Jessie Reyez Opens Up About Her Journey to Landing a Deal with Island Records

Jessie Reyez, 2017
Noam Galai/Getty Images

Jessie Reyez photographed at the 2017 Governors Ball Music Festival - Day 2 at Randall's Island on June 3, 2017 in New York City. 

Jessie Reyez could’ve given up the night five years ago that she was propositioned and threatened by a “big producer” whose name has never been revealed; instead she is sitting here with a record deal with Island Records.   

“I was this close to selling my soul that night; I was this close to breaking,” she says in the short film Gatekeeper: A True Story.

While discouraged and ever-cautious, she kept working and got a break when she enrolled in Toronto’s The Remix Project, a nonprofit educational arts academy for creative youth from low-income households. After a workshop there in 2014 by King Louie, the Chicago rapper asked her to sing on a track called “Living in the Sky.” Then she continued writing and recording, releasing a series of singles and videos that earned her views, accolades, a loyal management team and eventually a publishing deal and recording contract.

The video for the year-old “Figures” has been viewed on YouTube more than 7.4 million times and for ”Shutter Island” more than 2.4 million times. The eye-opening song "Gatekeeper” and companion short film about the potentially dangerous night she was promised a career in exchange for sex should receive millions of views but has not yet cracked one million combined. It’s an important 12 minutes for any aspiring female artist to watch, a piece she co-wrote with director Peter Huang, narrates and acts in. It’s hard to watch, knowing she went through that.

“If you’re not using your pussy, you ain’t serious about your fuckin’ dreams,” the do-you-know-who-the-fuck-I-am producer says in the film. “You’re fucking up your chance right now.” “My body’s my temple,” she says at one point.  

“Everything that’s in there happened,” Reyez tells Billboard.

But what d’ya know, she didn’t have to sell her soul to some creep to realize her childhood dream of becoming a singer. Today, her star is only rising. Her debut EP, Kiddo, has garnered more than 30 million streams since its April release. 

Over the summer, the 26-year-old performed “Figures” on the 2017 BET Awards and wrapped up a U.S. tour, which culminated back home in Toronto with a sold-out show at the Mod Club. She made her late-night talk show debut on The Tonight Show Starring Jimmy Fallon in August. She’s also featured on Calvin Harris' track “Hard to Love;” Romeo Santos' ballad “Un Vuelo a La” and Allan Rayman’s sultry “Repeat.” Last week she dropped her new video for “Blue Ribbon," and tonight (Sept. 5) she films an episode of George Stroumboulopoulos’ Apple Music series House of Strombo that will be released late September.

Watching you at soundcheck at Mod Club, you take your time. I think it was two hours. Are you a perfectionist?

Yes. I’m very meticulous. Yes. I am. I don’t know about perfection because sometimes I embrace flaws, but I do that in life. I feel like it’s who I am to embrace flaws, but what I am is meticulous in having things a certain way because I have a vision in my head and I just want it to be as accurate as possible. And I’m blessed to work with people that help me execute it.

It seems like a nice crew.

I love them. They’re all great.

One of your managers is setting up the T-shirts and you customize them?

There’s a specific design on them so I’m gonna use red paint and do little details on them. I feel like my objective in music is to take a hammer and nail and chip away a piece of my heart and give it to someone, so I feel with merch it’s a tangible parallel of that.

Speaking of a piece of your heart, being a woman in the music industry, I’ve been fortunate most of my mentors have been men that have always treated me with respect. I haven’t encountered what you wrote about in “Gatekeeper.” Kesha released that powerful song “Praying, ” music publicist Heathcliff Berru was publicly outed online for making unwanted sexual advances toward women, and in Canada former TV and radio host Jian Ghomeshi abused his power and position and was charged with sexual assault. It is really coming to light what a lot of young woman and girls go through who want to work in this industry, as artists and on the business side. The film is really emotional. The woman in the car [who fed you to the wolves], how real is that? It’s called Gatekeeper: A True Story.

Yeah, it was accurate. Everything in there happened, man, which is shitty because you would just hope the idea of sisterhood existed as strong as brotherhood does, you know? Sometimes it does and sometimes it doesn’t and this was a case where it clearly didn’t, but I never thought I’d look back at that and be like, 'I’m happy I went through it' because we were able to create something from it. Never did I think I’d look back to that night and be like, 'It had a purpose.'

It could have been a lot worse.

It could have been a lot worse. Oh yeah. I had to sit my mom down and warn her about what was coming out, my mom and dad, and they said the same thing too. What if you weren’t praying in the bathroom? I’m very spiritual and so is my family, so we are of the belief that because I had so much faith and was expressing so much gratitude that maybe the forces combined to help it not go down in the worst case scenario that it could have.

What got you through that, emotionally scathed but unharmed? You were strong enough to say no. What is it about you?

Nothing. I don’t think there’s anything special about me for deciding to not do it. I feel like humans, when you’re faced with decisions, you can go up and down, duality. That’s why I said when I wrote that song and we were deciding to put it out — and we were talking about how to put it out, I never wanted to put it out — we’re on this highest vibe of morality and I did it because of some heroic bullshit but it’s not true. It so happened I did it the same way other women who are strong and broken.

