A Timeline of Chappell Roan’s Rapid Rise From YouTube Covers to Global Stardom

It’s not over quite yet, but I have a feeling that 2024 will be remembered as the year of Chappell Roan. With her bright-red hair, ambitious drag-inspired looks, and her penchant for unabashedly queer pop songs, the 26-year-old openly lesbian artist has experienced a truly meteoric rise to mainstream stardom. From drawing record festival crowds to topping national charts — with a song about compulsory heterosexuality of all things! — it seems like you can’t blink without running into another Roan-related headline.

Despite her sudden rise, Roan’s ascent to stardom has in fact been at least 10 years in the making. The “Good Luck, Babe!” star has been putting out music for a decade, drawing on her small-town Missouri upbringing to deliver a love letter to the Midwestern and Southern LGBTQ+ community during a time when anti-drag and anti-LGBTQ+ legislation is sweeping the country. Still, her Gen Z ubiquity hasn’t stopped her from facing public backlash over her request for fan boundaries and criticisms of Democratic policies. Her stardom has raised questions about the unique contours of parasocial fandoms in the 2020s, especially given her young queer audience.

If you haven’t been a card-carrying member of the Pink Pony Club from the beginning, you might find yourself wondering how exactly we got here. So without further ado, allow me to guide you through Roan’s 10-year journey to pop stardom, from YouTube covers to her truly wild 2024 rise.

2014: Chappell Roan gets her start on YouTube

Like many Gen Z and young millennial stars, Roan got her start sharing music on YouTube as Kayleigh Rose. A teenager living in the small town of Willard, Missouri, she began uploading covers before sharing her original song “Die Young” in November 2014. In the moody, Lorde-esque track, Roan sings about a young protagonist’s journey “running with the devil” and losing herself “with a bottle and the bottom of an ashtray,” while still dreaming of finding love. During a September 2024 Rolling Stone cover story, she described the track as “the corniest song on Earth.”

Still, it wasn’t long before the song granted Roan a platform.

November 2014: Chappell Roan receives a shout-out from Troye Sivan

Roan and Sivan are currently making headlines for the Sweat tour and The Rise and Fall of a Midwest Princess respectively, but the “Rush” singer has actually been aware of Roan for a decade. Way back in 2014, Sivan took to X to shout out her song “Die Young.”

“I’ve had this 16 year old girl on repeat for 2 months,” he tweeted at the time. “You HAVE to listen to this, guys — go send some love.”

Sivan continued to hype Roan up in a follow-up tweet, writing, “LETS BLOW KAYLEIGH UP BC I HAVEN’T HEARD A VOICE LIKE THIS SINCE ADELE, NO EXAGGERATION.”

It’s an especially sweet shout-out given that Sivan also got his start on YouTube. Shortly afterward, Roan thanked the singer for the shout out, posting a screenshot of the song receiving over 15,000 YouTube views via an old Instagram account.

“Thank you so much to all who have supported my music and I!” she wrote at the time. “Also, thank you so much Troye Sivan.”

May 2015: Kayleigh Rose Amstutz signs with Atlantic Records and becomes Chappell Roan

Shortly after turning 17, Roan signed with Atlantic Records, officially taking on the stage name she uses today. The moniker pays tribute to her late grandfather, Dennis Chappell, whose favorite song was the classic country song “The Strawberry Roan.”

“People would always ask if I had a plan B,” Roan recalled in a 2017 short documentary. “And he never asked. He just knew I could do it.”

After signing with the label, Roan missed her senior year of high school to focus on music, an experience that she later admitted she had mixed feelings about. “I don’t miss high school… But I miss my youth,” she told Vanity Fair of the decision in 2023. “I mourn being a kid because my career took that away from me pretty immediately when I signed.”

September 22, 2017: Chappell Roan releases the EP School Nights

In late 2017, Roan released her EP School Nights, which features five songs: the aforementioned “Die Young,” “Good Hurt,” “Meantime,” “Sugar High,” and “Bad For You.”

“Sonically, I’d say that it’s very dark pop with some influences of the sixties and seventies,” Roan told AXS in a 2018 interview. “I really wanted to showcase a very moody vibe with [this] album.”

In other words, her musings about craving a “good hurt” and romancing a “beautiful boy” whose words are “made of poetry” are markedly different from the queer, camp-infused stylings that pervade The Rise and Fall of a Midwest Princess.

“I used to be very witchy, dark, serious,” Roan remembered during a 2023 interview with Amazon Music. “I was just emo and wanted to be a witch.”

