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Sleepy Hallow

One of the leading exponents of Brooklyn drill, the American rapper known as Sleepy Hallow was born Tegan Joshua Anthony Chambers on December 20, 1999. Though born in Jamaica, he relocated to the United States with his family as a child, settling in the Brooklyn neighborhood of Flatbush. He started rapping at the age of 12 inspired by Biggie Smalls, 50 Cent, and Kendrick Lamar, and joined the hip-hop collective Eight Tray Gangsta Crips alongside future collaborator Sheff G. In 2017, Sleepy Hallow was signed to Junior Galette’s Nula Entertainment and dropped a handful of tracks in collaboration with Sheff G, including “Disrespect,” “Haters Hurtin,” and “Panic,” the duo’s breakout single. His debut mixtape, Don’t Sleep, arrived in 2019 and found the artist steering away from the drill sound of his earlier work in favor of a trap-based aesthetic. Sleepy Hallow followed up in 2020 with the EP Black House and the mixtape Sleepy for President, which spawned the viral hit “Deep End Freestyle.” The track climbed to Number 80 on the Billboard and garnered the attention of RCA Records, who quickly signed the rapper to their roster. With the support of a major label, Sleepy Hallow released his studio debut Still Sleep? in 2021, reaching Number 83 on the Billboard 200.