I think it was my mom, and the way that I was raised, and me praying and me not wanting to break. I thought about it. I say in the video I thought about doing it. It’s not like I was adamant about the ‘No’ off the bat. I thought about it because I was thinking that this might be my only shot and this might be what it is, so if I say no now, the probability of me encountering this again within another year, another two years, the way he’s talking about it, it sounds like it’s probable so why am I going to say no? To say no a year later when nothing’s happened? When I’m 25 and I look around and I’ve made nothing of my life? Am I going to think back to today and I’ve wasted it? The possibility exists that I could have done it.

Many women keep that inside. But with people like you talking about it, it encourages others to share their stories. Maybe social media helps facilitate that.

I think so.

What made you decide to do it now at this early stage in your career, and have you had people say ‘Thank you. I’ve gone through this,’ which is giving you reinforcement?

Yeah, people have come up to me and expressed that they’ve gone through it and they said ‘Yes,’ or they’ve gone through it and they’ve said ‘No,’ or men who have said, 'I didn’t realize what kind of power I hold as a man in the industry and how you can yield that.' It’s interesting how it’s touched different people, but, again, it’s not like I set out with an objective to put it out and make it a pillar to help others. It wasn’t that. It was just the way I create other music too, is just talking about my experiences, talking about the shit that I went though, and keep it as honest as I can. The fact that It resonated with people has two sides: it’s dope that people resonate with it, but it’s shitty that so many people resonated with it at the same time, you know? But I think about how you said social media and the fact that the feminist movement is getting stronger by the day and it’s nice to see more of that ideal, sisterhood and unity.

So you kept working, kept writing and recording and handing out tapes.

[Laughs] Yeah.

When did you get that break?

I was bartending and busking in Florida at the time and I was blasting everybody on my Facebook with this video that I had made with me and my homie. There’s this old music video called "Why Should We," and the reason it was made is because I was on Skype with [producer/songwriter] Doc McKinney [The Weeknd, Esthero] and he was giving me advice because I was pissed that long distance I couldn’t get producers to send me shit as quick as I wanted, and I couldn’t get sessions as fast as I wanted, and I was waiting for beats. It’s easier if you’re in the same city and not even as a woman, it’s hard; it’s hard sometimes.

I was complaining, and he would let me complain and then he was like, 'Jess, you gotta do what you can with what you got. Grind as hard as you can ‘cause when people see you grinding like that, they’re not going to have a choice.' And I was like, okay. Cool.

Hearing that inspired me so much that I linked up with my buddy and we went to the beach and we shot a music video and that night I came home, went on Google, learned how to edit. It took me 48 hours to edit a three-minute clip. It took me 48 hours and I didn’t sleep because I was so excited to have a piece. 48 hours. Did it. Blasted it everywhere on Facebook, like spamming everyone and anyone I could think of and one of the people that got it was Mauricio who is now my manager, and at that point he was like, 'Hey this is kind of dope. If you’re serious about your music, there’s this thing called The Remix Project in Toronto, and it’s an art incubator and it’s basically like free school. If you don’t got money for studio, you don’t have the networks, they help you.'

So I took the weekend off at the bar, begged my bar manager, found a $50 flight on Spirit Airlines, flew over here, did the audition, flew back, covered some more shifts to make some more money, and then I got the word that I had made it into the program, and then I moved back home, and then that year I busted ass. They could testify because I used to beg for them to let me stay overnight and beg for them because I was learning how to engineer and learning how to produce — loosely, because it’s not my main thing — and working on my songwriting and working on my faults and working on how I could get my message clear and studying the greats and everything like that.

King Louie came to speak, came as a mentor, and this must have been three years ago — I always fuck up these timelines — then he liked some stuff and we ended up making a song together, and then Chance the Rapper heard it and then he tweeted about it and things have just been rolling since.

And at that point Mauricio [Ruiz] and Byron [Wilson] were friends because Byron also manages this lovely artist named SonReal, and Mauricio co-founded this thing called Mad Ruk Entertainment, a production agency in Toronto, and they were doing some videos for him, and they would just bounce ideas off each other and he sent him the music one day and he decided to send it to Jeremiah  [Jermi] Thomas at BMG. Jeremiah Thomas [was] one of the first people to ever champion me in L.A., ever, and to actually put his heart in it — because I have trust issues; I am a very private person when it comes to letting people be close to me for long because I feel like energy is very contagious, so you have to be very picky. He was consistent, and even though I wasn’t signing anything because I was so paranoid, he would follow through with things. They sent me to Sweden for a writing camp before I even had a contract with them because I still didn’t want to sign. I wanted to see how hard they were willing to ride.

This is publishing you’re talking about?

This is publishing.

Because you are with Island.

Yeah yeah, that’s also really, really new. And same thing because the way life really works is Jeremiah ended up going from BMG to Island during that same time, and I was nervous about going with any label for that same reason — because I’m so paranoid. It was like the universe was like, ‘Okay, so you already know this guy and this guy has already proven himself to you.’

Why are you uncomfortable or paranoid?

With people?

With the industry?

Just with everybody. With everybody. So the industry just falls under that umbrella. People at the corner store. Just cautious.


Not suspicious. Just guarded. Just guarded.