Just a few years ago, Chappell Roan was manning the window at a drive-through coffee shop, while living with her parents in Missouri. Today, she’s selling out venues across the world and drawing crowds that rival those that come to see the biggest musicians on the planet. It’s undeniable: the era of Chappell Roan has arrived.

A viral appearance on NPR’s Tiny Desk concert series in March, and high-profile performances at Coachella and the Governor’s Ball music festival in New York, confirmed her status as a newly-minted superstar. The iconic moments didn’t stop there. Roan is said to have drawn the largest crowd ever for a Lollapalooza set, estimated at 100,000 spectators, and she wasn’t even one of the headliners. An endless stream of chart-raiding hits have blown up on TikTok. The cheerleader-inspired ‘HOT TO GO!’ can be heard at football matches – indeed, you’d feel left out for not knowing its YMCA-style choreography.

Here’s the rub. The Missouri native – better known to her high school classmates as Kayleigh Rose Amstutz – may seem like an overnight sensation to some, but her career has been nearly a decade in the making. And along the way, on occasion, she’s had to overcome apparently insurmountable odds just to stay in the game.

Kayleigh got her start – like many young teens looking to soundtrack their angst – by uploading cover songs to YouTube. It wasn’t long before those videos piqued the interest of various record labels. Her first original song, ‘Die Young’, was uploaded in 2014: it was one she had penned at an arts summer camp which proved momentous for the budding songwriter.

The following year, Kayleigh travelled to New York and cut a deal with Atlantic Records. Hoping to adopt an alter-ego, she landed on the name Chappell Roan, at once an homage to her late grandfather (on her mother’s side) and a nod to her favourite song, ‘The Strawberry Roan’, by Curley Fletcher. 2017 saw the official release of her first single ‘Good Hurt’ and debut EP School Nights. At the time, the intention was to sing dark, brooding torch songs about the quasi-sadomasochistic thrill of being in love with bad boys. During those early days, she lived with her parents in Springfield, Missouri, flying to Los Angeles and New York when she needed to.

In 2018, armed with little more than her ambition, Chappell packed her bags and relocated to Tinseltown, hoping the move would help ignite her career. For a while, the trick seemed to work.

HOW KAYLEIGH BECAME CHAPPELL

Living among the SoCal freaks and angel-headed hipsters proved fruitful, granting Chappell the space and freedom to properly explore her personal identity. While navigating the Hollywood music industry, she met songwriter-producer Dan Nigro, who had worked with the likes of Kylie Minogue, Finneas, Lewis Capaldi and Caroline Polachek. With a newfound collaborator by her side, Chappell Roan appeared to hit the ground running. In 2020, she released ‘Pink Pony Club’, an anthem of self-acceptance inspired equally by a visit to the Abbey, a gay bar in West Hollywood, and her dreams of becoming a go-go dancer.

“God, what have you done?” the narrator’s mother asks in the chorus, to which the narrator responds, “Oh mama, I’m just having fun”. Although the song is in a minor key, Roan’s voice is joyous and exuberant: “On the stage in my heels, it’s where I belong.”

Two more singles followed, ‘Love Me Anyway’ and, in May 2020, ‘California’. Despite their undeniable pop quality, the releases weren’t successful enough to meet label demands. In what must be one of contemporary music’s most agonising “What the hell did we do that for?” moments, Atlantic Records dropped her in August of that year. Her boyfriend apparently broke up with her the very same week her music dreams juddered to a halt.

With little in immediate prospect in Los Angeles, she moved back home to Missouri and worked as a barista in a drive-through coffee dive to plot her next move. Upon recalibrating both her ideas and her plans, and saving enough to take the plunge again, she returned to LA to work on what would become The Rise And Fall Of A Midwest Princess. In the calm before the storm, she worked odd jobs – she was a nanny for a wealthy family, a production runner for HBO and a doughnut shop clerk – to stay afloat. She had decided she’d give music another shot for a year, with the intended compromise that if it didn’t work out, she’d enrol in college.

