Conan Gray and Olivia Rodrigo on Heartache, Meet-Cutes, and Growing Up in the Public Eye

Five years ago, a then 18-year-old Olivia Rodrigo texted Conan Gray to ask him out for a “COVID walk,” only to be ghosted. It took a dinner with Dan Nigro, who produced both of their debuts albums simultaneously, to set the record straight: Gray had mistaken Rodrigo for a different Olivia, the one who was his next-door neighbor back home in Georgetown, Texas. The rest is history: five years later, the two have danced on each other’s TikToks, performed together on tour, and posed side by side on the Met Gala red carpet. Last week, we reunited them once more, this time to talk about Gray’s fourth studio album, Wishbone, out today. What followed was a conversation between two singer-songwriters who have no qualms about wearing their hearts on their sleeves. “If you aren’t honest with yourself, then you’re not going to make honest music,” said Gray. “And people don’t like dishonest music.”—SIMON DWIHARTANA

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OLIVIA RODRIGO: This is going to be so fun. There’s so little that I actually don’t know about this album process, so I’m kind of a bad interviewer.

CONAN GRAY: I mean, there’s literally nobody on earth that I have asked more questions to about this album than you. We literally made this album together, literally down to picking singles, down to production elements, literally everything.

RODRIGO: Like me approving the cover art.

GRAY: Us listening to mixes being like, “I don’t know, that vocal sounds a little weird.”

RODRIGO: [Laughs] I know. I know.

GRAY: Wait, I have to take a brief moment. This is my cup right now. [Shows coffee mug]

RODRIGO: Oh, hell yeah. I got Conan that cup for… was it your birthday or something?

GRAY: Yeah. It says, “Not single, not taken, too busy playing Fortnite.”

RODRIGO: [Laughs] Okay, let’s get down to it. Actually, I think it would be nice to start with you talking about the name of the album and how that came to be, because I think that’s such an interesting story and it’s such an interesting word. The story behind it is so cool and I feel like not a lot of people know it and the airport of it all.

GRAY: Right. So I was on tour and I’d been thinking about naming my album Wishbone for probably six months, but I hadn’t really decided yet. I felt a little bit apprehensive, and I was just kind of getting cold feet about the album in general. I was kind of freaking out. I was like, “Okay, maybe it’s stupid. Maybe this is a dumb idea.” And I was finishing up the tour and that last week, that was when I was most doubting it. I was like, “I feel like the title is just not a good enough idea.” I thought of naming it Wishbone because the Wishbone ritual is something that I think is really interesting. It’s one of the only wishing rituals that requires two people. Every other wishing thing, like throwing a penny into a well or blowing a dandelion, is a solo experience. But with a Wishbone, it’s two people actively taking this moment to be like, “I might get my wish and you might get nothing, and let’s take a bet on each other and just agree to do this even though one of us is bound to lose.” Then on the very last day of my tour, I was literally going to the airport. It was 5:00 AM, I was on the way back home after finishing the very last show in Dallas, and I walked into the doors of the airport and, legitimately, a 30-foot tall wishbone was just standing right in front of me at the airport gate. I felt like it was the largest, most hilarious sign ever that I need to trust my gut. And I feel like a huge part of this whole album was just me trusting my gut. So that’s when I finalized the album title.

RODRIGO: That is so cool. That’s literally the universe just beating down on you.

GRAY: I know. We were literally losing our minds. I remember texting you immediately and being like, “What the hell is going on?”

RODRIGO: “What the fuck.” And you wrote a lot of these songs on tour too, which is kind of uncharacteristic. I feel like you wrote all the other ones at home or in the studio or whatever. What was the process like with traveling? And do you think traveling was more inspiring to you than it used to be? 

