Why Chappell Roan is an era-defining pop star

A writer-fanboy deep dive into our possible new Madonna

Several weeks back, while starting to prep my most recent long post – entitled Girls On Top for lack of something less obvious – I realized that for all my enthusiasm about “fun and feisty” female-fronted music being made all over the world, I was stuck for an act from the States to match the raucous and irreverent mood of Sailor Honeymoon or Lambrini Girls, Amyl & The Sniffers or Feast.

…Until, that is, I suddenly realized that I’d been looking in the wrong place. The answer was right in front of me, hiding in plain sight. The USA’s Girls on Top – those making music that is fun and feisty at the same time – are, literally, on top. On top of the charts, that is, which in the U.S. means pretty much on top of the world. To be clear, there are plenty young female Americans who, quoting again my previous piece, “excited and surprised me in 2024,” but there only a couple who “made me want to jump and down in the front rows, had me yearning to be super young and pogo strong.” They are, to a small extent, Olivia Rodrigo, but to a much larger extent, Chappell Roan. I will go further than that, and on the record. I believe Chappell Roan to be not just the most “fun and feisty,” but the most exciting, entertaining, intelligent, astute and sexually provocative female pop star since Madonna.

I should probably have assembled my own complementary image of Chappell Roan and Madonna, but this one, from the NYPost via Yahoo, was too good not to use.

Madonna, of course, has always served as a lightning rod for critics. Hell-bent on success at all costs, she made a career out of marrying her commercial ambition with her musical magpie-ism, borrowing from all bubbling underground genres with an acute awareness for crossover potential unseen since David Bowie. Additionally, her voice has always had its limitations and she doesn’t/didn’t play an instrument. And yet Madonna became a role model for a new generation of women in and out of music who admired her fierce independence and provocations, her fashion sense and her business sense, and um… Has anyone checked her back catalogue lately? (Matt Fish has; he is in the middle of revisiting and reviewing all fifteen studio albums.) Not even Taylor Swift has more U.S. Number 1 singles.

I suspect some of my readers, given that I rarely come across celebrations of pop stars like these on my Substack feed, might be as dismissive of Chappell Roan as with Madonna at first glimpse/glance/listen. After all, if it’s pop music, and it’s commercial, and it’s brash and bold and pushing all the right high-tech buttons in the studio and comes accompanied by high-budget videos, and especially if it’s sitting on top of the charts and it’s the under-age kids who are packing the arenas, there must be something wrong with it, right?

Wrong. Chappell Roan’s 2023 debut album The Rise and Fall of A Midwestern Princess was the break-out album of 2024 – and easily my Pop Album of 2024 - for a reason. Actually, make that a whole number of reasons. But before we break them down, let us dispense with any notion that this is not a proper Artiste in the making. Exhibit A is below the fold: Chappell Roan’s performance at NPR’s Tiny Desk Concert – the post-MTV Unplugged seal of approval that only gets granted if the artist can prove their acoustic mettle - from March 2024. Long-term NPR music critic Stephen Thompson, who was in the room, refers to it in the accompanying YouTube notes as “a stunning set … In every mood and every song, she’s utterly commanding — witty and whip-smart, vocally assured and charismatic beyond words.” I am not about to disagree.

Now that we have established Roan’s performing credentials, let’s bullet point what renders her such a femininomenon, to cite – and it will not be the last time – the opening track of that debut album…

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1) The Back Story

Chappell Roan is no overnight success. And I’m not talking here about the Rise and Fall…’s eight-month rise to the UK number one spot, or its 11-month crawl to America’s number two, though it’s refreshing in this age of seven-days-of-streams-and-we’re-on-to-the-next-thing that the rise of The Rise and Fall… can be measured in months. No, it was way back in 2014 that the 16-year-old-girl born as Kayleigh Rose Amstutz, who had, even then, long been uploading her performances to YouTube, first got “spotted,” specifically for her song “Die Young.” She subsequently signed to Atlantic Records as a 17-year-old, adopted the stage name Chappell Roan as tribute to her recently deceased grandfather, moved to LA from Missouri to try and make the big time, and released a lyrically interesting but musically unspectacular EP entitled “School Nights” at age 19,

The EP was passably popular, and Atlantic persisted, for a while. Roan, having come out as queer in the meantime, released a further trio of singles, all of them produced by Dan Nigro, who was already a/the (former indie rocker) Pre-eminent Pop Producer. But the singles failed to fully set the charts alight, and Atlantic dropped her. It’s not quite (at least not yet) like Decca turning down the Beatles, and 2020 was a, um, weird year all around, but two of those singles are included on the Rise and Fall, and one of them, “Pink Pony Club,” is as great a singalong pop anthem as ever a major record label failed to render a hit first time around. (Considering that USA Today named it one of the 10 Best Songs of 2020, and that it had racked up 10,000,000 Spotify streams a full year before her debut album was released, you do have to wonder at Atlantic’s short-sightedness.) In case you somehow haven’t heard it, and if you didn’t play through the Tiny Desk concert above to hear it in stripped-down form, here is the link to the official video from April 2020, and here she is delivering it on Saturday Night Live this past November, a monumental performance that even Lady Gaga would struggle to match.

