The Stunning Transformation Of Chappell Roan

Fans of pop music were unusually blessed in 2024, a year that saw new projects from massive names like Ariana Grande, Dua Lipa, Beyoncé, Charli XCX, Kesha, Katy Perry, and many more. Even though the market seemed incredibly crowded, the first half of 2024 was also a period dominated by an incredible pop culture story: the explosive rise in popularity of an artist named Chappell Roan.

"I'm the pop star of Goodwill. I'm a thrift store pop star. I'm a DIY queen, know what I mean?" she told Rolling Stone in 2022, a few years before her career really took off. "If a five-year-old could draw a pop star, it would be me," she joked. Indeed, Roan's still-burgeoning career has been marked by impressive shifts in her image — from a repressed, closeted Midwest singer-songwriter into a full-fledged, avant-garde queer pop superstar who switches up her look more than anyone since the early days of Lady Gaga.

Even though it may seem like Roan came out of nowhere, she's had a slow and steady rise to the top, putting in the work through a series of setbacks and struggles. This is the stunning transformation of Chappell Roan.

Chappell Roan was born Kayleigh Rose Amstutz in Missouri, and she always hated where she grew up. "I felt so out of place in my hometown. 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."

Thankfully, she found music as a way to cope with the struggle of growing up in a place where she knew she was different. "When I was younger, I really loved Karen Carpenter and I really wanted to emulate her. And then, I really love Stevie Nicks, her gravel and the vibrato she brought," Roan told the Associated Press. She also latched on to 2010s pop icons like Katy Perry and Lady Gaga, finding inspiration in their theatricality and songwriting.

For a while, though, she hid her budding musicality from her family. In a documentary shared to her YouTube channel, Roan's grandmother Barb reflected, "We heard her voice the first time at a junior high talent show." Her grandfather Denny chimed in, adding, "We didn't know she could sing." On Instagram years later, Roan shared a snap of her younger self, holding a cat and looking sad. In the caption, she wrote, "if only she knew how hard she would slay."

After Kayleigh Amstutz revealed her musical talent to her family, they supported her. Soon, as a teenager, she was flying to Los Angeles, laying the groundwork for a music career. Looking back in an interview with Rolling Stone, she revealed it was difficult. "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," she said. "I missed a lot of what would have been the end of my childhood to do this job."

To that end, she developed the Chappell Roan persona to help separate her real life from her stage self. In an interview with the Associated Press, she shared that having that separation allows her to be more sexual and open on stage, even if she doesn't feel that way. "I would say the mythology ... is just like being a girl from Midwest and experiencing, like, Hollywood," she explained. "But involved in that is self-exploration and freedom and finding a community that she didn't have before."

Through fashion choices that involve lots of thrifted clothes and music that makes mention of where she grew up, Roan ensured her pop persona paid homage to her upbringing. "I have to honor this place that raised me, no matter how I feel about it," she said in her YouTube documentary. "This job allows me to do and be whoever I want."

For the first few years of Chappell Roan's music career, the music she made was more indie singer-songwriter than the full-on pop music that would later send her career through the stratosphere. In 2017, she released an EP called "School Nights," which she took on tour in support of an artist called Declan McKenna. "It's very dark pop with some influences of the sixties and seventies," she explained in an interview with AXS. "I really wanted to showcase a very moody vibe with his album."

Even then, thanks to Roan's internet presence, she was beginning to find a fanbase. After opening for McKenna in early 2018, Roan realized there were already people out there who cared about the music she was making. "I had never cried on stage before until last night," she wrote in an emotional Facebook post. "Looking out and seeing people singing my songs with me is a feeling I can't describe. It is a dream come true."

Nowadays, Chappell Roan is known for sexual, proudly queer lyrics. During those early years in Los Angeles, however, she was often writing from a place of inexperience, having grown up in an area where she wasn't able to explore her true self. After all, she'd been immersed in midwestern church life, which isn't exactly known as an accepting community for queer people. "I'm saying that not as an observer," she told The Washington Post in 2023. "I was in it, and I know."

Speaking with Vanity Fair that same year, Roan revealed that several of her songs that mention lesbian relationships, like "Naked in Manhattan," were written as total fantasies. "I hadn't even kissed a girl or dated a girl when I wrote those songs," she confessed.

