For Canadian singer/songwriter Tobias Jesso Jr., 2015 was a dizzying year of spectacular success and total flame-out, pretty much all at once. In March of that year, he released his debut album, Goon, a collection of Laurel Canyon-y throwback piano-pop that critics loved. By the end of October, he realized he hated performing and canceled all his remaining tour dates, scrapping his career as a recording artist along with them.
But he didn’t have to wait long to find a new path. In November of 2015, Adele released 25, which included “When We Were Young,” a song Jesso wrote with her earlier that year in his very first professional co-writing session. It became a Top 20 hit, and Jesso has spent the last six years as an in-demand co-writer for artists from Florence and the Machine to Shawn Mendes to King Princess, culminating with a nomination this year for the first-ever Grammy for Songwriter of the Year.
Jesso acknowledges the improbability of it all. “I can see the made-for-TV version of my life for sure,” he says. In a recent in-depth conversation with Rolling Stone, he looks back at his winding career path, talks about his work this year with Adele, Harry Styles, and FKA Twigs, and more.
What was your life like in the year or so before you made Goon?
I was in bands and playing guitar and bass and I was struggling to accomplish anything or have anything stick. I felt like I was a self-sabotager who really wasn’t gonna amount to much. And then I was in L.A., overstaying my visa, just struggling to think of myself as a songwriter.
And I was like, God, give me a sign. I don’t believe in God really. But I was sort of like, give me a sign, universe, what’s the deal here? And I got hit by a car and I had to go to the hospital. And then my mom got cancer and it was like, everything is telling me I’m not supposed to be here. I’m supposed to be home where everything makes sense. So I went back to Vancouver. I think I was like 26 and turning 27. And then in Vancouver I had resigned myself to just giving up on the music dream. It was a very humbling experience. It was enough to make me reevaluate how I was doing things. I decided that I really hadn’t put too much effort into the learning of instruments. I’m a songwriter who doesn’t sing, who doesn’t really play the guitar that well, and who has more confidence than ability.
And somewhere in there you started to play piano?
Yeah, I started playing piano on my 27th birthday. And I wrote a song [that day] and I sang it. And it was funny, because it came so late in the game for me that I was kicking myself after I picked it up. Because the guitar never really made sense to me. If I was gonna learn a new chord, I would have to play that chord every week, or else I’d forget it because I didn’t really understand how the fret system made sense.
I was always just trying to get my ideas down very quickly, however I could. On guitar, I was way slower than I wanted to be. As soon as I started playing piano, it was like, oh my God, I can get my ideas out so fast. I was writing songs the first day because it was a lot easier for me to kind of fumble my way into what I wanted to hear than on the guitar. With bass, having a single note to write a song to, especially with how much I was not into the sound of my own voice, it was a little bit more difficult for me to get excited about something. Whereas the piano kind of felt finished. It was the full package to get those songs done.
I think that first song you wrote on piano that day was “Just A Dream,” which, like a lot of your songs, has a prominent use of a diminished chord in it — a real musical throwback.
Yeah, I’ve always been hooked on those. My favorite sort of Seventies-style music, the traditional sort of songwriting era of music, has every chord in the book. And I’m chasing that dream. So then I just started writing on piano and it made a lot of sense and I would go on these big long walks and just dream about, “Oh man, imagine this was the path. Imagine this was it. I’m writing songs. I can get my ideas out in the right way and I can translate them in the right way.” And as much as I didn’t like my voice, I wanted to listen to the songs. So I think that was the first time for me where I was like, “This makes sense, I want to hear it, so why wouldn’t other people want to hear it?”
It turned out that was right, and I got a record deal and moved down to L.A. to produce my album with JR White, who I would say is the first person who gave me a shot, who believed in me. I was like, “Okay, who’s gonna sing it?” And he was like, “you are gonna sing it.”
But it all started to go wrong pretty quickly, right?
The album came out and I just imploded. I didn’t want to be an artist anymore. I’ve always written songs and I’ve always loved it. It’s a great form of therapy and it’s a great form of creativity. And I think that at the time it became about, “Now I want you to go perform.” And I’m like, “But I’m a terrible performer.” And they’re like, “and we want you to do interviews.” I’m like, “That makes me really uncomfortable.” They’re like, “We want to put you in photo shoots and we wanna put you on TV…” I’m already very anxious. This is just driving me into a state of unknowable stress. You go on tour and I’m like, “Wait, why am I going on tour if I have to pay to go on tour?” And they’re like, “Because then you do two more [tours] and then it starts paying you.” And I’m like, “I never want to play shows. I never want to ever do that.” And they’re like, “That’s how you make money as an artist.” And I’m like, “I don’t care.” Everyone’s telling me I’d be an idiot not to take this opportunity. Even though it feels wrong to me.
Was there a final breaking point when you knew you were done as an artist?
Yeah, I had two tours booked. One of them was in Australia and one of them was in Japan. I think I had just done an American tour. What happened was I said, “I don’t want to go.” My managers were like, “Okay, let’s just give him some time.” I said, “No, no, I don’t want to go to those places and be miserable.” And then it turned into this sort of choice that I had to make, which was, the promoters need to be paid. So if you don’t go, you’re gonna owe a lot of money to the promoters. And I was like, “Okay, I don’t have any money. What are they gonna do? Break down my door?” And they’re like, “No, no, the label will have to pay for it, but then you won’t see any money from the record side of things.”
