The Midwestern Princess

When Chappell Roan joins me on a Zoom call, she’s fresh out of the shower, giving formidable pop star vibes even without the pink fringe and rhinestones. As she chats about needing to paint on her eyebrows, I see that I was correct in my assumption that the artist I’ve been obsessed with ever since a gay friend turned me on to 2020’s “Pink Pony Club” is as authentic as I thought.

“I just decorated my grinder, and I got pink rolling papers,” Roan shares. 

She uses cannabis to relax, preferring sativas over indicas, and has a taste for edibles. Currently, she needs to take the edge of settling into stardom.

“It helps me zen out,” Roan, born Kayleigh Rose Amstutz, says. “I play [The Legend of] Zelda like every fucking day.”

At the time of our interview, her first full-length album, The Rise and Fall of a Midwest Princess, was just over two weeks away from its release date of Sept. 22, 2023.

To gays and strippers of big cities and her home state of Missouri, Roan became a favorite thanks to “Pink Pony Club.” You must see the music video. Like, stop what you’re doing and open Roan’s YouTube channel right now. As queers and strippers already know, it’s a track that makes you happy to be alive while the world falls apart.

The song narrates a small-town girl’s journey to West Hollywood to pursue a career as a stripper, inspired by Roan’s visit to The Abbey, an iconic gay club in West Hollywood. She once said she wasn’t confident enough to follow the protagonist’s escape plan in real life (fans may disagree; Roan resonates boldness), so she wrote a song about it.

“Won’t make my mama proud, it’s gonna cause a scene, she sees her baby girl, I know she’s gonna scream…” builds Roan’s voice, hooking you from the intro and swelling into perhaps one of the most addictive pop tracks released in recent years.

While Roan is from Illinois, the song’s protagonist is leaving Tennessee, and the music video heavily features drag queens, currently under attack by conservative lawmakers in The Volunteer State. Roan has a knack for writing music that turns the spotlight on queer politics without an ounce of the cringe that so many pop stars exude when writing songs about LGBTQIA+ issues, perhaps because she means it.

Vulture described it as “the song of summer 2021,” and three years after its release, “Pink Pony Club” has over a million views on YouTube. However, despite its critical success and cult status, “Pink Pony Club” didn’t prove financially viable for Atlantic Records, leading to Roan’s departure from the label in 2020. Roan moved back home to take jobs as a nanny and at a doughnut shop and a drive-thru.

As a queer woman with a musical taste hungry for a track like “Pink Pony Club,” the disparity between her fame in certain circles while simultaneously getting dropped from her label was hard to wrap my head around, and a reminder that gay culture isn’t as mainstream as the conservatives out to ban drag queens want you to believe. I asked Roan about the incongruity. I can tell before she opens her mouth that she’s appreciative of the experience. This isn’t a woman ashamed to work a shift.

“You can have both,” Roan responds. “I worked at a drive-thru, and I happened to write a gay anthem that a lot of people connected to.”

Specifically, she worked at Scooter’s Coffee, which has a drive-thru kiosk that can whip your favorite candy bar into your coffee (in under a minute). Their menu consists of items sure to appeal to anyone reading with a case of the munchies.

“I don’t think there’s any shame that I felt whenever I had these jobs because it gave me a sense of camaraderie that I do not feel in the music industry. You clock in for a shift, you have all these inside jokes with your coworkers,” she reminisces. “I loved that. No one has any money. And then there was not a lot of pressure for me to use all this time to promote myself and make TikToks and shit because it was like, ‘Bitch I have a shift.’”

“Pink Pony Club” go-go dances further into the spotlight as one of the 14 tracks on The Rise and Fall of a Midwest Princess—Roan’s inaugural full-length album and her return to a major label, Island Records. The creation of the album involved the talents of Dan Nigro, previously best known as the lead singer and guitarist of the indie rock band As Tall as Lions, who also worked with Roan on “Pink Pony Club.” Now, thanks to his creative collaboration with Olivia Rodrigo (whom Chappell Roan is opening for on her U.S. GUTS tour), he has recently become a notable producer. This vibrant and audacious pop project is a tapestry of stories about finding love and self-discovery that’s relatable, witty, and downright hilarious, regardless of your orientation.

Roan can sing like a powerhouse. I can’t recall a pop star who’s managed to blend technical skill, witty songwriting, and an envelope-pushing aesthetic since Lady Gaga hit the scene in 2008 with The Fame. The gay community is already bragging that they were into Chappell Roan before anyone else. “The gays pick their icons,” Roan notes. “I mean, look what they did with the fucking Babadook. They want whatever is funny.”

Roan is very, very funny. Of course, part of what makes her so funny is that she’s relatable.

