A day in the life of Jessie Reyez, Toronto’s next big pop star

From Kensington Market to the 905, the breakout singer/songwriter shows us the spots that keep her grounded

JESSIE REYEZ with Savannah Ré at the Danforth Music Hall (147 Danforth), December 3 & 4, doors 7 pm, all ages. $25-$30. ticketmaster.ca.

Jessie Reyez is hungry. 

Sitting on the small covered patio of Perola’s, a Latin American grocery store in Kensington Market that’s been there since the 1960s, she rips open the tin foil of a freshly made pupusa and dumps a pile of hot sauce on her plate. 

“These are not actually Colombian, they’re El Salvadorian,” she says before taking a bite. “And they’re fire. Oh my god, I’m so happy. This sauce is lit!” 

It’s 5 pm on a hot September day and this is Reyez’s first proper meal of the day. 

I asked the Toronto singer/songwriter to take us somewhere significant to her, and she’s chosen Kensington as her first stop after our photo shoot. It’s where she used to busk with her acoustic guitar at the corner of Augusta and College and play open mic nights at The Supermarket. It’s also home to some of the city’s best Latin American food, which the Colombian-Canadian 27-year-old rarely gets to eat when she’s on tour. 

Like Bon Bon Bum, a deliriously sweet strawberry-flavoured Colombian lollipop with bubble gum in the centre. (She bought a family-sized bag.) For dessert after the pupusas, she buys a handful of churros from a sidewalk vendor across the street and passes me one.  

“These churros have dulce de leche inside,” she says, grinning. “They’re deep fried and they’re fucking fresh.”


Reyez at a corner she used to busk at in Kensington Market. “I used to play in front of a fruit stand. At night they’d put all the [produce] away and it would just be me sitting on the crates.”

Reyez has been touring for the better chunk of 2018, opening for PartyNextDoor in Europe, playing massive festivals like Lollapalooza and Afropunk in Brooklyn, and supporting Halsey’s arena tour across North America. Later this month she embarks on a headlining North American tour that ends with two hometown dates at the Danforth Music Hall in December. 

The tour is in support of her sophomore EP, Being Human In Public, a seven-song collection that finds Reyez deepening her relationship with R&B, pop and soul, even tapping Kehlani and Normani (formerly of Fifth Harmony) for a remix of her anti-slut-shaming rallying cry, Body Count. There are feminist anthems disguised as demure hymns, intimate confessionals and fiery indictments against misogyny. It’s both catchy and self-assured, a charismatic mix of raw bravado and vulnerability. 

Reyez has had a big year already – she’s collaborated with fellow breakout Torontonian Daniel Caesar, international stars Calvin Harris, Sam Smith and Eminem, and in Spanish with Romeo Santos. She also won the 2018 Juno Award for breakthrough artist of the year and was nominated for two MTV Video Music Awards. But with Being Human In Public and her biggest solo tour to date, Reyez seems finally poised to break out big on her own. 

It didn’t come out of nowhere. She spent years trying to network with producers and spamming music industry gatekeepers with demos.

“There are people who aren’t hungry enough. They don’t take advantage of the days they have or the hours they have to make their shit happen,” reflects Reyez. “I was hungry. I’m hungry still.” 

The hustle

Four years ago, Reyez was working as a bartender in Fort Lauderdale, where her family had relocated temporarily, writing lyrics on scrap receipts, busking on the beach and bribing DJs with free shots to play her songs. 

Before moving to Florida, she’d been hustling for her music since high school. She auditioned for a girl group when she was a teenager – she was rejected – and then later, burned mix CDs with her demos to hand out to big-name visiting DJs like Steve Aoki and Calvin Harris at the Guvernment. Years later, in a serendipitous full-circle moment, Harris and Reyez collaborated together on his songs Hard To Love and Promises, and co-wrote Dua Lipa’s multi-platinum single One Kiss. (And, no, Harris did not remember the time when Reyez climbed on her buddy’s shoulder and snuck onstage to give him her CD.) 

While in Florida, she was accepted to the Remix Project, an arts incubator for Toronto youth from marginalized communities that’s bred talents like WondaGurl and Rich Kidd, and moved back to the city. For nine months, Reyez worked non-stop, writing new songs while under the mentorship of Daniel Daley, one half of local R&B act dvsn.  

Last year Reyez released her debut studio EP, Kiddo, featuring the breakout single Figures (later re-released as a duet with Daniel Caesar). Over a sparse guitar melody, Reyez sings about the heartbreak of realizing an ex will never change, her voice sounding equally tender and fiercely fed up. On another standout single, Gatekeeper, Reyez recounts an experience with a predatory producer early in her career: “30 million people want a shot, how much would it take for you to spread those legs apart?” This past spring, she revealed on Twitter the “sleazeball” in the song was Noel Fisher (aka Detail), who produced Beyoncé’s Drunk In Love and 711.  

She’s been lauded by fans and journalists for speaking out, but Reyez, who released the track prior to the #MeToo reckoning, has said she didn’t write the song to necessarily spark a larger conversation about misogyny in the music industry. She’s always drawn from her own experiences. 

“When I write a song, it’s me talking about legit shit that I’ve been through. It’s me trying to make a copy of that moment in the studio. If I keep going back to the song a week later, I’m diluting that feeling,” says Reyez. “It might be more perfect, but it’s less raw and the rawness is what resonates the most with someone, because that’s what someone’s going through. They’re not going through some polished version of it.” 

Sola, for instance, is about failing to live up to the expectations of a former partner’s mother. “It’s about feeling like I don’t fit into a lot of the stereotypes [of what a girlfriend should be]: they’re so quiet, so submissive, they don’t make scenes in public and they forgive easily,” says Reyez. “Those women your mom would want for you. I’m not that type of chick.” 

