Sleepy Hallow
Biography
Tegan Joshua Anthony Chambers (born December 20, 1999), known professionally as Sleepy Hallow, is a Jamaican-American rapper and singer. He was born in Jamaica and later moved to the Flatbush section of Brooklyn, New York City. Around the age of 12, he began rapping and adopted the moniker "Sleepy Hallow" which was his street name. Chambers dropped out of high school in the ninth grade. He is a prominent figure in the Brooklyn drill scene.
Career Beginnings
Sleepy Hallow's career began to gain traction alongside his close friend and frequent collaborator, Sheff G. The two met in Flatbush and developed a strong friendship. They were signed to former NFL player Junior Galette's Nula Entertainment from 2017 to 2018. In 2017, they released singles like "Disrespect" and "Haters Hurtin". In 2019, Sleepy Hallow and Sheff G co-founded their own record label, Winners Circle Entertainment. That same year, Sleepy Hallow released his debut mixtape, *Don't Sleep*.
Rise to Prominence
In 2020, Sleepy Hallow released his second mixtape, *Sleepy for President*. The project featured the single "Deep End Freestyle" with Fousheé, which became a viral hit, partly due to its popularity on TikTok. The song peaked at number 80 on the Billboard Hot 100 and was certified gold by the RIAA. In August 2020, Winners Circle Entertainment entered into a partnership with RCA Records.
Studio Albums
His debut studio album, *Still Sleep?*, was released in June 2021. It included the highly successful single "2055", which was certified double platinum. A deluxe version of the album followed. His second studio album, *Boy Meets World*, was released in September 2023. This project was noted for its introspective and emotionally raw lyrics, with collaborations from artists like Fivio Foreign and Marshmello. He released another project titled *Read This When You Wake Up* in 2024.
Musical Style
Sleepy Hallow is recognized as a pioneer of the New York drill scene. His music often blends pop-savvy melodies with vivid storytelling about street life. He is also known for being one of the first drill artists in New York to go viral by using samples in his songs, a style that has been influential. His music is characterized by a melody-driven approach, his husky tone, and collaborations with producer Great John.