Chappell Roan and Bowen Yang on Queers, Fears, and Surviving Superstardom

It’s not easy being Chappell Roan. America’s newest pop star may have achieved peak fame, but the singer-songwriter still identifies as a queer kid from Missouri, struggling to make sense of her identity in a world that loves to scrutinize women. Since dropping her slow-burn hit The Rise and Fall of a Midwest Princess in 2023, the 26-year-old drag queen turned modern-day Kate Bush has spent the summer stealing festivals with her undeniable anthems while grappling with her new found fame, sometimes onstage. To help her make sense of it all, Chappell connected with big fan Bowen Yang, who had some advice for navigating queer superstardom.

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THURSDAY 1:30 PM JUNE 13, 2024 COLUMBIA, SC

BOWEN YANG: Chappell is doing the chic thing of blurring her Zoom background. Love it. But it looked like a beautiful animal just went past you?

CHAPPELL ROAN: That was my assistant Kyle.

YANG: Kyle? Well, he’s—they’re beautiful.

ROAN: They? [Laughs]

YANG: I cannot assume gender here.

ROAN: I know.

YANG: Where are you in the world right now?

ROAN: I just did Raleigh. I’m in Columbia, South Carolina. I’ve never been here. It’s great.

YANG: It’s great? [Laughs]

ROAN: I mean, it’s amazing. We’re doing every market we can, all the teeny ones, it’s crazy.

YANG: Okay. I don’t want to dig into what I think is a really beautiful moment that you had last night at your Raleigh show, but I hope you feel rewarded for being honest about what the last few months have been like for you.

ROAN: I’ve just gotten to the point where I have to stop lying to myself that this is—

YANG: Easy?

ROAN: Yeah. I was at Brooklyn Pride this weekend, and I was in a wig the whole time, and I was also on shrooms. I was like, “I need to stop lying to myself.” So I ripped the wig off, and I was like, “This is me.” [Laughs] It sounds so dramatic.

YANG: I love it.

ROAN: I was just like, this is really weird and really hard. In the past, honestly, eight weeks, my entire life has changed. It’s been really emotional because I’m not just singing pop music, it’s automatically political because I’m gay.

YANG: And we’re lucky that we have this point of view by default, but then you end up getting sucked into a whirlpool of other shit. Somehow you’ve ended up at the trash island in the Pacific, when all you wanted to do was get on a boat and sail.

ROAN: [Laughs] Yeah.

YANG: And anytime someone is like, “Wow, it’s all happening so fast, like, how do you feel?” That’s only reinforcing the sense of overwhelm. So if you can tune that out—not me giving you advice right off the fucking bat like I’m an elder.

ROAN: I appreciate advice. I don’t know anyone who’s going through this, personally. The biggest thing has been getting recognized, and just feeling not myself. And touring, it’s all-consuming. I’ve never given a fuck about the charts or being on the radio, but it’s so crazy how industry people are taking me more seriously than before. I’m like, “I’ve been doing this the whole time, bitch.”

YANG: Bitch!

ROAN: Like, my career doesn’t mean anything more now that I have a charting album and song. If anything, I’m just like, “Fuck you guys for not seeing what actually matters.” A chart is so fleeting. Everyone leaves the charts. I’m just like, “This is giving valedictorian.”

YANG: [Laughs] Were your grades good in school?

ROAN: They were fine.

YANG: Mine sucked.

ROAN: But everyone graduates. The valedictorian doesn’t really matter, and that’s kind of what I feel like right now. I’m like, “Cool. Maybe I’m valedictorian, but it’s weird that we’re graduating, and everyone’s going to move, so—”

YANG: I’m going to do something so fucking cringe, but I have to tell you, your vinyl is in my living room, front and center, because it’s just so pretty. Like the fucking sleeve, are you kidding me?

ROAN: Thank you. Me and my best friend made it, she creates everything.

YANG: I still have glitter stars all over my living room, and I’m like, “Don’t vacuum over it.” But you helped me through a lot of shit when I was fucking depressed. And I will always associate “Casual,” which is a horny song that is not even necessarily for someone like me, who unfortunately loves dick—anyway. There were so many 4 a.m. car trips to set for Wicked where I was blasting you. I remember drinking a glass of wine with Ariana Grande after we wrapped and being like, “You should get on Chappell Roan. She’s fucking awesome. Her live shows are incredible.”

