In June 2021, he released his first studio album, Still Sleep? The album includes the single, " 2055", which was released alongside a video that sees an animated Sleepy Hallow in an alternate, futuristic universe. Sleepy Hallow and Sheff G released the single "Tip Toe", produced by Great John. In August 2020, Winners Circle Entertainment started a partnership with RCA Records. The single has over 85 million streams and was certified gold by RIAA in August 2020. The mixtape featured the hit single " Deep End Freestyle" featuring FousheƩ which peaked on the US Billboard Hot 100 chart at number 80 on June 20, 2020. In 2020, he released his second mixtape, Sleepy for President. In the same year, Winners Circle Entertainment was founded, with Sleepy Hallow as one of the first signees. In 2019, Sleepy Hallow released his debut mixtape, Don't Sleep. He and Sheff G were signed to former NFL player, Junior Galette's music record label, Nula Entertainment from 2017 to 2018. He first met friend and collaborator Sheff G when the two were preparing to fight, but stopped when Sheff G was impressed with how Chambers carried himself.
Chambers dropped out of school in the ninth grade. He later picked the name "Sleepy Hallow" as his rap name as that was his name in the streets. As a child, Chambers immigrated from Jamaica to the Flatbush section of Brooklyn, New York City.