Soon, though, that all changed. After a night out at an iconic West Hollywood club called The Abbey, Roan felt the queer community opening up to her. "I danced my ass off and I didn't care; it was one of the most fun nights ever," she told Headliner, insisting she was sober the entire night in order to remember every detail. "There were go-go dancers on the table, and I walked in and it was the most spiritual experience. Everyone was having a great time; it was magical. I just felt like I belonged there, and that really changed my life." The night inspired "Pink Pony Club," an ode to the gay community. Chappell Roan had found her people.

When her single "Pink Pony Club" didn't become a smash hit, Chappell Roan was dropped by her label, and amid the onset of the COVID-19 pandemic, she had to move back home to Missouri. At first, she wasn't entirely upset about it; after all, she'd been unhappy in Los Angeles, in part because she was so young. "You can't do anything in LA or anywhere if you're under 21 'cause everyone just goes out and I was so sad," she told Vanity Fair. "I was just so f***ing young and it just sucked. But I did learn so much."

Being dropped by her label meant a chance to reset. "I was upset about my project not moving. I felt stuck and like no one was paying attention to me," Roan told Rolling Stone of that tough time back home, during which she worked at a coffee shop and thought about quitting music. She got back in touch with producer Dan Nigro, who gave her some tough love. "[Dan] was just looking at me and goes, 'You are going to run your career into the f***ing ground if you don't start doing s*** on your own.'"

That's exactly what Roan decided to do, and it paid off; after releasing several singles independently, she was signed once more, this time to a division of Island Records. Back to Los Angeles she went.

This time around, Chappell Roan had a new sound, closer to the glittery synth-pop she explored on "Pink Pony Club." She fine-tuned the Chappell Roan persona, too, making her stage character more akin to a drag queen. "I think Chappell's a drag-queen version of me because it's very larger-than-life. Kind of tacky, not afraid to say really lewd things. The songs are kind of the fairytale version of what happened in real life," she told Vanity Fair.

This time around, the queer themes in her music felt more authentic, too. "I'm not observing from the outside anymore," Roan reflected. "I feel like I'm in it. I am the queer community — it's allowed me to just feel queer, feel like a queer person and feel freedom in that."

It all led to the release of "The Rise and Fall of a Midwest Princess," Roan's debut album, which came out in September 2023. Her new music and her new aesthetic suddenly hit. "I was the thrift store pop girl — it was so drag," she told NME. "I learned how to embellish my own costumes. I was like, 'I'm gonna give it one more year — and if it doesn't work, I'll rethink.' But do you know what, it f***ing worked."

Back in 2022, when Olivia Rodrigo embarked on a world tour in support of her album "SOUR," she brought along Chappell Roan on a handful of dates as an opening act. The two have been friends ever since, as evidenced by a photo Roan posted to Instagram in February of that year. Roan was pictured alongside Rodrigo, Conan Gray, and Dan Nigro, a producer with credits on songs by both Roan and Rodrigo. "I feel so loved and supported," Roan wrote.

In 2023, as her career began to really take off, Roan told NYLON that she turned to the former "High School Musical: The Musical: The Series" star for advice about how to handle sudden fame; after all, Rodrigo had admitted to having an "identity crisis." "'I don't have the answers — I'm sorry. No one has the answers,'" she remembered Rodrigo telling her. That was an answer that worked for Roan. "She's so good at being a normal person when everything is abnormal around her," the "Femininomenon" singer said.

In 2024, Roan joined Rodrigo as the opener on The GUTS World Tour. On Instagram, she showered praise on her friend, writing, "thank you @oliviarodrigo for asking me I am very honored. I adore you and the community that surrounds your project." The tour turned out to be a pivotal one for Roan, giving her widespread exposure just as her music began to take off.

Throughout the early months of 2024, a number of Chappell Roan live performances went viral online, proving her talent to an online audience that maybe only heard her music on TikTok. In March, she performed an NPR Tiny Desk Concert, wearing an elaborate red wig, white face paint, and now-trademark blue eyeshadow. "the lipstick on the teeth, the matching eyeshadows, the insane wig- she's one of the most 'committed to the visuals' gen z artists out there!!!!!!!" one person commented on YouTube.

In April, she performed a set at Coachella that blew fans away. Thanks to the festival's livestream, fans around the world were able to watch as she bellowed the climactic bridge in "Good Luck, Babe!" As fans have noted on X, formerly Twitter, the moment corresponded with a major increase in her online streams.

At Governors Ball in New York in June 2024, Chappell Roan dressed as the Statue of Liberty for her set. She gave a moving speech about how far America still needs to go. After quoting from the poem engraved on the iconic statue, Roan added, "That means freedom in trans rights, that means freedom in women's rights ... and it especially means freedom for all oppressed people in occupied territories." A new pop star with an interesting visual sense, the live performance skills to back it up, and a willingness to get political — the crowd went wild.