I’m like, “Great. Then let them pay for it. I’m way more optimistic about moving back to Vancouver and just working for my friend at his moving company than I am to be miserable on the road having to drink a bottle of wine to get on stage.” And so I just said no. And when I knew that I had this huge bill I had to pay and everything, the decision was made for me. Maybe I am a self-sabotager.
But in this particular case, self-sabotage worked out.
Yeah, exactly. Would I do the same thing today? Yeah, I would. I felt like I was on the wrong path, and then the gut instinct was telling me to get back on the right path.
Was your drinking at the time self-medicating for anxiety?
I think it became that, because in the beginning I felt like a primadonna. I had all these things where it was, “No, I can’t do that.” They tried to figure out a way I could tour, so it became, what if you toured with a band? I got my friends who were musicians who played in a fantastic band and they became my band. We got a bus that I couldn’t afford, that I didn’t feel like I deserved. I’m spending all this money now just to satiate my own need for comfort, right? And that’s not working, right? So I’m still needing something else to go out on stage. And then it becomes like, oh, it’s a lot easier if I get a little tipsy and then I go out on stage. And then somebody tweets “he was drunk,” and then I feel ashamed about it. And I’m waking up hungover at 4 a.m. on a bus I can’t afford. It’s a pretty brutal cycle if it’s not something you think you want to be in any way a part of. It’s a dream for some people. It just wasn’t my dream.
In January of 2015 Adele tweeted about your song “How Could You Babe,” and soon after, you met up with her to write “When You Were Young” and “Lay Me Down” with her. Her album came out in November of that year, right around the time you finished what became your final tour. How did that timing impact things?
The Adele thing was the saving grace that kept me in L.A., no doubt. It almost was like, this is my ticket out of what I’m doing. And I don’t think she knew that when I met her. But I think the decision in my mind was made: If this works out, I’m out. And I haven’t looked back since and I haven’t released a thing [myself] since. Without Adele, I would be a laborer. That’s just a fact. I simply would not be where I am without what she did for my career, without a doubt.
To go over some of your work this year, I think Harry Styles’ “Boyfriends” was actually from something you had originally written for his previous album, 2019’s Fine Line, right?
I went into a session on the previous album, and I sat down with Harryand, and Tom [Hull, a.k.a. Kid Harpoon] and we were just playing around in the studio and getting to know each other. Harry just said to me, “Can you play me some songs of yours?”
I had a chord progression when I played it, I thought, oh, this is very much what I imagined would be like a Harry Styles sort of chord progression. And then the next day he sent me a text message and he said, “Could you send me those chords that you were playing around with?” So I sent him the chords and I didn’t hear anything about it. Then he hit me up [two years later] and he wrote me, “Hey man, just wanted to let you know I used some of those chords.” He changed it to suit the song that they wrote, and I really didn’t have anything to do with the melody or the lyrics. It’s a rare thing to have somebody like Harry take the time to reach out to a songwriter after two years.
How different did things feel with Adele this time?
They were different in that she was going through a divorce, but the same in that her process was identical to how I remembered it. My first session with her was the blueprint of how I want all of my sessions to go. She just came in and we just talked. And I got to know her and she got to know me. And she does not come across as a celebrity. She’s very down to earth. She’s just herself, and we were just having a chat and telling jokes and, and, talking about life. I was a massive fan of her. So obviously I had a bunch of those layers of fandom I needed to break down. And then it had been so long that she just was like, “Are we gonna write a song or what?” And I’m like, “I guess so.”
I don’t even think she knew it was my first session ever, and we started on “When We Were Young” and wrote that song. Or most of it. We wrote the bridge the next day. So I try to let that experience influence me and slow me down. So every time I’ve led with, let’s just be two people, you’re not a celebrity, I’m not a songwriter. We’re not here to fulfill some agenda. Let’s just sit here and, and let me just try to see if we can spark a conversation that gets us interested in each other. And I think that once I start to relate with somebody in that way, and hopefully they are relating with me, the real magic happens, the more intimate magic.
You’re credited on “To Be Loved” on Adele’s 30, but I would bet you wrote more songs that didn’t make the cut.
We definitely sat and wrote a bunch. My favorite thing I’ve ever done is sitting in a room and watching Adele figure out what she wants to do, because there’s no telling her what to do. There’s no even influencing her. She’s a master at knowing what’s right for her almost right away. It’s a very pure process. You’re just two people sitting in a room and I’ll be on the piano playing chords until something just starts to click and she goes, “Can you play that again?” And then it’s melody work and she gets into lyrics and a lot of the times she’ll be like, “What do you think of this?” And by the time she’s even said it, she knows, she knows if it needs to change or not.
