Sleepy Hallow

Not to be confused with Sleepy Hollow.

Tegan 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.

Sleepy Hallow
Sleepy Hallow in 2019
Background information
Birth name	Tegan Chambers
Born	Jamaica
Origin	Flatbush Brooklyn, New York City, U.S
Genres	East Coast Hip hop Brooklyn drill emo rap R&B
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 with RCA Records the following year. Chambers first saw recognition for his verse on the Sheff G's 2019 single, "Flow".^[2] 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.^[3] His 2021 single, "2055" peaked at number 51 on the chart.^[4]

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.^[5] 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.^[6]

Career

He, Sheff G, and DizzyGotBands were signed to former NFL player Junior Galette's music record label Nula Entertainment from 2017 to 2018.^[7]

In 2019, Sleepy Hallow released his debut mixtape, Don't Sleep.^[8] In the same year, Winners Circle Entertainment was founded, with Sleepy Hallow as one of the first signees.^[9]

In 2020, he released his second mixtape, Sleepy for President.^[10][11] 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.^[12] The single has over 85 million streams and was certified gold by RIAA in August 2020.^[13][3]

In August 2020, Winners Circle Entertainment started a partnership with RCA Records.^[14] Sleepy Hallow and Sheff G released the single "Tip Toe", produced by Great John.^[15]

In June 2021, he released his first studio album, Still Sleep?^[16] The album includes the single, "2055", which was released alongside a video that sees an animated Sleepy Hallow in an alternate, futuristic universe.^[16] The single would be certified double platinum in March 2022.^[17]

In September 2022, he released his single "2 Mins of Pain".^[18]

In November 2022, he released the single "Marie".^[19]

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.^[20]

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.^{[citation needed]}

On February 14, 2024, Sleepy Hallow released the single "Cupid's Guidance".^[21] On May 8, 2024, he released single "Winners In Paris".^[22]

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.^[23]

Chambers supported the Donald Trump 2024 presidential campaign, attending a rally in the Bronx alongside Sheff G.^[24]

Discography

Studio albums

List of studio albums, with selected chart positions, certifications and album names

Title	Album details	Peak chart positions								Certifications
		US [25]	US R&B/HH [26]	US Rap [27]	AUS [28]	CAN [29]	DEN [30]	NZ [31]	SWE [32]
Still Sleep?	Released: June 2, 2021 Label: Winners Circle, RCA Format: Digital download, streaming	16	10	9	90	15	38	39	50	RIAA: Gold[33] BPI: Silver[34] MC: Gold[35] RMNZ: Gold[36]
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[37] 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 [38]	US R&B/HH [39]	US Rap [40]	CAN [41]
Sleepy Hallow Presents: Sleepy for President[42]	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 [43]	AUS [28]	CAN [44]	IRE [45]	NZ [31]	SWE [32]	UK [46]	WW [47]
"Deep End Freestyle" (with Fousheé)	2020	80	—	69	—	—	—	93	—	RIAA: Platinum[33] BPI: Silver[34] RMNZ: Gold[48]	Sleepy Hallow Presents: Sleepy for President
"Don't Panic"		—	—	—	—	—	—	—	—
"Baddie Betty Boop"		—	—	—	—	—	—	—	—
"Anxiety Freestyle"		—	—	—	—	—	—	—	—
"Tip Toe" (with Sheff G)		—	—	—	—	—	—	—	—	RIAA: Gold[33]	Still Sleep?
"2055" (solo or remix featuring Coi Leray)[16]	2021	51	13	17	21	11	65	21	—	RIAA: 4× Platinum[33] ARIA: 2× Platinum[49] BPI: Platinum[34] MC: 4× Platinum[35] RMNZ: 2× Platinum [48]
"Die Young"[50] (featuring 347aidan)	2022	60	38	15	—	—[A]	—[B]	45	—	RIAA: Platinum[33] BPI: Silver[34] MC: Platinum[35] RMNZ: Gold[48]	Boy Meets World
"2 Mins of Pain" (featuring Alborosie)		—	—	—	—	—[C]	—	—	—		Non-album singles
"Marie"		—	—	—	—	—[D]	—	—	—
"Pain Talk" (featuring Lil Tjay)	2023	—	—	—	—	—[E]	—	—	—		Boy Meets World
"Good Girls Ain't No Fun"		—	—	—	—	—[F]	—	—	—
"GBG" (featuring Marshmello)		—	—	—	—	—[G]	—	—	—
"Anxiety" (featuring Doechii)		45	14	25	12	5	28	15	21	RIAA: Gold[33] MC: Platinum[35]
"Winners in Paris"	2024	—	—	—	—	—[H]	—	—	—		Read This When You Wake Up
"Calm 3"	2025	—	—	—	—	—[I]	—	—	—		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)
"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 [56]
"Breakin Bad (Okay)" (featuring Sheff G)	2019	—	RIAA: Gold[33]	Don't Sleep
"Molly" (featuring Sheff G)	2020	—	RIAA: Platinum[33] RMNZ: Gold[48]	Sleepy Hallow Presents: Sleepy For President
"Weight On Me" (with Sheff G)		—	RIAA: Gold[33] RMNZ: Gold[60]	One and Only
"Basketball Dreams (Intro)"		—	RIAA: Gold[33]	Still Sleep?
"Scrub"	2021	39 [61]
"1999"		—	RIAA: Gold[33]
"Lowkey"		—	RIAA: Gold[33]
"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

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[48]	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

Notes

1. "Die Young" did not enter the NZ Top 40 Singles Chart, but peaked at number five on the NZ Hot Singles Chart.^[51]
2. "Die Young" did not enter the Swedish Singellista Chart, but peaked at number 17 on the Swedish Heatseeker Chart.^[52]
3. "2 Mins of Pain" did not enter the NZ Top 40 Singles Chart, but peaked at number 36 on the NZ Hot Singles Chart.^[53]
4. "Marie" did not enter the NZ Top 40 Singles Chart, but peaked at number 16 on the NZ Hot Singles Chart.^[54]
5. "Pain Talk" did not enter the NZ Top 40 Singles Chart, but peaked at number 24 on the NZ Hot Singles Chart.^[55]
6. "Good Girls Ain't No Fun" did not enter the NZ Top 40 Singles Chart, but peaked at number 32 on the NZ Hot Singles Chart.^[56]
7. "GBG" did not enter the NZ Top 40 Singles Chart, but peaked at number 25 on the NZ Hot Singles Chart.^[57]
8. "Winners in Paris" did not enter the NZ Top 40 Singles Chart, but peaked at number 36 on the NZ Hot Singles Chart.^[58]
9. "Calm 3" did not enter the NZ Top 40 Singles Chart, but peaked at number 37 on the NZ Hot Singles Chart.^[59]