Sleepy Hallow
American rapper
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.
01Early 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.
02Career
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 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".
03Personal 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.
04Discography
Studio albums
| Title | Album details | Peak chart positions | Certifications | ||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| US |
US R&B/HH |
US Rap |
AUS |
CAN |
DEN |
NZ |
SWE | ||||
| Still Sleep? |
|
16 | 10 | 9 | 90 | 15 | 38 | 39 | 50 | ||
| Boy Meets World |
|
17 | 4 | 3 | 32 | 10 | , | 19 | , | ||
| Read This When You Wake Up |
|
, | , | , | , | , | , | , | , | ||
| ", " denotes a recording that did not chart or was not released in that territory. | |||||||||||
Mixtapes
| Title | Mixtape details | Peak chart positions | |||
|---|---|---|---|---|---|
| US |
US R&B/HH |
US Rap |
CAN | ||
| Sleepy Hallow Presents: Sleepy for President |
|
48 | 32 | 25 | 61 |
Singles
As lead artist
| Title | Year | Peak chart positions | Certifications | Album | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| US |
AUS |
CAN |
IRE |
NZ |
SWE |
UK |
WW | ||||
| "Deep End Freestyle" (with Fousheé) |
2020 | 80 | , | 69 | , | , | , | 93 | , |
|
Sleepy Hallow Presents: Sleepy for President |
| "Don't Panic" | , | , | , | , | , | , | , | , | |||
| "Baddie Betty Boop" | , | , | , | , | , | , | , | , | |||
| "Anxiety Freestyle" | , | , | , | , | , | , | , | , | |||
| "Tip Toe" (with Sheff G) |
, | , | , | , | , | , | , | , |
|
Still Sleep? | |
| "2055" (solo or remix featuring Coi Leray) |
2021 | 51 | 13 | 17 | 21 | 11 | 65 | 21 | , |
| |
| "Die Young" (featuring 347aidan) |
2022 | 60 | 38 | 15 | , | , | , | 45 | , |
|
Boy Meets World |
| "2 Mins of Pain" (featuring Alborosie) |
, | , | , | , | , | , | , | , | Non-album singles | ||
| "Marie" | , | , | , | , | , | , | , | , | |||
| "Pain Talk" (featuring Lil Tjay) |
2023 | , | , | , | , | , | , | , | , | Boy Meets World | |
| "Good Girls Ain't No Fun" | , | , | , | , | , | , | , | , | |||
| "GBG" (featuring Marshmello) |
, | , | , | , | , | , | , | , | |||
| "Anxiety" (featuring Doechii) |
45 | 14 | 25 | 12 | 5 | 28 | 15 | 21 |
| ||
| "Winners in Paris" | 2024 | , | , | , | , | , | , | , | , | Read This When You Wake Up | |
| "Calm 3" | 2025 | , | , | , | , | , | , | , | , | Non-album single | |
| ", " denotes a recording that did not chart or was not released in that territory. | |||||||||||
As featured artist
| Title | Year | Album |
|---|---|---|
| "Panic" (Sheff G featuring Sleepy Hallow and Double G) |
2017 | Non-album singles |
| "Hurtin'" (Sheff G featuring Sleepy Hallow) | ||
| "Automatic" (Sheff G featuring Sleepy Hallow) |
2018 | The Unluccy Luccy Kid |
| "Addicted to the Cash" (Sheff G featuring Sleepy Hallow) |
Non-album singles | |
| "Panic 2" (Sheff G featuring Sleepy Hallow) | ||
| "Panic 3" (Sheff G featuring Sleepy Hallow) | ||
| "Flows, Pt.2" (Sheff G featuring Sleepy Hallow) |
2019 | The Unluccy Luccy Kid |
| "Brazy" (J.I the Prince of N.Y featuring Sleepy Hallow) |
Non-album single | |
| "Make It Happen" (Sheff G featuring Sleepy Hallow) |
2020 | Just 4 Yall |
| "Goat Freestyle" (Eli Fross featuring Sleepy Hallow) |
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) |
The Golden Child |
Other charted and certified songs
| Title | Year | Peak chart positions | Certifications | Album | ||||||
|---|---|---|---|---|---|---|---|---|---|---|
| NZ Hot | ||||||||||
| "Breakin Bad (Okay)" (featuring Sheff G) |
2019 | , |
|
Don't Sleep | ||||||
| "Molly" (featuring Sheff G) |
2020 | , |
|
Sleepy Hallow Presents: Sleepy For President | ||||||
| "Weight On Me" (with Sheff G) |
, |
|
One and Only | |||||||
| "Basketball Dreams (Intro)" | , |
|
Still Sleep? | |||||||
| "Scrub" | 2021 | 39 |
||||||||
| "1999" | , |
| ||||||||
| "Lowkey" | , |
| ||||||||
| "Driver's Seat (Intro)" | 2023 | 25 | Boy Meets World | |||||||
| "All the Way" | 33 | |||||||||
| ", " denotes a recording that did not chart or was not released in that territory. | ||||||||||
Guest appearances
| Title | Year | Other artist(s) | Certifications | Album |
|---|---|---|---|---|
| "Flows" | 2019 | Sheff G |
|
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 Swish | Year of the H 3 | ||
| "Like Me" | 2022 | Sheff G | From The Can | |
| "Bad Breed" | ||||
| "Overseas" | Jay Bezzy, Sheff G |
Sources and credits
This article is adapted from the Wikipedia article “Sleepy Hallow”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Sleepy Hallow in 2019.png by DOGGTOWN DIGIT4L, CC BY 3.0
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