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.
Chappell Roan spent 7 years becoming an overnight success
How a Midwest princess played the long game and embraced queer joy.
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.”
“Don’t call me baby, and don’t call me Kayleigh,” she would say at the opening of her shows
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?