Tobias Jesso Jr.: The Best of What’s Next

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Tobias Jesso Jr. is a man with ideas. Four years ago, when the Vancouver native was living in Los Angeles and trying to spark a career writing songs for other artists, he one day decided that he would be good at thinking up concepts for reality TV shows. Thanks to friends of friends, an agent took interest and within a week, Jesso found himself meeting with execs at VH1, pitching titles such as Little Love.

“I can’t tell you the premise of it,” Jesso says, “but it was good.”

After a few weeks, when it was apparent that none of his show ideas were sticking, he gave up on that whim. Jesso, now 29, says he doesn’t watch television these days; therefore he’s not aware if any of the 20 to 30 ideas he pitched eventually were produced.

“If you see a show called The Skinny Chef, then you let me know,” he says.

“Hollywood,” a wry and weary voice-and-piano ballad that articulates Jesso’s ambivalence toward show business, is the centerpiece of his debut LP Goon, a work that’s been hailed for its kinship with the melodically robust ’70s output of singer-songwriters such as Harry Nilsson, Randy Newman, and Paul McCartney. “Hollywood” is informed by Jesso’s failure to find success as a songwriter during his first stint in L.A.

But there were other disappointments before that. In 2006, Jesso was playing bass in the Vancouver band, The Sessions, when it took first place in the worldwide battle-of-the-bands competition, Emergenza. Such notoriety led to The Sessions recording an EP with Metallica producer Bob Rock, but in 2008, the band’s singer left amid collective dissatisfaction with the direction of the music. That opened the door for Jesso and the other remaining members to move to Los Angeles and play behind upstart pop singer Melissa Cavatti—her father, also her financial backer, had seen a Sessions video—but after a year’s worth of rehearsals and only a couple shows, her ambition waned and she returned to school. Things came to a head for Jesso in 2012, after four years in Los Angeles: a day after surviving a hit-and-run while riding his bicycle, he found out that his mother had been diagnosed with cancer. If that weren’t enough, he also had experienced a recent breakup. He returned to Vancouver, embarrassed to tell his friends about his failings.

“Whenever they’re keeping up to date, you’re trying to say the best things that are going on,” Jesso explains. “You’re trying to be like, ‘Oh yeah, things are going great. I’m hopefully going to be doing this soon.’ You know, just trying to be the best that you can. And then, when you’re going home and you’re not taking anything back with you, it’s kinda like, ‘Well, here’s the real me.’ It’s like using an old photo on a dating profile.”

Jesso loves Vancouver, but he feels that L.A., where he’s currently based again, is where he found his independent self. To him, Vancouver is synonymous with living in his parents’ house. Growing up, he had envisioned getting out after high school.

“I was pretty ambitious, but I didn’t know toward what until later on,” Jesso says, reflecting on his adolescent years. “I didn’t really get into a band and start taking music seriously until I was in my 20s. So I was ambitious to do something with my life. I thought I wanted to do something that would last, but I had no idea what.”

He tried out for sports in high school but didn’t make any of the teams because of, he believes, his chubbiness. Though he stands at 6’7” now, a growth spurt of four inches came too late, when he was 18. He also lost about 50 pounds that year.

As a teen, Jesso developed interests in melodies and the intricacies of song structure, evaluating in his head the songs that older kids were playing at local live shows and then nitpicking tracks he heard on the radio, wondering if and how he could make them better. He imagined himself a song doctor of sorts but never considered writing for himself or gigging on his own. He decided that the spotlight wasn’t for him and that he’d prefer to write for other artists.

“I got the idea when I looked in the mirror and was like, ‘Yeah, you’re not that guy,’” Jesso recounts. “And I thought to myself, ‘I can’t really sing. If I went on American Idol, I’d be booed off or something.’ So I was not of the mindset that my voice or my musical abilities were really going to carry me further than my front door.”

