Like mentor and fellow Toronto native Drake, Roy Wood$ pursues a moody and atmospheric fusion of R&B and rap and frequently comes across as a sullen hedonist, though his approach is less pop-oriented. His 2017 debut album, Say Less, generated multimillions in streaming numbers, and he followed with a series of stand-alone tracks and 2020 EP Dem Times.

Within the span of one year, the singer, songwriter, and occasional rapper, born Denzel Spencer in Brampton, Ontario, signed to Drake's Warner-supported OVO Sound, premiered on the boutique label's radio show, and released his debut EP. Issued when Spencer was 20 years old, that six-track set registered at number 27 on Billboard's R&B/hip-hop chart, boosted by the Drake-assisted single "Drama." Waking at Dawn, Wood$' first full-length mixtape, followed in July 2016, synchronized with a U.S. tour beside Drake, Future, and labelmates dvsn. The album debuted at number 30 in Canada and at number 11 on Billboard's Top R&B/Hip-Hop Albums chart. An EP titled Nocturnal was out by the end of the year. In November 2017, Wood$ appeared on PnB Rock's "Low Key" around the same time PnB was featured on Wood$' own "Balance." The latter was among the tracks that led to the December release of Wood$' official debut LP, Say Less. The set broke into the Top 100 of the Billboard 200 and featured additional guests Jessie Ware, dvsn, and PartyNextDoor. Wood$' output was limited to singles for the years immediately following Say Less, including songs like 2018's "Russian Cream" and the 2019 Martin Solveig collaboration "Juliet & Romeo." In 2020, new EP Dem Times surfaced, and that year Wood$ also worked on material alongside Tm88, Swagger Rite, and Wiz Khalifa. Over the next two years, Wood$ released new songs "Touch You," "Speeding," and "Insecure." ~ Andy Kellman, Rovi