On “Red Wine Supernova,” Roan boasts to a potential new lover: “I heard you like magic; I got a wand and a rabbit,” in addition to proclaiming: “I don’t care that you’re a stoner.” I have to know. In addition to keeping your Hitachi charged, what are her tips for dating a stoner? She flips the question and answers for herself.

“You know what’s so crazy is that I’ve never dated a stoner. I haven’t dated many people. I hadn’t even kissed a girl at the time I wrote that song. I’ll say how to date me; I want someone I can giggle with,” Roan says, adding that making bracelets and playing video games are also the way to her heart.

There is a bright-eyed and bushy-tailed vibe to the aptly named Midwestern Princess album. Now that she has dived headfirst into the queer world, I ask her how it will impact her music. 

“I think that the ship of me being like, ‘What is this new thing, what are all my daydreams about being with a woman, it’s so magical the first time, etcetera,’ has sailed,” Roan says. “You only have the new experience one time. I captured that feeling in this album. But now, how I write is more confident, and being like, ‘Yeah. I am.’ Instead of ‘I want to be’ or ‘Am I?’”

Some of her fantasies are rooted in cultural references that all walks of life and orientations have likely masturbated to. On “Naked In Manhattan,” she croons: “Oh, I’ve never done it, let’s make it cinematic, like that one sex scene that’s in Mulholland Drive; I wanna know, baby, what is it like?”

But the angel princess (Roan even has a tramp stamp that reads “Princess”) shows off her devilish side on the album, which is delightfully dirty. In “Casual,” a most excellent sonic dissection of a situationship, she belts: “I’ve heard so many rumors that I’m just a girl that you bang on your couch,” later asking the same love interest: “Knee deep in the passenger seat and you’re eating me out, is it casual now?”

While in “Pink Pony Club,” Roan is a brunette wearing minimal makeup, now she’s a brazen redhead with makeup worthy of an art exhibit. But she’s still a pink pony girl. There’s one community she credits her style to: drag queens.

“Drag—100%. Drag inspires me,” Roan says. “Burlesque inspires me. I love camp. I want to look loud and fun. And a lot of it in the past has been just DIY.”

Noting how scrappy burlesque dancers and drag queens are (they can whip up a look made for TV in a bathroom stall with one sink and five other girls), Roan describes utilizing those crafting skills to create stage costumes. However, it didn’t stick.

“I did that all last tour. Then I was like, ‘Oh shit, I can’t do this again,’ because parts of my outfit were flying into the audience. It was just not sustainable because we’re playing like 40 shows this year. Now I can finally afford a stylist.”

True to her Midwestern princess style, these outfits contain pink cowgirl hats, fringe, pearls, rhinestones, and metallic looks fit for space. She’s currently on her own tour, The Midwest Princess Tour, which began last year and will run between February and April this year.

“I love touring. I love the grind of it all; most people hate it, and I get why, but I have a great time. I love it,” Roan says.

While album release parties typically happen in New York or Los Angeles, she had hers at home in Springfield, Illinois.

“The queer community is really struggling where I’m from to feel safe and accepted,” she says. “I was talking to a trans girl, and she was telling me how she’s just having trouble even getting hired because of transphobia.”

Roan is determined to give her community a break from the world’s harsh realities, if only for a brief respite.

“The best I can do is offer a safe space in their city for a couple of hours. And hire local drag queens, pay them, get them tipped by their local queer community,” she says.

A percentage of each ticket also goes to For The Gworls!, which curates parties to fundraise money to help Black transgender people pay for their rent, gender-affirming surgeries, additional medical costs, and travel assistance.

But FYI—anyone can come to shows to join the party. I ask Roan about her straight dude fans, which, yes, definitely exist. Any special message for the cishet guys before joining in on the queer-themed, costumed aerobic parties that are her concerts?

“You’ll be fine as long as you’re not homophobic and weird,” she says. “I want you there. I want cishet men at my shows. I want them there if they are down to party like in the way that we are. But no special message.”

However, get ready to dance. On “Super Graphic Ultra Modern Girl,” she shares sage advice: “You know what they say, never waste a Friday night on a first date. But there I was, in my heels with my hair straight, and so, I take him to this bar. This man wouldn’t dance… He doesn’t have what it takes to be with a girl like me.”

While she sounds like fabulous company to get stoned, make crafts, and play Zelda with, ultimately, she says being on stage is her favorite high.

“It feels the same to play a show. Amazing, and euphoric and bubbly,” Roan says.

But don’t get it twisted. Despite all the attention, Roan isn’t about to forget why it’s called The Midwest Princess Tour.

“I’m grateful for that time,” she says, of returning home after her first stint in Los Angeles. “It made me so happy that I understand what it’s like to clean a public restroom.”

This article was originally published in the January 2024 issue of High Times Magazine.