2017 to 2018: Chappell Roan books her first opening gigs

During her School Nights era, Roan nabbed her first major supporting gigs. In 2017, she toured as an opening act for Australian indie musician Vance Joy during the U.S. leg of his “Lay It On Me” tour. By early 2018, she began opening for English singer Declan McKenna.

Seeing McKenna perform helped inspire Roan to make the switch to more upbeat pop music herself.

“I hated performing my old EP on tour,” she told Vulture in 2023. “[...] And [Declan] would jump off the speakers, and throw balloons in the crowd, and have so much fun every night. I was like, ‘I want to do that. I don’t want to do what I’m doing. This is too serious. How do I have fun on stage? How do I make this a party?”

April 2020: Chappell Roan releases “Pink Pony Club”

“Pink Pony Club,” which ultimately became the first single from Roan’s debut album, tells the story of a young woman who trades her upbringing in conservative Tennessee for the freedom of performing in the neon-tinged eponymous, fictional West Hollywood gay bar. The track was inspired by Roan’s own trip to The Abbey in Los Angeles.

Ironically, what has become an anthem for gay clubbing and discovering oneself within the queer community was released in April 2020, when said locales were largely closed amid COVID-19 lockdowns. To make matters worse, Roan later revealed that her label didn’t even want to release the song at the time.

Luckily, the song has since received its flowers and then some. On TikTok, many fans have shared viral videos stitching a clip of Roan performing “Pink Pony Club” solo on a keyboard at a tiny 2021 Los Angeles fundraiser with more recent videos of passionate crowds screaming along to the song’s infectious post-bridge chorus.

“It feels so good to prove [Atlantic Records] wrong [about ‘Pink Pony Club’] because they weren’t just a little wrong,” Roan later told Rolling Stone. “They were really, really, really wrong. To know that my gut instinct was right is the best feeling in the world.”

August 2020: Atlantic Records drops Chappell Roan

Reportedly displeased with the performance of “Pink Pony Club” in the midst of the COVID-19 pandemic, Atlantic Records dropped Roan a few months after its release. That same week, her partner of four years broke up with her.

Roan ended up temporarily moving home to Missouri, where she was diagnosed with bipolar II disorder and started to piece her life and career back together while working at a drive-through coffee chain. In 2021, she moved back to L.A. and found work as a nanny and production assistant.

“I was like, I have to give this a shot, one more year,” Roan recalled to Paper magazine in June 2024. “If I fucking hate L.A. and make no money from music, then I’m just going to move to Nashville or something, go to school, because obviously, this is not for me. It kind of worked.”

2022: Chappell Roan goes independent

In 2021, Roan reconnected with producer Dan Nigro, with whom she had worked on “Pink Pony Club” and who had recently blown up thanks to his work on Olivia Rodrigo’s debut album Sour. When they reunited, she recalled Nigro giving her some tough love.

“I felt stuck and like no one was paying attention to me,” she told Rolling Stone in 2022. “[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.’”

From there, she began working on her first songs as an independent artist, resulting in now-viral tracks like “Naked In Manhattan,” “Femininomenon,” and “My Kink Is Karma.”

“Naked In Manhattan” marked Roan’s first time explicitly singing about her attraction toward women as she explored her own relationship with her queerness.

“I was dating a boy [when I wrote it],” she told the Los Angeles Times in 2023. “I had never even kissed a girl when these songs were written. It was all what I wished my life could be.”

In the long run, Roan has described going independent as “the best thing that could’ve happened to my career.” It was during this time that she began garnering newfound fans for her queer pop singles and scoring larger opening gigs on Rodrigo’s Sour tour as well as pop artist Fletcher’s North American tour in 2022.

“[Being independent] lit a fire under my ass,” the singer said during a January interview with Capital Buzz. “[...] I did what I always wanted to do… which is, like, release music whenever I wanted to, dress however I wanted to… I opened for Olivia one time as an independent artist. I got the Fletcher tour as an independent artist… I felt like, ‘Damn, I was meant to do this, because it’s working without a label.’”

2023: Chappell Roan signs with Amusement Records

Although she proved to herself that she could make it big as an independent artist, Roan ultimately decided to re-sign with a label again. In January 2023, she inked a deal with her frequent collaborator Nigro’s new label, Amusement Records, in partnership with Island Records.

“It got to a point where I could not [be a totally independent artist] anymore,” Roan told Capital Buzz. “I was like, ‘This project is too big. I can’t do it alone with my friends anymore.’ So I re-signed in January.”

