Chappell Roan’s Big Year: How the DIY Indie-Pop Star ‘Casual’-ly Thrived in Her Post-Label Era

As 2022 draws to a close, Billboard Pride is taking a look back at some the queer indie artists who saw their stars rise over the last 12 months. Below, pop singer Chappell Roan breaks down her big year.

When Chappell Roan markets herself as a “thrift store pop star,” she means that in its most literal sense. Even as she logs onto her Zoom account for an interview with Billboard, the 24-year-old singer is opening up a package she ordered online. “There is this girl on Etsy who makes rhinestoned disco cowgirl hats,” she says, tearing into the plastic wrapping in front of her. “So, I ordered one, because I’m going on tour and I have to start prep now for the outfits.”

As she finally opens the bag, she reveals a massive, disco ball-inspired cowboy hat covered in reflective panels and glittering gems. Roan’s jaw drops as she inspects it (“This is so sick,” she whispers), before looking slightly concerned as she dons the sparkling Stetson: “Ooh, that is heavy — I don’t think I can wear this on stage for long.”

Refining her tour outfits is just one small part of what Roan has been up to lately — the rising indie-pop singer-songwriter saw her hard work pay dividends in 2022. Releasing four singles throughout the year to increasing acclaim and growing her online following along the way, Roan is currently enjoying new heights of cultural recognition; her last single “Casual,” along with winding up on multiple “best of 2022” lists, boosted her profile online, with TikTok users quickly comparing pre-release teases of the track to Taylor Swift.

Looking back on her banner year, Roan acknowledges that it feels good to finally be recognized (“Last year I was working at a doughnut shop, so I’m doing great now,” she jokes), but she doesn’t feign shock at finally achieving a breakthrough. “It’s validating … but also not surprising to me,” she says, shrugging. “Like, yeah, I’ve been working my ass off for seven years! It’s about time!”

Back then, Roan was an aspiring singer-songwriter from Willard, Missouri who was simply trying to make it through high school while dreaming of a life in the music industry. After posting some of her music online, the singer traveled to New York City in 2015 for a set of showcases, where she ended up signing a deal with Atlantic Records.

Roan spent five years at Atlantic, workshopping her sound and releasing her debut EP School Nights in 2017. But after putting out what would go on to become her most successful song to date, the label decided to terminate their working relationship with the budding star, dropping Roan from their roster in 2020.

When asked about her time with Atlantic, Roan starts with diplomacy: “It was such an incredible learning experience for me, honestly.” Then, the singer gets real: “It was not great … I feel like once I was dropped, it lit such a fire and fury in me, I swear,” she recalls. “I learned that it’s just like, ‘Oh s–t, no one’s going to do anything for you — not your manager, not your label — if you don’t tell them what to do. No one can do this job for you.’ That’s when I started asking myself how much I could get away with.”

Fortunately for Roan, her time at the label did bear some significant fruit — it was at Atlantic that she first met her songwriting partner Dan Nigro, who has co-written each new release with the singer since her departure. Before he was writing generational breakup anthems for Olivia Rodrigo, the pop-rock auteur was working with Roan on her tracks, earning his first official credit with her for her queer-coded ode to stripping, “Pink Pony Club.”

Unencumbered by label expectations, the singer-songwriter finally began bringing her full creative vision to fruition in 2022. The first step, as she tells it, was nailing her presentation: Gone was an attempt at presenting a clean-cut facade, now replaced by a more effortless deconstruction of style. “Once I let go of trying to be this very well-managed, put-together pop girl, it felt like everything just fell into place,” Roan explains. “I leaned into the fact that my looks were tacky, and very obviously using fake diamonds and Gucci knockoffs. I leaned into my queerness for the first time. When I did that, the songs got easier to write, the shows got easier to design, and my aesthetic was finally there.”

While putting together a rapid-fire rollout schedule of singles throughout the year (including “Naked In Manhattan,” “My Kink Is Karma” and “Femininomenon”), Roan quickly began accruing a fiercely loyal following on TikTok. According to Roan, while she was promoting the release of “Naked in Manhattan” in January 2022, she gained over 30,000 followers in one month, with fans anxiously wondering when the song would come out.

Roan doesn’t see herself as a “TikTok artist” — not necessarily due to fears of pigeonholing, but rather out of a healthy dose of skepticism. “I go so back and forth with TikTok,” she says. “I gained a lot of speed at the beginning of the year with TikTok because I wasn’t busy; I had time to post twice a day, go live once a day, repeat. It doesn’t work when you’re busy.”

The singer knows that because she has, in fact, been busy — along with unveiling her new set of singles, Roan filled the latter half of her year with plenty of touring. After opening for Olivia Rodrigo in May at her San Francisco Sour Tour stop, Roan caught the attention of fellow queer singer-songwriter Fletcher, who offered Roan the opening spot on the second half of her Girl of My Dreams Tour. Embarking on 10 dates with Fletcher, Roan honed her live show in real time while her song “Casual” began to pick up steam online.

“I don’t even know what I discovered, besides the fact that this is incredibly hard,” Roan laughs, looking back on her time opening for Fletcher. “If I’ve learned anything, it’s that the live show is where the heartbeat of the project is. Luckily, it’s my favorite part of what I do — I like touring, but a lot of people hate it because it’s horrible and hard.”

The singer likes touring enough that she’s embarking on her own headlining tour in 2023. Spanning 20 dates through February and March, Roan will be traveling coast to coast with an ambitious performance goal — every show, she says, will be themed. “It’s already really hard to do that on an independent budget — but also coming up with that many different themes is insanely hard,” she says. “But, if the live show rocks, then everything else will trickle down.”

It’s also important to her to create a show worthy of the very queer fanbase she’s garnered — that means making tickets affordable (“College kids don’t have money!” she giggles), keeping her concert spaces safe, and donating $1 of every ticket sold to For the Gworls, a Black, trans-led organization dedicated to helping Black trans people pay for their rent and gender-affirming care. “If I can create a space where people can afford to come into a mostly queer space, and dress up and feel good and meet other queer people in a town where maybe there’s not a lot of other places to meet queer people — a.k.a. my hometown — then that is great,” she says. “That’s doing the world good.”

Her plan is working so far — streams for “Casual” are continuing to rise, approaching the 2 million mark before its second month out on DSPs. Meanwhile, the majority of dates for her headline tour have already sold out, with only a small number of tickets remaining at a few venues. “That’s actually crazy,” she says of her sold-out dates. “My numbers are not that big, comparatively, to other artists. So when things started selling out, it was like, ‘Oh, okay, this is pretty real. I did not know that I could sell out in a day.'”

Despite her building success, Roan is still trying to keep one foot firmly in reality — while being independent has its perks, she says, it’s also not sustainable for the kind of artist she wants to become. “I’m not perfectly fine with being indie, if I’m being honest,” she says. “I need money to hire more help, and I just can’t keep doing everything DIY. I cannot keep asking favors from my friends, it’s just not fair to everyone.”

But now, unlike when she was a 16-year-old signing her first record deal, Roan knows who she is and what she wants (opening for Miley Cyrus, for example, is on her to-do list). “I will not sign a deal unless it is the right deal for me, and it must be mutually beneficial,” she says. “I know that I can do it without a label, which gives me such empowerment to walk away there.”

She pauses, and smiles. “That’s the key, I think; this year has been empowering for me.”