Pressa — grew up in an environment that shaped both his voice and his music. He was raised in the Driftwood area of the Jane and Finch neighborhood in Toronto, Ontario, Canada, a community well‑known for its resilience as well as hardship. His background is multicultural: his mother is Filipino and his father Jamaican, but his father was incarcerated for much of his early life, leaving his mother and uncle to raise him and his older brother.
Growing up in Driftwood wasn’t easy. The neighborhood’s struggles, street realities, and tight‑knit community all fed into Pressa’s worldview and would later become the raw material for his music. As a youth, he faced the kinds of adversities many in his community knew all too well — instability at home, the pull of street influences, and brushes with the legal system.
Pressa first began rapping as a way to express his truth. Early tracks uploaded on YouTube and SoundCloud like “Wass Gang” (a tribute to his late friend Wassi) and “Deadmihana” amassed significant attention and millions of views, giving him his first breakout moments online.
His breakthrough came in 2016 with the single “Novacane,” produced by Murda Beatz, which helped him gain attention from major names in the industry — including Meek Mill, The Weeknd, and ultimately Drake. That exposure led to a chance to open on Drake’s Boy Meets World Tour in 2017 — a major milestone that brought his talent to crowds far beyond Toronto.
Despite ups and downs — including legal troubles in his early career — Pressa continued to release music rooted in his experiences. Tracks like “Canada Goose” featuring Tory Lanez and “420 in London” with Lil Uzi Vert expanded his international appeal. Over time, he cultivated a style defined by gritty storytelling, melodic hooks, and a high‑pitched delivery that became his signature voice in trap and hip‑hop.
In 2019, Pressa released his debut album Prestige (named after his father), which hit No. 1 on the iTunes Canada hip‑hop charts and solidified his place in the Canadian rap landscape. His subsequent EP Gardner Express and collaborations with artists across North America and the U.K. further showcased his versatility and ambition.
After years of building his catalog and refining his craft, Pressa dropped his latest full‑length project Press Machine II on December 5, 2025.
Notable features on the album include:
• Quintana Mills
• Bay Swag
• Hunxho
• Bundog
One of the standout songs and the centerpiece of the rollout is track 7 — “5K for the Draco.” The track has become a key anthem from the album, gaining attention for its catchy hook and compelling visual narrative in its official video.