It’s fascinating in that I feel like you’re a tool for her to get what she wants. And she’s so good at finding what she wants and she’s so good at it that you feel like a useful device. Not that she makes you feel like that, but I’m just trying to explain the experience for me, like sitting in a room and going, I can’t believe this is happening. She’s singing all these melodies and she’s saying all these things and they all are just amazing. But she’s filtering it herself. She doesn’t need anybody. She really doesn’t. So you’re really lucky if you’re in there.
“To Be Loved” is definitely an instant-classic Adele song. How did it come together?
When she sang the chorus for me, I was like, no-brainer. This sounds like her and what she wants to say is all there. We would just play around with it, verses and melodies and different chords and stuff until it locked in. It was a few days of getting that song right. And once we did, she recorded that on her laptop at the house that is now demolished that we used to write those songs in. Once she did that, she sang it through and I just barely, played the piano through. It felt solidified and it felt done, and it felt pretty, pretty good. So I think we both felt that that song was special and for different reasons.
You’re credited with playing on the song. Is the demo what we hear on the album?
We tried a version at Henson [Studios], but she wasn’t feeling her vocals there. She decided that she wanted to see if it was possible do it the way we had done [the demo]. So she asked if it would be possible to set up mics and record at the house. I asked Shawn Everett, who’s the best sound engineer and producer and sound person. Her sitting there singing that song, she only sang it a few times – and it took my breath away. I’ll remember that until I can’t remember anything.
You also worked with FKA Twigs and Omar Apollo, which shows you’re really expanding the breadth of what you’ve been doing.
I think that was one of the intentional moments of my career. The beginning of my career was front-loaded with Adele and Sia and Pink and John Legend and all of these huge, amazing superstars and it was primarily for ballads and mid tempo songs. Then I got very intentional: I really want to do pop. I would start going into these pop sessions. And I was depressed because I was like, “I can’t do this. This is way too hard.”
I canceled a month of sessions because I was just so disheartened at how good everyone was. Everyone had perfect pitch. They were so intentional: “Why don’t we do like a Maroon 5? What if it was like this?” And I’m like, “Man, that hook would take me two weeks to figure out. What’s going on here?” And then you try to find your way back to it. I got a really lucky break with getting invited into that Niall Horan session in the beginning of my sort of desire for pop. Luckily they made it a single off that album, which was the beginning.
But, I still feel like I’m just turning the wheels trying to keep up. There’s different things you want to focus on. The intention behind working with Twigs and Omar is that I wanted to branch out and make it more about the artist’s wants. How would I be in a situation with someone like Twigs who is a very critically acclaimed artist, but also a very abstract song artist? I wondered how someone like her does this, and I’m still asking that question, even though I’ve worked with her a bunch.
What were the Twigs sessions like?
She is just a well of ideas and I had never really worked that way where it wasn’t like trial and error and then solidifying. In most sessions, you’re trying to find a chorus, melody, or a chord progression. And once you’re all in agreeance, then you solidify. And with Twigs, it was like, “What about this melody?” You’re like, “Yeah, that’s great.” She goes, “Throw that over there. What about this melody?” You’re like, “‘”That’s really good.” She goes, “Great. Throw it over there.” And you’re like, oh my God, there’s no order. Everything is just thrown around in a fascinating way. Not in a bad way. It’s another way of working entirely. I don’t think I’ve ever left a Twigs session going, “This is exactly what the song is.” You leave she’s got it all in her head spinning around. But I was always like, wow, what a gift. To be able to take all of these fragments of ideas and put them together in such a beautiful way.
I heard you might have worked with Miley Cyrus this year.
Yeah, I did. Yeah. She’s amazing. I used to be really into music documentaries, like Harry Nilsson and all of that stuff. And I feel like I, myself, am a documentary camera and I’m getting to see all these artists in their process and it’s pretty surreal. I’m like, “Oh my God, I used to watch this stuff and now I’m watching this stuff for real.” If you hear Miley sing in front of you, I challenge anyone to not be moved by the force of what her voice is and her command over it.
Is your work with Miley done or are you going back with her? That was a while ago, and there’s still no new album.
Who knows? That’s part of the songwriter’s journey. You never really know. You’re there when you’re there, and then you’re not there when you’re not there. And right now I’m not there. So I don’t know but I’m hopeful.
Is there any way you’d consider going back to releasing music on your own as an artist?
I think that my relationship with myself probably would have to change. I don’t think I would ever promote an album the way that a label would, would want me to. There’s not enough in it for me. I know that sounds very selfish, but I just mean not monetarily, but psychologically. It’s too difficult. And who knows, maybe there’s a psychotherapy or I can take a big old ton of mushrooms and all of a sudden I’ll want to perform. But I’m always writing. I always have songs and I’ll play them for people. But it just doesn’t feel like a business that I want to get into. I’m really happy with the, the business I’m in, and you might think that that’s me depriving an audience, but my duty was never to the audience. I never felt that my duty was always to the artist. I always knew I was gonna let the audience down myself.
Does that mean you’re recording as well, privately?
Just voice notes. Yeah. Like I’ll have a new favorite song for a couple days and then I’ll forget about it.
Do any of the people you work with ever try to pep-talk you back into being an artist?
I have a lot of friends who would love to see me do another album, but they would also love to see me be happy. And I think that they know that those two cannot exist together.