Sleepy Hallow was born in Jamaica and grew up in Brooklyn before establishing himself as a key figure in melodic drill music during the late 2010s. Through his introspective lyrics and smooth haunting delivery, he achieved fame as part of the Winners Circle collective together with frequent collaborator Sheff G. His musical style combines direct narrative delivery with musical instrumentation to produce a unique sound that distinguishes him from other drill artists.

Sleepy Hallow received his first nati onal recognition through the platinum-certified single “Deep End Freestyle” (2020) which spread across social media platforms. Through his mesmerizing and emotional delivery Sleepy Hallow established himself as a fresh storytelling voice in hip-hop. His debut album Still Sleep? (2021) entered the Billboard 200 chart while his platinum-certified single “2055” demonstrated his skill in merging street credibility with melodic chorus elements.