Roan’s subsequent true rise since signing, first, a publishing deal with Sony that allowed her to resume working with Dan Nigro, and then a record deal with Island, is proof positive that failure is sometimes the best route to success, and that talent can out, regardless. (There is a caveat, namely that the person with said talent also has the fortitude, resilience and ambition to absorb that failure and come at it again, which is no easy ask). Several reasons have been put forth for the album’s subsequent success, including Roan’s friendship and affiliation with Olivia Rodrigo, for whom she opened on tour and with whom she shares Nigro’s production markings; the TikTok viral success of the word “femininomenon”; the solid commitment this time round of her record company; plus the generational calling card of an identity that manages to be beauty queen and beauty queer at exactly the same time. But let us now focus on the primary reason she is so popular...

2) The Songs

Roan’s present-day material runs the full gamut of modern pop. There are the floor-bangers like “Feminonomenon” (though only after a teasing build-up) and “Super Graphic Ultra Modern Girl.” There are the upbeat pop anthems: “Red Wine Supernova,” “HOT TO GO!” and “The Pink Pony Club.” There are the perfect mid-tempo pop songs: the non-album 2024 universal hit (her only US Top 10, surprisingly), “Good Luck, Babe!” and “Casual,” which would rank a 10/10 for craftmanship even before we discuss its lyrics (which we will). And there are proper ballads: “Coffee” is a song that transcends the rest of the album and I suspect will be getting cover versions in years to come.

Moreover, Chappell’s music is full of lovely little tricks and surprises. There is the sudden drop on the pre-chorus of her album’s opener “Femininomenon,” just as the song moves from Swift-like hit-by-numbers to indicate its possession of a real groove, at which Chappell shows up to demand someone “play a song with a fucking beat.” Second and third time round, because we know she’s going to repeat the trick, she increases her excitement (and her pitch) as the song does likewise, ending in a teen buzz of dancefloor delight. If it’s a trick that may yet grow old, it hasn’t done so yet.

There is also the ending to 2024’s “Good Luck, Babe!” to which the lyrics – “you’d have to stop the world just to stop the feeling” – are applied literally, as the song slows to a crawl, and her voice drops an octave in the process. It’s the inverse of what attracted me to Sailor Honeymoon’s “F**x Urself,” it’s unusual, and it works a charm. And it really doesn’t matter if these “arts of surprise” (I cited both on my recent Masterclass for the Songwriting Academy) were her idea or Dan Nigro’s, anymore than we should worry what George Martin suggested to the Beatles or Martin Hannett to Joy Division. What matters is ultimately the song at the heart of it, and the fact that both Franz Ferdinand and Sabrina Carpenter covered “Good Luck, Babe!” at the BBC last year (for different shows on different channels), confirms that Chappell Roan’s songwriting credibility is already established among those who aspire to be her peers.

While I am happy to share them above, neither cover version can quite pull off that vari-speed slow down and octave drop, and Carpenter barely tries. So here, as reference, is the original version in its original super retro lo-fi promo video form.

3) The Voice

Ever since Cher made autotune infamous with “Believe” over a quarter century ago, the modern pop star – specifically, the modern female pop star – has had to defend themselves against mansplaining accusations of studio manipulation. But while all is fair inside the control room anyway, Chappell Roan is the real deal. If the vocal delivery on the singles “Pink Pony Club” or “Good Luck, Babe!” don’t do it for you, may I refer you back to the live presentations shown up above; I was especially bowled over by that performance on SNL. And I’m clearly not the only one, having come across a series of You Tube presentations by self-identified “pro vocal coach” Tim Welch, whose channel is dedicated to “live, raw, visceral real human vocals,” and whose analysis of Chappell’s SNL performance involved isolating her vocals from the rest of the band, demonstrating the (very slight) imperfections that render great music human.

