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Toronto's Jessie Reyez Connects with King Louie on Unlikely Terms

She went from dancing in Toronto, to having her heart broken, to bartending in Miami. Learn Jessie's story and how she managed to work with Chicago's King Louie.

The phrase "you never get a second chance at a first impression" holds doubly true for artists who came onto the scene at a time when most of the world is plugged directly into the internet. With the ability to get an artist’s entire body of work with the swipe of a finger, acts are going to great lengths to make sure that a potential fan’s first experience with them is a favorable one. But sometimes, an artist’s past mistakes can be the very thing that makes them so appealing to the general population. And for Toronto’s Jessie, those past mistakes are what propelled her into a career in music and got her featured on a record with Chicago's King Louie.


Born Jessica Reyez, the Colombian singer-songwriter grew up bouncing around different regions of Toronto, moving around North York before finally settling in Brampton. She danced to hip-hop music throughout her high school career and her scholastics suffered as a result. “I’d get out at school at 3:00 PM, show up to dance practice at 6:30 PM, practice for three hours till 9:00 PM, get home at midnight, and try to do whatever homework I could before getting back up for 7:00 AM. But I did it because I liked dancing, and I loved the music,” she explained. After hitting puberty, Jessie found herself in a serious relationship that lasted throughout her years in high school, and for a while everything seemed to be going well. But when her boyfriend told her that he was going to be going to be continuing his education in a different country, Jessie’s world shattered. “Me and him got together and fell in love, and when it went to shit when I was 17, it hit me hard as fuck. That’s when I started to write about, real pain, I guess.”

She buried herself in the music room for the remainder of her high school career. “I stopped going to classes and just went to the music class, just locked in the piano room,” she told me. “Thankfully my music teacher totally understood me and he would look out for me. It took me a year and a half to get out of my depression, but that time helped me create things I didn’t know I was capable of.” Soon after graduating, Jessie turned her pain into poetry as she performed her songs around the streets and clubs of Toronto. But just as she was beginning to make headway into the local music scene, Jessie found out that she had to move to Miami. After applying for American visas 18 years prior, Jessie’s family had finally been approved, and she could either live on her own in Canada or join them in Florida. “I ended up moving to Miami and bartending, but the party atmosphere is a black hole down there,” she said. “People party all the time, and if you’re working in the industry, you’re sleeping all day and at the club all night, day after day. I did that for a year, I completely neglected my music. The only musical thing I did was playing the guitar at the beach when everyone was coming down after a long night.” Suddenly, the pursuit of a career in music seemed to be slipping farther away from Jessie’s reach as she looked around and saw like-minded people around her slipping deeper into the nightlife quagmire. “I saw people in the Miami bar scene who were in it for ten years, 15 years, just used to that easy money and fast money, but it’s a lie.” Noticing that she was stagnant and on the verge of moving backwards, Jessie recognized that she needed to make a change. All she needed was a catalyst.


While in Miami, Jessie recruited a friend to shoot a music video for one of the songs she recorded before leaving Toronto. But since she was in a hurry to have it be released, Jessie took the task of editing the video into her own hands, something she had never had practice doing before. “I got so scared of wasting time that I got a sense of urgency,” she said. “I had never done any video editing before, but it took me 48 hours to edit a three and half minute video.” She sent the final version to everyone in her Facebook network, and soon it reached a few thousand views. One of the people she sent it to referred Jessie to Toronto’s Remix Project, an arts academy that helps youth from low-income households study the craft of music, photography, and business. Jessie applied to the music program on a whim, and a few months later, she was accepted into the program’s upcoming semester. This shift marked much-needed change in her life and started her on a new direction where the primary focus was music. “It took me out of the environment of clubs and brought me into a focused setting where everyone is a dreamer and ambitious and taking advantage of their opportunity,” she said. She branded herself as Jessie, pronounced “Yessie,” a name that riffs on the Colombian pronunciation of her real name, and set out to learn as much as she could from her peers at The Remix Project.

“The main focus of The Remix Project is to connect like-minded individuals and to create win-win situations for artists in all mediums,” explains Gavin Sheppard, founder of The Remix Project. This mantra is what led to Jessie’s first collaboration with a major artist, King Louie, which came to fruition during an impromptu jam session. Prior to a workshop that King Louie was leading for young creatives in Toronto, Gavin played Louie and his manager some music from the enrolled participants. While playing Jessie’s song “Status”, she happened to walk by and saw King Louie visibly enjoying what he was listening to. “That song is called 'Status,' right?” asked Louie, “like, subtweets?” Elated that he understood the concept of her single, Jessie left The Remix Project on cloud nine. The following day, Jessie gets a text from Gavin: “King Louie wants to work with you before he flies out.”

“We went to a house that belonged to a Remix alumni,” said Jessie, “and all of King Louie’s camp is there, so we start talking about music and the industry. Then Gavin’s like, ‘maybe you should play something live’ so I pull out my guitar and starting humming the song he heard at The Remix Project the other day.” King Louie starts freestyling over the guitar strums, and his management records the impromptu jam session on their phones for reference. Less than 24 hours after returning to Chicago, King Louie submits his verse for the song, and “Living In The Sky” was born.

Now, Jessie is looking to capitalize off this newfound buzz by using it as the launching pad for the musical career she’s always wanted. Her upcoming album, The Archives, will be a collection of music that draws inspiration from her entire life, from the breakup that shaped her way of dealing with pain, to her time with the despots of South Beach, to her eventual return home. “I’m appreciating every single bit of success I get, no matter how small. If you let yourself get emotionally fucked up, you’ll screw your energy up and attract negative shit. So I’m just learning to appreciate everything as it comes in. I know something bigger is coming for me, I’m not worried.”

Slava Pastuk is a writer living in Toronto - @SlavaP