“Dude, I have four weeks until shit hits the fan,” Chappell Roan, the 25-year-old singer-songwriter, tells me, a month out from her full-length album debut, The Rise and Fall of a Midwest Princess. It’s aptly named: At 17, Roan (born Kayleigh Rose Amstutz) signed with Atlantic Records after being discovered on YouTube. She moved to Los Angeles where she lived until the record label dropped her when her 2020 single, “Pink Pony Club,” didn’t hit the numbers the label had hoped for.

Roan returned to the midwest, where she continued to write songs—just this time between her various gigs in rural Missouri, sometimes between serving customers at a drive-through coffee shop. A bipolar disorder diagnosis around this time provided Roan not only with an explanation for being what she calls a “depressed kid,” but also with a clearer road map for treatment. Toward the end of 2020, Roan determined that she couldn’t write music while “depressed on a farm.” Label-less, she moved back to LA and released songs as an indie artist. This time, Roan’s writing revealed a new tone: bops punctured with synths overlaid with lyrics that put Roan’s queerness at their center. Her glitter-drenched audiences assembled as longtime groupies at sold-out venues at her shows. Amusement/Island Records signed Roan this year.

Vanity Fair spoke with Roan as she prepared to hit the road in support of her album, out September 22.

This interview has been edited and condensed for clarity.

Vanity Fair: When you started putting your videos on YouTube, did you just want to share them? Or were you like, “I kind of would love to get ‘discovered’”?

Chappell Roan: I was just sharing it. I didn't know that I was gonna get discovered months after that. It was very dramatic.

Your deal with Atlantic Records didn't last as long as maybe that younger version of you had hoped, but you missed all of your senior year of high school once you were signed. Is there a part of you that mourns not having that last year?

I don't miss high school. I was such a depressed kid, so I don't miss that. But I miss my youth. I mourn being a kid because my career took that away from me pretty immediately when I signed. But I also didn't know how to protect myself. I didn't know how to protect my youth and my mental health. And I wasn't diagnosed yet with bipolar. I feel like I did miss out on having friends. I didn't have a lot of friends and I feel like I would've made more. That's why I wish I would've gone to college, just because I would have so many friends. But now I have a ton and it's great.

You were thrown into a professional world where everyone is older than you are.

I didn't have anyone who wasn't like six or seven years older than I was. It was so crazy because the youngest person I knew at the time was Emily Warren, who's now a massive songwriter, but she was 23 and I felt so attached to her. And even me being 17, that's still really little. You can't do anything. You can't do anything in LA or anywhere if you're under 21 'cause everyone just goes out and I was so sad. I was just so fucking young and it just sucked. But I did learn so much.

When you moved back home after the deal fell through, you ended up working on an album, really on a new sound, in a place where you didn’t feel like you belonged. What was that experience like? Was there any dissonance?

It felt like I needed to get out of Missouri to finish the rest of the songs that needed to be written. I couldn't write pop songs when I was depressed on a farm. I just needed to get out of there. I was working the drive-through and I would just think of little song melodies and write on my Notes app. And that's kind of how I kept the flame going. It didn't really explode until I moved back to LA and got a job. [laughs]

I'd love to know how both versions of you informed one another. There's stuff that you’ve sung about that you hadn't yet experienced and stuff that you're experiencing that you're not necessarily going to share onstage.

I think Chappell’s a drag-queen version of me because it's very larger-than-life. Kind of tacky, not afraid to say really lewd things. The songs are kind of the fairytale version of what happened in real life. A lot of the songs are just enhanced versions of what happened or maybe they never happened at all. With “Pink Pony Club,” I was inspired by a gay club, but obviously I'm not from Tennessee and I've never danced on stage at a club. Same with “Naked in Manhattan” and “Red Wine Supernova.” I hadn't even kissed a girl or dated a girl when I wrote those songs. That version of me is really fun to play, but it's very exhausting. Being a queen is just like–you’re in makeup and hair and you exude all your energy and you're very dramatic.