4) The Persona

Chappell Roan is not just a nom de plume, adopted as a family tribute. It’s a makeover, a fiction, a persona. As my son Noel noted when we watched that Tiny Desk concert together, where it is on hyper display, Chappell Roan is an act. To be specific, it is Kayleigh Rose as drag queen, by her own definition. “Drag is like a spa for my soul,” she told The Guardian a few months back, a perfectly succinct summary of why we should all dress up now and then.

To get a deeper understanding on Kayleigh’s understanding of her Chappell Roan role-playing, there is this interview with Tom Power, which I found as enlightening as I did refreshing.

By comparison, it took Vince Fournier some heavy alcoholism to learn the same about his alter ego Alice Cooper (when “I finally realized that character belongs on stage, and [I should] play him to the hilt [on stage], but don't be him off stage, then I was able to lead a normal life”).

5) The Lyrics

If we ended it here we’d already have ourselves a decent modern pop star. But it’s with her words that Kayleigh as Chappell proves properly transgressive in a way that neither the aforementioned Bowie or Madonna were capable of getting away with at the time. Have you checked the arm-waving chorus of “Casual,” the opening song on that Tiny Desk concert?

“We're knee deep in the passenger seat and you're eating me out
Is it casual now?”

Alannis Morrissette, um, well no, the pun is too obvious, and let’s move on before asking how many 14-year-olds fully understand what’s going on here. To be clear, I fell for “Casual” long before I grasped its storyline (of a relationship moving beyond intended speed) and embraced the sheer cujones of those words. Maybe I am now listening too intently, because I am also hearing in the song “Femininomenon” something beyond its well-worn if accurate trope that boys often make lousy, unreliable boyfriends: namely, that they aren’t capable of giving girls “what you need” – which, per the actual chorus, would appear to be to “make a bitch go on and on.” Lily Allen had a hit in this vein called “Not Fair,” in which she similarly decried her boyfriend’s inability to “make me scream.” Far be it from me to assert that “Femininomenon” is also about the female orgasm, because a Google search on such a connection comes up short, but if I do hear as much, maybe that reflects on my own youthful years as a lousy boyfriend.

I also recognize the old younger me in the undercelebrated “Coffee.” In my version of this familiar tale, former partners vow to become “just friends” but inevitably, as soon as alcohol enters the equation, so does sex, and with it the inevitable recycling of the relationship as something more messy. Chappell Roan’s story is similar, but one in which she still loves her ex, who does not reciprocate, and her verses are smart enough to place each hook-up in a different physical environment (the jazz bar, the park) even though the chorus remains the same:

“I'll meet you for coffee 'cause if we have wine
You'll say that you want me, I know that's a lie
If I didn't love you, it would be fine
I'll meet you for coffee, only for coffee
Nowhere else is safe, every place leads back to your place.”

(Below: a pre break-out performance of “Coffee” at the Bowery Ballroom in 2022.)

We could go on – “Red Wine Supernova” is as explicit as they get, with references to wands and rabbits of the bedroom kind as well as a straight-up invitation to fucking - but fortunately, Roan has more to sing about than carnal behavior. “Pink Pony Club” is a modern (and future) classic not only for of its pop-perfect musical construction and production, but because of its lyrical self-emancipation, which for this Tennessee girl was found dancing as a drag queen on stages in Santa Monica and West Hollywood. Roan raises the specter of her strict Christian upbringing by imagining her mother seeing her on that stage and exclaiming “Oh, what have you done?” and her own happily defiant response, “It’s where I belong.” The delicious irony of this four-year old sleeper classic is that its subsequent hit status has allowed Kayleigh to indulge her inner drag queen on the biggest stages in the world, and for her parents to come around and be “so supportive,” per that Guardian interview. “It’s just cool to see my family get excited about things that we never thought were possible.”

Clubbing is also the subject of “After Midnight.” Written as a response to her parents protectively telling her when younger, that nothing good ever happens after midnight, Roan proudly proclaims the opposite: “Everything good happens after midnight,” runs the chorus, which she rhymes with starting a bar fight. Chappell Roan is no one’s pussy.

6) The Person

I could have called this “flamboyance” or “confrontation” but I would like to instead offset the earlier subtitle. Part of what makes Roan such a great role model – and it’s evident that her fans see her as such – is the outright openness of the true person (Kayleigh) behind the drag persona (Chappell). In speaking so honestly about the problems of her upbringing – difficult but not generally unique - Roan connects with kids and teens globally. In telling truth to power about the music business – “in this industry, you really flourish if you don’t protect yourself,” she tells Tom Power – she warns future wanna-be pop stars of the exploitation they’ll face if they don’t put their own well-being first. In employing an all female band, she helps put paid to a tired but once conventionally-believed myth about musical differences between the sexes.