Inch by inch, Roan was beginning to develop a cult following, without any official backing from the music industry. ‘Pink Pony Club’ was on its way to becoming a bona fide sleeper hit, as it took off on TikTok. Meanwhile, Nigro had been helping Olivia Rodrigo craft and release her debut album, Sour.

In November 2021, as Rodrigo scaled the charts, powerfully embossing Nigro’s burgeoning reputation, he and Roan reunited. She may have been feeling spurned by the industry, but Roan credits Nigro with reigniting the spark she needed to start working for herself, on her own terms. “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. So she did.

In March 2022, a newly liberated Chappell unveiled ‘Naked In Manhattan’, her first song as an independent artist. She shot the accompanying music video dressed in thrift-store clothing, with friends, on the streets of New York. The song sees Roan crushing on a girlfriend, hoping to finally cross the line and kiss her. “Boys suck, and girls I’ve never tried it,” she sings.

In real life, she noted the authenticity of those lyrics. “I was dating a boy then,” Roan told The Los Angeles Times last August. “I had never even kissed a girl when these songs were written. It was all what I wished my life could be.”

‘These songs’ refers to both ‘Naked In Manhattan’ and ‘Red Wine Supernova’. In a sense, ‘Naked In Manhattan’ continues the aesthetic thread Roan first established in ‘Pink Pony Club’ – but takes it to entirely new levels. It’s Roan’s first explicitly queer song, ‘Pony Club’ having buried the coming-out lead in plausible deniability.

Meanwhile, the charming video for the single debuts the “secondhand-chic pop star” drag persona that would become her calling card: crimson curls, a burlesque pin-up raunchiness, and elaborate hyper-femme outfits cobbled together from thrift-store finds. It was a flashing marquee, signalling that Roan had, at long last, found an image she was comfortable with.

‘Red Wine Supernova’ left no room whatsoever for speculation. There’s six songwriters credited, including Chappell and Dan. But the intent is clearly hers.

 “I like (I like) what you like (what you like),” she sings, with a little bit of help from the backing vocalists. “Long hair (no bra) that’s my type (that’s right) / You just told me, want me to fuck you / Baby, I will ‘cause I really want to.”

NASTY ELECTION CAMPAIGN

In March 2022, Chappell Roan was announced as the opener for Olivia Rodrigo and Fletcher, on their respective US tours. She continued releasing independent singles, with ‘My Kink Is Karma’ in May 2022, followed by ‘Casual’ in October. In February 2023, Roan officially launched her own US national tour.

A month later, she announced that she had signed to Nigro’s new label, Amusement Records, in partnership with Island Records. According to Roan, by then, she had a wealth of options to choose from. In September 2023, she released her debut album, The Rise And Fall Of A Midwest Princess, and once again set off on tour as Olivia Rodrigo’s opener. At the start of 2024, the record was still a sleeper, but it had captured the hearts of queer listeners, and was on its way to becoming a cult classic.

There’s a moment in the music industry when people suddenly realise about an artist: there really is something happening here. And so it proved. A staggering round of festival performances provided the live ammunition. Chappell’s follow-up single, ‘Good Luck, Babe!’, went to No.1 in Ireland, No.2 in the UK and No.4 in the US, Canada and Australia. It was arguably the single most important breakthrough of the year. By June, Midwest Princess had bounded up the charts, first peaking at No.1 in Ireland. It was No.1 also in the UK and New Zealand, No.2 in the US and the Netherlands, and No.3 in Canada and Australia. After years of trying on personas that didn’t fit, of working shoddy day jobs and scrambling to keep her musical dreams afloat, her moment had finally arrived.

Hindsight is often 20/20. Looking back over Roan’s career, it becomes clear that her music truly thrived – and her career started to take off – once she gained a stronger sense of self, intertwined with Roan defining herself as a queer woman. The drag outfits and a strong, direct appeal to queer women – and queer young women in particular – struck a chord, with fans happily getting into the spirit of her shows by dressing up flamboyantly to match looks that are pre-ordained by Roan herself.

Mind you, she traces the root of it all, amusingly, back to childhood...

