Sleepy Hallow

An early pioneer of Brooklyn's drill scene, rapper Sleepy Hallow made his name with the iconic "Panic" set of singles, pushing the genre's sonics forward alongside close collaborator Sheff G. He broke through to mainstream audiences and chart success first with his 2020 single "Deep End Freestyle," then with the expanded production and songwriting of his 2021 debut studio album, Still Sleep?, and once more with 2022's "Die Young." In 2023 he released his second album, Boy Meets World, revealing even more of himself with emotionally naked lyricism and introspective looks at loss and mental health struggles. Tracks like "Winners in Paris" and "Yes Freestyle" appeared in 2024.

Born in Jamaica and raised in Brooklyn, New York, Sleepy Hallow kicked off his musical career with a string of singles, demonstrating his kinship with local collaborator Sheff G on early tracks like "Disrespect" (July 2017) and "Haters Hurtin" (August 2017). At the forefront of Brooklyn's emerging drill scene, the duo's early material reconfigured the British drill beats of AXL and MKthePlug within a New York context, adding local slang and alternate flows to the U.K. style. Together with DoubleG, the pair soon released the iconic single "Panic," which would become the first of a series as the rappers continued to develop their sonics. After closing out 2017 with "Saucin" and the collaboration "Glocc wit a Sticc," Sleepy joined with Sheff again in January the next year for "Attic," followed shortly by a second installment in the "Panic" series. Continuing to build his brand on bassy vocals and brutal imagery, the rapper moved through 2018 with a mix of solo and Sheff G-assisted singles, with a third release in the "Panic" series becoming the duo's biggest hit to date.

2019 saw Sleepy work heavily on two full-length projects, and he was featured seven times on Sheff's debut, The Unluccy Luccky Kid, before issuing his own debut mixtape, Don't Sleep. While both tapes retained the pair's charisma and signature flows, they swerved significantly away from their drill roots, instead landing variably on the trap spectrum. While still primarily focused on trap, Sleepy's 2020 offerings were more diverse in their approach: both his second tape, Sleepy for President, and The Black House EP ranged from guitar-driven introspection to experimental drill styles. He soon found his biggest hit to date with "Deep End Freestyle," a minimal track that found international success through its use in viral video content. The newfound attention around the song led to Sleepy Hallow signing on with RCA.

Now backed by a major label, Sleepy began work on a proper studio album. Led by the hit single "2055," his full-length debut, Still Sleep?, arrived in June 2021, boasting elevated production and even more advances beyond the standard drill elements. It was also a commercial success, hitting number 16 on the Billboard 200 on its way to gold status. Sleepy returned to making singles with 2022's "Die Young." Featuring 347Aidan, the track appeared on Billboard's Hot Rap Songs chart. "2 Minutes of Pain" (with Alborosie) and "Marie" were released that year, and "Pain Talk" (with Lil Tjay) arrived in 2023. These singles set the scene for a second studio album, Boy Meets World, which was released in September of 2023. The album included appearances from Fivio Foreign, Doechii, Marshmello, and others, and rose to the number 17 slot on the U.S. Billboard 200 chart. Over the next year, Sleepy issued solo singles like "Cupid's Guidance" and "Winners in Paris," and he teamed up again with Sheff G for 2024's "Yes Freestyle." ~ David Crone