After emigrating from Jamaica to Brooklyn, New York, Sleepy Hallow real name Tegan Chambers found himself jump-starting his musical career alongside local collaborator, Sheff G, who would end up being his long-time friend, aiding in each other's success. The two went to school together, although they weren't exactly friends - Sheff G was originally planning on jumping Chambers with nearly 50 other people. However, things took a turn when Chambers began defending himself, apparently surprising Sheff G. Chambers has shared in interviews he wasn’t much of a troublemaker at school, although after having to serve three weeks in juvenile detention for the possession of marijuana, his performance in school began to decline. He did manage to get his diploma with a GPA of 2.2.
Some of Sleepy Hallow's early tracks got him discovered by former NFL player Junior Galette’s record label, Nula Entertainment. Both Sleepy and Sheff G were signed to the label, but after a year, in 2019, the two left and created their own label, Winner’s Circle Entertainment. With the rights to most of his music, Sleepy has accumulated quite a large fortune with a net worth estimated to be a couple million.
Sleepy released his debut mixtape in 2019, Don’t Sleep, and his second mixtape, Sleepy for President, the following year. In August of 2020, “Deep End Freestyle” featuring Fousheé, which appeared on Sleepy for President, was certified gold with over 85 million streams. The track found international success as a trending sound on TikTok with thousands of videos hyping up the beat. During that same month, Winner’s Circle Entertainment announced its partnership with RCA Records.