ROAN: I appreciate that. I’ve been like, “Oh, my god. People are legitimately excited about this album.” Like, “Dang, gay people do care.” [Laughs]

YANG: Gay people care. And as long as you have a queer fan base—yes, all humankind is a little bit toxic, a little bit unethical, immoral, whatever—but the queers are going to make sure you’re okay. That’s the guardrail.

ROAN: I agree. Queer people are forgiving, and the fact that I’m not trying to be a perfect person all the time—

YANG: Perfect is boring. Right now, in pop music, we want a rough edge. We want something to grip onto.

ROAN: Yeah. I never really expected it to grow this big. I feel like I peaked a couple of years ago. Back then, I was like, “I sold out Bowery Ballroom and that’s crazy.” It’s been amazing to do bigger shows, and open for Olivia [Rodrigo], but everything right now is truly icing on the cake. Me trying to navigate this, I feel very supported. Because I’ve never not been myself. I’m really glad the persona that I have, the drag version, is still very much me.

YANG: What’s probably such a weird mindfuck is, like, “Pink Pony Club” came out April 2020, like, the most ironic time for a song about a queer club to come out. It’s like, “Well, I can’t hear this while I’m out so it’s totally internal,” which is beautiful. It’s yours. You feel self-possessed in that work. But then, it’s this gradual thing where you release song after song, and people really respond to it. But in the last few weeks this floodgate has opened, and now people are coming to you, and consuming you in a way that you did not necessarily anticipate, which is all at once.

ROAN: Yeah. It exploded within a matter of four weeks. All of a sudden I had an album charting that came out in September.

YANG: Yeah, and so it feels arrhythmic. It’s not the timeline that makes sense to anybody.

ROAN: Totally.

YANG: I don’t know what the release plan with “The Subway” is, but I feel like if you want that to just be a song that you sing live for a while, and not have it released—

ROAN: That’s how I did the first album and it fucking worked.

YANG: Yeah.

ROAN: My career has worked because I’ve done it my way, and I’ve not compromised morals and time. I have not succumbed to the pressure. Like, “Bitch! I’m not doing a brand deal if it doesn’t feel right. I don’t care how much you’re paying me.” That’s why I can sleep at night.

YANG: Speaking of sleep, I know you have insomnia. Have you been sleeping okay on the tour?

ROAN: Kind of. I sleep for a long time on the bus, but I’ve been talking to this girl that I have a crush on, so I don’t sleep anymore.

YANG: Goddamn it. This is why crushes are great, but they suck a little bit.

ROAN: It’s my favorite part of life, having a crush on someone. It’s the best thing ever when you are at the beginning of a relationship and talking on FaceTime for eight hours a day.

YANG: In a way, that makes it worth it when the crush fades away; all you care about is that feeling. It doesn’t matter what comes next, necessarily.

ROAN: Yeah. I’m a relationship girl. I’ve never dated someone less than a year. So I always cherish the honeymoon phase.

YANG: Well, then I’m glad you have that.

ROAN: Right, I’m excited about my job, yes, but I’m actually excited about a girl, and that’s so fun. I had my best friend who made the album cover with me. She came on tour for five days, and that makes me feel normal, and those are the things I love. It’s just my fucking friends; that’s what makes all this amazing.

YANG: Yeah, keep them close. This is a hard left: Are you going to act soon? Maybe acting is the thing that takes you away from all the craziness, if it does hit a level that’s not tenable.

ROAN: I say this with peace, and love, and blessings. Actors are fucking crazy.

YANG: We’re crazy!

ROAN: I don’t feel that way about you.

YANG: You can, I’m crazy. [Laughs]

ROAN: I don’t know you, but I know that you’re not the vibe I’m talking about. Like, I get so freaked out by film people. I’ve been asked in the past couple of weeks, like, “You want the lead in XYZ?” and I’m like, “No.”

YANG: No.