In the wider world at large, Kayleigh/Chappell pushsed back on Kamala Harris’s adoption of the “femininomenon” meme, disappointed by the Democrat candidate’s stance on Palestine, speaking for that part of her generation that feels utterly disconnected to the leftist power structure. While I may feel disappointed in turn, given who we have ended up with (again) – a white racist male who is hardly going to be the trans-supportive politician we could have had and which Chappell says we so need, and who will be far less a friend of the Palestinians than Harris – I appreciate the integrity. (Besides, if Taylor Swift’s endorsement couldn’t get Harris elected, then…)

Putting some of the suddenly incoming money where her beliefs lie, Roan donated £1 per ticket sale from her recent UK tour for an LGBTQ+ charity, and raises funds for Palestinian aid agencies at the merch tables. She also gives her gigs specific themes, providing a licensed invitation to her young audience to dress accordingly. And by proving willing to talk openly about the problems of sudden global fame (the loss of thrift-shopping without a security detail being a much-missed former everyday occurrence), while simultaneously acknowledging its advantages (living out an “11-year-old boy version of myself” at the MTV VMA Awards, see below), Roan shows a worldly involvement and a personal engagement that reminds us there is a human behind those heroes that every generation throws up the pop chart. Her performances, her persona, her outspokenness, her public embrace of queerdom and trans rights, her blending of the commercial with the confrontational, truly makes her a star for the ages. Or, at least, for this age. And that, especially if you are young, is the only age that matters.

7) The Joie de Vivre

Finally, I can’t let it all go without getting to the heart of why some of us love pop music so fucking much: because it’s fun! I started out buying 45s in the glam-rock era of the early 1970s, when everyone from the aforementioned Alice Cooper and David Bowie through to Sweet and Slade and, had I known them at the time, the New York Dolls, was exploring their inner drag queen. That period was glorious and I would not swap it for all the coffee in Zanzibar. Everything I have stated above about Chappell Roan is important, but at the end of the day – as with the male artists just referenced, plus Madonna, Lady Gaga and anyone else you may think pertinent to this conversation – the music is “really all disco.”

And this brings me back to Olivia Rodrigo, readily denied her own acceptance as a quality singer-songwriter because she grew up in public as a Disney star. Her 2021 breakout single “Driver’s License” was itself a great teen anthem born out of her own version of universally experienced heartbreak, but she is no Chappell Roan. Nor should she be. I love her latest single “Obsessed,” and I dig that the second studio album to which it has now been appended - Guts (Spilled) - starts with the E-for-expletive “All American Bitch” and ends with the E-for-expletive “So American.” But Rodrigo is not transgressive: she is straight, she is conventionally pretty, and she plays that role because it's the honest role. But so we can be clear, she too has talent to back up her success, having taken piano and singing lessons along with her acting lessons as a child, and we will prove as much with the same NPR endorsement with which we introduced Chappell up top.

Indeed, Olivia Rodrigo has much to do with Chappell Roan’s monumental success. When Daniel Nigro produced “Driver’s License” and was immediately, inevitably, hired to produce an accompanying debut album (Sour, also 2021), it temporarily severed his connection with the then label-less Roan, who could have harbored jealousy or animosity to Rodrigo, five full years her junior and still just 21 at the time of my writing this. No such thing appears to have happened. Chappell and Nigro reconnected once Sour was finished and Roan secured a fresh publishing deal, and the result was, of course, The Rise and Fall of a Midwestern Princess. Rodrigo subsequently took Roan out as support act on her Guts tour, and if she harbors any jealousy in turn that Nigro’s Midas Touch is gaining more attention right now with her former opening act, she too is not showing it. There is room for them both in this world.

There is, however, barely a stage big enough to contain their collective energy, which is why their guest, surprise and encore appearances together work best on the catwalks and sidewalks of the modern-day arena/stadium stages, not those of an old-fashioned Top of the Pops. Nonetheless, when, over the recent holiday period, I watched this clip of Olivia Rodrigo and Chappell Roan performing the latter’s “HOT TO GO!” it brought me back to the dressed-up pop stars of my own childhood. Specifically, it was the one modern-day performance I watched in December 2024 that brought out the child of December 1973, and the gloriously inane delight of singing alone to Slade’s “Merry Xmas Everybody” and Wizzard’s “I Wish It Could Be Christmas Everyday.” For those who celebrate, this clip below is like Christmas everyday. May pop music always be this fun. And feisty.