reach critical mass.

Everything changed, Roan has said in interviews, when she left Missouri to live full time in Los Angeles on her own in 2018. For the first time, she was able to separate herself from the conservative ideology of her childhood.

“I was told this city is demonic and Satanists live here,” Roan told NME this February. “But when I got to West Hollywood, it opened my eyes [to the fact] that everything I was afraid of wasn’t always true — especially [what I’d been told] about the queer community. Going to gay clubs for the first time, it felt spiritual.” 

It was also in LA that Roan met the man who would become her primary creative collaborator: Dan Nigro, a music producer and former indie frontman. He and Roan  began collaborating just a few months before Nigro broke out in a huge way for his work on Olivia Rodrigo’s “Driver’s License.”

The first collaboration Nigro and Roan released together was “Pink Pony Club,” which dropped in April 2020. There, we start to see the beginning of what we now know as Chappell Roan: hair worn loose and curly, vulnerability pushed forward but shame exuberantly chased away. 

“Pink Pony Club” is a story song Roan has said was inspired by her first trip to the Abbey, an institution in LA’s gay nightlife scene. She was transfixed by the go-go dancers, and so she wrote a song about a woman from a small town who leaves her scandalized mother behind to become a stripper at the Pink Pony Club. Roan had sung all her previous songs in the deep indie girl slur that was popular at the time, but she does “Pink Pony Club” in a voice so precise it starts to feel like a burlesque. 

“God, what have you done?” wails the narrator’s mother in the chorus, with Roan coming down hard on the d’s and the t’s, her falsetto bright and airy. “Oh mama, I’m just having fun,” the narrator responds, and although the song is in a minor key, Roan’s voice is joyous: “On the stage in my heels, it’s where I belong.” 

Unfortunately for Roan, April 2020 was not a time that welcomed raucous odes to the dance club. When “Pink Pony Club” dropped into the traumatic early days of the pandemic, it sank like a stone.

The song was also unpopular at her label, which disapproved of Roan turning her back so abruptly on the aesthetic she’d begun to craft in School Nights. Roan released only two more songs with Atlantic: the light love ballad “Love Me Anyway” and the melancholy “California.” 

“California” is a sort of response to and inverse of “Pink Pony Club.” Like its predecessor, it tells the story of a dreamer who left her small town for a love of delicious sin in LA. Unlike the main character in “Pink Pony Club,” the narrator of “California” feels increasingly like she’s failed by coming to the city and that everything she’s sacrificed has been for nothing. “Won’t make my mama proud,” Roan sings with mounting excitement in “Pink Pony Club.” “I let you down,” she sings on a down note in “California.”

Ten days after “California” was released, in August 2020, Atlantic officially dropped Roan from the label. Her music, they said, was underperforming. The same week, her relationship with the man she’d been seeing for four and a half years ended.

The Midwest princess rises

“I felt like a failure, but I knew deep down I wasn’t,” Roan told the Guardian in 2023. She moved back home to Willard, Missouri, got a job working the drive-thru window at a coffee kiosk, and plotted her next move. She wanted to give herself time to recalibrate and save money before going back to LA and trying music again. She would give herself a year there to make it before giving in and enrolling in college. 

Still, little by little, Roan was beginning to develop a cult following, without any official backing from the music industry. “Pink Pony Club” was becoming a bona fide sleeper hit as it took off across TikTok and through word of mouth.

“Here’s a totally reasonable proposal for song of summer 2021: a single that dropped more than a full year ago, in April 2020, to essentially no fanfare, by a 21-year-old singer-songwriter who hasn’t even cracked 4,000 followers on Twitter,” announced Vulture in 2021, describing “Pink Pony Club” as “a pop hit from an alternate timeline that somehow ended up in ours by accident.” The song wasn’t charting yet, not even close, but it was starting to get attention in all the right places. 

Meanwhile, Nigro had been helping Olivia Rodrigo craft and release her hit debut studio album, Sour. In November 2021, with Rodrigo launched, Nigro and Roan reunited. Roan was feeling listless and ignored, she says, and Nigro gave her the impetus she needed to start working for herself. “[Dan] was just looking at me and goes ‘You are going to run your career into the fucking ground if you don’t start doing shit on your own,’” Roan told Rolling Stone in 2023. 

In March 2022, Roan released “Naked in Manhattan,” her first song as an independent artist, without the backing of a music label. She shot the accompanying video with friends in thrifted wardrobe on the streets of New York City. 

