Tegan Joshua Anthony Chambers (born December 20, 1999), known professionally asSleepy Hallow,^[2] is a Jamaican-American rapper and singer-songwriter who specializes inBrooklyn drill.^[3] Born in Jamaica, Chambers was raised inFar Rockaway,Queens,New York City, alongside frequent collaboratorSheff G.^[4][5]

Sleepy Hallow
Sleepy Hallow in 2019
Background information
Birth name	Tegan Joshua Anthony Chambers
Born	(1999-12-20)December 20, 1999 (age 25) Jamaica
Origin	Far Rockaway,New York City, U.S
Genres	East Coast Hip hop Brooklyn drill
Occupations	Rapper songwriter
Years active	2017–present
Labels	Winners Circle RCA[1]
Website	winnerscirclestore.com

Signing with Winners Circle Entertainment in 2019, the label entered a joint venture withRCA Records the following year. Chambers first saw recognition for his 2019 single, "Flows" (with Sheff G).^[6] His 2020 single, "Deep End Freestyle" (featuringFousheé) received platinum certification by theRecording Industry Association of America (RIAA) and marked his first entry on theBillboard Hot 100.^[7] His 2021 single, "2055" peaked at number 51 on the chart.^[8]

As a child, Chambers immigrated from Jamaica to theFlatbush section ofBrooklyn, 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.^[9] He first met friend and collaboratorSheff G when the two were preparing to fight, but stopped when Sheff G was impressed with how Chambers carried himself.^[10]

He, Sheff G, and DizzyGotBands were signed to formerNFL playerJunior Galette's music record label Nula Entertainment from 2017 to 2018.^[11]

In 2019, Sleepy Hallow released his debut mixtape,Don't Sleep.^[12] In the same year, Winners Circle Entertainment was founded, with Sleepy Hallow as one of the first signees.^[13]

In 2020, he released his second mixtape,Sleepy for President.^[14][15] The mixtape featured the hit single "Deep End Freestyle" featuringFousheé, which peaked on the U.S.Billboard Hot 100 chart at number 80 on June 20, 2020.^[16] The single has over 85 million streams and wascertified gold byRIAA in August 2020.^[17][7]

In August 2020, Winners Circle Entertainment started a partnership withRCA Records.^[18] Sleepy Hallow and Sheff G released the single "Tip Toe", produced by Great John.^[19]

In June 2021, he released his first studio album,Still Sleep?^[20] The album includes the single, "2055", which was released alongside a video that sees an animated Sleepy Hallow in an alternate, futuristic universe.^[20] The single would be certified double platinum in March 2022.^[21]

In May 2022, he released his single "Die Young", which features Canadian rapper347aidan, and was considered the best Shortest Trend Song onInstagram in July 2023 according to YouTubersJordan and Salish Matter, Peyton Delu, and the Royalty Family, as well as "one of the best songs onSpotify" byKansas City Chiefs andMiami Dolphins receiverTyreek Hill.

In September 2022, he released his single "2 Mins of Pain".^[22]

In November 2022, he released the single "Marie".^[23]

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.^[24]

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" featuringMarshmello and "Anxiety" featuringDoechii.^{[citation needed]}

On February 14, 2024, Sleepy Hallow released the single "Cupid's Guidance".^[25] On May 8, 2024, he released single "Winners In Paris".^[26]

On May 15, 2023, Chambers was indicted along with 32 other alleged gang members including Sheff G for a multitude of gang conspiracy charges.^[27]

• Read This When You Wake Up (2024)^[40]

• Sleepy Hallow atIMDb