# Sleepy Hallow

Tegan Joshua Anthony Chambers (born December 20, 1999), 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 the Far Rockaway queens, 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 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", 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, and was considered the best Shortest Trend Song on Instagram in July 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.

## Discography
### Studio albums

List of studio albums, with selected chart positions :
| Title | Album details | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Certifications |
| Title | Album details | US | US R&B/HH | US Rap | AUS | CAN | DEN | NZ | SWE | Certifications |
| Still Sleep? | Released: June 2, 2021 Label: Winners Circle, RCA Format: Digital download, streaming | 16 | 10 | 9 | 90 | 15 | 38 | 39 | 50 | RIAA: Gold MC: 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 (2024)

### Mixtapes

| Title | Mixtape details | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions |
| Title | Mixtape details | US | US R&B/HH | US Rap | 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 | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Certifications | Album |
| Title | Year | US | AUS | CAN | IRE | NZ | SWE | UK | WW | Certifications | Album |
| "Deep End Freestyle" (with Fousheé) | 2020 | 80 | — | 69 | — | — | — | 93 | — | RIAA: Platinum BPI: Silver | Sleepy Hallow Presents: Sleepy for President |
| "Don't Panic" | 2020 | — | — | — | — | — | — | — | — | | Sleepy Hallow Presents: Sleepy for President |
| "Baddie Betty Boop" | 2020 | — | — | — | — | — | — | — | — | | Sleepy Hallow Presents: Sleepy for President |
| "Anxiety Freestyle" | 2020 | — | — | — | — | — | — | — | — | | Sleepy Hallow Presents: Sleepy for President |
| "Tip Toe" (with Sheff G) | 2020 | — | — | — | — | — | — | — | — | RIAA: Gold | Still Sleep? |
| "2055" (solo or remix featuring Coi Leray) | 2021 | 51 | 13 | 17 | 21 | 11 | 65 | 21 | — | RIAA: 4× Platinum ARIA: 2× Platinum BPI: Platinum MC: 4× Platinum | Still Sleep? |
| "Die Young" (featuring 347aidan) | 2022 | 60 | 38 | 15 | — | — | — | 45 | — | RIAA: Platinum MC: Platinum | Boy Meets World |
| "2 Mins of Pain" (featuring Alborosie) | 2022 | — | — | — | — | — | — | — | — | | Non-album singles |
| "Marie" | 2022 | — | — | — | — | — | — | — | — | | Non-album singles |
| "Pain Talk" (featuring Lil Tjay) | 2023 | — | — | — | — | — | — | — | — | | Boy Meets World |
| "Good Girls Ain't No Fun" | 2023 | — | — | — | — | — | — | — | — | | Boy Meets World |
| "GBG" (featuring Marshmello) | 2023 | — | — | — | — | — | — | — | — | | Boy Meets World |
| "Anxiety" (featuring Doechii) | 2023 | 45 | 14 | 25 | 12 | 5 | 28 | 15 | 21 | | Boy Meets World |
| "Winners in Paris" | 2024 | — | — | — | — | — | — | — | — | | Non-album single |
| "—" denotes a recording that did not chart or was not released in that territory. ||||||||||||

#### As featured artist

List of singles as a featured artist, showing year released and album name :
| Title | Year | Album |
| "Panic" (Sheff G featuring Sleepy Hallow and Double G) | 2017 | Non-album singles |
| "Hurtin'" (Sheff G featuring Sleepy Hallow) | 2017 | Non-album singles |
| "Automatic" (Sheff G featuring Sleepy Hallow) | 2018 | The Unluccy Luccy Kid |
| "Addicted to the Cash" (Sheff G featuring Sleepy Hallow) | 2018 | Non-album singles |
| "Panic 2" (Sheff G featuring Sleepy Hallow) | 2018 | Non-album singles |
| "Panic 3" (Sheff G featuring Sleepy Hallow) | 2018 | Non-album singles |
| "Flows, Pt.2" (Sheff G featuring Sleepy Hallow) | 2019 | The Unluccy Luccy Kid |
| "Brazy" (J.I the Prince of N.Y featuring Sleepy Hallow) | 2019 | Non-album single |
| "Make It Happen" (Sheff G featuring Sleepy Hallow) | 2020 | Just 4 Yall |
| "Goat Freestyle" (Eli Fross featuring Sleepy Hallow) | 2020 | Cesar |
| "Run It Up" (Sheff G featuring Sleepy Hallow and A Boogie wit da Hoodie) | 2021 | From The Can |
| "No Love" (Fredo Bang featuring Sleepy Hallow) | 2022 | Two-Face Bang 2 |
| "Bad Days" (Eli Fross featuring Sleepy Hallow) | 2022 | The Golden Child |

### Other charted and certified songs

| Title | Year | Peak chart positions | Certifications | Album |
| Title | Year | NZ Hot | Certifications | Album |
| "Breakin Bad (Okay)" (featuring Sheff G) | 2019 | — | RIAA: Gold | Don't Sleep |
| "Molly" (featuring Sheff G) | 2020 | — | RIAA: Gold | Sleepy Hallow Presents: Sleepy For President |
| "Weight On Me" (with Sheff G) | 2020 | — | RIAA: Gold | One and Only |
| "Basketball Dreams (Intro)" | | — | RIAA: Gold | Still Sleep? |
| "Scrub" | 2021 | 39 | | Still Sleep? |
| "1999" | 2021 | — | RIAA: Gold | Still Sleep? |
| "Lowkey" | 2021 | — | RIAA: Gold | Still Sleep? |
| "Driver's Seat (Intro)" | 2023 | 25 | | Boy Meets World |
| "All the Way" | 2023 | 33 | | Boy Meets World |
| "—" 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 and album name :
| Title | Year | Other artist(s) | Album |
| "Flows" | 2019 | Sheff G | The Unluccy Luccy Kid |
| "Demon Flow" | 2020 | Yak Yola, Sheff G | Misunderstood |
| "Wet Em Up Pt.2" | 2020 | Lil Tjay, Sheff G | State of Emergency |
| "Lil Big Bro Shit" | 2020 | Sheff G | One and Only |
| "Head Tap" | 2020 | Pressa, Sheff G | Gardner |
| "Goat Freestyle" | 2020 | Eli Fross | Cesar |
| "2020 Vision" | 2021 | DJ Drewski, Sheff G | Seat at the Table |
| "Steppas Freestyle" | 2021 | Eli Fross | The Book of Eli |
| "Run Up" | 2021 | Hamo Crime, mauley G, Sheff G, Rah Swish | Year of the H 3 |
| "Like Me" | 2022 | Sheff G | From The Can |
| "Bad Breed" | 2022 | Sheff G | From The Can |
| "Overseas" | 2022 | Jay Bezzy, Sheff G | From The Can |