Sleepy Hallow

Tegan Joshua Anthony Chambers, known professionally as Sleepy Hallow, is a Jamaican-American rapper and singer-songwriter who specializes in Brooklyn drill. Born in Jamaica, Chambers was raised in Flatbush, Brooklyn, New York City, alongside frequent collaborator and co-founder of Winners Circle Entertainment Sheff G.

Raised in Flatbust alongside Sheff G, Sleepy Hallow emerged from Brooklyn's drill scene with a sound that balanced the genre's aggressive percussion with melodic sensibility—a contrast that defined his early collaborations with late peer Pop Smoke. His partnership with Sheff G through Winners Circle Entertainment solidified the duo's place as drill architects during the genre's rapid ascent in the late 2010s, while solo efforts like *Don't Sleep* (2019) and *Still Sleep?* (2021) proved he could command attention beyond group dynamics. Where many drill rappers traded in one-dimensional menace, Sleepy Hallow's catalog reveals an artist experimenting with vulnerability and introspection, positioning him not just as a scene fixture but as someone willing to complicate the genre's aesthetic.