The Rise and Rise of a Midwestern Princess
Chappell Roan's meteoric rise to pop stardom has been thrilling to watch—but with her unstoppable ascent, could a dramatic fall be just around the corner?
Chappell Roan seemed to appear out of nowhere, and just as quickly, she dominated the summer as the US's biggest pop sensation. Despite Taylor Swift and Billie Eilish both recently releasing record-breaking albums, Chappell achieved the seemingly impossible: her album, “The Rise and Fall of a Midwestern Princess,” soared to the number one spot on US Spotify, displacing both superstars from the top.
Chappell’s Spotify success is just one of her many incredible achievements over the past few months. Summer festival organizers—who booked her when she was still an emerging name—had to scramble to re-accommodate her in the lineup to match the massive crowds she has been drawing. In June, Bonnaroo had to move her to the biggest stage at the last minute as the anticipated public for her gig surpassed 55,000 people. Her afternoon show at Chicago’s Lollapalooza in early August drew the largest crowd in the festival’s 33-year history—a remarkable feat, considering Lollapalooza is North America’s highest-attended festival and has seven international editions, all booking major A-list artists.
Not since Olivia Rodrigo's breakout in early 2021 has there been such a rapid pop takeover. So, who exactly is Chappell Roan, and how did she pull off this incredible feat?
Well, first things first: it wasn’t fast at all.
From the Trailer Park to a Record Deal
Raised in a conservative, unglamorous town, Chappell Roan found solace in singing. Her talent quickly opened doors, leading to a record deal before she even graduated high school. From the trailer park to a major recording contract, it could have been a rags-to-riches Cinderella story. But real life is more complicated than that.
Chappell was born Kayleigh Amstutz in 1998, part of a working-class, conservative religious family in small-town Missouri. She struggled to connect with her upbringing, which involved attending church three times a week, where she was taught that being gay was a sin. In a few interviews, she described her childhood home as a trailer park. Amidst a disorienting, unglamorous daily life, the young girl found solace in singing and pop music. Her confidence in her talent soared after receiving thunderous applause at her middle school talent show. This success sparked her interest in exploring her theatrical and musical side, leading her to attend an arts summer camp in Michigan.
Venturing outside her conservative small town for the first time, she met countless creative young people, and the experience deepened her passion for music. At camp, she wrote her first original song, “Die Young.” Soon, she started posting videos of her original material on YouTube and, in no time, traveled to New York City for a series of showcases for music executives. By May 2015, at only 17, she had signed a deal with Atlantic Records.
With her record contract in hand, she started spending more time in L.A., ready to leave behind the name and hometown that never felt like hers. To mark this new chapter, she adopted a new identity inspired by her late grandfather (Dennis K. Chappell) and his favorite song (“The Strawberry Roan”).
Kayleigh Amstutz was now Chappell Roan.
The Come-Up
After leaving Kayleigh behind, Chappell began her professional singing career. But will the indie Tumblr darling path she was molded into take her anywhere?
After two years of traveling between Missouri, L.A., and New York for recording and training, Chappell finally released her debut single in the summer of 2017. By September, she had dropped an EP titled School Nights. The image she and the label crafted was far from her current aesthetic—straight black hair and long white gowns gave her a witchy vibe. She deepened her voice, stretched vowels, and embraced the distinct “cursive singing” style that defined indie girls of that time.
The reasoning behind this look was clear. Commercial success isn’t about blazing a new trail but rather winning over the public with a sense of familiarity. Chappell followed the lead of successful alternative music darlings of the Tumblr era, like Florence & the Machine and Halsey. At first glance, it made sense. Chappell had an alternative edge and sultry beauty, in contrast to the tanned, voluptuous look of a mainstream pop star. Her writing had depth, so adopting the indie Tumblr girl approach seemed logical.
Her first single, “Good Hurt,” was about the sadomasochistic thrill of falling in love with a bad boy. It embodied many trends of the era, but it’s hard to find any connection to the Chappell we came to know years later.
Despite significant opportunities—touring with alternative rock band Vance Joy and British singer/songwriter Declan McKenna—she failed to resonate.
Given the circumstances, her lack of success was expected. At that point, Chappell had already found her artistic name. But besides the name, who was she? Chappell seemed lost.
Self-Discovery
After a permanent move to L.A., the young artist finds her place in the world and meets the man who’ll decisively change her career. Unfortunately, that may not be enough.
