Sleepy Hallow

Biography

Tegan Joshua Anthony Chambers, known professionally as Sleepy Hallow, is a Jamaican-American rapper and singer-songwriter who specializes in Brooklyn drill. Born in Jamaica, Chambers was raised in Flatbush, Brooklyn, New York City, alongside frequent collaborator and co-founder of Winners Circle Entertainment 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 verse on the Sheff G's 2019 single, "Flow". His 2020 single, "Deep End Freestyle×Deep End Freestyle3 April 2020 · SingleSpotifyYouTube Music (search)Tracklist · 1 track1Deep End Freestyle1:55" (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×Don't Sleep31 October 2019 · Studio albumSpotify (search)YouTube Music (search)Tracklist · 14 tracks1Movie (Intro)1:4422 Fake3:063Breakin Bad (Okay)2:114I Get Luv1:435Bestie2:306Calling2:047Pray 4OR2:598Dis Summah3:009Tension2:2910Get Low2:0911Demons2:0112Switch Up2:2413Agony2:2914187 (Outro)2:19. 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×Deep End Freestyle3 April 2020 · SingleSpotifyYouTube Music (search)Tracklist · 1 track1Deep End Freestyle1:55" featuring Fousheé, which peaked on the U.S. 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×Tip Toe12 August 2020 · SingleSpotify (search)YouTube Music (search)Tracklist · 1 track1Tip Toe3:01", produced by Great John.
In June 2021, he released his first studio album, Still Sleep?×Still Sleep?2 June 2021 · Studio albumSpotifyYouTube Music (search)Tracklist · 14 tracks1Basketball Dreams (intro)1:3222 Sauce3:0934or Daze2:34420552:045Make You (Snake Proof)1:586Equal3:037Scrub2:538Sleepy Freestyle2:159Chicken2:0910Mi no sabe1:191119993:2812Murda She Wrote2:0613Low Key2:3814Tip Toe3:01 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 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×Boy Meets World15 September 2023 · Studio albumSpotifyYouTube Music (search)Tracklist · 18 tracks1Driver’s Seat (intro)2:392Good Girls Ain’t No Fun2:233Motion2:284ADHD1:435All the Way2:406Damn2:117A N X I E T Y2:298Cash & Chow2:329GBG2:1110OTR Freestyle2:2011Goodbye2:1712BWV3:0813For You1:5914Pain Talk2:3715Die Young2:2916Self Control3:0617Perky Man2:0918Purple Heart2:10", 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".

Personal life

On May 15, 2023, Chambers was indicted along with 32 other alleged gang members including Sheff G for a multitude of gang conspiracy charges. After serving a 8 month sentence, he was released in June of 2026.
Chambers supported the Donald Trump 2024 presidential campaign, attending a rally in the Bronx alongside Sheff G.