GRAY: I feel like for most songwriters, it’s kind of hard to write on tour because there’s just so much going on. I’ve never been able to write on tour. But then I think something kind of changed in me in the past two years where all of a sudden I was able to write songs on tour. I think I just got to a point where touring wasn’t so terrifying so I was able to relax and write songs on my days off. But I was also in such a strange head space on my last tour. I was really discovering myself and I felt like I needed to write the songs to figure my brain out, basically. I was in a very special place. 

RODRIGO: We talked about how you felt that Wishbone was a lot about just trusting your gut as an artist and as a person. Can you talk more about that and why this album feels different in that respect?

GRAY: I’ve definitely had immense amounts of doubt my whole life. Like, always. But with this album and this time in my life, I just realized there really is no option in life other than just being yourself. I think for a lot of your youth, you try on different hats and see who you can become to hopefully end up at a place that is very genuinely you. But for me, there have been times in my life where I’ve put on hats not out of experimentation, but more out of hiding. And with this album, I was just tired of it. I actually can’t give a fuck anymore. I’m just going to make something that I like and I think is cool. And if I’m not even being myself, I’m not sure people would even relate in any way whatsoever, so I just have to be honest and real. And it’s so interesting how when you’re not really quite being yourself, you don’t see it in the moment. You can’t really tell that something is wrong.

RODRIGO: You can only see it in hindsight.

GRAY: This whole album was me just saying, “If people don’t like this true version of me, then I literally do not care at all.” And even if I do care, I’m going to choose to ignore it because I need to make an album that is honest and real, that is a true reflection of me as a person. It was time to give up the jig.

RODRIGO: What would you say to Conan five years ago, post-making this album? What advice would you give him?

GRAY: Conan five years ago… whoa.

RODRIGO: What were you doing five years ago?

GRAY: Five years ago was around when I first met you, honestly.

RODRIGO: Yeah. Kid Krow was just coming out.

GRAY: That’s so weird to think about. We were such different versions of each other, but also kind of not. When I look back at pictures of us from when we were that age, I very much still see the exact same version of ourselves existing. I would say, “Nobody cares as much as you think they do, so just be yourself. Don’t be afraid to make mistakes. If you aren’t honest with yourself, then you’re not going to make honest music. And people don’t like dishonest music. Everyone makes mistakes and everybody has those days.” And now I’m quoting Hannah Montana.

RODRIGO: [Laughs] Oh, that’s good. That was actually another one of the questions that I was going to ask. Do you want to talk about that? The story of how we met?

GRAY: Oh my gosh.

RODRIGO: Our meet-cute.

GRAY: Well, actually, I slid in the DMs. We must not forget.

RODRIGO: I totally forgot about that, actually.

GRAY: I originally slid in the DM because I had heard “All I Want” on my TikTok, and this was probably a year before we ever even met, I think. I was like, “Oh my gosh, this song is so good.” And then I saw in the comments and people were like, “Oh, she wrote this herself.” I was so excited and just so impressed. So I messaged you, something along the lines of, “You’re amazing, and I think it’s so cool that you write your songs by yourself.” Is that what I said?

RODRIGO: Yeah, something like that.

GRAY: You were like, 16?

RODRIGO: Yeah.

GRAY: You started working with Dan [Nigro] and I was making my second album with him, and then COVID happened so we literally saw nobody even vaguely in our age range for an entire year. But you were leaving the studio one day. I think you were kind of midway through Sour? I was walking in and I remember seeing you and being like, “Oh my god, a person.”

RODRIGO: [Laughs] We were so isolated at the time.

GRAY: The only person we saw was Dan.

RODRIGO: Yeah.

GRAY: Literally.

RODRIGO: Yeah. And my parents, because I lived at home. I was so young.

GRAY: Should we talk about the text?

RODRIGO: Oh, yeah.

GRAY: You gave me your number, and I had a childhood neighbor growing up named Olivia. So I received a text from from an Olivia a week later and it’s like, “Hey, want to hang out?” And I was like, “What? Why is my childhood neighbor texting me to hang out in Texas? She knows that I moved. Does she think I’m back home or something?” I literally was so weirded out because this was my neighbor. Like, we weren’t super close friends or anything. So I just ignored it fully.