Sola is the first song Reyez has ever written in Spanish, which adds another layer of intimacy. “When I sing in Spanish, my tone is different. I feel more relaxed because that’s how I speak to my family,” says Reyez. “It feels like my default.”

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Samuel Engelking

Born in Toronto, Reyez grew up near Jane and Driftwood and then moved to Brampton when she was around seven. “When I went to school, I didn’t know a lick of English, but it was okay because there were so many immigrants in the area, a lot of the kids didn’t speak a lick of English either,” says Reyez. “It was normal to have a wicked accent.” 

In contrast to her multicultural peers in Toronto, her class in Brampton was mostly made up of white kids. “I didn’t understand why other kids would make fun of my accent, but that shit’s a blessing. It made me stronger and it made my skin thicker for the shit you have to deal with as an adult.”

It also helps that Reyez has such a tight-knit family. She’s much closer with her parents than your average 27-year-old selling out concerts across North America. When she won her Juno this year, she brought them onstage to accept her award. They catered the release party for Kiddo, and when they can swing it, Reyez also brings them on tour. 

After our mini-culinary tour of Kensington, we drive to her brother’s house in Vaughan, and her whole family is there to welcome her: her brother, sister-in-law, four nieces and nephews, and her parents. 

She opens the front door, lifts up her smallest niece in her arms and snuggles up next to her on an oversized armchair. She’s clearly most relaxed when she’s with her family, laughing with her nieces and nephews and speaking in rapid Spanish to her parents, even as I prod them for embarrassing stories of Reyez as a child. (The best ones I get: her putting on performances for her parents pretending to be Cuban singer Celia Cruz or how when her older brother was obsessed with Snow’s Informer, he’d hear little three-year-old, pig-tailed Jessie trying to sing along from down the hallway). 

On touring with their daughter, Reyez’s father says, “In the beginning, we wanted to stand in the front, right close to the stage. But sometimes [the audience] starts moving too much, doing some wave, and we didn’t like it there any more,” he laughs.

Raw energy

Sitting on a bench on King East after our photo shoot, Reyez scoops up her mass of dark wavy black hair and ties it into a half bun with a red velvet scrunchie – her signature look, turned into a cartoon on her latest single art. Reyez says she’s “aching for the music” to come out and anticipating the album’s response. But in a way, she’s already in the midst of it. 

Although Being Human In Public comes out next week (October 19, on Island/FMLY), Reyez has been releasing tracks for the past couple of months. In the age of surprise album releases, it’s an almost anticlimactic approach to a record drop, but it’s one that Reyez and her team thought about carefully. 

“The way we consume music, the way we consume everything, has changed. You used to sit down and watch a video, but now you just swipe through stuff. It’s hard to get someone to sit down and listen to an album in its entirety,” Reyez says. “I feel like once you prove yourself as an artist that can deliver a fucking full dose, like Beyoncé or Kendrick… I want to work toward that.” 

Ironically, despite Reyez’s fears that her songs might get swiped past on Instagram by a listener with a short attention span, it’s on those very platforms where people are discovering her. Before she officially released the track Fuck Being Friends, concertgoers were already singing along to the chorus, recognizing it from YouTube videos and Instagram clips from past performances. 

When I bring this up, that maybe she’s underestimating the devotion of her fans, she admits, “I know I’m my own worst critic. I just want to get better.” 

She talks about getting better a lot: how she should be better at guitar since her dad taught her how to play when she was 10 how even though she’s trying to eat healthier on tour, she has a “weak tongue” for junk food how she should meditate and do yoga more because it’s good for her mental health how she’s constantly working at becoming a better songwriter. 


Reyez with her niece (left), sister-in-law, brother, mother, niece, father and two nephews at her brother’s house in Vaughan.

It’s not that she’s self-deprecating or naively ignorant of her talent. She has a seemingly insatiable desire to keep hustling and pushing herself into new territory, something she’s been doing for the past decade. She’s radically self-aware, which might explain the title of her EP.

“It means being honest in situations where you feel like other people have masks on. It means holding your flaws out for strangers to see,” says Reyez. “That was the driving theme behind the album. I feel like people can smell bullshit or when something’s not sincere, so I never want to do that.” 

Backed by a major label and with her popularity growing, remaining true to herself has become even more important. She’s a self-proclaimed control freak and has been practising relinquishing control to members of her team. She used to be obsessed with setting up her own merch table, fiddling with T-shirts while she should’ve been warming up backstage. Now, she lets someone else do it. 

For the past two years, she’s been on “artists to watch” lists and getting shout-outs from Elton John and Steven Tyler, but so far in her career, Reyez’s highest chart-toppers have been collaborations with other artists. These days, though, Reyez’s ascent feels inevitable. The question is whether she can make the leap to full mainstream pop stardom. (In a city where the biggest hip-hop and R&B breakouts have been men – Drake, the Weeknd, Daniel Caesar, etc. – Reyez would be a welcome change.)

In Toronto, at least, her star power is obvious. I witness it myself as we walk through Kensington, where multiple groups of young women approach her for selfies. One woman, who I initially assumed was a long-time friend because of how warmly Reyez embraced her, gushes that she’s recently moved from Saskatchewan to pursue music and that Reyez is one of her musical inspirations. 

It’s not uncommon for her to get approached by fans, but Reyez is visibly overwhelmed by the experience today. For the first time during our interview, she’s at a loss for words when I ask how she’s feeling. So I ask what she said to the young woman.

“I told her that [Kensington] is where I started playing shows and that I used to busk here. It’s the craziest when it happens… it’s surreal and it gives me so much joy and pure energy,” Reyez says, before taking a long pause. “It always humbles me.”

samanthae@nowtoronto.com | @SamEdwardsTO

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