After finishing high school, Reyez decided not to apply to college. She wanted to devote her live to music, dreaming of becoming famous. Jessie earned money by doing different jobs. In the evenings, she performed at the local Toronto clubs and even on the streets. At that time, her parents acquired permission to live and work in the United States, and the family moved to Miami. In the USA, Reyez got a job as a waiter in a bar. She performed at Florida beaches, playing the guitar and singing.
No matter how hard Jessie tried, she couldn’t get the attention of any labels or managers. She decided to ask a friend to help create a music video. Later, Jessie edited the video and uploaded it to Facebook. The video collected thousands of views. One of the viewers advised the singer to try to get into The Remix Project Academy of Recording Arts. The project helped talented artists with low budgets to find their way around the music industry.
In 2014, Jessie returned to Canada. A few months after moving, she was accepted to the project. One of the girl’s recordings caught the attention of a Chicago singer King Louie, who offered her collaboration. Together, they recorded a single “Living in the Sky”, which helped the artist become popular. She started getting collaboration offers from such artists as Chance the Rapper, Diplo, Skrillex, and Babyface.
In 2015, Jessie worked with London Future to record “Hold Your Fire”. In 2016, together with Tim Suby, Reyez recorded “K Goodnight”. The same year, she presented two solo singles, “Shutter Island” and “Figures”. The latter reached the 32nd spot on Rhythmic Chart and came in 58th on Canadian Hot 100.
In April 2017, Jessie released her debut EP, Kiddo, which featured 7 tracks. It settled on the 83rd spot on Canadian Albums Chart. Critics gave high scores to the lyrics of the songs, in which the singer talked about music industry morals. Soon a documentary “Gatekeeper” came out, in which Jessie talked about the producer Noel Fisher, who was infamous for the sexual harassment scandal in the music industry. At that time, many fans tried to book Jessie Reyez for private events.
The same year, Jessie helped Calvin Harris record a new single “Hard to Love”, which was part of his album, Funk Wav Bounces Vol. 1. The single climbed to the 30th spot of The Dance/Electronic Songs Chart. By the end of the year, Jessie released two singles, “Phone Calls” and “Cotton Candy”. In 2018, she presented her new EP, Being Human in Public.
In 2017, at iHeartRadio Much Music Video Awards, Reyez was nominated for Best New Canadian Artist. In 2018, she won a June Award for Breakthrough Artist of the Year.