Chappell Roan’s Glittering Ascent: Following Her Journey from Ground Zero to the Grammy Stage

It's May of 2020, three months after my senior portrait graced the screen of my virtual graduation, cheered on from my living room couch, I found myself on the other side of the country - alone. After high school, I had taken the leap to move out of my suburban Midwest town and venture to the big, bustling city of Los Angeles to attend the University of Southern California. I aimed to study music business, and if anywhere was the place to be, it was here. Surrounded by musicians on every corner, shows every day of the week, and a major music venue sitting next door to my brick-laid apartment complex. This was the place, I was in it.

But as we all know, 2020 brought with it challenges unforeseen and unnavigable, especially for an 18-year-old, anxious girl from a town named after buffalos. Campus was closed, all classes remained online. My roommates, morally ambiguous at best, had nothing remotely relatable let alone compatible to offer. The only social affordances were parties where COVID spread faster than news of a new Taylor Swift re-release. So, while my roommates raged night after night and made friends on every floor of our plague-ridden apartment complex, I stayed in my beige room and listened to music with my tried and true Sony headphones - canceling out the noise around me.

For all my life I was known as a popstar enthusiast - namely following Katy Perry through every endeavor, tour stop, album release, you name it. Bubble-gum pop has always been a second language to me. My way of life was live shows and with the pandemic, everything was on hold. The main way I found community and connection was put on the back burner. So as I sat, alone, enclosed in my 12x12 dorm room, sterile, where the same four walls seemed to inch closer each day, the industrial carpet wearing thin beneath my feet and the single window, barely large enough to let in the Southern California sunshine, served as a constant reminder of the world moving on without me. I thought to myself - what now?

I began to find solace in my solitude and I listened to as much music as I could. Being in college, paying in the thousands for a degree meant I got $5 off Spotify Premium - score! With nearly every track ever recorded at my literal fingertips, I found myself immersed in the discovery of small emerging artists. 

The exact date and circumstances leave my mind, but I was probably eating a bag of Orville Redenbacher microwavable kettle corn, rocking back and forth on the anti-suicide chair that lovingly came with my furnished apartment - when I heard it for the first time, "Pink Pony Club".

The song opened softly - a gentle piano melody carrying a voice that held both vulnerability and quiet determination. In her raw, honest tone, I heard echoes of my own story: a small-town girl daring to imagine a life beyond familiar boundaries. As she sang about leaving Tennessee for LA, about finding a place where she could shed the weight of hometown judgment and embrace her true self, each verse felt like reading pages from my own journal. Her lyrics about a place 'where boys and girls can all be queens every single day' resonated deep within me - a fellow queer soul who had also sought refuge in LA's promise of acceptance. The narrative built slowly, deliberately, her voice gaining confidence with each line about breaking free from expectations and finding somewhere to celebrate rather than hide who you are. The lyrics weren't just words floating through my headphones - they were the same dreams I'd whispered to myself late at night, the same yearning for a community where my queerness could flourish, the same fears I'd pushed against when booking that one-way ticket to California. Here was someone who understood not just the magnetic pull of possibility, but the specific ache of needing to find your people, your place, your permission to shine.

As the pre-chorus picks up, the song transforms melodic piano chords into a euphoric explosion of pulsing beats and crystalline synths, Chappell's voice somehow captures both the grit and glamour of LA nightlife. The chorus was like a confetti cannon of sound - theatrical, bold, and absolutely unapologetic in its pop sensibilities, all while Roan's voice commanded the track with the confidence of someone who had already made it big. The raw energy and authenticity of her performance resonated through every note, making it impossible not to be swept away by the magic she was creating. Chills spread across my skin.

I was so moved, I broke a rule that I held myself accountable to - as a professional fangirl - I slid into Chappell's DMs. At this point, June 19th of 2020 to be precise, no blue checkmark sat next to her name, and her followers were just under eight thousand. I wrote: 

“Just want to let you know I'm absolutely OBSESSED with PPC [Pink Pony Club]..."You are so insanely talented" 

"Thank you so much ✨💖✨," she replied.

Little did I know that the underground, indie song I was applauding would be part of Chappell's inaugural Grammy performance four and a half years later, where the audience, made up of industry legends from Taylor Swift to Stevie Wonder, would be belting the chorus. A song about queer joy, liberation, and communal celebration on the mainstage, just weeks after the American government denounced transgender identities, imposing harm and erasure to the whole LGBTQ+ community.

As the weeks and months went on, I delved further into her discography, which at that point consisted of a grunge, gospel-esque EP, the sound, completely opposite of "Pink Pony Club". I followed her socials, all of which were incredibly uncurated and personable, and her monthly streams barely surpassed ten thousand. It was still the early months of the pandemic; she wasn't performing, and I learned years later, was dropped from her label. In the meantime, Roan was working at a Highland Park doughnut shop I actually frequented - Donut Friend - they have a great gluten-free selection for anyone wondering.

