Sleepy Hallow

Tegan Joshua Anthony Chambers (born December 20, 1999), known professionally as Sleepy Hallow, is an American rapper who specializes in Brooklyn drill. Born in Jamaica, Chambers was raised in the Flatbush section of Brooklyn, New York City alongside frequent collaborator Sheff G.

Signing with Winners Circle Entertainment in 2019, the label entered a joint venture with RCA Records the following year. Chambers first saw recognition for his 2019 single, "Flows" (with Sheff G). His 2020 single, "Deep End Freestyle" (featuring Fousheé) received platinum certification by the Recording Industry Association of America (RIAA) and marked his first entry on the Billboard Hot 100. His 2021 single, "2055" peaked at number 51 on the chart.

Early life
As a child, Chambers immigrated from Jamaica to the Flatbush section of Brooklyn, New York City. Around the age of 12, he started to rap. He later picked the name "Sleepy Hallow" as his rap name as that was his name in the streets. Chambers dropped out of school in the ninth grade. 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.

Career
He, Sheff G, and DizzyGotBands were signed to former NFL player Junior Galette's music record label Nula Entertainment from 2017 to 2018.

In 2019, Sleepy Hallow released his debut mixtape, Don't Sleep. In the same year, Winners Circle Entertainment was founded, with Sleepy Hallow as one of the first signees.

In 2020, he released his second mixtape, Sleepy for President. The mixtape featured the hit single "Deep End Freestyle" featuring Fousheé, which peaked on the US Billboard Hot 100 chart at number 80 on June 20, 2020. The single has over 85 million streams and was certified gold by RIAA in August 2020.

In August 2020, Winners Circle Entertainment started a partnership with RCA Records. Sleepy Hallow and Sheff G released the single "Tip Toe", produced by Great John.

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. The single would be certified double platinum in March 2022.

In May 2022, he released his single "Die Young", which features Canadian rapper 347aidan. Which was considered the best Shortest Trend Song on Instagram in July of 2023 according to youtubers Jordan and Salish Matter, Peyton Delu, and the Royalty Family, as well as "one of the best songs on Spotify" by Kansas City Chiefs and Miami Dolphins receiver Tyreek Hill.

In September 2022, he released his single "2 Mins of Pain".

In November 2022, he released the single "Marie".

In May 2023, Sleepy Hallow was charged in a 140-count indictment, as the district attorney's office said the gang is linked to 12 shootings and a murder that was caught on camera.

On September 15, 2023, Sleepy Hallow released “Boy Meets World", his second studio album since getting out of jail. It features songs such as "GBG" featuring Marshmello and "Anxiety" featuring Doechii.

On February 14, 2024, Sleepy Hallow released the single "Cupid's Guidance". On May 8, 2024, he released single "Winners In Paris".

Legal issues
On May 15, 2023, Chambers was indicted along with 32 other alleged gang members including Sheff G for a multitude of gang conspiracy charges.

On May 30, 2023, Chambers announced on his Instagram story that he has been released on bail, and is now waiting for the trial to start.