Sleepy Hallow Biography (2026): Real Name, Age, Jamaican Roots, Brooklyn Story, Songs, Albums, Sheff G, Girlfriend and Latest Music
Sleepy Hallow Biography (2026): Real Name, Age, Jamaican Roots, Brooklyn Story, Songs, Albums, Sheff G, Girlfriend and Latest Music
Artist Spotlight · Updated October 27, 2026
9Some rappers have to shout to make you listen. Sleepy Hallow has never really needed to.
He can jump on a heavy drill beat, deliver a few lines in that deep, relaxed voice, and somehow make the entire song feel effortless. That's the kind of sound that helped turn a young Jamaican-born artist growing up in Brooklyn into an internationally recognized rapper.
If you've heard 2055, Deep End Freestyle, Die Young, Molly, ANXIETY or Weight On Me, you've already experienced what makes Sleepy Hallow different.
His music can be catchy and playful one minute, then surprisingly emotional the next. He talks about growing up, relationships, street life, friendship, ambition and the pressure that comes with success.
And here's something fans might be happy to hear: Sleepy Hallow is back releasing music in 2026. His September single Loaded arrived after a run of new songs, including Fine with Kyle Rich and WTW? First Day Out. A follow-up to his breakthrough Still Sleep? project has also been announced.
Audible Treats+1 Listen on Spotify Instagram Apple Music
Artist Spotlight · Updated October 27, 2026
Some rappers have to shout to make you listen. Sleepy Hallow has never really needed to.
He can jump on a heavy drill beat, deliver a few lines in that deep, relaxed voice, and somehow make the entire song feel effortless. That's the kind of sound that helped turn a young Jamaican-born artist growing up in Brooklyn into an internationally recognized rapper.
If you've heard 2055, Deep End Freestyle, Die Young, Molly, ANXIETY or Weight On Me, you've already experienced what makes Sleepy Hallow different.
His music can be catchy and playful one minute, then surprisingly emotional the next. He talks about growing up, relationships, street life, friendship, ambition and the pressure that comes with success.
And here's something fans might be happy to hear: Sleepy Hallow is back releasing music in 2026. His September single Loaded arrived after a run of new songs, including Fine with Kyle Rich and WTW? First Day Out. A follow-up to his breakthrough Still Sleep? project has also been announced.
Who is Sleepy Hallow?
Sleepy Hallow is a Jamaican-American rapper, singer and songwriter best known for helping shape the Brooklyn drill sound alongside his longtime friend and music partner, Sheff G.
His full name is Tegan Joshua Anthony Chambers, and he was born on December 20, 1999, in Jamaica. He moved to Brooklyn, New York, as a child and grew up in East Flatbush.
At 26 years old in October 2026, he already has several major projects, a billion-stream hit and a catalogue that has attracted listeners far beyond New York.
What makes him stand out is his combination of low-pitched vocals, smooth flows and imaginative production. Instead of sticking to one kind of drill beat, he experiments with samples, guitars, dreamy melodies and even pop-inspired sounds.
Sleepy Hallow is a Jamaican-American rapper, singer and songwriter best known for helping shape the Brooklyn drill sound alongside his longtime friend and music partner, Sheff G.
His full name is Tegan Joshua Anthony Chambers, and he was born on December 20, 1999, in Jamaica. He moved to Brooklyn, New York, as a child and grew up in East Flatbush.
At 26 years old in October 2026, he already has several major projects, a billion-stream hit and a catalogue that has attracted listeners far beyond New York.
What makes him stand out is his combination of low-pitched vocals, smooth flows and imaginative production. Instead of sticking to one kind of drill beat, he experiments with samples, guitars, dreamy melodies and even pop-inspired sounds.