I am very introverted. I love being alone. I love playing video games by myself. My favorite thing to do is get really high and play Fortnite or Mario. Even doing Chappell’s makeup and drag makeup takes hours. The colors. The first six months of this year I didn't wear color [offstage] because I couldn't handle it. I felt like I needed to go the complete opposite so I could calm down. I only had gray, white, or black that I wore every day.

Same with my room. My room has calming colors and I have a storage unit where I keep all my boas and everything so I don't have to look at it 'cause it's so much. I found it to be pretty exhausting just interacting with so many people a night. Not anything they did wrong, but my soul was just so overwhelmed. Shows really take it out of you. It's a really emotional rollercoaster being on tour, so it's hard to play the character all the time.

How has sharing your queerness through music informed how you feel about yourself?

I had to catch up to the music. I had to catch up to kissing a girl or dating girl just to actually feel what it felt like. And I feel that the project has really allowed me to explore parts of myself that I wouldn't have if I hadn't chosen this specific path. I could be really brash and really loud and really dressed however I wanted to and almost made it on purpose a drag version of myself so I can be whatever I want.

It allows me to feel really safe exploring those aspects of myself. I’d never be able to do that if I took myself super seriously with pop. I think that the project has allowed me to be a part of the queer community in a deeper way because I'm not observing from the outside anymore. I feel like I'm in it. I am the queer community–it's allowed me to just feel queer, feel like a queer person and feel freedom in that. It's allowed me to feel safe on stage with the audience because I know a lot of people in the audience are queer and they just want to be there and have a good time.

I think culturally there can be a lot of shame of like, “well, if you haven't done something physically, romantically”—whatever it might be—“then you're not X, Y, Z.”

That's a constant. You just hear that about bi people all the time.

Obviously I'm queer, I'm dating a woman, but I think people just wanna party. I mean Britney [Spears]’s straight and she's a gay icon, you know? Like, there's so many straight people that are gay icons. I think it's more so about the art.

You met a lot of your creative team attending summer camp in Washington. What was attending camp like for you as a young person?

It built my music career because whenever I was in the music camps, I learned how to write songs. I felt it was the first time I'd ever been around creative kids. Like, truly people who were passionate about writing poems and being emotional. I just didn't have that growing up. I had friends in theater, but the writing was different. I had so many people at camp that I felt like I belonged. There are people out there that think and feel like me.

I went to church camp too and that was not it.

How old were you?

Probably like nine through 13.

Was that musical too?

It was like, go to camp, learn bible verses, have a fun game? Worship, go swimming, eat dinner, go worship again. Go to sleep and pray.

What's your relationship now with religion, if you have one?

I feel like it's evolving. I don't identify with the Christian Church anymore right now, but I'm really glad that I was part of that community because I understand them. I understand that perspective. I know where they're coming from. I have a different understanding when it comes to really confusing things that most people are like, “what the fuck?”

I saw a clip of you teaching your grandparents the “Hot to Go!” dance. What was that like?

It was so cute. They're so into the [Chappell Roan] world from a very surface level perspective, 'cause they won't go deeper because I think it's a lot. I mean I know it's a lot. My grandma literally said it's a little too much, which I understand. The lyrics are really a lot to listen to sometimes if you know me. But they were so down to learn it. And we interviewed them for the mini doc that we have coming out for episode two. They're just really proud of me and they always have been.

That's so special. The song and dance remind me a little of Miley Cyrus’s “Hoedown Throwdown.”

I wanted a cheer song. So literally what I did was google classic cheerleading cheers. And I just picked Hot to Go. There is a Hot to Go dance, but it's not the one that I made up. I wanted to be a cheerleader so bad because I always thought they were just so cool and so hot and I don't know, they were just so sassy at my school. I never had the confidence to try out because I just thought I wouldn't, I didn't belong. And so it's another dream-come-true vibes. It follows the same path as how my other songs are like dreams come true.