After Chappell Roan's career exploded in popularity throughout the first half of 2024, she struggled to keep up. After one performance shortly after her mega-viral Governors Ball set, Roan cried onstage while talking about how strange everything felt. "I guess I just want to be honest," she said in a YouTube clip, her voice catching. "I think that my career is just kind of going really fast, and it's really hard to keep up."

In an interview with Glamour, Roan elaborated on how she's had to set boundaries with fans in order to protect her mental health. While her early tours featured meet-and-greet options for fans to hang out with her backstage, she quickly found that a lot of fans had a tendency to overshare, telling her very emotional stories moments before she had to go on stage and perform.

"Toward the end, I was having panic attacks between the meet-and-greets and the shows, because of how intense the stories were that people were telling me," she recalled. "The meet-and-greets, I don't think I can do that again. I know a lot of artists, as you grow, they can't do it anymore. Because of this. Oh, my God, the boundaries, there's none, you know?"

Through a series of performances in 2024, Chappell Roan became known as someone who would dress outrageously, transforming her look for each show. For years, Roan has paid homage to the drag community, and she began wearing looks honoring some, including "Pink Flamingos" star Divine. After she mimicked Divine's red dress and iconic makeup from that film, Roan quoted from the John Waters movie and wrote on Instagram, "Filth is my politics! Filth is my life! ... inspired by Divine the most beautiful woman in the world, almost."

Shortly thereafter, she wore a leopard-print look that resembled Divine's outfit in Waters' film "Female Trouble." In the corresponding Instagram post for that look, Roan went into more detail about what Divine meant to her. "i like to believe madame divine was watching over the performance and she was the one who set off the fireworks during casual," she wrote. "divine if you are reading this from heaven...come down and haunt me sometime."

When Roan appeared on "The Tonight Show Starring Jimmy Fallon," she shouted out another drag legend: "RuPaul's Drag Race" winner Sasha Colby, who was an icon in the queer community even before she competed on the show. Colby calls herself "your favorite drag queen's favorite drag queen," and Roan adopted her confidence, naming herself "your favorite artist's favorite artist." She told Fallon, "It just hit me through the heart. I hope Sasha Colby one day watches me."

Almost a year after "The Rise and Fall of a Midwest Princess" was released, as her popularity exploded, Chappell Roan's music hit the Billboard charts for the first time. Her album finally vaulted into the upper reaches of the chart, even though it didn't hit the Billboard 200 at all when it was first released. Billboard pointed out her entire catalogue was receiving about 3 million streams a week at the beginning of 2024, several months after "Midwest Princess" was released. By June, however, only six months into the year, she was racking up a staggering 68.36 million streams a week.

"The Rise and Fall of a Midwest Princess" wasn't the only Chappell Roan offering to impact Billboard; several singles hit the Hot 100, too. As an account called ChappellCharts noted on X, formerly Twitter, "Pink Pony Club" finally charted ... four years after her label dropped her for not being an immediate smash. 

One twitter user offered up a theory as to why Roan's music was finally taking off, after all this time. "People are starving for something authentic and cool in pop again," they wrote. "She's filling a void!"

Chappell Roan calls herself "your favorite artist's favorite artist," and there's a good chance that's quite literally true. In addition to her friendship with Olivia Rodrigo, plenty of other big-name artists have lined up to support Roan's rise to superstardom. For example, after she covered "Bad Romance" at a 2024 concert, Lady Gaga noticed the video going around TikTok. "I love Chappell," she commented, followed by a string of black heart emojis.

Sabrina Carpenter, who experienced a massive surge in popularity in 2024 too, covered Roan's single "Good Luck, Babe!" for the BBC. After Roan's Statue of Liberty costume went mega-viral, fans photoshopped her into a meme about the upcoming "Wicked" film, catching the attention of star Ariana Grande. "I really ♡ @chappellroan," she wrote on her Instagram Story. Fans on X, formerly Twitter have noticed that SZA often comments on Roan's Instagram photos, and Kesha tweeted that she was excited about seeing Roan at Lollapalooza.

She has the attention of some industry legends, too. Elton John is known for befriending younger artists, and he's a massive fan of Roan. On Instagram, he shared a photo of the two hanging out. "The BEST evening of pizza and outrageous laughter with the fiercely fabulous @chappellroan," the "Crocodile Rock" singer wrote. "Love her, love her, love her." Surely that love for Roan will only continue to spread as her career continues.