Sleepy Hallow

About

Tegan Joshua Anthony Chambers, known as Sleepy Hallow, was born on December 20, 1999, in Jamaica and raised in Brooklyn, New York. Immigrating as a child, he started rapping around age 12 and later adopted the name Sleepy Hallow from his street nickname. Dropping out of school in ninth grade, he first gained attention with his 2019 single "Flows" featuring Sheff G. Sleepy Hallow's 2020 hit "Deep End Freestyle" achieved platinum status and marked his Billboard Hot 100 debut. His 2021 single "2055" peaked at number 51 on the chart and was certified quadruple platinum. Despite a rising career, Sleepy Hallow faced legal troubles in 2023, including a 140-count indictment linked to gang activity. His discography includes the mixtapes Don't Sleep (2019) and Sleepy for President (2020), as well as studio albums Still Sleep? (2021) and Boy Meets World (2023).