Sleepy Hallow's quick facts
Information
Details
Full name
Tegan Joshua Anthony Chambers
Stage name
Sleepy Hallow
Date of birth
December 20, 1999
Age
26 years old
Birth country
Jamaica
Hometown
East Flatbush, Brooklyn, New York
Nationality
Jamaican-American
Occupation
Rapper, singer and songwriter
Genres
Brooklyn drill, hip-hop, trap, melodic rap
Active since
Approximately 2017
Record labels
Winners Circle Entertainment, RCA Records
Frequent producer
Great John
Closest musical collaborator
Sheff G
Breakthrough song
Deep End Freestyle
Biggest Spotify hit
2055
Latest released single
Loaded (September 25, 2026)
Most recent studio album
Read This When You Wake Up (2024)
Instagram
Spotify
Information | Details |
|---|---|
Full name | Tegan Joshua Anthony Chambers |
Stage name | Sleepy Hallow |
Date of birth | December 20, 1999 |
Age | 26 years old |
Birth country | Jamaica |
Hometown | East Flatbush, Brooklyn, New York |
Nationality | Jamaican-American |
Occupation | Rapper, singer and songwriter |
Genres | Brooklyn drill, hip-hop, trap, melodic rap |
Active since | Approximately 2017 |
Record labels | Winners Circle Entertainment, RCA Records |
Frequent producer | Great John |
Closest musical collaborator | Sheff G |
Breakthrough song | Deep End Freestyle |
Biggest Spotify hit | 2055 |
Latest released single | Loaded (September 25, 2026) |
Most recent studio album | Read This When You Wake Up (2024) |
Spotify |
From Jamaica to Brooklyn: Where Sleepy Hallow's story began
8Sleepy Hallow wasn't born in New York, even though Brooklyn is a huge part of his identity.
He was born in Jamaica and moved to Brooklyn with his mother and siblings when he was about five years old. The family settled in East Flatbush, an area that would influence both his personality and the music he later created.
His Jamaican background meant music was always close by. He grew up hearing Caribbean sounds as well as American hip-hop, including artists associated with Young Money, Drake and Kanye West.
In an interview, he explained that he loved the feeling of listening to a beat and being transported somewhere else in his mind.
He began experimenting with rap around the age of 12, long before anybody outside his neighborhood knew his name.
Growing up wasn't always straightforward. He experienced trouble during his teenage years and spent time in juvenile detention. But music gradually became something he could concentrate on and build a future around.
A major turning point came when he connected with another young Brooklyn rapper, Sheff G.
Their partnership would eventually help change the sound of New York drill.
Read more about his upbringing in XXL's Sleepy Hallow interview and his conversation about growing up and musical influences.
XXL Mag+1
Sleepy Hallow wasn't born in New York, even though Brooklyn is a huge part of his identity.
He was born in Jamaica and moved to Brooklyn with his mother and siblings when he was about five years old. The family settled in East Flatbush, an area that would influence both his personality and the music he later created.
His Jamaican background meant music was always close by. He grew up hearing Caribbean sounds as well as American hip-hop, including artists associated with Young Money, Drake and Kanye West.
In an interview, he explained that he loved the feeling of listening to a beat and being transported somewhere else in his mind.
He began experimenting with rap around the age of 12, long before anybody outside his neighborhood knew his name.
Growing up wasn't always straightforward. He experienced trouble during his teenage years and spent time in juvenile detention. But music gradually became something he could concentrate on and build a future around.
A major turning point came when he connected with another young Brooklyn rapper, Sheff G.
Their partnership would eventually help change the sound of New York drill.
Read more about his upbringing in XXL's Sleepy Hallow interview and his conversation about growing up and musical influences.
How Sleepy Hallow met Sheff G
6You can't tell the full story of Sleepy Hallow without talking about Sheff G.
Today, they're known as two of the important voices behind Brooklyn drill. But their friendship didn't begin as a music-business partnership.
According to accounts shared in interviews, the two first crossed paths during a disagreement that almost turned into a fight. Instead, they developed respect for each other and eventually became close friends.
That friendship turned into music.
Songs such as Panic, Disrespect, Flows, Tip Toe and Breakin Bad (Okay) helped the pair build a following.
They were among the artists bringing a distinctly Brooklyn sound to drill music, combining hard-hitting bass, UK-inspired production and local street slang.
