Sleepy Hallow – Lyrics, Songs & Albums

About Sleepy Hallow

Sleepy Hallow is a Brooklyn-based rapper known for blending gritty drill beats with melodic flows and introspective lyrics. Born in Jamaica and raised in the Flatbush section of Brooklyn, Sleepy is part of the rising wave of New York drill artists, yet stands apart due to his signature blend of raw street storytelling and melodic delivery.

He rose to prominence alongside frequent collaborator Sheff G, with whom he helped define the Brooklyn drill scene under the Winners Circle Entertainment label. Tracks like “Deep End Freestyle” and “2055” brought him mainstream recognition, with “2055” going Platinum and becoming a viral hit on platforms like TikTok.

Sleepy Hallow’s music often explores themes of street life, loyalty, paranoia, and the pursuit of success, all delivered in his emotionally detached yet catchy style.