February 2023: Chappell Roan kicks off her first headline tour, “Naked in North America”

From February to March 2023, Roan embarked on her first-ever headlining national tour, cheekily named after “Naked in Manhattan.” Each of the tour’s 20 sold-out stops had their own dress-up themes for concertgoers — a tradition that has persisted across her tours. The openers were all local drag queens, an idea that Roan got from fellow queer artist Orville Peck.

“It’s a really great way to engage the local queer community to that city,” she told People in September 2023. “I encourage people to tip the queens, that’s redistributing funds within the community there, and also it just gives a platform for the drag queens. Some of these queens have never performed in front of a crowd that big before, and it’s just fun.”

September 22, 2023: Chappell Roan releases The Rise and Fall of a Midwest Princess

Exactly six years after putting out School Nights, Roan released her debut album, The Rise and Fall of a Midwest Princess. It garnered widespread acclaim, appearing in year-end best album lists from publications like The A.V. Club, Vogue, Rolling Stone, TIME, and Billboard.

Pitchfork’s Olivia Horn gave the album a 7.2 out of 10, writing, “The pop singer’s full-length debut is a bold and uproarious introduction, buoyed by sturdy songcraft and steely indifference to good taste.”

October 2023: Chappell Roan starts watching Drag Race

From referencing Sasha Colby’s famous refrain, “I’m your favorite drag queen’s favorite drag queen” at Coachella weekend two to dressing up as Divine in Pink Flamingos during a Kentuckiana Pride performance, Roan has been open about how much she loves and is inspired by drag artists.

However, her identification with drag is still relatively new. As she told The Face in September, she first started watching RuPaul’s Drag Race in October of last year (“I was really confused by the ‘reading,’” she said, “Like, that’s so mean!”).

During an October 2023 appearance on the podcast Q With Tom Power, she added that she didn’t truly consider herself a drag queen until one of the queens opening for her at a London show, Crayola, assured her that she was one.

“There was something that switched,” Roan recalled. “I really have taken that on as an identity, and it’s been very freeing to be like, ‘Oh, Chappell Roan is my drag project.’ And I think that’s also helped personally to separate it as a job and as like a project.”

February to April 2024: Chappell Roan blows up on the Rodrigo’s “GUTS” tour and beyond

After meeting through Nigro and briefly working together on Rodrigo’s Sour tour, the two worked together once again when Roan provided backing vocals on three songs on Rodrigo’s sophomore album Guts: “Lacy,” “Obsessed,” and “Bad Idea, Right?” Given their history, it was unsurprising when Rodrigo picked Roan as one of her openers on her Guts tour from February to April 2024. What was more surprising was just how much Roan exploded into the mainstream while doing so.

As Billboard reported at the time, the singer’s streaming catalog received a 32% bump during the first weekend of the Guts tour alone, jumping from 941,000 streams between February 17 to 18 to 1.24 million streams between February 24 and 25.

In between tour stops, Roan’s star continued to rise with a series of well-timed media appearances. In February, she was a musical guest on The Late Show With Stephen Colbert, singing “Red Wine Supernova” against a vintage Valentine-esque backdrop. In March, she graced NPR’s legendary Tiny Desk, serving high femme camp in a frilly hot pink dress, sky-high red wig, and lipstick-stained teeth.

April 5, 2024: Chappell Roan releases “Good Luck, Babe!”

Described by Roan as “the first song of the next chapter,” “Good Luck, Babe!” finds her grappling with the pain of loving another woman who seemingly refuses to publicly acknowledge her feelings for her or her queerness in general. Featuring ’80s synth riffs and a stirring falsetto, the song builds into a striking bridge in which Roan imagines her lover’s unfulfilled heterosexual future, singing, “When you wake up next to him in the middle of the night / With your head in your hands / You’re nothing more than his wife.”

“I knew exactly what I wanted. I wrote it in three minutes,” Roan told Rolling Stone in April. “I felt so much anger. I was so upset. It all came out, and I didn’t add anything when I wrote it all done. It was a perfect storm.”

Somehow, a pop song about compulsory heterosexuality didn’t just become “gay famous,” to borrow a phrase from Saturday Night Live. Instead, it became one the defining songs of summer 2024, reaching far beyond everyone already aware of the lesbian Masterdoc’s existence. It topped the Pop Airplay Chart five months after its release! It has been covered by the likes of Sabrina Carpenter and the Jonas Brothers! It has become an anthem for queer Stardew Valley gamers! Talk about impact.

April 2024: Chappell takes Coachella

Hard as it may be to believe now, Roan didn’t even play her first music festival until this year’s Coachella, performing both weekends on April 12 and 19, respectively. The first weekend, Roan took the internet by storm with her viral set, performing in a shirt that read “Eat Me,” a harness that was a pretty obvious homage to a strap-on, and makeup that she later described to Vogue as, “What if Paris Hilton and James St. James or Walt Cassidy became one and put on a drag show?”

