A Midwest Princess and the Art of Where You Are

I’m trudging through the streets of Chicago on a school night and there’s ass out everywhere this fine Thursday night. A friend and I are amid the daily exodus of fellow festivalgoers from Grant Park as Lollapalooza comes to an end for the day. The Windy City sees this crowd come and go every summer during the first weekend of August, at the peak of its humid summer. Toasty and toasted from the hot summer day, we beeline back to the hotel for some well-deserved air conditioning time.

“One more hour before Chappell Roan drops The Subway,” I announced, pulling Spotify up on my phone prematurely as the cell signal slowly seeped back into my device. I’d just seen the superstar the year before, in 2024, at the exact same venue, decked out in lucha libre gear. During her performance, she went through her album’s discography, but she also graced attendees with a live rendition of her at-the-time unreleased single The Subway

That’s when a girl, freshly tanned from the first in a series of hot outdoor days, turned around and smiled at me: “It’s already out!” 

I queued it up immediately and listened on the walk home.

This was in summer of 2025, a few years after Chappell Roan’s release of her debut album The Rise and Fall of a Midwest Princess on September 22nd, 2023. The album’s initial reception was met with limited but enthusiastic fanfare, circulating mostly among online popheads to begin. Her global fame didn’t truly skyrocket until she toured as an opener for Olivia Rodrigo for the GUTS Tour in spring of the following year. Around the same time, she also dropped “Good Luck, Babe!” which spiked in Billboard’s Hot 100, and alongside it came Chappell’s rise to stardom herself. Coupled with subsequent performances at Coachella and the aforementioned Lollapalooza, Chappell had suddenly and randomly become an unstoppable sleeper hit in the pop culture sphere.

You’d be lying if you were reading this and said you didn’t know who Chappell Roan was – her presence has been culturally loud and omnipresent. She’s graced everything from advertisements, to wedding receptions, to short-form video since her rise to stardom – all algorithmically designed to capture your attention. But not without reason; in her debut album, Chappell Roan nailed the formula of the catchy, high-energy pop song, following closely in the footsteps of other pop heavy hitters of the 2010s. Add in a little scripted dancey-dance to HOT-TO-GO and some relatable lyrics slapped on and you’ve got yourself a fastpass to the top of the charts.

To me, though, Chappell’s impact has always been her skill in evoking such a compelling sense of setting and place through her music and songwriting. One mindful listen through the album and her surface themes are obvious: in The Rise and Fall of a Midwest Princess, the listener undergoes Chappell’s journey away from home and her foray into the coasts, her agony over the decision to leave her little Midwestern town, and the excitement to experience what coastal California has to offer. There’s palpable excitement, there’s unease, and sprinkled in between is the devastation of determining where you are, where you should be, and how to be what you’re supposed to be. It’s a well seasoned crock pot of everything to experience in your twenties.

Let’s go back to the beginning. I’m trudging through the hilly streets of Chicago, burnt and crispy despite the two pounds of sunscreen I swear I slathered on mindfully throughout the day, and I’m probably pissing off my fellow constituents by playing The Subway out loud on my phone after everyone had just fought tooth and nail to flee the festival grounds and catch the next L train. The studio version of The Subway begins with the distinct sound of – obviously – a subway train rumbling through a tunnel before opening into a description of a brief encounter with an ex, a flash of green hair swinging by as they pass one another as strangers on a subway platform. Chappell is, of course, inconsolable. Lyrically, the encounter is brief, but the sounds and ideas are a direct and distinct call to the subway stations and transit culture of New York City.

NYC’s commuter culture is unique in that it’s the most populous city in the United States while maintaining the highest rate of public transit commuters out of any major city in the nation, at approximately 55% of all workers not working from home utilizing public transit.

The Subway’s intro is brimming with a familiar melancholy, that of seeing that one person you didn’t want to. Or maybe, the person you wanted to see the most. I couldn’t name to you the number of times an ex’s name has popped up in a notification and my stomach fell out of my ass and onto the floor. For a lovergirl like me, I chased it. I’ve stalked social media posts, changed my normal walking course to potentially pass by where they might be, curated Instagram stories with agonizing deliberation just to pray to see their name pop up on the “viewed” list. And so what? Chappell Roan’s release of The Subway is a fun, riled up reminder that we share so much in common.

When the single dropped, I was coming off the tail end of a devastating but otherwise mundane breakup. He was from Ohio, living in Texas, and had seen more dead deer on the side of highways than commuter trains. And I’m from California, where the metro line was more of a marketplace for skeevy taser salesmen than an efficient form of locomotion to get you from the place you are to the place you need to go. All that to say: in no circumstances have he or I ever circumnavigated a city together on a train. We’re car-pilled. But the sensation of the song is so powerful, it’s like I lived that subway experience myself. In a way, I have.

