THE RISE OF CHAPPELL ROAN: BEHIND THE SCENES

On a bone-chilling late-August afternoon in San Francisco, Chappell Roan was in the middle of what’s become routine for her: headlining a festival on which she wasn’t the headliner.

There were still three acts to follow her on the main stage at Outside Lands, but the tens of thousands of pink-hatted fans packed into Golden Gate Park were clearly there to share in the joy of Roan’s unexpected rise from major-label washout to queer cult act to pop superstar. Roan, by now famous for her cosplay stage outfits (Statue of Liberty at Gov Ball, luchador at Lollapalooza), was dressed as a drum majorette, donning the same spangly onesie she wore in the video for “HOT TO GO!,” released, she announced from the stage, exactly one year prior.

Then, Roan (born Kayleigh Rose Amstutz) was getting set to drop The Rise and Fall of a Midwest Princess, her first long-player since the release of a moribund five-song EP on Atlantic Records in 2017. Preceded by a series of singles independently released on her collaborator Daniel Nigro’s Amusement Records, the randy and often hilarious Rise and Fall, issued in September 2023 by Amusement/Island, sold some 7k copies in its first week. “Which,” notes Island Co-CEO Justin Eshak, “is obviously not a lot.”

The album gained some traction with critics and in the LGBTQ+ community, but it wasn’t until a Februrary-April run of opening arena dates with fellow Nigro collaborator Olivia Rodrigo and a March NPR Tiny Desk Concert that word-of-mouth began to spread more widely. Still, it took the release of a new song, untethered to either the current or an upcoming album, for Roan to become a femininomenon: “Good Luck, Babe!,” a rueful kiss-off to a romantic partner in denial and an instant queer anthem.

Once “Good Luck, Babe!” took off on streaming services, the floodgates opened. Soon, Rise and Fall tracks “Pink Pony Club,” “HOT TO GO!” and “Red Wine Supernova” were crashing the Spotify Top 50, 80,000 people were performing the “YMCA”-like choreography for “GO!” at Lollapalooza and the album was ascending to its current, #2 spot on the chart. Next up: An MTV Video Music Awards performance and all-but-certain multiple Grammy nominations.

Here is the behind-the-scenes account, told by her key collaborators, team members and executives, of how Chappell Roan became the feel-good music story of 2024.

1. “Am I taking crazy pills here?”

Nigro: I met Kayleigh in October 2018. She had just switched over to be managed by Nick Bobetsky. My manager, Ian McEvily, had worked with Nick. Kayleigh was just starting to do some sessions. On the very first day that we met, we wrote “Love Me Anyway,” and I thought she was amazing. So we booked two more days, and we wrote “California.” And at that point, I was convinced she was my favorite songwriter that I had ever worked with, and “California” was one of the most important songs that I had ever written. I was so excited about those two songs that I wanted to play them for her label at the time, Atlantic.

So I invited them over. I printed out the lyrics to “California,” which is all a cappella for the first 20 seconds. I wanted them to sit in the room and listen to the song and look at the lyrics. But one of the A&R people didn't show up to the meeting. That was the first of many disappointments trying to get them to be involved in the project. Then they canceled another meeting. And then we made “Pink Pony Club,” and they were, like, It's cool, but we don't really like the concept of the song. I remember thinking, am I taking crazy pills here?

Roan and Nigro, Bobetsky and Roan's Princess cover

Bobetsky: ​​I met Kayleigh almost six years ago. She'd had management and they had parted ways. Atlantic had signed her as a teenager, and they sent her music to me, after her first EP. Her talent was very clear, but she was still very much figuring out who she was. She had been in a lot of writing rooms that were not necessarily the best fit for her, a lot of rooms that she didn't relate to.

Eshak: She’d had a pretty negative experience. It’s hard sometimes when artists get signed really young and they're still formulating things.

Bobetsky: Look, it's hard to develop an artist in any big building. Atlantic had known her for many years, and it was hard for them to trust her when she started to evolve. She’s talked about this, but she was sick of singing depressing songs. She was, like, I want to have fun. I want to feel important.

Justin Tranter, songwriter: I met Chappell through Kate LaBrel, who works on the label side of my business. She doesn't normally suggest sessions for me. But she's, like, “Hey, there's this girl named Chappell Roan. Listen to her song ‘Pink Pony Club.’ I know some people on her team, if you want to work with her. I just think it's right up your alley.” And so I listened to "Pink Pony Club," and I was, like, Oh yeah, this is possibly the best song ever written. It's like an American Songbook standard.

I did a couple sessions with her; this is about two and a half years ago. On one of those dates with her and Dan, we wrote "My Kink Is Karma."

Bobetsky: “Pink Pony Club” was the one where, when we all heard it, we looked at each other and we're, like, This is unbelievable.

