Why Tobias Jesso Jr. is stepping back into the spotlight

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To get it out of the way: Yes, Tobias Jesso Jr. has heard about gooning.

The singer, who is 40, was surprised to hear someone suggest his earlier work was about masturbation, but they weren’t entirely wrong. A recent viral essay in Harper’s explained that, among Gen Z, the term ‘goon’ – originally popularized by his 2015 album of the same name – now refers to prolonged masturbation that leads to a trance-like state.

I was really struck by how honest Jesso was. He admitted he’d never tried whatever that was, and then cheerfully explained where his nickname, ‘Goon,’ came from – the movie ‘The Goonies,’ which he clearly loves! He even laughed about it, but then added with a shrug that he’s okay with it if it helps him sell more records. It’s just a really genuine and funny moment.

It might surprise some people that Jesso is releasing a new album. His first record, “Goon,” was well-received by critics and musicians, who often compared his style to classic singer-songwriters like Randy Newman, Harry Nilsson, and early Paul McCartney. However, Jesso wasn’t comfortable with the demands of being a performer and quickly stopped his solo career to focus on writing songs for others.

He’s become a highly successful songwriter, creating popular songs for major artists like Adele, Niall Horan, Harry Styles, and Dua Lipa. He won a Grammy Award for Songwriter of the Year in 2023 and recently received another nomination, recognized for his work with artists including Justin Bieber (“Daisies”), Haim (“Relationships”), and Olivia Dean (“Man I Need”).

He’s released a new album called “Shine,” a surprising follow-up to his first. Primarily featuring just his voice and piano, it’s a sincere and thoughtful project that showcases his ability to convey vulnerability with power.

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Vancouver native Jesso, now based in Los Angeles, recently revealed his new album with a music video for his song “I Love You.” The video stars Riley Keough and Dakota Johnson, both longtime friends of Jesso’s dating back to when he moved to Los Angeles around 2008.

He contacted the popular girls and jokingly asked if he could leverage their fame to boost views on his video. He explains that the video starts with them, but quickly shifts focus to him, and they aren’t shown again after that initial shot.

Says Keough, a former girlfriend: “It was a very Tobias ask.”

What prompted his return to public life? Jesso explains it was a difficult breakup that caused him to feel incredibly depressed. We’re talking in a comfortable room overlooking a beautiful garden, with a bowl of persimmons and a record – a copy of Paul McCartney’s “McCartney II” – visible among a collection of vinyl records.

I’ve noticed Jesso has a little gray in his hair now, but his approach to songwriting is still amazing. He told me he makes a point of leaving all his personal problems at the door when he starts working with an artist. He’s completely focused on helping them write the song they envision. It’s that selfless attitude that everyone loves about him, and it’s led to some incredibly powerful songs, like Adele’s ‘To Be Loved’ – a really moving song about the pain of divorce on her last album.

For the first time in his ten years of working as a voice actor, Jesso found it difficult to perform earlier this year. He explains that he felt so down that even saying a single line could make him cry, and he sometimes struggled to get the words out.

I was so surprised to hear he took six weeks off just to deal with everything he was going through! It really came through in the new songs. They’re super personal – he sings about his own heartbreak, like in ‘Rain’ where he describes seeing the love fade from someone’s eyes, but also about really tough stuff like his mom’s dementia and being a dad to his son, even after the split with his ex-wife. It’s honestly really moving to hear him be so open.

Music

A new biography about the 81-year-old songwriter and composer has been written by Robert Hilburn, who used to review pop music for The Times.

When it came to recording his music, Jesso naturally wanted to go all out. He explains, “I’m a bit of a dreamer, and I started thinking about all the people who could help me now, compared to ten years ago.” He initially reached out to various studios and made commitments, but those plans eventually fell through. “Everything I tried over those weeks just didn’t work out,” he says.

