Jessie Reyez's ambition cannot be questioned. Her willingness to rise above the bullsh*t of love and life is felt throughout her dynamic single "Figures" and debut LP Kiddo. The singer has shared pieces of her story in passionate harmonies, but now it can be seen from the ones who know her best.

As part of Vevo's LIFT program, the 26-year-old spent six weeks with the brand to deliver her story in Becoming, the mockumentary-style series about budding superstars. Former subjects include Lorde, Sam Smith and Jidenna.

From her upbringing in Toronto to her time throughout the scene in Florida, no stone went unturned.

Here are just a few gems we learned from her Becoming short film.


Jessie Was the Flyest Cheerleader 


The singer's old cheerleading coach, Jorie Brown, remembered her boomkack moves and glowing personality. "She always had a spunk, like rough around the edges but in a good way," Brown said. "If you watch the old rehearsals, everyone's in their basketball shorts and Jessie's in shorts and a crop top."

Her Work Ethic Comes From Her Precious Parents 

Illustrations help paint a portrait of her Colombian parents, who, like many migrants, worked dozens of jobs to provide their family with a good life. "The first job I had when we came to Canada was a cleaner," her mother said. "I worked as a babysitter, and later we worked as gardeners."

He father had his fair share of gigs as well. "I was a tool maker, a dishwasher, and in the hotel washing pots. They were so big I had to get in them! I [even] collected worms. Fifteen dollars for 1,000 worms, but I would catch only 700 a night."

Between their jobs, they supported Jessie, even when she moved to Florida for a change of scenery.

She Dodged Club Security So Calvin Harris Could Hear Her Demo


"I got my bag and filled it with my sh**ty little mixtape, and we went in," Jessie said about an early club experience in 2014. After successfully passing off her demo to a DJ, she went to another room where another DJ was playing.

"We went to the next room, and as soon as security turned their head I ran up and tried to give [it to the] DJ, but one of his guys ended up taking it. The security saw me but I just ran into the crowd, and that DJ was Calvin Harris." While she doesn't share if he remembered that moment, the two ended up working together on his beautiful Funk Wave Bounces Vol. 1 project earlier this year.

"You have the good voice, you have the content, you have the audience and you have the melody," Harris says of Jessie's talent. "When you hit the spots, all of those things, you have a really impactful important artist. A lot of people see that in you."

Her Eureka Moment Came While Bartending in Florida  


"It hit me like, 'What are you doing? Why aren't you doing music?'" she says of her time in Florida. Fresh out of high school, Jessie got caught up in her gig as a bartender and the tempting scene life. "What good is going to one session a week and working the rest? It's gonna get you exactly that. Ten or 20 percent of what you want. So I just started hustling more."

After meeting her manager, Jessie returned to Toronto to join The Remix Project, a program dedicated on helping talented at-risk youth. Her mentor turned out to be Daniel Daley from DVSN. She also found a friend in volunteer and Grammy-winning producer King Louie.

"Figures" Still Gives Her the Feels

"I was all depressed because my ex cheated on me. It was hard for me to get over that," she says of the inspiration behind her breakout single. "Sometimes if I feel the songs are too much, it hurts, but then I open my eyes, people are singing along or crying, and the 7-year-old in me is like, 'Yeahhh.'"

Jessie joins fellow LIFT artists Khalid, Julia Michaels and Aminé in California this month for a special Halloween-themed show. She will also join PARTYNEXTDOOR for his Infinity Tour in February 2018.

For now, learn more about the talented soul in the short film above.