The next weekend, she once again set social media abuzz when she took the stage in a pink butterfly get-up complete with six-feet-wide wings.

Summer 2024: Chappell Roan is quite literally everywhere

Calling Roan’s rise to superstardom “meteoric” would be something of an understatement. Mere months after she began gaining a large following on the Guts tour, the musician was suddenly in the center of the public zeitgeist as summer festival season kicked off.

In June, she performed at New York City’s Governors Ball in full Statue of Liberty drag, complete with green head-to-toe makeup. During the concert, she revealed that she had turned down an offer to perform at the White House during Pride month, saying, “We want liberty, justice, and freedom for all. When you do that, that’s when I’ll come.”

Flash forward to August, and sources close to Lollapalooza were telling CNN that Roan’s set at the Chicago-based festival is believed to be the biggest Lolla set of all time, despite her not even being a headliner.

Roan capped off a truly monumental summer by taking home the MTV Video Music Award for Best New Artist at this year’s ceremony on September 11. She dedicated her win to “the queer and trans people who fuel pop” and closed with a shout-out to “queer kids in the Midwest watching right now.”

“I see you, I understand you because I am one of you,” she said. “And don’t ever let anyone tell you that you can't be exactly who you want to be.”

Chappell Roan Dedicates Her VMAs Win to the “Queer and Trans People Who Fuel Pop”

The Midwest Princess sent a special message to “all the queer kids in the Midwest watching right now.”

August 2024: Chappell Roan sets boundaries

To this day, it seems like female stars can’t explode into the mainstream without inevitably facing some sort of public backlash, warranted or not. Unfortunately, Roan has been met with her own decidedly unwarranted series of controversies after spending months in the public eye non-stop. On August 23, she took to Instagram to call out “predatory behavior (disguised as ‘superfan’ behavior) that has become normalized because of the way women who are well-known have been treated in the past.”

The star reiterated her point in a series of TikTok videos, saying, “I don’t care that abuse, harassment, stalking, whatever, is a normal thing to do to people who are famous… that does not make it okay.”

In her Rolling Stone cover story, Roan elaborated on the harassment she has faced over the past few months, including a stalker who’s shown up to her parents’ home and her hotel room, a man who berated her about not signing an autograph at an airport until police showed up, and a fan grabbing her and nonconsensually kissing her while she celebrated a friend’s birthday at a bar in August.

However, plenty of people still took issue with Roan publicly drawing boundaries, driving home the reckoning with near-religious fandom and parasociality that has become the subject of much conversation over the past few years.

Yet shortly afterward, internet users relentlessly went after Roan once again after a quote from her aforementioned cover story went viral saying that she doesn’t feel pressured to endorse someone in the 2024 presidential election due to “problems on both sides” (while still encouraging people to vote). The singer clarified in a TikTok that she will be voting for Vice President Kamala Harris in November’s election but takes issue with “some of the left's completely transphobic and completely genocidal views,” referencing the Biden administration’s support of Israel’s continued siege on Gaza.

As the wave of backlash continued, Roah — who has been open about living with bipolar II disorder and severe depression — pulled out of her scheduled performance at the New York City edition of All Things Go Festival a day before the event, stating that “I need a few days to prioritize my health.”

Despite facing extreme highs and lows of stardom in such a condensed period of time, Roan has remained clear-eyed about why she does what she does to begin with. Mere days after All Things Go, she got back on the road, performing in Franklin, Tennessee on Monday, October 1. During the concert, she once again reaffirmed her connection with queer and trans people outside of the coasts.

“I know how hard it is to be queer in the Midwest and South. I understand. And so I’m very grateful I can be here,” she said. “[...] And I just have to remind myself that this is why I do it… I hope you know that you are wanted here, and you’re welcome here.”

September 2024: Chappell Roan is tapped for Saturday Night Live

Appearing on Saturday Night Live as a musical guest is a major milestone for young up-and-coming artists, and it’s one Roan is slated to achieve in early November. On September 18, the iconic comedy show announced that she would appear as a musical guest alongside host John Mulaney during the November 2 episode. One cast member who’s undoubtedly stoked for Roan’s SNL debut? Cast member Bowen Yang, who has been pushing to get her on the show since long before her career blew up.

While chatting with Roan for an August Interview magazine feature, Yang shared that he tried to get the singer on SNL during the 2023-2024 season. “I was texting the SNL bookers… being like, ‘There’s this girl, Chappell Roan. I think she’d be incredible for the show,’” he recalled.

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