Nigro: When we made “Pink Pony Club,” I was convinced Chappell was a superstar. I was actually sad after we wrote the song, because I loved it so much, and I remember thinking, This song needs to be played for thousands of people. This song needs to be embraced and sung along to. But how do we get there? Because we're not there.

Jennifer Knoepfle, Co-Head of U.S. A&R, UMPG: I did a joint venture with Dan for Chappell when I was at Sony Music Publishing. He and I had been discussing doing some kind of partnership, and he was, like, I'd really love to do one with Chappell.

Majid, Roan and Eshak feel the enchantment

2. “It was fucking bonkers”

Nigro: Chappell got dropped by Atlantic at some point in 2020. The first time we talked about it, I said, "This is going to be the most exciting time ever. Because now we have no restrictions. We don't have to listen to anybody. We can A&R the entire album ourselves; we can choose the singles; we can put them out whenever we want." And we started to formulate Rise and Fall.

Chappell’s an incredible singer. Her voice, her tone, is insane. She's a great lyricist. She writes amazing concepts. I’m really good with melodies and chords, and we really complement each other. She would come in with concepts of what she wanted to write about, and we would sit at the piano and hash out the melodic structure. We’re both really into pop music, and we’re on the same page about structuring melodies in a certain way. We found a perfect groove together. She and I A&R’ed the album. And we started releasing songs independently.

Knoepfle: I started to think about people who might be good for Chappell, who had the right disposition and sensitivities to what she had already been through. And I thought Justin Eshak should hear it. I felt he would get it.

Eshak: The first person who told me about Chappell was Jenn Knoepfle. She thought it would be something I would like. She sent it to me, and then I sent it to [A&R exec] Caroline Ellis, whose taste I really value. She was into it. And then we played it for [label Co-CEO] Imran [Majid], and he loved it.

She had already been dropping singles. “My Kink Is Karma” was already out. “Naked in Manhattan” was already out. “California” was already out. “Pink Pony Club” was already out. The album was pretty fully formed by the time we heard it. It was almost, like, Is she going to do a deal at all? Because she didn't have the greatest experience at a major label previously.

Nigro: We brought the record to Island and kind of said, "This is our album. These are the songs we want to release. This is how we want to do it. This is our publicist. This is our creative director. We have the whole package. We just need a partner."

Majid: At that point, Justin and I were the new kids on the block. There wasn’t any recent success we could point to. But I think we had the right temperament and understanding.

Eshak: Imran and I went to see her at the Bowery Ballroom in August 2022. And it was really kind of notable, because she was selling out the Bowery without a label. We went on a Saturday night and it was fucking bonkers. People were losing their minds. Imran and I were, like, If we can take what's happening right here at Bowery and bring that story to the world, this is going to work.

Majid: It was one of those moments. It felt like the walls were gonna rip open.

Nigro: Island understood the project the best. My pitch to Justin was, this is not a linear album. Like, you can't go into this record and think because “Pink Pony Club” was released years ago [in 2020], it's not a single. So when the time comes for these songs to become singles, we need your word that you will push all of these songs that have already been released.

Knoepfle: I saw her in spring 2022, at a small club in downtown L.A. called Resident. I went down there with my colleague Scout Easley, and that was the first time that I saw her play in this new iteration of what she was doing. [Editor’s note: Easley, Sony Music Publishing’s Senior Director of Creative A&R, co-signed Roan with Knoepfle. Roan remains signed to SMP.] It was really compelling. Then I saw her a couple months later at the Troubadour. And she had all these people in the audience who were dressed like her. And that was really shocking to see, for someone who was still a burgeoning artist.

Jackie Nalpant, agent, Wasserman: It’s like The Rocky Horror Picture Show: Everyone comes in their favorite Chappell costume.

Eshak: Chappell had a club run, and the tickets blew out right away. We would invite people to these sold-out shows, and then people would look on Spotify or Apple and they're, like, Where are the streams?

Majid: When Olivia Rodrigo announced her tour with Chappell opening, Chappell started trending on Twitter, which she had never done before.

Eshak: Olivia was vocal in her support for Chappell from the beginning. Even at the show that Imran and I went to at the Bowery, Olivia was there.

3. “The song took on a life of its own”

Nigro: Chappell, Justin Tranter and I wrote “Good Luck, Babe!” in late 2022, when we made the album. We just never finished it. Chappell and I couldn’t crack the code on the song. First, it was just a verse and a chorus. Like, a minute-long idea. That’s how a lot of our songs happen. We write a little piece of it, then we go back with fresh ears and go, it needs to be faster, or the key needs to change, whatever. And then we change the key, and then we change the key again. In the case of “Good Luck,” we tried to change the key too many times, and we got frustrated. We put it away, and then we opened it up a few months later, and we were, like, Oh wait, the original key was better. And then we sang it, and we're, like, Is it too fast? We probably opened it up four separate times trying to figure out what it was.

