Sleepy Hallow

Born in Jamaica, Chambers immigrated as a child to Flatbush, Brooklyn, where he began rapping at the age of 12. He adopted the stage name “Sleepy Hallow” from his street nickname and dropped out of school in ninth grade. He met Sheff G in his early teens, and the two initially prepared to fight before bonding over mutual respect, eventually forming a close friendship and musical partnership.

Sleepy’s early music journey began under Nula Entertainment, a label owned by former NFL player Junior Galette, where he and Sheff G were signed from 2017 to 2018. In 2019, he released his debut mixtape Don’t Sleep, the same year Winners Circle Entertainment was founded, with Sleepy as a foundational artist. The label entered a joint venture with RCA Records in 2020.

Sleepy gained widespread attention in 2020 with the release of “Deep End Freestyle” featuring Fousheé. The song went viral, earned RIAA platinum certification, and marked his first Billboard Hot 100 entry. That same year, he dropped his second mixtape, Sleepy for President, further establishing his reputation.

In 2021, he released his debut studio album, Still Sleep?, featuring the breakout hit “2055”, which peaked at No. 51 on the Billboard Hot 100 and was certified double platinum in 2022. He continued his momentum with singles like “Die Young” featuring 347aidan, and “Tip Toe” with Sheff G, showcasing his ability to blend melodic emotion with hard-hitting drill.

Sleepy’s career was briefly halted in 2023 when he was indicted in a 140-count gang-related case linked to multiple shootings and one murder. Following his release, he returned to music stronger than ever, releasing his second studio album, Boy Meets World, on September 15, 2023. The project featured notable collaborations, including “GBG” with Marshmello and “Anxiety” with Doechii.

In 2024, he continued his resurgence with singles such as “Cupid’s Guidance” and “Winners in Paris”, solidifying his place in hip-hop’s new wave.

With a gritty backstory and a raw, melodic style, Sleepy Hallow remains a standout voice in the Brooklyn drill scene and a rising force in mainstream rap.