Hailing from Brampton, Ontario, Roy Woods (stylized as Roy Wood$) has been rapping since he was 14-years old, and began gaining a foothold in the industry in 2014 by releasing singles on SoundCloud. Woods became one of the many artists in Drake’s musical sphere in 2015, when Drake premiered Woods’ breakout song, “Drama.” The song also included a feature from Drake himself, thus helping to jumpstart Woods’ musical career when it peaked at No. 2 on the Billboard Hot 200. With his newly-minted Drake co-sign, Woods released his debut EP, Exis, in July 2015 as an official OVO family member.
Woods released a full-length mixtape, Waking At Dawn, one year later and toured the U.S. with Drake, Future, and R&B duo dvsn. Woods’ initial releases proved his talent as both a singer and songwriter, setting the stage for his 2017 debut album, Say Less, which incorporated features from artists by the likes of PartyNextDoor, Jessie Ware, and labelmates dvsn. Woods’ sultry lyrics and soothing vocals have established the GTA artist as one of R&B’s rising stars, with him carving out a lane of his own within the genre. Among Woods’ most popular songs are, “How I Feel,” “Gwan Big Up Urself,” and “Why.” One of hip-hop’s most exciting young prospects, Woods often incorporates dancehall and Afrobeats in his music, in a nod to his Guayanese descent.