“The whole project is to honour my 10-year-old self,” Roan told Paper Mag in June. “My whole persona is just me trying to honour that version of myself that I was never allowed to be.”

The juggernaut of fame, of course, always comes with a price. In drag, it is generally understood that you do not approach a queen for a picture when she’s out of costume. Roan has made it clear that when she stops being Chappell and starts being Kayleigh, she prefers to be left alone. Despite this, she’s been subject to stalking and similar behaviour from fans.

For a while, it appeared that Chappell might be overwhelmed by the sheer magnitude of her fame. In a feisty response to those who were intruding thoughtlessly on her space – and her sanity – Chappell said in a TikTok message that she doesn’t “give a fuck” if she’s described as “selfish” for declining hugs and photos with strangers. “That’s not normal,” she says of those who demand a photo. “That’s weird. That’s fucking weird.”

Many people understood. But it didn’t go down well with some. “How rude she must be to deny fans a selfie!” one fan commented. “Famous people shouldn’t bat an eyelash at being hounded by devotees, because it comes with the job!”

Over the summer, in an attempt to wrestle back control, she posted more TikToks calling out obsessive fans. “If you saw a random woman on the street, would you yell at her from the car window? Would you harass her in public?” she implored in one post. “I’m a random bitch. You’re a random bitch. Just think about it.” Her impassioned pleas for respect and privacy are both refreshingly unmediated and genuinely earnest – a far cry from the sanitised PR gloop of so many celebrities. In an industry where precision trumps passion, Chappell Roan is once again challenging expectations.

Her pushback placed an onus on fans to make sense of it all, resulting in some fraught  discourse. Fanbases were once seen as loyal and mostly uncritical. What an artist did in other aspects of their lives was more ammunition for fascination. And if an artist erred, well then they were easily forgiven.  But the emergence of stan culture has shifted the relationship between artists and their fans into something far messier and more conditional. Loyalties can, and sometimes do, collapse along innumerable fault lines.

We saw what happened to Lizzo, when she was accused by three of her former dancers of sexual harassment, disability discrimination and even assault. Overnight, she went from being feted as queen of body-positive pop to outcast in danger of permanent cancellation.

In a climate of political correctness, dialled up to the nth degree, even a position conscientiously held can be used against you. In her Rolling Stone cover story, Roan mentioned her decision to decline an invitation to perform at the White House’s Pride celebration, and that she had considered accepting an invitation to join in a protest against the Biden administration’s collusion in the assault by Israel on Gaza and the death of tens of thousands of Palestinians. In an interview with The Guardian, she indicated that she wouldn’t endorse any candidate in the upcoming presidential election.

All of this led to a series of bad faith misinterpretations, with some absurdly suggesting that she supported Donald Trump. Recognising that she needed to kill any opportunity for the Trump campaign to use her name,  Roan declared that she would vote for Kamala Harris as the lesser of two evils. But she remained adamant in refusing to endorse the policies of the Democratic Party: a party, in power, “that has failed people like me and you — and more so Palestine and more so every marginalised community in the world.”

Clearly, it takes courage, in the febrile context of an especially nasty election campaign to nail your colours so clearly to the mast – not least given the added viciousness of the Zionist lobby that supports the genocidal intent of the current Israeli government.  But there were other less predictable critics.

Real Time talking head Bill Maher – a liberal who has been openly critical of the tenets of Islam – lampooned Roan’s support for Palestinians, suggesting that she would be “thrown off a roof in Gaza”. She became the butt of a joke on Saturday Night Live which mocked her comments about intrusive fans, comparing her to the viral Moo Deng, the pygmy baby hippo that TikTok has turned into a viral superstar.

However righteous the desire to poke fun at our superstars might be, the fact that Chappell is completely right about the failure of US President, Joe Biden, to rein in the appalling, genocidal excesses of the Netanyahu government should not be beside the point.

CELEBRATING DRAG AND QUEERNESS

What’s too often neglected in these media slagging exercises is the sweepingly positive impact she’s had. For many in the queer community, she has emerged as a new patron saint of candour – including in her insistence on the right to privacy.