But while Sheff G often leaned into a more direct, aggressive delivery, Sleepy Hallow developed a relaxed, melodic style.
The difference worked perfectly.
They also became closely associated with Winners Circle Entertainment, the music collective and label that helped establish their careers.
Their friendship, business partnership and musical chemistry have remained important parts of their public identities.
For a deeper look at their connection, read Complex's interview with Sleepy Hallow and his AllMusic biography.
You can't tell the full story of Sleepy Hallow without talking about Sheff G.
Today, they're known as two of the important voices behind Brooklyn drill. But their friendship didn't begin as a music-business partnership.
According to accounts shared in interviews, the two first crossed paths during a disagreement that almost turned into a fight. Instead, they developed respect for each other and eventually became close friends.
That friendship turned into music.
Songs such as Panic, Disrespect, Flows, Tip Toe and Breakin Bad (Okay) helped the pair build a following.
They were among the artists bringing a distinctly Brooklyn sound to drill music, combining hard-hitting bass, UK-inspired production and local street slang.
But while Sheff G often leaned into a more direct, aggressive delivery, Sleepy Hallow developed a relaxed, melodic style.
The difference worked perfectly.
They also became closely associated with Winners Circle Entertainment, the music collective and label that helped establish their careers.
Their friendship, business partnership and musical chemistry have remained important parts of their public identities.
For a deeper look at their connection, read Complex's interview with Sleepy Hallow and his AllMusic biography.
How Sleepy Hallow became famous
Deep End Freestyle: The viral breakthrough
In 2020, Sleepy Hallow released Deep End Freestyle, a short but memorable recording built around a vocal sample from singer Fousheé.
The sample added a haunting feeling to the instrumental, while Sleepy's relaxed flow made the track unusually catchy.
The song caught fire on social media, especially TikTok, introducing him to listeners who had never followed the Brooklyn drill scene.
It became his first song to enter the Billboard Hot 100 and was certified platinum in the United States.
The recording also helped draw attention to Fousheé, whose sampled vocals later became associated with her own breakthrough song Deep End.
In 2020, Sleepy Hallow released Deep End Freestyle, a short but memorable recording built around a vocal sample from singer Fousheé.
The sample added a haunting feeling to the instrumental, while Sleepy's relaxed flow made the track unusually catchy.
The song caught fire on social media, especially TikTok, introducing him to listeners who had never followed the Brooklyn drill scene.
It became his first song to enter the Billboard Hot 100 and was certified platinum in the United States.
The recording also helped draw attention to Fousheé, whose sampled vocals later became associated with her own breakthrough song Deep End.
2055: The song that took him global
Then came 2055 in 2021.
This is the song that made Sleepy Hallow impossible for many mainstream listeners to ignore.
Produced by Great John, 2055 features a dreamy melody, a distinctive instrumental and some of Sleepy's most recognizable vocal delivery.
Rather than sounding like an ordinary aggressive drill song, it feels almost like a futuristic, floating soundtrack.
The song reached No. 51 on the Billboard Hot 100 and went on to exceed one billion Spotify streams.
It also showed that Sleepy could appeal to people who didn't usually listen to drill music.
Then came 2055 in 2021.
This is the song that made Sleepy Hallow impossible for many mainstream listeners to ignore.
Produced by Great John, 2055 features a dreamy melody, a distinctive instrumental and some of Sleepy's most recognizable vocal delivery.
Rather than sounding like an ordinary aggressive drill song, it feels almost like a futuristic, floating soundtrack.
The song reached No. 51 on the Billboard Hot 100 and went on to exceed one billion Spotify streams.
It also showed that Sleepy could appeal to people who didn't usually listen to drill music.
Die Young and the emotional side of Sleepy Hallow
In 2022, Sleepy released Die Young, featuring Canadian singer and rapper 347aidan.
The song explores fear, survival and the uncertainty of life. Its emotional melody helped it become another major streaming success.
These three songs — Deep End Freestyle, 2055 and Die Young — are excellent starting points for anybody discovering his music.
You can find all three through his Apple Music catalogue and Spotify artist page.