Tranter: When Chappell started talking about the subject matter she wanted to write about with “Good Luck, Babe!,” I was pretty emotional that I got to write about a personal experience of hers, but something that I went through many times. About someone who has feelings for you, but they aren't ready to accept that. Straight people have felt that feeling so many times—you know, your love interest has feelings for you, but for whatever reason, they can't handle them—but for us as queer people, it's a very specific thing that carries a different kind of weight.

Nigro: It wasn't until December 2023, a year later, Chappell came over for a session, and she was, like, “Can you open up ‘Good Luck’?” At the time it was called “Good Luck.” And we're, like, It needs to be a little slower. And then she sang a vocal performance. And we were both, like, Ooh, that vocal performance feels pretty good. Then I started adding in the synth strings that happen in the pre-chorus. We went away for the holidays, came back, and I kind of doctored up the strings with a bunch of MIDI strings and got it to a place where we both felt pretty good about it. In January, we said, This is the next song we're going to release. And then we wrote the bridge—well, she wrote most of the bridge; that’s her. I invited my friend Paul Cartwright over, who plays strings, and he went to town. He took my arrangement and made it 10 times better. And that was it. We finished the song in February.

Majid: When “Good Luck, Babe!” came out in April, I was flying to Dallas. The song came out at midnight, and I was up at, like, four in the morning. The streams weren't extraordinary, but they were so much higher than she normally did. I just remember sending a text that said: “Wow!” And the song just took on a life of its own.

Eshak: We always loved the song. Dan's production is incredible, and Kayleigh and Justin’s writing is so great. The bridge on that song! But we didn't have any sort of indicators pre-release that it was going to be this big hit.

Nigro: Did I think it was going to be a hit? I did not. I will admit that I did not know. I don't think anybody felt like this was the song that was going to change everything.

Majid: People who weren't in the know were, like, Okay guys, she's got to go back to the studio to record a follow-up. We're, like, No, no, no. We have an album already filled with “follow-ups.”

Eshak: A very common strategy nowadays is for artists to release deluxe editions. We’ve all seen this a million times. And so we had a conversation with management: Why don't we use “Good Luck” as an opportunity to put out a deluxe? But Kayleigh was, like, I’m down to put out music, but I just want to put out “Good Luck” as another single. I want to keep on rolling the same way that I’ve rolled. I give a ton of credit to her because a lot of people would be, like, Now I have to change the way that I've done things. And she was, like, No, I want to keep doing it the way that I’ve been doing it. So our strategy became, let's not overly “major label” this.

4. “Our first gay icon who is actually gay”

Tranter: I'm 99.9% sure that Chappell is our first superstar who came out before their superstardom. And did so while the world is trying to create barbaric legislation to take away queer people's rights. To have our first queer superstar, in this moment? It's crazy.

Bobetsky: Kayleigh was always really focused on creating safe spaces for queer kids at her concerts.

Eshak: Artists like Madonna and Lady Gaga, they’re very important in the queer community. But they’re not openly queer, right? I think that's why it's important to her and Dan that “Pink Pony Club” is having such a big moment right now. It’s an origin story about her self-discovery. It’s a classic hero's journey.

Tranter: To help launch our first openly queer superstar as they walk into fame, our first gay icon who is actually gay? As a queer person, to be a tiny, tiny part of it… I can't believe this is my life.

Eshak: “Good Luck, Babe!” is an anthem for the queer community. But it's one of those rare songs that crosses over and now it's just like an anthem for everybody. That’s one of the things that's so fascinating about Chappell: If you look at things on the surface, it doesn’t seem to be something that's designed for the masses. But it just works.

Tranter, Ellis, Nalpant, Mosiman, Knoepfle

5. “It just hasn’t stopped”

Kiely Mosiman, agent, Wasserman: Coachella was the kickoff.

Nalpant: Her set the first weekend was crowded. The second weekend, you couldn’t get near the tent.

Mosiman: After that, everything got bigger and bigger. Gov Ball was the next real moment. Then Bonnaroo, then Lollapalooza, then Outside Lands. It just hasn’t stopped.

Bobetsky: Lollapalooza was one where, like, everyone was celebrating it. Lollapalooza's social media was celebrating it. News outlets were celebrating it. Obviously, the fans were celebrating it.

Nalpant: She's an anomaly. Usually there’s backlash when this happens, but there’s none. Instead, at every festival, another headliner is singing her song.

Mosiman: I honestly don’t think I would compare her to anything or anyone. We used to try, and the next day, it’s bigger.

Eshak: There are a lot of great people who are dedicated to this project. Kayleigh, obviously, first and foremost. Her manager, Nick, and Ruby Anton from Nick's team. Dan and his manager, Ian. Caroline Ellis. Natasha Kilibarda, who's a product manager on our team, has been incredible. [Island SVP Commerce] Marshall Nolan, too.

Majid: It’s funny, two weeks can completely change the trajectory of a label. There’s two and a half years behind the scenes that go along with it. But it happened in two weeks.