“It’s fabulous to see Chappell setting boundaries,” the Irish cabaret provocateur SexyTadhg tells me. “I think women have not always had the opportunity to voice their grievances, especially in the music industry. I think it’s absolutely fantastic that she has the power to hop on TikTok and say, ‘Actually this is my boundary and I don’t like it when you do this, so please stop’. It’s important for artists to be taken seriously in this way.”

SexyTadhg was first introduced to Chappell Roan’s music in a queue at Dublin Airport, just before boarding a flight to New York. Upon seeing the artwork for the album Rise And Fall Of A Midwest Princess – where an unenthused, yet undeniably fabulous Chappell cradles a bouquet of pink silk roses in her dressing room – SexyTadhg was immediately stricken.

Chappell Roan - The Rise and Fall of a Midwest Princess (2023)

“After seeing the cover art, I was like, ‘Oh… who is this diva?’,” they recall. “I listened to ‘Casual’ just before hopping on the plane, and had one of those ‘Oh my God’ epiphanies. She was just so vulnerable. I hadn’t heard that story being sung about in such detail and with such honesty.”

Naturally, the first song SexyTadhg played as the plane touched down in the Big Apple was ‘Naked In Manhattan’. That particular queer-girl bop became an anthem for many reasons, at least one of which is the unabashed queerness channelled into her singalong narratives.

“For a long time, queer artists have always felt the need to either take out information so that people don’t know that their songs are about the queer experience,” SexyTadhg continues, “or maybe they change pronouns to make it more palatable for a mainstream audience. The fact she hasn’t dulled or diminished her story, and is still incredibly successful, is so inspiring.

“You know, for a lot of queer people, you might relate to the music. But to actually hear yourself in a song is a real privilege, which I think a lot of straight people have taken for granted for a long time. But now we actually get to have it – and it’s really beautiful.”

In this way, Chappell Roan is a beacon of hope for many. At a time when drag bans and anti-LGBTQ+ legislation and rhetoric are reaching new peaks in the US, Russia and elsewhere – though, so far, Ireland is thankfully exempt – Roan has turned her concerts into opportunities to celebrate drag, and queerness in general, by enlisting queens as her openers.

“It’s just a great way to engage the local queer community in that city,” she explained to People. “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.”

A VERY GAY OLYMPICS

As she geared up for the European leg of her Midwest Princess tour, Roan sent out the bat signal for Irish drag artists to apply for the Dublin opening slot at the 3Olympia Theatre. It was an apparently straightforward process, with Roan posting a humble Google form to her X, where artists could throw their names in the ring. SexyTadhg immediately caught wind and launched a social media campaign, with a viral video to boot. In the end, SexyTadhg didn’t get the gig with Chappell.

“It got such a bigger, better response than I ever hoped for,” SexyTadhg reflects on his video. “In the grand scheme of the internet, I think the Instagram video got 30,000 views, which is amazing for Irish internet. That’s like ‘the mortgage is done’, superstar kind of levels. It got so much support from the Irish community, the audience and the artists. The video did end up getting to Chappell’s team, which was exactly what it needed to do. But, you know, it wasn’t the time, it wasn’t the moment.”

Instead, the support slot went to Haus Of Wig, the drag trio comprising Shaqira Knightly, Donna Fella and Naomi Diamond.

“Once the submission form was active, we filled it out separately and hoped for the best,” Naomi Diamond tells me. “We didn’t really do too much campaigning. We were just like, ‘Let’s see who gets it’, because there’s so much drag talent in Ireland and anyone would have deserved it.

“So it was a case of letting it be, and luckily it worked out in our favour. The fact that we got to do it together made it extra special, because we’ve always done drag together since the start, so it was a real pinch-me moment for all of us.”

For the show, in a powerful display of just how devoted fans are to Roan, the hordes gathered early in the streets around the 3Olympia, dressed proudly in hot-pink leotards, pearl-studded wigs and pink cowboy hats.