RODRIGO: And I was so sad. I was like, “Can we go on a COVID walk one of these days?” So pure. And I was like, “God, he fucking hates me. I don’t even warrant a response.”

GRAY: I shot you down. [Laughs]

RODRIGO: Rejected.

GRAY: I was so confused. But I don’t really exactly remember what happened next. I think we ended up having dinner at Dan’s house.

RODRIGO: And I think I brought it up. I was like, “Oh, I texted you.” And you were like, “Oh my God. I thought that was a different girl. Holy shit.” And so Conan changed my contact name to all caps, “OLIVIA FUCKING RODRIGO,” because that’s who this bitch is and and it’s still that in your phone.

GRAY: To this day. I did not make the mistake of thinking about my neighbor Olivia. But shout out to my neighbor, Olivia.

RODRIGO: Love you, girl.

GRAY: [Laughs] Love you, girl.

RODRIGO: Speaking of Texas, we should talk about the music videos, which I love. I think they’re so beautiful and so well-done.

GRAY: So the music videos were so meta and strange because, in so many ways, I think they’re a reflection of a piece of my childhood that I kind of got a version of, but not quite. In a weird way, it feels like kind of rewriting my history or something. But I think what was most important to me was that I made a love story that felt like a reflection of the arc of the album. The beginning of the album starts from a place of butterflies and wondering if someone likes you.

RODRIGO: And then it devolves.

GRAY: it devolves into different places. I just really needed to place these music videos back home in my home state, Texas, because visually I feel like I’ve returned home in a way. I mean, you’ve seen me through so many versions of life but, at the end of the day, Texas is always home. So yeah, I shot these music videos of these two childhood best friends essentially realizing that maybe they weren’t just friends and that something has kind of changed and we watched them break up and have this very Texas summer romance.

RODRIGO: It made me want to go to Texas so bad.

GRAY: I know, we still have never—

RODRIGO: No, we have to do it. Wait, did you always know that you were going to do the kiss? Was that one of the initial ideas, or did it kind of evolve into that?

GRAY: I knew I needed the kiss. I knew I had to approach Corey [Fogelmanis] because I knew I wanted a kiss and it had to be someone that I know I can kiss and not feel freaked out about. So yeah, he was the first and only person I felt like I could have asked to do the videos, and we had such a great time.

RODRIGO: Wait, is there one more video coming out with the album?

GRAY: One more.

RODRIGO: Are we allowed to know what song it’s for?

GRAY: Do we know, actually? I don’t really know.

RODRIGO: How did you come up with the names again? I feel like you’ve told me this, but—

GRAY: Actually, this is lore that I didn’t really explain. Basically, I knew I wanted a W name and a B name.

RODRIGO: Oh.

GRAY: For Wishbone.

RODRIGO: Smarty. Okay.

GRAY: But I actually came up with the names because of James Dean and Marlon Brando. The family name on James Dean’s mother’s side is Wilson. And I don’t know, something about them as these pieces of Hollywood history, what they kind of portrayed felt so American. And also, we shot the second two videos in a town called Marfa, which is very well known for being the filming location of a very, very famous movie from the time called Giant that has James Dean in it. I just knew they had to be these old Hollywood names, and Wilson and Brando just came to me while I was doing my research.

RODRIGO: I love those names. What inspired the sailor outfits? Why was that the aesthetic you were going for? I never knew this.

GRAY: Remember when I first started making this album and we kept calling it “Conan’s Big Adventure”? When we were all like, “Oh yeah, this is going to be my album where I fully grab life by the balls.” And when I was thinking about “Conan’s Big Adventure,” obviously quite a stupid title, but it did actually seem indicative of how I felt at the time. And I was like, “Okay, what do I associate with adventure?” And I was like, “I guess sailing.” I’m not a sailor in my own life, but it felt like I saw it immediately. The imagery of me being in the sailor outfit and kind of stealing this wishbone and taking it for myself. It felt like, Indiana Jones-esque or something.