I was often 1/30 or so in her intimate TikTok live streams, from her little bedroom, with her guinea pigs, twin bed, and singular rack of avant-garde wardrobe. She spoke freely, sharing everything from her dislike of Charlie Puth to her plans for the future. I recall her playing demos of the songs she was creating with producer Dan Nigro—one of the first to hear the raw, stripped-down version of what would become the hit "Red Wine Supernova," still in its unfinished, unmastered state.

During a whirlwind trip to New York, I made a pilgrimage to the Stonewall Inn - the legendary Greenwich Village bar where the modern LGBTQ+ rights movement was born in 1969, when patrons, led by trans women of color, fought back against police harassment in what became known as the Stonewall Riots. Though I only had a few precious minutes to spare, I knew I had to step inside these hallowed walls, to breathe the same air where our community's fight for dignity and recognition first erupted into the mainstream consciousness.

As I pushed open the door, my heart nearly stopped - the opening synths of "Pink Pony Club" filled the historic space. The song that had become my personal anthem of queer liberation was playing in the very birthplace of queer liberation itself. It felt like the universe was winking at me. This wasn't a radio hit or a Billboard chart-topper - this was a relatively unknown artist's song about finding freedom in queerness, playing in the most significant queer space in American history. Tears welled up in my eyes as I ordered my drink, the bartender noticing my emotional state. Through happy sniffles, I gushed about Chappell, about the coincidence, about how perfect this moment felt. He listened with the patient understanding of someone who had witnessed countless similar moments of queer joy and revelation within these walls, as generations of LGBTQ+ people found their way to this sacred space. For those few minutes, time seemed to stand still, "Pink Pony Club" echoing off walls that had witnessed the birth of a movement, now bearing witness to its continuing evolution through art and music.

As I made friends throughout the year, I shared my adoration for Chappell with all of them, and they quickly became hooked - we would spend countless nights doing karaoke in my living room to "Pink Pony Club," - we sounded awful, except for Jenny, who happened to major in Opera arts of all things. They reaffirmed my belief that "Chappell is going to be the next big thing."

By 2022, I had returned to LA after a long and eventful summer when Chappell announced her first solo show - ever. Tickets were $15, and I felt like the luckiest girl in the world to be living in the music capital of the country, being the only place she would perform. Though none of my friends were convinced enough to go with me, I attended the Troubador show alone, where she premiered an abundance of her works-in-progress to an intimate crowd of early believers. 

Walking into the venue that night, I was immediately enveloped by a sea of pink cowboy hats and boots, each person more bedazzled than the last. The 500 person room sparkled with endless rhinestones catching the dim lights, creating a constellation of queer joy right in the heart of LA. Fellow fans had transformed themselves into their own versions of the Pink Pony Club dancers - some sporting metallic fringe that swayed with every movement, others wearing carefully crafted cowgirl outfits that would make Dolly Parton proud.

As Chappell took the stage, the energy shifted from excited chatter to electric anticipation. Here we were, a room full of queer people singing about West Hollywood's promise of freedom and acceptance, while standing in the very place the song celebrated. For me, as a lesbian who was still finding her footing in the community, this was transformative. It was one of my first experiences being in a space where queerness wasn't just accepted but celebrated as the main event. The room was filled with people who understood the weight of lyrics about leaving small towns for the promise of finding your people. Every person around me had their own version of that story, their own Pink Pony Club they'd been searching for.

Chappell herself embodied this spirit of unapologetic authenticity. Between songs, she shared stories of her own journey, her voice carrying the same raw honesty that made her music so powerful. She wasn't just performing for the queer community; she was creating a safe space for us, championing our stories, and reflecting our experiences back to us through her art. In a time when anti-LGBTQ+ sentiment was on the rise, having an artist so boldly and joyfully celebrate queer identity felt like a radical act of resistance through pure, unbridled joy.

It was a night I will never forget.

A week later, I was attending the first meeting for a campus concert committee called Femfest, a student-run, female-fronted music festival. After icebreakers and a logistics breakout session, they asked, "Does anyone have any small, female artists they'd be interested in booking for our show?" My hand shot up instantly.

"Chappell Roan!" I immediately exclaimed.

There were murmurs rippling through the room: a third of students asking "Who's that?", another group whispering "Oh, I think I know her," and the leaders exchanging excited glances, saying "Wait, that is an amazing idea!"

I was on the digital media committee, so I had little knowledge of the behind-the-scenes happenings in the weeks that followed, but I'll never forget sitting with my friends when they leaned in close and whispered, "Have you heard the news? You can't tell anyone... Chappell is booked for Femfest, she's the headliner."

