Teagan Joshua Anthony Chambers, known as Sleepy Hallow, is an American rapper and songwriter. He was born on 20 December 1999 in Jamaica.
As a child, Chambers immigrated from Jamaica to the Flatbush neighbourhood of Brooklyn, New York. Around the age of 12, he began rapping. He later chose the name ‘Sleepy Hallow’ as his rap pseudonym because that was the name he was called on the streets. Chambers dropped out of school in ninth grade.
In 2017-2018, he and Sheff G signed with Junior Galette's music label Nula Entertainment. In 2019, Sleepy Hallow released his debut mixtape Don't Sleep. That same year, Winners Circle Entertainment was founded, with Sleepy Hallow being one of the first signees.
In 2020, he released his second mixtape, Sleepy for President. The mixtape included the hit single ‘Deep End Freestyle’ featuring Foshi, which reached No. 80 on the US Billboard Hot 100 chart on 20 June 2020. The single has been listened to over 85 million times and was certified gold by the RIAA in August 2020. 2
In June 2021, he released his first studio album Still Sleep?