The only sound left was the warm, rich tone of an old Steinway piano. He’d found it on Craigslist for just $800 and had it lovingly restored. He keeps it in a simple, tidy studio above his den, and it’s there he recorded “Shine,” singing and playing the piano live at the same time.

A few other musicians contribute to the album, most notably on the song “I Love You.” It features an energetic drum solo near the end played by Jesso’s friend, Kane Ritchotte. Jesso says the idea for the solo came to him after taking psychedelic mushrooms. He spontaneously asked his assistant to start recording, and the drum fill was what he improvised.

I was chatting when he suddenly pulled out his phone and showed me something incredible. It was Jesso, right there in the same room as us – a video of him, eyes wide, silently mimicking the drum patterns that Ritchotte would perfectly recreate later on. It was a really strange and amazing thing to see.

Jesso explains the song is about searching for someone’s vulnerable, childlike side, lost in a confusing maze. The singer is desperately trying to reach them and express their love. Feeling blocked and frustrated, they wish the maze would simply disappear. The lyrics, ‘Shatter the cracks wide open / And say, “I love you”,’ represent a breakthrough, and the powerful drumbeat at that moment symbolizes the walls of the maze collapsing.

Beyond the impressive drumming, Jesso’s voice truly shines on this album. His heartfelt and vulnerable singing creates a deeply personal connection, like he’s performing just for you at the piano.

Jesso feels self-conscious about his voice, a feeling Keough notes has been present since his younger days playing in bands. She always admired his voice, but he didn’t seem to appreciate it himself. Keough finds this particularly interesting, as Jesso is generally a very confident person.

When asked about Jesso releasing a sequel to “Goon,” she admitted she was initially surprised by the first movie itself.

Jesso initially felt his singing wasn’t strong enough to do his own songs justice, leading him to collaborate with other artists. However, he’s now realized that his voice is actually the perfect fit for his music.

Hearing the finished recording wasn’t easy for Jesso. After recording “Shine,” he asked his friend Shawn Everett to mix it, but the result was unsettling – every flaw in his voice was painfully obvious. “It felt incredibly vulnerable,” Jesso explains.

He texted Everett, apologizing and explaining he couldn’t release the record in its current state. He recalls telling Everett that making the record had forced him to reveal more of himself than he was comfortable with. When he got home, he smoked marijuana and sat on the couch, hoping to get high enough to listen to the record and distance himself from it. He laughs, remembering that when he finally put on the headphones, it was the most powerful musical experience of his life.

Who did you think was singing? I wasn’t sure – maybe someone around 50, or even a young woman with a deep voice. It didn’t really matter though, because it wasn’t me, so I wasn’t being critical of the singing.

It’s funny, because the album “Shine” feels incredibly authentic – like a true representation of myself. I kept it simple, without any artificial enhancements like auto-tune or editing. It’s just my voice, the best take I could do. In contrast, the album “Goon” relied on things I wasn’t really capable of doing on my own.

The film ‘Goon’ involved a larger team of players and producers. This presented a challenge because I wondered how to effectively rework something I hadn’t originally created entirely on my own.

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Considering how difficult the experience after your last book, “Goon,” was, I was curious if you’d set any boundaries for yourself this time around.

To be clear, I won’t be doing a book tour – absolutely not. I’ve heard many artists say they feel most like themselves when performing, and I understand that feeling. But I’ve tried performing both sober and while drinking, and it just doesn’t work for me. It doesn’t feel natural.

I’m still figuring some things out in therapy, but performing and singing feels strange because it’s like I’m claiming to be a ‘singer,’ which doesn’t quite feel right. I’m much more comfortable identifying as a songwriter. It’s like I feel embarrassed presenting myself as something I’m not fully confident I can deliver on.

For this album, it was important to me to be authentic and true to myself. That’s why I’m fine with imperfections – a slightly off-key note or a tempo that varies a bit. Even though I can play the songs exactly as they are on the recording, I don’t feel driven to perform live. I’m not interested in building a traditional fan-artist connection. I’m grateful that making music isn’t how I earn a living, which allows me to approach it differently.