This experience brought about a deeper dig into Chappell’s lyrical catalogue. Let’s go back to even more beginning-er: in April of 2020, Chappell Roan released Pink Pony Club, an instantly recognizable hit to anyone that has had functional nerve endings in their ears during the last few years. In it, Chappell Roan describes the departure of a girl from her home landlocked state (Tennessee, because it rhymed better than her home state Missouri per a reddit user during a live) to coastal California, and depicts her subject as a go-go dancer at a bar in West Hollywood. At the other end of 3,000 miles, her heavily conservative mother clutches her pearls at the thought – scantily clad and dancing for work, unbecoming of a good, traditional girl! Our protagonist assures her she’s having fun, she’s living the call of the coast, and she’s by no means forgotten her roots in the south and misses her all the time. But nothing will stop her from being the girl she needed to be, where she could only truly be at the Pink Pony Club.

While it’s not a one-for-one to her life, the song is heavily inspired by Chappell Roan’s first visit to The Abbey, a gay bar in West Hollywood. The visit inspired the singer to become a go-go dancer herself, but felt she was not confident enough to do so, birthing a song from the experience instead. The song channels her desire succinctly – the song’s refrain lets the listener know she’ll always choose herself first, that she’ll keep dancing and expressing herself this way regardless of what her mother wants for her. This comes before and after a dip into the song’s final bridge, consoling her dramatic mother who was certainly born and raised in a different time and place: she still loves her and Tennessee, they’re always on her mind. There’s little in common between a West Hollywood gay bar and a small southern town, so there’s an implication that our song’s protagonist has abandoned her roots. Pink Pony Club’s bridge brings solace to the frenzied mother. She assures her that she brings Tennessee with her, and just because she’s not there right now, she will always choose to be who she really is: a southern girl in a coastal gay bar.

Then, the last few decades saw unprecedented technological advancement, a technological revolution. The Pew Research Center estimates that approximately 52% of Americans utilized the internet in the year 2000, which has since skyrocketed to 93.1% of Americans in 2025 per DataReportal. With that evolution came social media usage, short form content and pop culture news which has transformed our level and frequency of media consumption. All that to say: young queer people are engaging with queer media at a higher rate than ever before, fighting the feeling of communal discomfort around the environments they were raised around to embrace a digital acceptance. When these online communities congregate in person, they find themselves congregating particularly near the coasts, away from the jeering stares of Middle America.

And so it is! West Hollywood comprises a specific queer culture, of which The Abbey is distinctly a part of. I can’t speak too much on it myself as someone who is not queer – but the feeling is clear. Chappell Roan spells it out for us through the lens of a girl working for herself, her dreams, and her life. It’s the California dream, which she takes on while proudly wearing her roots on her sleeve.

If Pink Pony Club describes the rise of the Midwest Princess, then a later track details her descent. In May of 2020, just a month after the release of Pink Pony Club, Chappell released California, a track presenting as a foil to Pink Pony Club. In contrast to the latter, this song laments the death of Chappell’s dreams as she is chewed up and churned out by the reality of the entertainment industry. Her description of the golden state is charmed, but not necessarily positive – there’s no brown leaves in California (a reference to California Dreamin’ by The Mamas and The Papas), there’s no seasons in exchange for her massive sacrifice. She came to the state to chase a dream that has stretched herself across half the country, and she’s understandably tired.

When she talks about Missouri, her descriptions are quite literally full of death – dried up, amber clay roads. A dying town, where the foliage is brown and dead and ready to return to the earth for the year. It’s the Middle America that many are intimately familiar and bored with. But after the heavy disillusionment coming from California, Chappell looks back and remembers that despite the lack of life, it’s still home.

Some time in my twenties, I left my home state of California to go on a cross-country road trip with my dog and a half-baked plan. I zipped through the deserts of Arizona, the wastelands of West Texas, the swamps of Florida. I zoomed back up the eastern seaboard, spent time in the country’s capital, and checked out the universities around Boston. During this time, I met lots of different kinds of people. My favorite was my ex boyfriend. He was visiting Texas on a coincidental trip. We met, drank through a series of bars on 6th Street, and fell in love. This massively derailed a portion of my trip – in a good way – and a while later I wedged his tiny Midwestern town into my itinerary for a few months, between Washington D.C. and Boston.

He spoke positively and defensively of his hometown, and I can see why. The difference between my dingy, high-density apartment in California and his big house backed up to the woods was stark. And worth more than anything I could afford in California, it was peaceful. It was quiet. The people were friendly and different from me. My dog could run around in the snow, something he’d never seen before and wasn’t exactly familiar to me either. It was just not California, looming overhead with its steel gray buildings and overwhelming pressure. It was Ohio, and at the time it was green and white and I got to share it with a cool guy I met on a trip.

Chappell Roan probably feels the same way about Missouri.

Incidentally, California’s total commercial failure led to Atlantic Records dropping Chappell Roan, subsequently sending her home to Missouri to work odd jobs while she worked on music independently. 

During an interview with Variety, Chappell Roan touches upon her Midwestern roots and how it impacts who she is. “Thank God I came from the Midwest because I understand people,” she commented. “I have family who have complete opposite views of my views and values, and they still support my project. I have this perspective that I think people on the coasts don’t have of the people there. I know where they’re coming from. It’s just not that black-and-white.”