ROAN: I appreciate it, but literally, no. I originally started doing music because I wanted to get my foot in the door for acting, and then I moved to Los Angeles, and I was like, “Fuck that.” The industry is legitimately so scary, and it is so out of my control. I can put out music whenever I want. I don’t have to wait for a casting director to be like, “It would be great if we cast you, and then we’ll decide your schedule for the next three months.”

YANG: Totally.

ROAN: I think it would have to be really specific and really silly. I would maybe do a cameo.

YANG: Okay, good to know. Filmmakers out there, you heard it here first. Make it silly. Make it a cameo.

ROAN: [Laughs] Yeah. I’ve been trained how to act, but it’s the most stressful thing in the world to me. I would rather get arrested.

YANG: [Laughs] You’d rather be in jail.

ROAN: Yeah, because I know how to operate myself in jail.

YANG: That’s the pull quote: “I’m in jail, but at least I’m not acting.” I mean, you’re right. It’s thankless. Sometimes you feel like it’s out of your control. With music, you can write a music video treatment for “Casual,” and be like, “I want it to be me and this mermaid girl fucking.”

ROAN: [Laughs]

YANG: You can write your own fantasy and be in it. Watching “Casual” makes me go, “Oh, she has the goods, if she wants to do it.”

ROAN: Yeah. It would really have to be the right thing and the right timing.

YANG: Yeah.

ROAN: The next year is booked out. It’s crazy.

YANG: Does the next year being booked out feel good, bad, or neutral?

ROAN: I’m just very lucky that I have the leverage to say no and yes. I mean, it’s awesome knowing that I have a job.

YANG: Yeah, you definitely have a job, but it’s the same job you’ve always had.

ROAN: It is. But also, I’ve never been guaranteed money before. That’s the difference. I’ve always been a writer, but I didn’t start making money to pay my rent until last year.

YANG: Right. This is me fucking kissing ass the whole way through, and I’m fine with it. So you played Brooklyn Steel two nights; you played a Tuesday and a Wednesday.

ROAN: Yes.

YANG: I didn’t buy tickets to the shows because I was like, “Fuck, I’m working at SNL.” But I was texting the SNL bookers months before being like, “There’s this girl, Chappell Roan. I think she’d be incredible for the show.” And then, the night came and I played hooky for the first time, because they were like, “Do you want to come with us?” The next night, my friends were like, “We’re going,” and I was like, “Well, I’m going again.” I saw you two nights in a row and I have no regrets. I think you have your heels in everybody, and it’s going to be this reciprocal thing where everyone’s just going to make sure you’re okay. There’s already video essays on YouTube of people being like, “Everyone stop being weird about Chappell. Just let her cook.”

ROAN: Yeah. [Laughs] I appreciate you.

YANG: You’re at the stage now that maybe is starting to sunset a bit, where everyone’s like, “Oh, my god. I haven’t heard of this person. Who is she?” Now, that’s going to reach a sort of critical mass, where then it becomes about the next thing.

ROAN: It’s great because now, it’s not just about releasing these singles. Now it’s like, “What the fuck is she going to wear to XYZ?” and, “What is she going to say?” So I’ve set that up great because it’s new information in the media once a week, so people are distracted from being like, “When are you going to release new music?” I feel protected, in a way.

YANG: Good. It can’t seem too dangerous, you know what I mean?

ROAN: Yeah.

YANG: And it won’t be. Okay, is that our time? Anything you want to be immortalized in Interview magazine? [Laughs] I’m putting so much emphasis and weight on this.

ROAN: I hope I look back at this time and still stand behind all the nos that I’ve said, because I say no to pretty much everything right now. I don’t want to fucking go back into the mental hospital because I don’t know how to handle my emotions. I hope I don’t look back and I’m like, “Damn, if I just would’ve sucked it up and pushed a little harder.” I don’t think I will, but I’m always scared of that.

YANG: Yeah?

ROAN: I’m just trying my best to honor my feelings, and I hope that my future self is still on that train.

YANG: I have almost never regretted a no. Not that you and I are the same person, or remotely doing the same thing, but have you ever felt like, ahh damn, I should have followed that person in the crush fantasy?