RODRIGO: Oh, that’s so cool. I actually didn’t know that. What are you looking forward to most about this tour? Is there any song in particular that you’re like, “Ooh, I hope this one goes crazy live”?

GRAY: Well, “Romeo” has been really fun.

RODRIGO: That’s one of my favorites.

GRAY: Yeah, it’s a fun one to scream along to. And I’m least looking forward to not seeing you for two months.

RODRIGO: Oh my god.

GRAY: But it’ll be worth it. I’m also really looking forward to “My World.”

RODRIGO: “My World” is my favorite, I think. One of my favorites.

GRAY: You’re a “My World” truther.

RODRIGO: I am a “My World” truther. I’ll die on that hill. I also love “Class Clown.” What’s your favorite?

GRAY: I think “Class Clown” is my favorite. I just feel like that’s the one that really hits home in almost a too-much way.

RODRIGO: Yeah, where it’s a little scary to sing. Also, shout out to “Vodka Cranberry.” That was my drink.

GRAY: I really can’t even tell you if I’ve ever even had one. Wait, I have a question.

RODRIGO: Oh, for me?

GRAY: Yeah, I have a question for you.

RODRIGO: Oh my god. Okay…

GRAY: What was the most surprising part of this album to you? What were you most surprised when the album, now that the album’s done, what are you most surprised about it?

RODRIGO: Oh, my God. I don’t know. To be honest, I remember being a little worried. You seemed so obsessed with this album and you weren’t doing anything else. You were just eating, breathing, and sleeping this album. And I’m like, “Oh, I just don’t know if that’s really healthy.” Sometimes when I do that, I just don’t write good songs. And I remember when you first played me the demos, I was like, “Damn, these are so good.” It all sounded great in theory, but until I heard the demos, I didn’t really fully contextualize it. And I remember hearing it and being like, “Wow.” I just remember being so proud of you. And I remember being like, “You better promote this album. Every breakfast you have, I want it to be on a morning show. Every conversation you have is going to be on a podcast because this album has got to be heard.”

GRAY: Yeah, I remember when I was kind of getting towards the end of it, I was getting tired. You were like, “You better promote. You have to work hard.”

RODRIGO: It’s just so good. And I hope as many people hear it as possible because it feels so pertinent and heartfelt. Maybe this is too much information to be giving, but we notoriously give each other bad advice sometimes about samples. On Superache, you played me “Memories,” which turned out to be the biggest hit on the album. Everyone loved it. And I remember hearing it for the first time being like, “I just think you have better songs.” And then similarly, when I played you Guts, I played you “Vampire” and I was like, “Isn’t this good?” And he’s like, “Not for a first single.”

GRAY: I was like, “It’s okay.”

RODRIGO: We’re notoriously wrong about each other’s songs. We’re just too close to it and can’t see the forest of the trees.

GRAY: Way too close. But you know who was always rooting for “Vodka Cranberry”?

RODRIGO: Who?

GRAY: Your mom.

RODRIGO: My mom loved it. My mom’s such a huge Conan fan. My whole family, actually. They travel miles to see you in concert.

GRAY: That’s real family for real.

RODRIGO: I love those songs so much, but this was the first time I’d seen that part of you that I know so well, this positive, joyous, strong-willed Conan. It’s the first time I’ve seen it represented in a song, and it was so special because I just felt like people got to know you better the way that I know you. [Pauses] Oh, that makes me emotional.

GRAY: Oh, shoot. Wait, I’m actually tearing up. [Laughs]

RODRIGO: I know. [Laughs] I mean, you and I both write a lot of sad music, but I think maybe one misconception about us is that we’re actually very optimistic people.

RODRIGO: And super happy. Never a day without giggling, laughing.

GRAY: About the dumbest thing you’ve ever heard.