The nationwide contest, hosted by Kelly Clarkson and Snoop Dogg, pitted musicians from states and U.S. territories against one another, televised on Mondays and voted on by viewers.
And even though Jesso, who was representing Illinois on the show’s debut season, didn’t tally enough votes to reach the semifinals, he’s optimistic about the opportunity.
“I feel like it went well. I had a lot of fun. It was a great time,” he said. “Just being on the Universal lot is kind of incredibly fun in itself. And, for me, the experience was generally positive.
“By the way, one of the coolest moments of the show for me was when Snoop Dogg sang my song back.”
Jesso’s performance featured his new tune, “Lifeline,” a lively, soulful pop piece that belies its roots in a dark time for the singer when his mother was diagnosed with cancer and personal and business relationships were drifting through stormy territory, all during the pandemic.
“I felt very much like all of my pillars that I had depended on, the heaviest being of course my mom, were falling apart. And I felt like I just needed a lifeline,” he recalled. “The other thing that happened during the pandemic is I got a chance to step back and write a lot and redefine what I’m trying to say and how I’m trying to say it, and what type of music I’m trying to put out in the world.
“I love soul singers. And I love this huge arena-filling vibe. This Elton John, Queen, powerhouse-vocal, stadium-sized vibe,” he explained. “And I love crafting pop songs because that’s what I’ve been training to do since I got out of school. I wanted to mash it all together, and I wanted to tell big, loud emotional stories. So the pandemic gave me an opportunity to step back and say ‘OK, that’s the sound I want.’ And ‘Lifeline’ felt like a really great place to start to introduce that.”
Jesso, a New Trier grad who grew up in Highland Park and later Glencoe as Justin Stein, emphasized the contest is just another step in the process for him.
“It’s a long haul, and I have a very work-hard, grind-it-out, Chicago Midwestern mentality about it,” he said. “I’m not here to be a flash in the pan in the music industry. I’m here to be here for a while.
“And if this is my moment, then great. And if this isn’t my moment, that’s OK, because I’m going to keep creating moments that I care about and things that make me happy. And hopefully, because they connect with me, eventually they will connect and people will respond.”
As a performer, Jesso’s been connecting with audiences on stage since his early childhood. His upbringing reads like a guide to Chicago and North Shore theater, with roles at Marriott Lincolnshire, Apple Tree Theatre, Porchlight, Ravinia and theaters in the city, as well as classes at Writers’ Theatre and numerous school productions.
“I was the kid who always went for the plastic microphone over the toy football,” he said. “That was just me. I was a performer kid.”
Through connections he formed around musical theater in Chicago, Jesso also scored a spot in “Camelot” at the Lincoln Center, had a role in the 2010 movie “Master Harold … and the Boys,” and toured as an opening act with Radio Disney artists for a year between high school and college.
“I just kind of fell into these different weird pockets through the Chicago scene, both in theater and in music,” he said.
Jesso’s experiences at New York University’s Meisner Studio and the Clive Davis Institute of Recorded Music gave him the knowledge to redefine who he was and refine his path in the business, he said. And after learning some of the back end of the music industry through an internship at EMI Music Publishing, Jesso leaned into songwriting as a way to earn legitimacy as an artist. He found success co-writing songs for Ricky Martin (including the Latin Grammy-nominated “Vente Pa’ Ca”), Armin Van Buren and the Backstreet Boys. But his big break came when he presented a song to Norwegian producer Kygo, who insisted his label keep Jesso’s recorded vocals on the eventual smash track “Stargazing.” That lead to a deal with Sony and a start to his own career.
Around that time Jesso (who was still going by Justin Stein) adopted the stage nickname of his great-grandfather Jesse Cohen, who had performed jazz around Chicago and played piano for Al Capone.
“He wasn’t doing anything mobster-esque, but he was like the entertainment for the mobsters. So that’s a little fun history,” he said. “When I started making the transition to being an artist, I decided to adopt that moniker because I felt very connected to it and him and felt like since I was starting a new chapter, it needed a new presence.”
With his reality TV run over for now and three new singles (including earlier releases “Clarity” and “400 Trillion”) out this year, Jesso has earned some time to focus on the upcoming “Lifeline” video and new music before heading out on a European tour in June.
“I’m really excited to go down that path and see what happens with ‘Lifeline’ and the television show setting up this new sound,” he said. “It’s in your face. It’s soulful stadium pop that’s supposed to point the ship in the right direction. And I feel like that and the show will help me do that.”