One of the leading exponents of Brooklyn drill, American rapper Sleepy Hallow was born Tegan Joshua Anthony Chambers on December 20, 1999. Born in Jamaica, he relocated to the United States with his family as a child, settling in the Brooklyn neighbourhood of Flatbush. Inspired by artists such as Biggie Smalls, 50 Cent, and Kendrick Lamar, he started rapping at the age of 12, before joining 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 the duo’s breakout single, “Panic.” His debut mixtape, Don’t Sleep, arrived in 2019, with the rapper steering away from his earlier drill-inspired work in favour of a more trap-based sound. 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 charts 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 9 on the rap charts with lead single “2055” charting around the world, attracting notable attention in Australia and New Zealand, reaching number 13 and 11 respectively and attaining double platinum status. He followed this success with “Die Young”, a collaboration with Canadian rapper 347aidan, the first single from his 2023 sophomore album, Boy Meets World, which was released in September, seeing him land at number 3 and 4 on the US Rap and US R&B/Hip Hop charts.