In 2018, at 20 years old, Chappell moved full-time to L.A. Growing up, she had heard the city characterized as demonic and full of Satanists. But, to her surprise, she felt right at home and, most importantly, free. For the first time, she could dress however she wanted without fear of standing out. After missing her senior year of high school due to work commitments, she finally had a chance to experience a second adolescence, diving into nightlife and drag culture. She described discovering the gay clubs in West Hollywood as “spiritual.” It was then that the real Chappell Roan began to emerge.
Equally crucial as her move to California was meeting young producer Dan Nigro. Born and raised in Long Island, Nigro had some success as the lead singer of an indie band in his late teens before transitioning to production. His name first gained attention in 2011 when, at 29, he co-produced the buzzed-about debut album Night Time, My Time by indie darling Sky Ferreira. From then on, he worked with up-and-coming alternative and pop artists. He and Chappell immediately hit it off when they were introduced in October 2018.
Throughout 2019, Roan kept a low profile as Atlantic put her career on hold after her initial releases failed to generate much buzz. However, by early 2020, Nigro—her creative partner—had played a key role in two acclaimed records that helped establish indie stars: Caroline Polachek’s Pang (2019) and Conan Gray’s Kid Krow (2020). At that point, Roan had been on the back burner since 2018, but Nigro’s success and her connection to him prompted Atlantic to reconsider her as the indie-alt pop star they envisioned.
Rock Bottom
All the elements that took Chappell to stardom started to align. However, the timing was off, and instead of fame, it led her to hit rock bottom.
Written in late 2018, the first song Nigro and Roan created together, “Pink Pony Club,” was finally released in April 2020. Loosely based on her own life, the song, which she idealized after her first night out at The Abbey nightclub, narrated the story of a small-town girl from Tennessee who finds her place in a gay club in Santa Monica. It marked a significant departure from the indie angsty pop Chappell had done up to that point. Instead of the indie vocal fry, the powerful synth-pop ballad featured layered vocals that showcased Roan’s impressive range. The accompanying video also presents her in a new light, dancing around a bar in rhinestone outfits alongside drag queens.
Atlantic Records was surprised by the sudden shift in her style and mildly displeased, fearing she’d lose the few fans she already had. Still, they allowed her and Nigro to pursue their vision. After “Pink Pony Club,” she released two other Nigro-produced tracks, “Love Me Anyway” and “California,” but neither found success. Meanwhile, the world was coming to a halt due to COVID. There was uncertainty in the air, and none of her songs had broken through. In August 2020, the same week her boyfriend broke up with her, her label, unable to turn her into a profitable act after five years, dropped her.
With no money, no boyfriend, and no job, Chappell returned to her parents’ home in Missouri and found blue-collar jobs to support herself. Although she felt she was at rock bottom, she took this time to recalibrate before going back to L.A. to resume her career and music ambitions.
While Chappell worked as a barista and in a donut shop, Dan Nigro’s life was about to change radically.
Chain Reaction
The worldwide success of an emerging artist triggers a chain reaction that makes Chappell’s pop career viable once again.
While Chappell’s career was hitting a dead end, another young artist was moving fast: Olivia Rodrigo had found success as a child actress, booked a leading role on Disney Channel, and, in 2018, at 16, was cast as the lead in a Disney streaming show based on High School Musical. With a deep passion for music, she convinced producers to let her collaborate on the show’s soundtrack with one original song she had written. To everyone’s surprise, the song “All I Ask” became a massive TikTok viral sensation, and Olivia, who until then was just a teen actress, was sought after by major labels. Universal’s Interscope Records quickly signed her.
Before the labels came into play, Dan Nigro had already recognized Rodrigo’s impressive talent when he discovered an Instagram video in which she sang a snippet of one of her unreleased songs, “Happier.” He sent her a DM inviting her to collaborate. By the time she scored her Interscope deal, Nigro was already her producer. Her first solo single, “Drivers’ License,” was released in early 2021 and surpassed all expectations, becoming an international phenomenon and hitting #1 worldwide. Suddenly, Nigro was the creative partner of the world’s hottest pop star.
With “Drivers’ License” breaking all kinds of records, the label fast-tracked an album, and Nigro and Rodrigo got to work. Her debut album, SOUR, was released in May, and once again, it became a worldwide sensation. Up to that point, Nigro was a well-respected producer, but now he was one of the hottest hitmakers in the world. Indirectly, this benefited Nigro’s other protégé, Chappell.
Even before this whirlwind unfolded, “Pink Pony Club” was already starting to get noticed. In December 2020, a month before Rodrigo’s debut single, USA Today highlighted the song as one of the strongest of the year. Once Nigro became the hottest name in music production, the acclaim for Chappell’s track intensified, with Vulture billing it “the song of the summer.”
