Roy Woods

Like mentor and fellow Toronto native Drake, Roy Wood$ cultivates a brooding, atmospheric blend of R&B and rap that often projects the persona of a brooding pleasure-seeker, yet steers clear of mainstream pop conventions. His first studio album, Say Less, arrived in 2017 and amassed multimillions of streams, after which he issued standalone singles before unveiling the 2020 EP Dem Times. The follow-up full-length Mixed Emotions surfaced in 2023, succeeded the next year by Rolling Stone.

Born Denzel Spencer in Brampton, Ontario, the singer, songwriter, and part-time rapper secured a deal with Drake’s Warner-backed OVO Sound, made his debut on the imprint’s radio program, and dropped his first EP—all inside a single calendar year. The six-song project, released when Spencer was 20, climbed to number 27 on Billboard’s R&B/hip-hop chart, propelled in part by the Drake-featured single “Drama.” July 2016 brought the full-length mixtape Waking at Dawn, timed with a U.S. tour supporting Drake, Future, and labelmates dvsn; it entered at number 30 in Canada and number 11 on Billboard’s Top R&B/Hip-Hop Albums chart. By year’s end, the Nocturnal EP had also appeared. In November 2017 Wood$ joined PnB Rock on “Low Key” while PnB Rock appeared on Wood$’ own “Balance,” the latter helping pave the way for the December arrival of official debut LP Say Less. That set reached the Billboard 200’s Top 100 and included guest spots from Jessie Ware, dvsn, and PartyNextDoor. Wood$ concentrated on singles in the immediate aftermath of Say Less, among them 2018’s “Russian Cream” and the 2019 Martin Solveig collaboration “Juliet & Romeo.” Dem Times arrived in 2020, the same year Wood$ collaborated with Tm88, Swagger Rite, and Wiz Khalifa. Across the following two years he issued “Touch You,” “Speeding,” and “Insecure,” all of which were included on the 2023 sophomore album Mixed Emotions. The seven-track Rolling Stone followed in 2024, featuring 03 Greedo on “Nobody Else.”