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Chartbreaker: JESSIA Turned Her Insecurities Into a Hit (And a Record Deal)

Inside one wild month when the rising pop singer gained attention on TikTok, released her breakout hit "I'm not Pretty" and signed a high-profile recording contract with Ryan Tedder and Brandon…

On Jan. 1, JESSIA took to TikTok — as she had over 100 times since joining the platform in April 2020 — to sing the chorus of what would become her breakout hit, “I’m not Pretty.” Filming from the driver’s seat of her car, she says with a laugh in the New Year’s Day clip, “I don’t know if this is total trash or actually a bop, but here we go!”

The answer was a resounding “bop.” Of the 11 million-plus views on that initial clip, one was from songwriter-producer Elijah Woods, who took the seed of the song and helped the Canadian singer-songwriter (born Jessika Harling) flesh it out, showing the process on TikTok for followers to watch in real time. They wrote the song in two days and released it three days later. A sassy dance challenge choreographed by TikTok user @jambledore soon followed.

“I was making fun of people, like, ‘Oh, January 1st, you think it’s just a reset button and everything changes,’” says JESSIA. “And then, literally, everything changed.”


Even though she was personally having a “real bitter day” when she wrote the chorus — “You know, after Christmas, when you’ve eaten your weight in, like, everything?” — JESSIA discovered that listeners were connecting to the song’s “it’s OK to not feel OK” message for a range of reasons, whether it was postpartum moms struggling with baby weight or teenage boys with body dysmorphia.

“The song is talking about not being pretty and not feeling your best — that sucks that people feel this way,” she says. “But it’s also really beautiful that we’ve created this amazing community where everyone’s like, ‘Yeah, I got a belly and I got a bum, let’s just keep on moving on with our lives.'”

The buzz around the song caught the attention of singer-songwriter Ryan Tedder, who DM’d the aspiring pop star asking her to send more material. “I won’t sign a writer that’s not an artist, and I won’t sign an artist that’s not a writer,” says Tedder. “She was both in full spades — and I’m convinced had she not been living on an island off the coast of Vancouver, there’s no shot I would have had a chance of getting her. It would have been a feeding frenzy.” Adds JESSIA: “He gave a s–t. They say don’t meet your idols, but I’m very happy that I met him.”

Silverstein, JESSIA and Tedder
From left: Silverstein, JESSIA and Tedder photographed on May 19, 2021 in Los Angeles. Martha Galvan

He did face some competition, but by Jan. 31, Tedder’s Artist Driven Records and Brandon Silverstein’s S10 Entertainment record-label division signed JESSIA in partnership with Republic Records. Her manager, Studio 44’s JR Antoine, had come on just over a year ago. Ben Facey, Republic Records EVP, global marketing & digital strategy, says JESSIA’s music “popped” the first time he heard her, adding “her sound, her songwriting, her tenacity, her voice, her individuality stood out to such an incredible degree.”

Since then, things have only grown for the “I’m not Pretty” singer, including a Bebe Rexha remix released in April, while the original now soundtracks a body-positive Dove Self-Esteem Project campaign on TikTok. “I’m not Pretty” has racked up 49.4 million on-demand U.S. streams through May 27, according to MRC Data, and JESSIA topped the Canada Emerging Artists chart on May 8. Perhaps most affirming, though, are the steady stream of texts she now receives: “I constantly get messages like, ‘You were playing in Home Hardware!’ or ‘We haven’t talked in five years, but way to go, girl!’”

On June 4, she’ll release her first follow-up single, the bubbly IDGAF anthem “I Should Quit,” which she teased on social media this week, previewing the punchy lyric: “I’m a woman who doesn’t listen to her friends.” She feels like the success of “I’m not Pretty” has given her license to address any and every topic in her music moving forward, saying, “I remember writing these lyrics and being like, ‘Is this too much? Can I actually say this?’ And now that it’s gotten such a good audience and a great response, I kind of broke all the barriers.”

Tedder, who’s had both Zoom and in-person songwriting sessions with JESSIA, has high hopes, saying he “fundamentally believes that what’s coming next is bigger than ‘I’m not Pretty.'” Silverstein (who manages Normani and Anitta) adds, “We signed her off of the other music. There’s so many artists that are coming off of TikTok to have these one-hit-wonder type moments, and we wanted to make sure that she had a real career as a songwriter and artist.”

JESSIA photographed on May 19, 2021 in Los Angeles. Martha Galvan

With her career transpiring almost exclusively in a pandemic, JESSIA is especially looking forward to getting her songs in front of a crowd for the first time. “The music side of everything is all ready and it’s perfect, but I haven’t performed in like a year, so I’m trying to brush it all up in my bedroom mirror into a hairbrush,” she laughs. “I can’t wait to play for fans and feel the energy, because I’m going live on TikTok and Instagram, and your screen just fills with hearts … but having applause? I’m super stoked.”

She had a pretty big virtual audience back in February during her Zoom signing party, when more than 100 people from Republic, Artist Driven Records and S10 all gathered to welcome her to the family. “I was in my high school bedroom where I used to dream about this moment,” she says, “and I’m just sitting there and having champagne at 10 in the morning and like, ‘What is my life right now?'”

A version of this story will appear in the June 5, 2021, issue of Billboard.