I think there's value in admitting a sort of sadness, or a feeling of missing out, in being transparent about that. I imagine that's what a lot of your fans feel. You're giving your fans this permission to honor their younger selves and be proud of who they are.

I accepted this branding–I hate to call it branding–by doing inner child work with my therapist. That's how I got to this conclusion that I needed to be a tacky pop star [laughs]. I had to let go of the adult in me that thought, ‘oh, I need to be so sophisticated and serious and so good at everything or else I'm not good enough.’ And it's like when you're a kid, when you're playing dress up you’re never thinking about anything. You're just thinking like, oh my god, they're so pretty. That's how I view my project. Is this what would've made little me happy? And so I'm really attracted to sparkly things and cheetah print and I was really into Britney Spears and Barbie and just hyper girly. I wanted everything to be pink, purple sparkle. And then once I got into fifth grade, it was like basketball shorts. I hate being tomboy vibes. But I just go back to that version of myself 'cause it is when I felt the most happy.

I was free. And I just loved it. And the dress up part, pretend part, the art, making and sewing little things, taking photos. That was my favorite part of my childhood. And so that's kind of what I'm recreating with this project. So it's from inner child work. And that was really difficult to get through because I had a really difficult childhood mentally because of my disorder.

You've had to learn to live with it and having a diagnosis can be really helpful in terms of, “oh, like this explains things.”

It explains things and gets me on meds. Bipolar disorder is one of the hardest to treat because you just don't know what's gonna make you feel better. I mean, it took me two years to find the right medications and holy cow, it was so hard because I just felt, I was like, “is it the bipolarity? Is it the meds not working? Is it my period?” There were so many things that I was so confused. And finally I found a place that I feel good about my meds. I'm in therapy. I really try to like, take care of myself. But, oh my god, it's so hard with this job because there's no checking out. There's no like clocking in and out. I worked at a doughnut shop for a long time and I loved it because I would just leave work and I would just go watch TV and it was great. But I feel like this is just really hard to take a step away from, especially on tour.

You're working 24/7 for months.

You live with your coworkers and you're like this close to them all the time. And you're in a bunk bed with them.

Camp!

Camp, but not in a fun way. [laugh]

How are you feeling about the tour?

Not to be a bitch, but I'm not surprised. I'm not surprised that it's still going so well. The shows are really fucking fun and awesome and the music is really good.

I don't feel like super surprised by this stuff. The thing, the biggest news of the year that fucking was hit me like a wave was the fact that Urban Outfitters is selling my vinyl. Like, 'cause I was like, oh fuck. That's a big deal for 16-year-old me. Like that's crazy. But everything else I'm just like, yeah.

It’s just very validating to be like, oh, my gut was right. My gut was actually right. I am so excited. I've never done a bus tour. I've never been able to afford it, but I can and that's a game changer. I just played London in June, but we're going back, and we might go to Australia. If it wasn't so dangerous, I would literally wrap the bus in something like, fucking crazy. But it's just so dangerous 'cause people know where you are. I am just so excited. I love touring. It's my favorite part of my job, which is very rare and most people fucking hate it and it's so bad. The shows are so fun for me and for the audiences and I love my band and I just have a great team and the merch is so cute. This project is really fun. The worst part is that it's sometimes, or most of the time, overwhelming and exhausting.

I saw that you are helping people who can't afford tickets to your tour.

We have a scholarship for a couple hundred people who just didn't have money right now. I get it. I worked part-time and at minimum wage it was fucking horrible. We engage with the local queer community and we give back. The shows all have three local drag queens. I really encourage tipping the queens and paying the queens. Especially with drag right now, it's just like such a fucking ridiculous mess for no reason. Another thing that we do is we give a percentage to a Black trans charity called For the Gworls, which is out of New York. It's really important to know that not only are you coming to a concert for yourself, but you are supporting the community.