ROAN: I said no for a long time to a crush. And then I said yes, and I’m really glad that I did. But my biggest regret in life is that I gave up a full-ride scholarship to an arts high school called Interlochen.

YANG: I know Interlochen!

ROAN: They were like, “We want you, bitch,” and I was like, “I love my hick boyfriend, who’s a dairy farmer, going nowhere.” So I said no. I look back, and I’m like, “Damn, all that for a Marine?”

YANG: [Laughs] No regrets.

ROAN: It just would’ve been sick to save myself from a lot of queer violence. But at the same time, I would not be the Midwest princess I am today if I had been around art kids. I look at my life and I’m like, “Everything was exactly as it should have been.”

YANG: Aw.

ROAN: Gov Ball [Where Roan spoke up for trans rights] was really hard. It was hard to be like, “I’m going to say something that a lot of my family is going to be like, ‘Wow, you crossed the line.’” It’s emotional because I believe what I said, and what’s sad is that me believing in who I am, and what I stand for, rubs against a lot of my home.

YANG: That’s tough.

ROAN: But it’s like with queerness—I always cry during [RuPaul’s] Drag Race. There’s always some bitch that has a Roxxxy Andrews story that everyone makes fun of, which is fucking crazy. [Laughs]

YANG: It’s fucked up. If you joke about Roxxxy Andrews getting left at the bus stop your heart is black.

ROAN: But every season there’s a bitch who’s like, “I left everything I knew because my heart found a chosen family who loved me and stood behind me.” I feel like that is such a common thing for the queer community, like, “It’s okay if my blood family doesn’t fuck with me because I have the bitches at Pieces who will welcome me every fucking time. And not only do they welcome me, I feel like I’m cherished, and enthusiastically accepted.”

YANG: And it ends up being about control if family members, whether queer or blood, are trying to steer you in a certain direction. I’m like, “We’re related, and you’ve known me my whole life, but you have never been right about me being out. You’ve never been right about me pursuing comedy.” And so, love and respect is a beautiful boundary to draw.

ROAN: Do you feel like you’ve proven everyone wrong, or do you feel like people are still like, “Nah.”

YANG: They’re great now. It’s just my parents and my sister in the U.S., and then everyone else is overseas. I still have not had a conversation with them about me being out and gay, and I feel like they have complicated opinions about that. But all in due time.

ROAN: Because sometimes people are like, “Oh, you’re gay and you’re going nowhere.” But if you’re gay and successful, maybe that is better than being gay.

YANG: I think if one thing was misaligned in my “journey” to this, like if I wasn’t doing okay, then me being queer would’ve been the evidence that I am not a fully realized or lovable person. That feels conditional, but we can never know, and maybe we don’t have to know. These are just things that we’ll work through with our respective families. But until then, you have the chosen ones. I feel like you weave that mythology of moving to a city, meeting queer people, into your music better than anybody right now. Watching you and Elton [John] talk to each other is really special because I feel like you guys are from the same sort of lineage. I’m glad that you think that everything is happening the way it should. The only way is through.

ROAN: Right.

YANG: So I fucking love you. I know we don’t know each other that well, but I’m following you for the rest of time. You’re incredible. Enjoy it.

ROAN: Thank you. A lot of people only take me seriously because people like you validate that I’m important. So I’m very grateful that you’ve enthusiastically supported me, in a fun way. Like, you’ve talked about my mythology as you say—my story. That is something that I don’t get a lot of.

YANG: Well, it comes very easily.

ROAN: Thank you.

YANG: Love you, Chappell.

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Hair: John Novotny using Oribe at Opus Beauty.

Makeup: Rommy Najor using MAC Cosmetics at Forward Artists.

Nails: Juan Alvear using Essie at Opus Beauty.

Set Design: Cooper Vasquez at Frank Reps.

Lighting Technician: Amina Gingold.

Photography Assistants: Lourdes Salazar and Maxwell Menzies.

Fashion Assistant: Emily Drake.

Hair Assistant: Destiny Molina.

Set Design Assistant: Brett Lindell.

Production Assistant: Jordan Santisteban.

Post-production: Melissa Franco.

Location: Gary’s Loft.