I’m a contra-Chappell in that I was born and raised in California, in a (subjectively) little town nestled in the foothills of the San Gabriel Mountains, then spent time in the Midwest, albeit not for too long. Much of my childhood was spent frolicking around Los Angeles and the neighboring towns. The Los Angeles of my mind is probably much different than it is from the Chappells of the world. It wasn’t glitz and glamour and industry to me and the people around me – it was just hard to find parking. It wasn’t until I showed my Ohioan ex-boyfriend a picture of my hometown that he looked at me in shock and asked: “You just look up at that mountain all the time?” Before that, I’d never even given it a second glance. I grew up mostly peeved at how far away we were from the beach (40 minutes!).

When I finally made the drive home, I pulled up to my apartment and looked up. They had blocked the view of the mountain with a luxury mid-rise.

I’ve been wanting to move away again since I came home. When I talk about it with friends, though, they mostly don’t understand it; why the desire to move out of California? California has everything, what even is there in x state or y state? Haven’t you seen enough? Isn’t it just boring and lame outside of California?

I wouldn’t argue that California is not the best state in the United States. It’s got the highest GDP of all the states by quite a margin, the second largest number of unique ecoregions of nature (and the highest number of unique ecoregions out of all states that aren’t Alaska), and has some of the highest rates of year-round comfortable weather in the world (subjective, of course). There’s things to do if you like art or food or music, and special events or tours always make sure they zoom through California, so you’re never in an indie artist’s Instagram comments begging for them to come to LA.

But during my travels, I spent time with my ex’s friends and his family. I saw how they were kind and neighborly, how they were similar to me, how they were dissimilar to me. I watched my dog paw through thick layers of untrodden snow, and how his dog didn’t give a single shit about the snow and how he’d rather get those blasted skunks out of his goddamn yard. The squirrels were black, and his backyard led out into a small stretch of woods that had seen generations of dumb kids romping around with dirt bikes and other stupid, dangerous bullshit. I sat in his garage and I drank Yuengling. I watched his dad blast a kerosene heater to fend off the chill and smoke cigars at midnight. I think a lot of people might have found it boring, and maybe it was, but I look back at it fondly. I could understand why people want to live like this. Maybe for forever, or maybe not forever, but I want it for myself some too.

Before I made it back to California, I helped my ex-boyfriend move to Texas. We tried the long distance thing for a bit, but the destabilization of his life led to some push and pull, and we ended up breaking things off. Then, summer happened and Chappell Roan released The Subway. The song crawled its way up to my top song for 2025. And I decided it was time to leave.

But for a while it was 2024, and I’m at a bar with my friends and a boyfriend I loved at the other end of my phone. The Touch Tunes queue was plagued, just inundated with Pink Pony Club and Red Wine Supernova on repeat. The drinks were flowing. I was in Ohio, or LA, or Miami, or anywhere where the people could congregate to drink and be idiots together. I was amid a crowd of strangers that loved the same music as me in the biggest city in the Midwest. I was at a pool hall with a bunch of divorced dads. I was on the beach with my equally heartbroken friends and telling them all that we’ll get ‘em next time. I’m everywhere in the United States listening to a girl like me who had bravely adventured from her tiny town to the jeering steel skyscrapers of Los Angeles to talk about the art of where she is, how those things shape the person she wants to be, and how she tries to live up to those every day.

Behind Chappell Roan’s character lies Kayleigh Rose Amstutz, the real daughter of a veterinarian from Willard, Missouri. She’s a girl, not unlike me, and she had a lot of decisions to make, not unlike me, and she probably regretted a lot of them, not unlike me. She probably went back and forth a lot, and probably really ruminated on where she wanted to be versus where she needed to be. Along the way, she probably got a lot of encouragement to stay in one place, or leave another place, or just give up and come home. Take it from her herself in her Reddit AMA: LA is hard. In your tumultuous twenties, you might experience the same.

My ex and I got back together, so I was lying through most of this piece. There’s more calls, check-ins, and decisions to make now more than ever as we figure out the core of our issue: how can we close this thousand mile gap? How can I be close to him again while remaining me and wear my roots on my sleeve? It’s silly and fun and unserious pop music, but sometimes the radio’s on and Chappell Roan is playing for the trillionth time but I’m reminded that I’ll make right choices, wrong choices, and stupid choices about where to be like she and every other girl before me did.

My family immigrated to the United States a few decades ago seeking a better life with more opportunity – in retrospect, it trivializes my decision on where I want to be. Human migration is a well-documented pattern observed in peoples since the beginning of history. Evidence of migration is scrawled on cave walls, inked in scrolls, and most compellingly it’s shared through song and dance and art. Pop music will continue to carry on that legacy for as long as it continues to exist. Chappell Roan wrote The Rise and Fall of a Midwest Princess to share a multi-faceted reflection on her journey to the coast. I trust that wherever I go, I’ll continue to hear her at the local bars, surrounded by girls figuring themselves out too.