Jesso’s mother, who recovered from her cancer, used to work as a teacher’s aide with disabled children and kids with learning disabilities, usually one-on-one in the classroom. His father was a software engineer. “Me and my friends used to joke around that maybe he was in the CIA or something,” Jesso says. His brother also works in computers, and Jesso calls him once a month with new ideas for apps. For five to 10 minutes, he’s able to convince his brother that he’s conceived an innovation, until his brother does some research and breaks the news that similar apps already exist.

After returning to Vancouver in 2012, with his musical equipment left behind in storage in L.A., Jesso began tinkering on his sister’s old portable piano. His sister, today an academic pursuing her doctorate, was born blind.

“Blind people like doing stuff with their hands,” Jesso says. “I think she bought a piano because she wanted to explore. She does all kinds of things, but I don’t know that it was a particularly good investment based on the fact that she just bought it and left it at my parents’ house.”

On the contrary, the piano turned out to be a life-altering investment, as Jesso used it to write the ballad “Just a Dream,” the song that set him on his path to becoming his own artist. In L.A., Jesso had been flirting with various styles of music, writing mostly on acoustic guitar. “Just a Dream,” which appears on Goon, was inspired by a dream story and depicts a father singing to his one-day-old daughter about the life lessons he wishes he could impart. Jesso posted the song to YouTube and got a positive response.

“I always thought that being able to write any style of song was being a songwriter,” Jesso says. “It just wasn’t the authentic me. When I went to write the piano song, that was the first time where I was like, ‘Well, this definitely isn’t cool.’ And that was the one that got the interest.”

In Vancouver, Jesso began to shop his demos to artists as they came through town to perform. Via email, he found a producer and mentor in Chet “JR” White of Girls, a band that Jesso had admired before it broke up in 2012. White wound up producing most of Goon, preserving the intimate, bare-bones aesthetic that worked so effectively on Jesso’s demos. Two of Goon’s tracks were produced by Patrick Carney of The Black Keyes, and one, “Without You,” was produced by Ariel Rechtshaid with Danielle Haim guesting on drums.

Jesso’s favorite artist, Adele, endorsed him with her first Tweet of 2015, linking to his video for the Goon track, “How Could You Babe.” In February, he performed the song on The Tonight Show backed by The Roots and three background singers, each of whom he encouraged to take solo turns. When they suggested that he take a fourth solo, he replied, “Hell no.” Jesso describes the performance as both nerve-wracking and a dream come true. He confesses that performing makes him “nervous as hell” and that promotional obligations such as traveling and photo shoots take him out of his comfort zone. There’s a dichotomy to him, perhaps reflective of his time spent between Vancouver and Los Angeles. From one angle, he’s the brash idea man with ambitions too big for Vancouver. From another perspective, he’s the reflective songwriter perfectly happy to create outside of the spotlight. For Jesso, the experience of selling his music is entirely different from pitching reality TV shows.

“If you put me in a room to pitch a movie, I think I’d walk out of there with a $20 million check to make a blockbuster for the ages—because I’m delusional,” Jesso says. “I don’t really know what it takes, so I can believe in that fantasy. But with music, I’d spent a lot of time doing it, and I knew the ins and outs, and I knew it wasn’t so easy. I’d worked really hard at making myself prepared enough to be ready for opportunity. It’s still scary to reach out for opportunity, especially when you’ve worked so hard at something. When you haven’t worked at it, you’ve got nothing to lose. I spent maybe five days thinking of reality shows, so if they turn ‘em down, what’s the big deal? But with music, it was my identifier. That was my life. That was what I would tell my friends that I did. So it’s a little more personal and a little harder to fail with.”

The lyrics to Jesso’s love songs are oftentimes disarmingly direct. He admits that a few of the compositions on Goon were written about his ex-girlfriend in Los Angeles, while a couple others are about a friend he’s known since childhood. Rather than fearing expressions of vulnerability in his music, he maintains a healthy perspective about it.

“I’ve always been pretty open,” he says. “If you put yourself out there, and people don’t like you, well, then they don’t like you. It’s better than not putting yourself out there and them liking you for not knowing you. So I just put myself out there maybe as much as I can, and if people like it, then those are my kind of people.”