With Rodrigo’s success, it took a while for Nigro to find the time to meet Roan again. To focus on songwriting, she returned to Missouri, where she penned songs while working at a drive-through. In November 2021, the two finally reunited. At that point, Chappell was feeling frustrated, ignored, and lost. Nigro did not mince his words, advising her to take matters into her own hands instead of waiting for opportunities to arise. Otherwise, she’d “fuck her career into the ground.” Right after, they went back to work on music.
Career Takeoff (Phase 1)
After six years, Chappell’s career finally started moving forward. But stardom still wasn’t in the cards.
Following Nigro’s advice, Chappell took control of her destiny. By early 2022, her standing as a pop star was stronger, partly due to her association with Nigro. Around that time, she earned a publishing deal with Sony. In March, she officially restarted her career with the release of “Naked in Manhattan.” Although she left behind her indie alt-girl aesthetics, this time, she was indeed an independent artist.
Her partnership with Nigro established the sound she wanted to make. Now, it was time to define her aesthetic. For the first time in her career, she began wearing her hair in the now-iconic red-engine color. Inspired by drag queens and the colorful vibe of Katy Perry’s Teenage Dream, one of her favorite albums growing up, she scoured thrift shops for bright, campy outfits, creating vibrant and kitschy looks. She learned how to do makeup like the drag queens she admired. “If a five-year-old could draw a pop star, it would be me,” was how she defined her style for Rolling Stone.
Chappell also leaned fully into her queer identity. While “Pink Pony Club” was a coming-out of sorts, she became more literal. “Naked in Manhattan” was about kissing a girl for the first time. In her dance-pop anthem “Femininomenon,” she oscillates between feeling something is missing in her sexual encounters with men and the ease of dealing with women. “Red Wine Super Nova” explores having a crush on a girl and mustering the courage to ask her out.
Curiously, while Chappell enthusiastically wrote about queer love, she still had no same-sex experience. As she told NME, she was writing about the girl she wanted to be and the experiences she longed for while grappling with her fears and some internalized homophobia.
Regardless, these songs — along with other bops such as “Casual” and “My Kink is Karma” — made their way to streaming services and began gaining traction on TikTok. In the fall of 2022, she opened for Fletcher, an indie queer artist. Shortly after, she booked her solo tour. In February 2023, she embarked on the 20-city “Naked in North America” tour across theaters in the US. As she took the stage, she finally found her footing and understood who she was as an artist. A drag queen fanatic, she had a local drag queen opening each one of the dates, while also starting to define herself as a drag artist.
Stardom wasn’t on the horizon yet, but things were moving quickly, and Chappell was finding success within her niche. It was time to take the next step and release her debut album.
Hot to Go
Chappell Roan’s career is on the rise, but one thing is missing: money. After finally landing a major deal, the star is hot to go. The long-awaited release of her first album can only mean mainstream fame, right? Well…
As 2023 dawned, Chappell knew it was time to drop her first album. However, to do it her way, she needed one thing: money. So, she went shopping for a record label.
This time, Chappell had something new: leverage. She had independently built a respectable career with a publishing deal, minor TikTok hits, a niche following that led to a sold-out tour and a strong social media presence, and one of the world’s hottest producers as her creative partner. In many ways, she was precisely what executives wanted—a safe bet. Nine labels offered her a deal. In the end, she chose Universal’s Island Records, which agreed to partner with Nigro’s newly-established imprint, Amusement Records. Nigro, her biggest cheerleader, set up the label solely to support her.
With money, a major label, and an enthusiastic team, Roan was “Hot to Go,” as announced by her first post-signing single in August. The following month, her album “The Rise and Fall of a Midwest Princess”—four years in the making—was finally out.
The 14-track album was unapologetically pop, nodding to both the colorful mid-2000s pop that she grew up with, and the late-80s sound that came before and made Madonna a star. The production was sleek, and the lyrics were tongue-in-cheek yet revealing, taking listeners on her journey of self-discovery. The songs could make you emotional but also amused at her witness.
“I heard you like magic; I got a wand and a rabbit,” she sings in “Red Wine Super Nova,” in a clever reference to two famous vibrating toys. In “Hot to Go,” she isn’t shy about her intentions: “Baby, do you like this beat? I made it so you sleep with me.” From her increasingly hysterical interruptions asking for a beat change in “Femininomenom” to her dealing with her internalized homophobia in “Naked in Manhattan” (“Touch me, baby, put your lips on mine / Could go to hell but we’ll probably be fine”), it’s impossible to go through the album without cracking a few smiles. Critics praised “The Rise and Fall of a Midwestern Princess” as a great debut.