I nearly fell out of my chair.

At one of our club meetings, the official reveal happened, and I acted equally surprised, though my heart was racing with insider knowledge. My adrenaline was rushing, and I'm pretty sure there was a standing ovation - or at least there was one in my head.

Chappell's album wasn't yet released, and most people were unaware of her existence. Though unsigned, her name began appearing in niche corners of the pop world. Roan secured a spot opening for FLETCHER, a cultural icon in the lesbian community, on the "Girl of My Dreams" tour. Though FLETCHER's intense, bold persona and in-your-face pop style often left me feeling both fascinated and slightly overwhelmed, I was among the first to secure tickets with my new roommates, who by this point couldn't resist the opportunity to see Chappell perform.

The show was packed - even JoJo Siwa made an appearance. Yet, among the thousands, I was part of a mere handful who knew every word to every Chappell song, while the rest of the crowd waited restlessly for FLETCHER to take over. Chappell's stage setup was minimalist: just her, a guitarist, a backing track, and a dream. In her provocative version of a motorcycle suit, complete with assless chaps, patches reading "My vibrator has two wheels," "cunt," "I love my wife," and a denim thong, her stage presence needed nothing more. Even battling alcohol poisoning and a lost voice, she commanded attention, but the majority of the audience didn't give in - not yet, at least. I'd imagine they must regret that now.

Being a queer artist doesn't automatically guarantee the embrace of the LGBTQ+ community - the FLETCHER fans' indifference proved that much. It wasn't until Chappell opened for pop sensation Olivia Rodrigo that the mainstream world began to take notice.

The first few arena shows mirrored the FLETCHER crowd's response - uninterested audiences impatiently awaiting the main act. But with each passing week, more and more showgoers learned the HOT-TO-GO dance, and by the time her leg of the tour ended, entire stadiums were H-O-T-T-O-G-O-ing in unison. Chappell's debut album, "The Rise and Fall of a Midwest Princess," found itself atop the Billboard 100, a feat unfathomable for most artists, let alone an indie artist with few industry connections. Her numbers began to climb, and her name was coming out of the mouths of megastars like Elton John.

As the semester continued, the Femfest team and I worked tirelessly, ensuring each aspect of the experience was meaningful for both our audience and talent. I collaborated with the branding and social media team to create teasers and visuals announcing Chappell's headlining slot. We fundraised, diligently tackled the logistical challenges of planning a music festival on a private college campus, and recruited friends and their friends to attend the show.

I told everyone, "You have to come - Chappell Roan is performing and you won't want to miss it. She really is going to be big, I guarantee it."

What some of my newfound college acquaintances didn't know was that I had a history of predicting pop stardom - I'd done it with Billie Eilish when I saw her blue-haired, teenage self perform to a room of less than 1,000 in 2017.

The day of Femfest was imbued with glittering anticipation. I photographed Chappell during her soundcheck, where she commanded the stage in a purple sweatsuit, her hair casually undone, offering cues to the tech team and her band. I couldn't believe my eyes or ears. I was watching my favorite artist in real time, sharing this precious moment with just a handful of girls from the Femfest team - witnesses to the precursor of history.

As showtime approached, I learned the digital media team would be the only ones working directly with Chappell, photographing her in the green room after her set. Working the camera, I got more than just barricade access - my media pass put me in front of it, giving me a view better than any superfan could dream of.

I stood in position, DSLR camera from the journalism school's student center steady in my hands, as the anticipation built. After the student DJs and opening acts cleared the stage, the atmosphere shifted palpably.

Chappell emerged like a vision in a glittering black ensemble that reminded me of my former figure skating days - all sparkle and drama - complete with silver and black gym shoes, her signature red curls framing her face like a fiery halo. The stage filled with fog as a recorded voice memo, intimate as a late-night voicemail, played through the speakers while her guitarist strummed deep, resonant chords.

When she opened with "Naked in Manhattan," my heart soared. As a working photographer, I forced myself to remain professional, suppressing the urge to jump and scream, though inside I was having my own private concert of epic proportions. The audience, mostly unfamiliar with her music at first, swayed curiously, drawn in by her magnetic presence.

Her cover of Alanis Morissette's "You Oughta Know" was transcendent, her voice diving deep into guttural depths before soaring to stiletto-high heights. Through "Casual" and a premiere of "Red Wine Supernova," she built momentum until "Pink Pony Club" erupted as the finale, transforming the initially reserved crowd into a moshpit full of joy

Tears glistened in her eyes as she finished her first-ever festival performance, and I fought back my own as I made my way to the green room for post-show photos. She introduced herself sweetly as "Kayleigh," her gratitude genuine and overwhelming as she promised to remember this night forever. When I mentioned being a long-time supporter, her face lit up with sincere appreciation.