AllMusic+1
In 2022, Sleepy released Die Young, featuring Canadian singer and rapper 347aidan.
The song explores fear, survival and the uncertainty of life. Its emotional melody helped it become another major streaming success.
These three songs — Deep End Freestyle, 2055 and Die Young — are excellent starting points for anybody discovering his music.
You can find all three through his Apple Music catalogue and Spotify artist page.
Sleepy Hallow's complete albums and discography
Sleepy Hallow's musical journey is interesting because you can actually hear him growing as an artist.
His earliest projects sound like a hungry young rapper trying to establish himself in Brooklyn. As his career develops, the production becomes more adventurous, the melodies more memorable, and the stories increasingly personal.
Here's how his albums and mixtapes fit together.
Sleepy Hallow's musical journey is interesting because you can actually hear him growing as an artist.
His earliest projects sound like a hungry young rapper trying to establish himself in Brooklyn. As his career develops, the production becomes more adventurous, the melodies more memorable, and the stories increasingly personal.
Here's how his albums and mixtapes fit together.
1. DON'T SLEEP (2019)
DON'T SLEEP
October 31, 2019 · 14 tracks · Mixtape
This is the project that introduced many listeners to Sleepy Hallow as a solo artist. It's full of raw Brooklyn energy, catchy flows and collaborations with Sheff G.
Breakin Bad (Okay), Bestie and Pray 4OR are among its standout records.
Complete tracklist
Movie (Intro)
2 Fake
Breakin Bad (Okay) — with Sheff G
I Get Luv
Bestie
Calling
Pray 4OR — with Sheff G
Dis Summah
Tension
Get Low — with ABG Neal
Demons — with Sheff G
Switch Up
Agony
187 (Outro)
DON'T SLEEP
October 31, 2019 · 14 tracks · Mixtape
This is the project that introduced many listeners to Sleepy Hallow as a solo artist. It's full of raw Brooklyn energy, catchy flows and collaborations with Sheff G.
Breakin Bad (Okay), Bestie and Pray 4OR are among its standout records.
Complete tracklist
Movie (Intro)
2 Fake
Breakin Bad (Okay) — with Sheff G
I Get Luv
Bestie
Calling
Pray 4OR — with Sheff G
Dis Summah
Tension
Get Low — with ABG Neal
Demons — with Sheff G
Switch Up
Agony
187 (Outro)
2. Sleepy Hallow Presents: Sleepy for President (2020)
Sleepy Hallow Presents: Sleepy for President
June 5, 2020 · 12 tracks · Approximately 28 minutes
This is one of Sleepy's most important early projects.
It includes Deep End Freestyle, the viral song that pushed his music into the mainstream, and Molly, another fan favourite with Sheff G.
Complete tracklist
Deep End Freestyle — featuring Fousheé
Molly — with Sheff G
6am in NY
Water — featuring Sheff G
Don't Panic — featuring Sheff G
Baddie Betty Boop — with Fivio Foreign
BMH
Nauseous — with Jay Critch
Bankroll
Bad Luck
Anxiety Freestyle
All In (Outro)
What makes this mixtape so enjoyable is its variety. Some songs have a relaxed, almost playful feeling, while others sound much darker.
It's a great starting point if you want to hear how Sleepy Hallow started experimenting beyond traditional drill.
Sleepy Hallow Presents: Sleepy for President
June 5, 2020 · 12 tracks · Approximately 28 minutes
This is one of Sleepy's most important early projects.
It includes Deep End Freestyle, the viral song that pushed his music into the mainstream, and Molly, another fan favourite with Sheff G.
Complete tracklist
Deep End Freestyle — featuring Fousheé
Molly — with Sheff G
6am in NY
Water — featuring Sheff G
Don't Panic — featuring Sheff G
Baddie Betty Boop — with Fivio Foreign
BMH
Nauseous — with Jay Critch
Bankroll
Bad Luck
Anxiety Freestyle
All In (Outro)
What makes this mixtape so enjoyable is its variety. Some songs have a relaxed, almost playful feeling, while others sound much darker.
