Sleepy Hallow

Sleepy Hallow, born Tegan Joshua Anthony Chambers, is an American rapper from Flatbush, Brooklyn, and a leading figure in New York's Brooklyn drill scene. Raised in a Jamaican family, he began rapping as a preteen and adopted the stage name that referenced his reputation on the streets of his neighborhood. He rose alongside close collaborator and friend Sheff G, with whom he shared early affiliations before both artists launched their solo careers.

His breakout came in 2019-2020 with the viral single «Deep End Freestyle», which found massive traction on TikTok and helped propel his mixtape «Sleepy for President» into the spotlight. As one of the earliest signees to Winner Circle Entertainment, Sleepy Hallow became a central voice of the Brooklyn drill sound, marked by moody, minor-key production, melodic half-sung hooks, and laid-back yet menacing delivery.

Building on his mixtape run that began with «Don't Sleep», he expanded into full-length projects and further hits like «2055» and «Lowkey», blending drill's dark atmosphere with more melodic, R&B-inflected songwriting. His work has helped push Brooklyn drill toward wider mainstream recognition while retaining the genre's signature tension and street-rooted storytelling.