The song sees Roan crushing on a girl friend, hoping to finally cross the line and kiss her. “Boys suck, and girls I’ve never tried,” she sings. In real life, she says, the lyric was true when she wrote it. “I was dating a boy then,” Roan told the LA Times last August. “I had never even kissed a girl when these songs [“Naked in Manhattan” and “Red Wine Supernova”] were written. It was all what I wished my life could be.”

“Naked in Manhattan” continues the aesthetic project Roan found in “Pink Pony Club” and develops it. It’s Roan’s first explicitly queer song. (“Pony Club” covers its coming-out narrative in a thin veil of plausible deniability.) It’s also the first to feature the spoken word interlude that would become a go-to move for her. The accompanying video also debuts the “thrift store pop star” drag queen style that became her calling card: fire engine red hair, elaborate hyper-femme outfits cobbled together from thrift store pieces, a pinup girl burlesque cheekiness. It was a sign that Roan had at last found a new image that she loved. 

In March 2022, Roan was announced as the opener for Olivia Rodrigo and Fletcher. She continued releasing independent singles: “Karma” and “Femininomenon” in August 2022, and “Casual” in October. In February 2023, she launched her own national tour.

All the while, she was developing the character of “Chappell Roan” beyond just a stage name into a fully distinct persona like those used by the drag queens she had come to idolize. “Don’t call me baby, and don’t call me Kayleigh,” she would say at the opening of her shows. When she was performing, she stopped being Kayleigh and Chappell took over.

Chappell was all the things Kayleigh was ashamed of, made newly exuberant and joyful. She wore clownish white-face makeup because “that’s what the country boys called gay people in my hometown. Clowns.” She plays campily with the signifiers of her small-town background: yodeling vocal trills and camo-print merch. Perhaps most significantly, she is unapologetically sexual in ways that her creator cannot quite bring herself to be.

“I have such a difficult time — as Kayleigh — with sex,” she said in an interview with Polyester Zine in 2023. “I have a hard time watching sex scenes or flirting with people! I get really uncomfortable with hyper sexual things. But as the drag queen that I play, Chappell, she’s not like that – she is very confident and comfortable singing about those things.”

In March 2023, Roan announced that she had signed to Nigro’s new label, Amusement Records, in partnership with Island Records.

According to Roan, by then, she had options. “I met with nine labels and I went in with the attitude [of], ‘This is what I need — the only thing I need right now is money,’” she told NME. “So if you don’t give me this, this and this, I’m just not going to sign with you because I can keep going on my own. I was very picky and I had a fuck ton of leverage.”

Roan wasn’t wrong. She had all that leverage because it was clear that her moment was arriving. Now, after years of trying on personas that didn’t quite fit, of working bad day jobs and living with roommates, of scrabbling studio time and music videos together without a label to back her, it’s finally here.

A drag queen pop star in a time of moral panic

Looking back over the arc of Roan’s career, it becomes clear that her music got really good and her career started to take off once she had a strong sense of who she was as an individual. That sense of self is intertwined with Roan defining herself as a queer woman.

The energy of The Rise and Fall of a Midwest Princess comes from the palpable joy of finding oneself and rejecting old beliefs. “Touch me, baby, put your lips on mine,” Roan instructs her sapphic crush in “Naked in Manhattan,” adding with a verbal shrug, “Could go to hell but we’ll probably be fine.” The Chappell Roan of “Good Hurt” might have believed she would go to hell if she kissed a girl. The Chappell Roan of “Naked in Manhattan” doesn’t much care either way, even if the person who wrote the lyrics hasn’t quite gotten there herself yet.

If Midwest Princess is a celebration of finding oneself, Chappell Roan the character is the personification of that glee. Chappell, with her white-face makeup and princessy gowns that are just a little off, expresses what her creator longs for and cannot quite reach herself.

“The whole project is to honor my 10-year-old self. My whole persona is just me trying to honor that version of myself that I was never allowed to be,” she told Paper in June. 

It is probably not just coincidence that America fell in love with Chappell Roan at the same time that drag shows are becoming criminalized. As lawmakers position drag queens as monstrous threats to children, Roan stands for drag as the thing that saved an unhappy child, a joy, a marvelous act of creation. Her artistic project is about finding her self-identity, and as soon as she found that self, she made her a drag queen.

What makes Chappell Roan so compelling to watch is that as a character, she stands for a profound release, an unshaming. She is the artistic culmination of a long search for self-discovery, and you can hear the joy and celebration of that search in the music. 

That is, she’s the culmination for now. Who knows what’s coming next?