Confessions of a ‘Midwest Princess’: How Chappell Roan’s Debut Album Arose From the ‘Deep Pits of Hell’ to Become a ‘Dream Come True’

When Chappell Roan calls from Los Angeles, the singer-songwriter is picking up matcha on her way back from a morning pilates class.

“I like, kind of hate myself because of that sentence,” Roan tells Variety. “I’m literally in Silverlake — that’s even worse. If I was in Beverly Hills it would be so typical, but ugh, I’m that bitch on the east side.”

The 25-year-old has certainly come a long way from her home of Willard, Mo., a small Midwestern town with a population of only 6,000. Though Roan has clearly adapted to the L.A. lifestyle of athleisure and overpriced drinks, she’ll always carry a piece of the Midwest with her — hence the title of her debut album, “The Rise and Fall of a Midwest Princess,” out this weekend.

“I knew I needed to put the Midwest in there just because it’s so important to my project,” Roan says. “It influences the music, my fashion, my lyrics, the energy around it. It’s important for me to capture the Midwestern aspect. I don’t want to lose that part of me. I thought I really did when I was younger, but now I don’t anymore.”

Born Kayleigh Amstutz, Roan had what she calls a “really depressed” childhood. “I was diagnosed bipolar when I was 22, but as a child I think my parents just thought I was being a brat, so I had such a difficult time,” she says. Growing up in a Christian household, Roan describes herself as a “goody two-shoes” who “wanted everyone to like me.”

“I just wanted to feel like a good person, but I had this part of me that wanted to escape so bad. I just wanted to scream,” she adds. “I snuck out a lot, but I still went to church three times a week, you know what I mean? So it was just this dichotomy of trying to be a good girl, but also wanting to freaking light things on fire.”

Music provided some solace. Listening to the unique mix of campy, sin-soaked bangers and yearning ballads on “Midwest Princess,” one might think Roan had grown up listening to early-aughts pop princesses and songwriters like Joni Mitchell and Carole King. Instead, Roan says she “got really into hip-hop.”

“I downloaded Pandora and I would sit in my bathroom and just listen to Drake,” she says. “It was just a brand new world that I had not been exposed to ever. Hip-hop made me feel really cool, and was a place where I could put all these angsty feelings. It still makes me feel that way. The song that sparked me writing music was ‘Stay’ by Rihanna. I was like, ‘I want to make songs like this.’ And then I didn’t start making music that I liked until I was 21 or 22.”

Roan’s career had a fairy-tale beginning: After posting videos of herself singing covers on YouTube, she was signed to Atlantic Records at just 17 years old and moved to Hollywood to pursue her dream. She released her first EP, the folk-leaning “School Nights,” in 2017 and began touring as the opening act for artists like Vance Joy and Declan McKenna. But on the inside, Roan was lost.

“It happened so fast and I just wasn’t ready,” she says. “It’s so cliché, but one weekend I was playing coffee shops and the next weekend I was signed to Atlantic Records. It was very, very unhinged and really scary. I just genuinely didn’t know what I was doing, and I didn’t feel like I had a lot of help.”

Roan says she “hated all that music” from her first EP, and set out to discover who she really was as an artist. Come 2020, and she had started working with Dan Nigro — the songwriter and producer who was about to make it big with his work on Olivia Rodrigo’s breakout album “Sour.” In April of that year, they released their first collaboration “Pink Pony Club,” a euphoric, synth-heavy track inspired by Roan’s own experience going out in West Hollywood and finally living life as a queer woman, but she was nervous about how it would be received.

“I was embarrassed by it because I was like, ‘This is so cheesy!’ And at that point, I was confusing cheesy and campy,” she says. “I literally delivered it to the label and they were like, ‘No.’ They said no for a year, and I believed them. I felt so defeated.”

Later that year, Roan was dropped by the label. Add the COVID-19 pandemic and a breakup with her boyfriend of four years to the mix, and she ended up moving back in with her parents in Missouri and working at a drive-through coffee kiosk. (“It’s the classic Midwestern thing where it’s like, ‘We can make any candy bar you want into a frappé!’ It was not my favorite,” she recalls.) Though it didn’t feel like it at the time, slowly but surely, Roan was reinventing herself — while also unexpectedly gaining a newfound appreciation for her Midwestern upbringing.

“Thank God I came from the Midwest because I understand the people,” Roan says. “I have family who have complete opposite views of my views and my 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.”

Eventually, Roan saved up enough money to move back to L.A., where she worked a series of odd jobs — nanny, production assistant on an HBO show, cashier at an emo-themed donut shop — before she scored a publishing deal with Sony and was able to focus on making new music with Nigro. Her next single, “Naked in Manhattan,” was released completely independently with a DIY music video shot by her friend and visual artist Ryan Clemens.

“We had no plan and ran around New York shooting me in a bunch of different outfits that I thrifted. It was just so fun and so freeing, and it was the first time that I was like, ‘Oh, I think this is what it should feel like,’” Roan says. “I learned how to do drag makeup and how to bedazzle and sew a little bit. There were so many things I had to learn out of necessity, and that’s what built this project.”

Nearly a decade in the making, “The Rise and Fall of a Midwest Princess” is, according to Roan, the “absolute opposite” of her first EP. “I love this music, and that’s a big difference between my EP and now,” Roan says. “I rose from the ashes of losing all my money and moving back in with my parents and working the drive-through — this beautiful project came to life from the deep pits of hell.”

Produced entirely by Nigro (and released through his Island Records imprint, Amusement), the project incorporates the slew of singles Roan has put out over the last year, including “My Kink Is Karma,” “Femininomenon,” “Casual,” “Kaleidoscope,” “Red Wine Supernova” and “Hot to Go!,” as well as a handful of brand-new tracks. It’s a rollercoaster of genre-shifting sounds and raw emotion — ranging from the sexed-up and slick “After Midnight” to the indie-pop trimmings of “Guilty Pleasure” — but most of all, it’s pure fun and solidifies Roan as one of the most inventive pop artists of the current moment.

“It’s a dream come true,” Roan says of the album. “Like, I always dreamed of being able to feel this feeling, and I just happen to be able to sing and it came out in music. I think it would have come out of me one way or another, in some art form, but thank God it’s music because it’s so fun.”

Roan has worked hard to build a live show to match the theatrical quality of her music, complete with different dress-up themes for every date. Her latest stint kicks off on Sept. 25 and is set to fully sell out — and next year, she’ll join Rodrigo on the road for her highly anticipated “Guts” tour. Roan is also continuing her tradition of having local drag queens as the opening act for each show, with a percentage of every ticket benefitting For the Gworls, a Black trans-led charity.

“I love the queer community. When queer people are together, it’s the happiest, most vibrant feeling,” Roan says. “The shows are a way for me to give a safe space to queer people and to have fun and dress up. It feels like magic on stage. I’m literally getting teary-eyed because it’s everything I ever wanted.”