Naturally, the logical next step was stardom.
The album didn’t even chart on the Billboard Top 200.
The Olivia Connection
Having a bond with one of the world’s biggest popstars might help.
Right after releasing her debut album, Chappell embarked on her second tour. Backed by her label, she performed not only in the US and Canada but also in Australia, Paris, Berlin, Amsterdam, and London. As she wrapped up the tour with two nights at the iconic gay club Heaven in London, she felt on top of the world.
Did Chappell want mainstream fame? She wasn’t sure. Was it expected with her major label deal? Definitely. For the young queer artist, performing at Heaven might have been the pinnacle, but there was still money to be made. At that point, her album hadn’t even cracked the top 200 of any official chart, and with the Nigro connection, the industry wanted the next Olivia Rodrigo.
Of course, that connection was quickly leveraged. Two weeks before Chappell’s album launch, Rodrigo released GUTS, her highly anticipated follow-up to her multi-platinum debut. She also announced her first arena tour, with up-and-coming acts as openers. For the first 24 North American stops, that act was Chappell.
Chappell’s connection with Olivia went beyond the professional—they formed a friendship. In May 2022, while still unsigned, Roan was chosen to open Olivia’s concert in San Francisco. By December, Olivia was in the audience at Chappell’s first solo concert in New York City.
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Joining Olivia on tour, however, was a massive deal. At that point, Chappell was an alt LGBT-aligned artist with a niche following. The GUTS tour meant her first taste of mainstream exposure.
Career Takeoff (Phase 2)
For two years, Chappell’s career was gaining steam. In 2024, it finally took off.
As Chappell joined Olivia Rodrigo on tour, her streams started showing exponential growth. Rodrigo’s fans began to discover Chappell not only through the concert but also thanks to social media. On Instagram and TikTok, their cute friendship often went viral, like when, for her last night on tour, Roan surprised Olivia at the fan interaction portion of her concert.
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The buzz spread beyond Rodrigo’s fanbase. In late March, her NPR Tiny Desk performance quickly gained attention. By early April, "The Rise and Fall of a Midwest Princess" finally debuted at #127 on the Billboard 200. Days later, she released her first new single since the album "Good Luck Babe," which instantly hit Spotify’s US Top 50. The release was timed to coincide with her performance at the country’s most influential festival, Coachella. Her set at the California music bonanza soon went viral.
From there, things accelerated as the public discovered her album. Her "Midwest Princess" tour sold out. When she was announced as the headliner for a Pride concert in Kentucky, all 25,000 tickets sold out for the first time in the event’s history. As the summer festival season began, Chappell was the hottest act in the country. A drag-inspired artist, she captivated audiences not just with her stage presence and vocals but also with her creative costumes. The last time a new act made such a splash was over 14 years ago, when Lady Gaga, also known for her performances and outfits, became a global phenomenon. Even Google got in on the Chappell-mania, with search results labeling her "your favorite artist’s favorite artist," a nod to how she introduced herself during live shows (and a reference to her favorite drag queen).
Chappell’s success seems like a logical outcome. She’s a talented artist creating irresistible pop, with a natural stage presence honed by years of training before the masses discovered her. She is everything pop fans want: fresh, young, and current, utterly new while also being from the same lineage as former stars of the moment, like Madonna and Lady Gaga.
As a gay artist, she’s a powerful symbol for many. While LGBTQ+ stars — Connan Gray, Troye Sivan, Girl in Red, Boygenius, Rennee Repp — have been big on the indie scene (and some on the periphery of mainstream acclaim), Chappell might be the first in decades to truly take over the charts.
Chappell’s ascent mirrors a broader trend where pop culture responds to the moral panics of its time. During the Trump years, when Latino immigrants were targeted, Spanish-language music became mainstream in the U.S., exemplified by Bad Bunny’s rise as the world’s top artist. More recently, with trans and drag queens becoming targets in conservative discourse, Chappell’s success serves as an antidote, with the fervor around her being particularly strong in the South and in her native Midwest, conservative areas of the country where LGBTQ rights are in peril. Her emergence aligns with the current cultural moment and where young people stand.
In one of her most recent viral performances, she stood on stage at the Governor Ball festival in New York dressed as the Statue of Liberty while telling the audience why she refused an invite to perform at a Pride event at the White House.