It's a great starting point if you want to hear how Sleepy Hallow started experimenting beyond traditional drill.
3. The Black House (2020)
The Black House
July 31, 2020 · Five-track EP
A short project from Sleepy's early period that includes Perc Talkin, Somebody and Quarantine Boo.
Although not as commercially recognised as his later albums, it offers another look at his development.
The Black House
July 31, 2020 · Five-track EP
A short project from Sleepy's early period that includes Perc Talkin, Somebody and Quarantine Boo.
Although not as commercially recognised as his later albums, it offers another look at his development.
4. Still Sleep? (2021)
Still Sleep?
June 2, 2021 · 14 tracks · 34 minutes
This was the album that truly elevated Sleepy Hallow's solo career.
It features his biggest song, 2055, alongside 2 Sauce, 1999, Low Key and Basketball Dreams.
The album reached No. 16 on the Billboard 200 and later earned a gold certification in the United States.
Complete tracklist
Basketball Dreams (Intro)
2 Sauce
4or Daze
2055
Make You (Snake Proof)
Equal
Scrub
Sleepy Freestyle
Chicken
Mi No Sabe
1999
Murda She Wrote
Low Key (Bonus)
Tip Toe (Bonus) — with Sheff G
The album's success helped prove that Brooklyn drill artists could achieve mainstream popularity while experimenting with different musical styles.
A deluxe edition followed later in 2021, expanding the collection with additional recordings, including Luv Em All.
Still Sleep?
June 2, 2021 · 14 tracks · 34 minutes
This was the album that truly elevated Sleepy Hallow's solo career.
It features his biggest song, 2055, alongside 2 Sauce, 1999, Low Key and Basketball Dreams.
The album reached No. 16 on the Billboard 200 and later earned a gold certification in the United States.
Complete tracklist
Basketball Dreams (Intro)
2 Sauce
4or Daze
2055
Make You (Snake Proof)
Equal
Scrub
Sleepy Freestyle
Chicken
Mi No Sabe
1999
Murda She Wrote
Low Key (Bonus)
Tip Toe (Bonus) — with Sheff G
The album's success helped prove that Brooklyn drill artists could achieve mainstream popularity while experimenting with different musical styles.
A deluxe edition followed later in 2021, expanding the collection with additional recordings, including Luv Em All.
5. Boy Meets World (2023)
Boy Meets World
September 15, 2023 · 18 tracks · Approximately 43 minutes
This album brought a more emotional side of Sleepy Hallow into focus.
He explored relationships, personal pressure and mental health, moving comfortably between energetic drill records and softer melodies.
One of its most popular tracks, ANXIETY, features Doechii.
Among the album's songs are Driver's Seat (Intro), Good Girls Ain't No Fun, Motion, ADHD, All The Way, Damn, ANXIETY and Cash & Chow.
The album reached No. 17 on the Billboard 200.
It's a particularly good project for listeners who enjoy Sleepy Hallow's melodic side rather than only his early drill recordings.
AllMusic+1
Boy Meets World
September 15, 2023 · 18 tracks · Approximately 43 minutes
This album brought a more emotional side of Sleepy Hallow into focus.
He explored relationships, personal pressure and mental health, moving comfortably between energetic drill records and softer melodies.
One of its most popular tracks, ANXIETY, features Doechii.
Among the album's songs are Driver's Seat (Intro), Good Girls Ain't No Fun, Motion, ADHD, All The Way, Damn, ANXIETY and Cash & Chow.
The album reached No. 17 on the Billboard 200.
It's a particularly good project for listeners who enjoy Sleepy Hallow's melodic side rather than only his early drill recordings.
6. Read This When You Wake Up (2024)
Read This When You Wake Up
December 2024 · 20 tracks · Approximately 49 minutes
One of his most varied albums, this project moves between heavy beats, emotional melodies and relaxed, atmospheric production.
Featured artists include Babyface Ray, Sheff G, Jay Bezzy, Gray Hawken and B.B. Sofia.
