By Robert Moran

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Like a preordained dot-to-dot, everything’s suddenly lining up perfectly for Chappell Roan. Just days ahead of the release of her excellent debut album The Rise and Fall of a Midwest Princess, the 25-year-old – real name Kayleigh Rose Amstutz – chalked up a feature on what’s currently the biggest album in the world, Olivia Rodrigo’s Guts.

Signed to Amusement Records, the Island Records imprint of her main collaborator Dan Nigro – the hit producer famed for his Grammy-winning work with Rodrigo – it was all a sort of favour for a friend, but one that points towards a bigger platform to come.

“Everything just clicked, the very second I let go of trying to be taken seriously,” says Chappell Roan of her circuitous journey to pop.Credit: Ryan Clemens

“It wasn’t even, like, a favour; [Olivia] doesn’t need anything from me,” Roan laughs over Zoom from Los Angeles, her curls tumbling like red slinkies. “She is such an angel. I really look up to her, how she handles herself with such grace and tact. It’s very much an honour to be part of some of her songs, just way in the back there.”

She’ll now be opening for Rodrigo on her massive world tour, set to commence in February 2024. It’s amusing imagining how Roan’s explicit songs about, well, being “knee-deep on the passenger side, and you’re eating me out” (Casual) might play to Olivia’s youthful fanbase and their parents. Is she anxious?

“I mean, it’s not like Olivia’s stuff is buttoned up. Especially with Guts now, she does not give a f—. They know what they’re getting into,” Roan laughs. “Yes, my music’s a lot more crass, much more lewd. But I don’t think it’s, like, that far off?”

The ridiculously catchy hook off Feminomenon – a directive to “make it hot like Papa John” – and a lovelorn country ballad like Picture You – with its singalong, “the things I do when I picture you” – might make a parent blush, but she’s right. Kids are sophisticated these days. They’re watching Euphoria, they know about these things.

“Like, I grew up on Nicki [Minaj] and Kesha,” says Roan. “Kesha was my mum’s worst nightmare, just like, ‘F— yeah, party and drugs!’ And I was like, yes, yes! Just 12-years-old and obsessed with it. I think that kids just, like, f—ing love pop music.”

With The Rise and Fall of a Midwest Princess, Roan is ready to be Kesha for the queer kids. Fuelled by her theatre kid exuberance, yet able to juggle both outlandish hilarity and heart-tugging bitterness (often within the space of the same track, as on the majestic Casual), the album – like Rodrigo’s, entirely produced by Nigro – flows on Roan’s fearless force of personality. I can hardly remember last week, but it has to be the funnest pop album of the year.

Romantic, bitter, funny: Chappell Roan’s The Rise and Fall of a Midwest Princess.

“I just embody the pop star I wanted to be when I was little; it’s a caricature of a pop star,” says Roan of her approach to her “obnoxious” songs and flamboyant aesthetics, which are such a detailed part of Chappell’s appeal she once half-joked that the only Grammy she wants to win is “for album packaging”. “Drag and burlesque have always been a huge through line for me, but there’s also nods to Bratz dolls and Hannah Montana and that pop star cliche. In my head, Chappell Roan is like a drag queen; I think that’s where all those larger than life colours and outfits and songs come from.”

That the album is such an assured debut belies Roan’s circuitous journey to this moment; hers is not an overnight success. “Oh no, it’s taken a decade to get here,” she says with deadpan severity. “I tell everyone, it takes a decade.”

The album’s earliest single Pink Pony Club, a bouncy pop fable about a girl from a conservative small town who finds her queer spiritual awakening among the bright lights and dreams of Los Angeles (specifically, West Hollywood’s landmark gay club The Abbey), echoes Roan’s own real-life journey.

At just 17, off the strength of songs she’d uploaded to YouTube, she earned a contract with Atlantic Records, resulting in the 2017 EP, School Nights. “It was very brooding, teen angst. A bit Lorde-esque. I mean, I was 17. I just had no idea what I wanted,” Roan says of her earlier work.

“All I really had at that time was, like, I could sing – I had a unique sound – and I could write songs that were sad and had some sort of structure to them. There was a hint of, ‘Okay, maybe if I worked really hard at this for a long time, maybe I’ll get it.’ But I was really lost and so alone because I was a minor in the music industry, where kids just shouldn’t be.”

In 2020, five years into her contract, when Roan was 22, Atlantic dropped her. While many young artists might seek to bury the perceived shame of major label failure, Roan calls it the “best thing that happened to me in my career”.

“I don’t even see it as a failure,” she says. “I had a ton of experience under my belt and had proved to myself that I could do so much on my own at such a young age. And so, it was good that it happened. I had to go back home and work the drive-thru and it’s like, fine, that’s what happens. It took me a few years to get back on my feet – and, like, here we are.”

She’s blase about it now, but I wonder if at that point it felt like the end of the journey? For any aspiring artist, the goal is always to attract major label backing. So to get there and have it all taken away…

“Just because you get signed to a label doesn’t mean you’ve made anything,” says Roan. “Being signed to a label meant less for me than when I was dropped. Once I was dropped, I was free: I could do whatever I wanted, I could move at any pace I wanted. Yes, I didn’t have financial help but I just made it work, always.”

She’s admitted she was close to giving up. Back home in Missouri, she wondered if “maybe I wasn’t supposed to be an artist, or maybe I wasn’t supposed to be in music at all”. “I just wasn’t happy,” says Roan. “It did not make me happy to write music or talk about music or anything.”

Moving back to Los Angeles in October 2020, working shifts at a donut shop to make ends meet, she gave herself one last shot to phoenix her pop star dreams. “I told myself, if by the end of next year I don’t feel like this is right, then I’m gonna move to Nashville to be a writer, or just go to school to be an aesthetician,” Chappell recalls. Seven months into that move, she signed a publishing deal with Sony that meant she could dedicate all her time to music again. Earlier this year, she signed to Nigro’s imprint on Island.

“There’s only so much you can take. It was two years of horrible grind, just hoping something would f—ing happen, until it did,” she says of the struggle to make Chappell Roan work. “But I think I needed so many years to become free in writing this type of music, just because it is pretty bold.

“It also took a lot of, like, letting go: of trying to be cool, or sophisticated, so people would think I was this serious artist. Once I let that go, all the songs flooded in and the aesthetic and everything just clicked, the very second I let go of trying to be taken seriously.”

Much like The Rise and Fall of a Midwest Princess, there’s a celebratory turn in Roan’s story, in the self-discovery and identity – and artistic success – she uncovered via pop. Even so, returning home to Missouri now is a challenge, she says.

“I don’t know if people are accepting. I definitely dress differently when I go home. I don’t try to draw much attention, just because it’s not worth it. I don’t live there anymore, I don’t need to prove anything to anyone.”

Still, she’s aware of what Chappell Roan – like the pop stars who birthed her – can represent. “I’m a queer woman who grew up in the Bible Belt, in a small town, in a Christian household, who identified as straight and very lady-like, et cetera,” she says. “Now it’s like, ‘This is who I am!’, you know? I became this and it’s okay and I’m still here. I left home and I had no money and, like, everything turned out okay!”

Chappell Roan’s The Rise and Fall of a Midwest Princess is out on Friday. Her upcoming tour includes shows at Sydney’s Liberty Hall on November 24, Brisbane’s Powerhouse on November 25 and Melbourne’s 170 Russell on November 26.

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