Sleepy Hallow

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" (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 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. 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.

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".

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.

Discography Studio albums + List of studio albums, with selected chart positions, certifications and album names Title Album details Peak chart positions Certifications US USR&B/HH USRap AUS CAN DEN NZ SWE Still Sleep? Released: June 2, 2021 Label: Winners Circle, RCA Format: Digital download, streaming 16 10 9 90 15 38 39 50 RIAA: Gold BPI: Silver MC: Gold RMNZ: Gold Boy Meets World Released: September 15, 2023 Label: Winners Circle, RCA Format: Digital download, streaming 17 4 3 32 10 — 19 — Read This When You Wake Up Released: December 13, 2024 Label: Winners Circle, RCA Format: Digital download, streaming — — — — — — — — "—" denotes a recording that did not chart or was not released in that territory.

Mixtapes + Title Mixtape details Peak chart positions US USR&B/HH USRap CAN Sleepy Hallow Presents: Sleepy for President Released: June 5, 2020 Label: Winners Circle, Empire Format: Digital download, streaming 48 32 25 61

Singles As lead artist + List of singles, with selected chart positions, showing year released and album name Title Year Peak chart positions Certifications Album US AUS IRE NZ WW "Deep End Freestyle" 2020 80 — 69 — — — 93 — RIAA: Platinum Sleepy Hallow Presents: Sleepy for President "Don't Panic" — — — — — — — — "Baddie Betty Boop" — — — — — — — — "Anxiety Freestyle" — — — — — — — — "Tip Toe" — — — — — — — — RIAA: Gold — Read This When You Wake Up "Calm 3" 2025 — — — — — — — — "—" denotes a recording that did not chart or was not released in that territory.

As featured artist

Other charted and certified songs +TitleYearPeak chart positionsCertificationsAlbum NZHot "1999"— RIAA: Gold "Lowkey"— RIAA: Gold "Driver's Seat (Intro)" 202325 Boy Meets World"All the Way"33 "—" denotes a recording that did not chart or was not released in that territory.

Guest appearances + List of non-single guest appearances, with other performing artists, showing year released, certifications and album name Title Year Other artist(s) Certifications Album "Flows" 2019 Sheff G RMNZ: Gold The Unluccy Luccy Kid "Demon Flow" 2020 Yak Yola, Sheff G Misunderstood "Wet Em Up Pt.2" Lil Tjay, Sheff G State of Emergency "Lil Big Bro Shit" Sheff G One and Only "Head Tap" Pressa, Sheff G Gardner "Goat Freestyle" Eli Fross Cesar "2020 Vision" 2021 DJ Drewski, Sheff G Seat at the Table "Steppas Freestyle" Eli Fross The Book of Eli "Run Up"Hamo Crime, mauley G, Sheff G, Rah SwishYear of the H 3 "Like Me" 2022 Sheff G From The Can "Bad Breed" "Overseas" Jay Bezzy, Sheff G