After your album “Goon,” you started focusing on songwriting as your primary career. Because of that, I don’t feel the need to approach everything with such intense seriousness. I’m still dedicated to the creative side of things and happy to put in the effort to make good art.

However, I wasn’t doing this purely for the sake of achieving success. It’s strange to admit, but while working on the album – like when I was on the 73rd take and trying to remember a previous version – I’d think, ‘I could be at work right now, potentially earning much more money than this album will ever generate.’

It’s almost definitely true. Unlike “Shine,” which didn’t seem promising, I still wanted to do it, and that felt right. However, if I don’t think something is worthwhile, I absolutely won’t do it.

I reread something I wrote about your show at South by Southwest in 2015. It reminded me that you had to start your song “True Love” five different times! Oh man, that was something.

The audience didn’t seem to mind the mistake at all, actually they found it endearing. Looking back, if I were performing now, I think I’d appreciate being able to show vulnerability. It’s natural, and I recognize that’s a good thing. But at the time, I couldn’t handle the thought of people misinterpreting it. I wasn’t seeing it as a genuine moment; I was convinced I was failing as a performer and pretending to be okay. Even though the crowd enjoyed it, I didn’t want to hear praise about it being funny. I was searching for the negative comments, the ones confirming my fears that I was a disappointment, and that’s exactly what I expected to find.

Keough agrees with Jesso’s view of how his current situation differs from what it was a decade ago.

She believes his previous film, ‘Goon,’ would have forced him to conform to expectations as an actor. In contrast, ‘Shine’ comes after his Grammy wins and successful songwriting, allowing him greater artistic freedom because there’s less pressure to perform a certain way. He’s moved from being a newcomer, like a barista, to an established artist.

Jesso recently felt like he was nearing burnout with his music. He says he was almost ready to quit because he didn’t want to keep repeating the same formula for success – he didn’t want to just chase another hit song that sounded like the last one.

He explains he’s not referring to collaborations like the one with Dua Lipa, for whom he wrote on her 2024 album, “Radical Optimism.” He says, “Working with Dua was fantastic.” Instead, he’s talking about the typical songwriting process of attending pitch meetings and trying to get songs noticed. He adds that this approach hasn’t worked well for him, and as you become more successful with producers, you’re often pushed into this kind of formulaic songwriting.

His experience working with Justin Bieber earlier this year was completely different. Jesso describes the creative sessions for Bieber’s experimental albums, “Swag” and “Swag II,” as incredibly energetic and full of ideas. They traveled to France, the Bahamas, and Iceland while working on the project, before Jesso started focusing on his own album, “Shine.”

Honestly, watching Justin perform brought me to tears more than once. It wasn’t flashy or clever – it was just pure, genuine emotion, and after being in the music industry for so long, that was incredibly refreshing. It actually reminded me why I loved pop music in the first place, and totally renewed my faith in it.

It’s a funny situation, actually. Jesso’s planning to move to Australia soon, and honestly, it’s all about being closer to his son, Ellsworth. Ellsworth is living there with Jesso’s ex-wife, who you might know – she’s the fantastic Australian singer-songwriter, Emma Louise. As a film fan, I always appreciate a good story about family, and this feels like the start of one.

He explains that divorce is about compromise. One major issue was his ex-wife’s desire for their son, Ellsworth, to attend school in Australia. While it felt right for her, he didn’t think it was the best career move. However, he’d agreed to it and wanted to see it through, at least try to make it work.

Releasing the album and moving to Australia so close together feels like a major turning point for me,” Jesso says. “I think I’m finally overcoming my fear of making music and opening myself up to new challenges. I have no idea what I’ll be doing in Australia, but I’m hoping to find some work. If not, I might end up spending all my time brainstorming TV show ideas with the groundskeeper!”

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2025-11-22 14:33