On the night, when Haus Of Wig settled in their dressing rooms, collectively they were a bundle of nerves, such is the sheer gravity of getting to open for an artist like Chappell Roan all the more so in the kind of venue she’ll likely never play again, given the scale of her ever-mounting popularity.

That was until their manager abruptly barged in with the kind of news that would make any diehard fan scream with glee. But for the Haus Of Wig ladies, it meant a moment of debilitating paralysis. In a matter of a few minutes, they were told, Chappell Roan herself would pop by the dressing room to greet her openers, shortly before they were due onstage. Then came a knock on the door, and in shuffled the divine Chappell, dressed in a camouflage t-shirt and her flame-red curls clipped back.

“I’d like to say I remember the rest, but I think we all blacked out that night,” Donna Fella laughs. “Sometimes people say you shouldn’t meet your favourite celebrity because you’ll be disappointed, but with Chappell, it was nothing but greatness. There’s a lot of people who would let fame go to their head, but she was the complete opposite. She was so relaxed and chill. It was all so wild.”

“I think the most beautiful thing out of it all was the community element,” Shaqira Knightly adds. “We felt like people really rallied behind us. Annie Queeries basically said it was like watching an Irish athlete go to the Olympics and win the gold medal.”

“It was a very gay Olympics,” Donna chimes in.

“Exactly, and that really was so special,” Shaqira continues. “It was a really beautiful thing because, you know, it’d be too easy to be down and out about representation, but the community really showed up.”

Haus Of Wig’s kinship with Chappell Roan’s music runs deep. As the world started falling in love with Chappell, so did they.

“It’s a really magical time for pop music,” Donna Fella remarks. “I think this year has been the first in a long time that we’ve been fed so regularly by the girls, and especially Chappell. You could feel a bubbling roar around her. It’s rare to be a part of the wave, when an artist is rising like that.

“The way in which she’s risen is very unique and doesn’t happen all the time. I think that forming a community and having such a strong identity – in terms of handling and expressing your art, on your own terms – is very empowering, especially for queer artists. The command that someone can have – be it on the stage, in their music or with their presentation – is really captivating.”

“I think she strikes a chord because there’s something very fresh about her sound, something very unapologetic and a bit uncharted,” Shaqira Knightly adds. “She’s not doing conventional stuff and, as drag artists, we’re never doing anything conventional. I think it’s really beautiful to see that it doesn’t matter on what scale you’re doing it. The intent is still kind of the same, and look at what it’s done for her over the last year.”

COMMUNITY OF PEOPLE

Every few years, a new It girl emerges to fulfil the pop-stardom prophecy. Madonna, Kylie, Britney, Gaga, Taylor – the list is growing. Chappell Roan has tacked herself onto that list in remarkably short order and with more powerful effect than most. What makes her so compelling is that, as a character, she is carrying the torch for a profound release, an unravelling of shame and restraint. She stands as the artistic zenith of a long journey towards self-discovery. Her exuberance on finding her true self comes across in the music.

As the fan favourite ‘Pink Pony Club’ stipulates, we are here on Earth – however cosmically brief – to find a place to call home and treasure it forever. How we might get there differs from person to person. We unearth ourselves along the fringes, our arms outstretched in catharsis. All we can do is keep on dancing until we find it.

Chappell Roan fans gather at 3Olympia Theatre. Copyright Miguel Ruiz.

What the future holds is unclear, but one thing is for sure: Chappell Roan has at once shifted the narrative of celebrity; elevated the expression of queerness in art and popular culture; and rearranged the landscape of pop music altogether. The arduous journey she took to get here is a reflection not only of her work ethic, but of her pop relatability and the spill-your-guts honesty of her lyricism.

“I think her music has created a community within itself,” SexyTadhg observes. “Chappell Roan fans have been plucked out of the general population and brought together. That, in itself, creates a community of people who relate to each other and are of a similar personality. Sometimes there are people who have not felt that community at home, growing up in their small hometown or in school.

“So I think the biggest impact of her music is that it’s very healing for queer people to hear their story. It not only makes us feel less alone, it also prevents loneliness from ever happening again.”