“I’m in drag as the biggest queen of all. But in case you’ve forgotten, etched on my pretty little toes are the words ‘Give me your tired, your poor, your huddled masses yearning to breathe free,’” she said, referencing the 1903 plaque on the statue’s pedestal. “That means freedom and trans rights, that means freedom and women’s rights, and it especially means freedom for all oppressed people in occupied territories.
“When you do that, that’s when I’ll come,” she concluded as the public roared.
Growing Pains
Chappell Roan wanted pop stardom. She may be having buyer’s remorse.
Of course, Chappell wanted success, but she always struggled with the idea of mainstream fame.
In May 2022, she opened up about her mental health and dealing with Bipolarity in an Instagram post. One year later, she wrote another post about her struggles. “I’m grateful I have the means to afford therapy and occasional time off. Everything is very exciting right now, and I’m realizing that success actually makes me quite uncomfortable and self-conscious, and I’m not sure why yet.”
Even though she hadn’t yet hit the mainstream, the success and attention already felt overwhelming. At the time, she went to Olivia Rodrigo for advice.
“I asked [Rodrigo], ‘When you were getting big, did you talk to Billie Eilish? What did you do?’ And she was like, ‘I don’t have the answers—I’m sorry. No one has the answers,’” Roan shared in a July 2023 interview with NYLON. “I don’t feel like a normal person right now, and I’m not even near where [Olivia] is.”
Now, Chappell is a bona fide superstar, with her album currently at #1 on the US Spotify charts and “Good Luck Babe” as the most streamed song in the country. She has five other songs in the top 40, and her debut album just hit #2 on the Billboard charts almost a year after its launch.
However, things haven’t gotten any easier. During a solo concert in Raleigh in June, she choked up while sharing that she was having a “really hard time.”
“I just feel a little off today because I think that my career’s just kind of gone really fast, and it’s really hard to keep up,” she tearfully confessed. “This is all I’ve ever wanted; it’s just heavy sometimes."
Chappell had never faced controversy until her discomfort with certain aspects of fame abruptly changed that. In a highly divisive TikTok video posted this week, she expressed her frustrations about excessive fan behavior, defending her right to say “no” to photo requests and to feel annoyed by fans shouting at her from their car windows. She emphasized that while such behavior is often normalized, and many believe it comes with the job, she refuses to accept it. “I don’t want whatever the fuck you think you’re entitled to when you see a celebrity,” she stated.
Her conclusion? “I’m a random bitch, you’re a random bitch. Just think about that for a second, okay?”.
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The TikTok video garnered 2 million likes, with many fans supporting her decision to assert her boundaries. Ironically, the overwhelmingly positive reaction to her outburst is just an extension of the very culture she criticized. After all, only in celebrity culture would millions coddle you for what is essentially an unreasonable complaint.
Being a celebrity is a choice. Becoming one means accepting the terms and conditions of what allows your rise: celebrity culture. The essence of celebrity lies in charming people with your charisma, fostering a sense of familiarity and adulation. It’s because people idolize you that they’ll spend hundreds on your merchandise, devote their time to consuming your work, and drop the equivalent of a monthly wage on your concert ticket. There are countless perks: more money than most will encounter in their lifetime, incredible opportunities, and a great deal of comfort. However, there are also downsides: annoying fans and a lack of privacy. Yes, people will ask for photos and shout at you. You will have to make sacrifices. But that’s simply a result of your own choices. Because, no matter what you tell yourself, you are not a random bitch.
Like many aspects of capitalism, celebrity culture is toxic. And we’re all victims of it. While celebrities reap direct benefits from this system, the fans who harass them for a photo are also victims, albeit ones who gain far less.
In other words, Chappell’s annoyance with fame is understandable. In many respects, she is right. But if she isn’t willing to make the sacrifices that fame requires, shouldn’t she consider saying no to big festivals and deleting her social media? If it bothers her so much, do the people around her—who are ensuring she becomes one of the biggest names of the year—truly have her best interests in mind?
While social media debated the merits of her controversial venting, Chappell seemed to make peace with fame. Last Wednesday, she appeared as a surprise guest at Olivia Rodrigo’s concert in L.A. Together, they performed “Hot to Go” as the 20,000 crowd cheered loudly.
The night could serve as a lesson for the young star. After all, if you want to revel in the parasocial relationship that brings a crowd of thousands to shout your name, you must be prepared to deal with the inevitable annoying fans haranguing you for a selfie. One does not exist without the other.