It was one of the greatest nights of my life, made even more special by the knowledge of what was to come - just a week later, I saw her again in a venue three times larger, with announcements of Lollapalooza and Coachella on the horizon. She was on the cusp of something extraordinary, and we all knew it.

As summer turned to fall, Chappell Roan's ascent became impossible to ignore. Each week brought new coverage - Pitchfork analysis, NPR features, local news stations scrambling to claim her as their hometown hero. When Rolling Stone put her on the cover, draped in blush pink and wearing nails sharp enough to could claw their way through a stampede, it was evident her starpower had been solidified. The girl who once worked at a donut shop was now staring back at magazine readers from grocery store checkouts across America.

By the time festival season rolled around, in Palm Desert, Coachella's Mojave tent couldn't even contain her growing fanbase - the crowd spilled out far beyond its boundaries, a tapestry of pink cowboy hats and branded bandanas stretching as far as the eye could see. But nothing could have prepared me, or the festival workers for Lollapalooza. In a last-minute shuffle that would prove prophetic, organizers moved her from a side stage to the main stage, swapping spots with none other than Kesha. When over 100,000 people showed up - setting a festival record - I couldn't help but remember watching her perform to barely 100 people just a year earlier. The same songs, the same artist, but now her message of queer joy and self-discovery was reaching multitudes.

The following weekend, I found myself in rural Iowa (of all places) at Hinterland Music Festival, fighting through scorching heat and what would later turn out to be sun poisoning. But nothing could keep me away. As Chappell, dressed as a nun (because of course she was), led upwards of 10,000 people in the HOT-TO-GO dance, tears streamed down my face. It felt like yesterday when she was teaching the moves to an indifferent FLETCHER crowd, and now here we were, thousands strong, moving in joyful unison.

Six Grammy nominations, SNL performances, late-night show appearances - Chappell transformed from an underground artist into a cultural phenomenon. But superstardom came with its thorns. As an outspoken queer woman, the backlash was swift and severe. When she stood her ground against disrespectful paparazzi on the red carpet, they painted her as difficult. When she declined to make a presidential endorsement, focusing instead on LGBTQ+ rights and artist healthcare, critics called her apolitical. The online hatred grew so intense she had to withdraw from several festivals, which only fueled more vitriol.

But here's the thing about Chappell Roan - she never asked to prove herself to anyone. Setting boundaries as a woman in music shouldn't invite punishment. She's doing what's best for her mental health, a small-town girl who found herself rocket-launched into superstardom. The industry's treatment of her exemplifies a larger problem: the expectation that female artists should be eternally grateful, eternally accessible, eternally accommodating. It's time we respected women in music as full human beings, not commodities for consumption.

Last night, 4.5 years after I first heard "Pink Pony Club," I watched Chappell perform it at the 67th Grammy Awards. Accepting her Best New Artist award in princess attire (though she's nobody's damsel in distress), she used her platform to advocate for artist healthcare and security, speaking truth to power about being dropped from her label with no safety net. The small-town girl who once worked at Donut Friend now stood on music's biggest stage, using her voice not just to sing, but to demand change.

Watching Chappell's journey has been more than just witnessing an artist's rise to fame - it's been a masterclass in authenticity, resilience, and the power of staying true to yourself. As a music lover, I've seen how genuine artistry can still triumph in an industry often driven by algorithms and TikTok trends. As a queer woman, I've watched her create spaces where our stories aren't just told but celebrated. She's shown that success doesn't require compromising who you are - in fact, it often comes from embracing it fully, rhinestones and all.

From those early DM exchanges to Grammy night, from intimate venue shows to record-breaking festival crowds, I've had the privilege of watching a star not just rise, but reshape the very landscape she rose into. Chappell Roan didn't just find her place in the music industry; she created a new one, making room for all the weird, wonderful, and unapologetically queer artists who will follow in her sequin-studded footsteps.

In a world where anti-LGBTQ+ legislation continues to sweep across America, where drag shows face bans and trans youth are denied healthcare, having Chappell Roan dominate the pop landscape feels like a revolution dressed in rhinestones. Here's an artist who doesn't just wave the rainbow flag when it's profitable - she embodies queer joy as an out lesbian who performs in drag, who speaks up for trans rights from festival stages and Grammy podiums alike. She's proof that you can reach the pinnacle of pop music while being unabashedly, radiantly queer. Every time she steps on stage in her elaborate drag, every time she uses her platform to amplify trans voices, she's showing queer kids everywhere that they don't have to choose between authenticity and success. In an industry that often asks artists to tone themselves down for mass appeal, Chappell turned herself up to eleven and made the mainstream come to her. She's not just making pop music - she's making history, one sequined, subversive, spectacular performance at a time.