Complete tracklist
Melatonin
Alfebet
Madness
Winners In Paris
Tat My Name
Mmm
Top Tier — featuring Babyface Ray
Ain't Nun — featuring Dracodontjam
Call Me — featuring Sheff G
Upgrade My Life
Picture Me
Party Crasher
Drowning (Beverly Hills)
LAX — featuring Jay Bezzy
2AM in LA
Nostalgia — featuring Gray Hawken
All Mine
She Like (Fashion)
Like Practice — featuring Jay Bezzy
Last Song — featuring B.B. Sofia
The streaming release is dated December 12–13, 2024, depending on the music service and location.
Spotify+1
Read This When You Wake Up
December 2024 · 20 tracks · Approximately 49 minutes
One of his most varied albums, this project moves between heavy beats, emotional melodies and relaxed, atmospheric production.
Featured artists include Babyface Ray, Sheff G, Jay Bezzy, Gray Hawken and B.B. Sofia.
Complete tracklist
Melatonin
Alfebet
Madness
Winners In Paris
Tat My Name
Mmm
Top Tier — featuring Babyface Ray
Ain't Nun — featuring Dracodontjam
Call Me — featuring Sheff G
Upgrade My Life
Picture Me
Party Crasher
Drowning (Beverly Hills)
LAX — featuring Jay Bezzy
2AM in LA
Nostalgia — featuring Gray Hawken
All Mine
She Like (Fashion)
Like Practice — featuring Jay Bezzy
Last Song — featuring B.B. Sofia
The streaming release is dated December 12–13, 2024, depending on the music service and location.
Sleepy Hallow's latest songs in 2026
8After a quieter period, Sleepy Hallow returned to releasing music regularly in 2026.
The new songs have reminded listeners of the relaxed delivery and memorable hooks that made him popular in the first place.
Release
Date
Details
Baby I
2026
Collaboration with Sheff G
Young & Dumb
2026
Melodic solo single
WTW? First Day Out
July 17, 2026
Two-track release
Fine
August 2026
Featuring Kyle Richh
Loaded
September 25, 2026
Produced by Great John
After a quieter period, Sleepy Hallow returned to releasing music regularly in 2026.
The new songs have reminded listeners of the relaxed delivery and memorable hooks that made him popular in the first place.
Release | Date | Details |
|---|---|---|
Baby I | 2026 | Collaboration with Sheff G |
Young & Dumb | 2026 | Melodic solo single |
WTW? First Day Out | July 17, 2026 | Two-track release |
Fine | August 2026 | Featuring Kyle Richh |
Loaded | September 25, 2026 | Produced by Great John |
Loaded — September 2026
Loaded is Sleepy Hallow's latest confirmed single as of October 27, 2026.
Produced by Great John, the song combines dreamy production with Sleepy's recognisable melodic delivery.
The music video was filmed in Miami and features scenes aboard a yacht and inside a luxury apartment.
It's a polished return to the kind of sound his fans enjoy.
Listen: Loaded — official streaming links.
Loaded is Sleepy Hallow's latest confirmed single as of October 27, 2026.
Produced by Great John, the song combines dreamy production with Sleepy's recognisable melodic delivery.
The music video was filmed in Miami and features scenes aboard a yacht and inside a luxury apartment.
It's a polished return to the kind of sound his fans enjoy.
Listen: Loaded — official streaming links.
Fine — featuring Kyle Richh
Fine brings Sleepy together with Kyle Richh.
The song connects two generations of New York drill, pairing Sleepy's established style with one of the newer names in the city's rap scene.
Listen: Fine — official streaming links.
Fine brings Sleepy together with Kyle Richh.
The song connects two generations of New York drill, pairing Sleepy's established style with one of the newer names in the city's rap scene.
Listen: Fine — official streaming links.
WTW? First Day Out
This two-song release arrived July 17, 2026.
It includes:
WTW? Freestyle — 2:49
First Day Out — featuring Annalise Azadian — 2:45
The release marked an important return following Sleepy's recent incarceration.
Listen: WTW? First Day Out on Spotify.
This two-song release arrived July 17, 2026.
It includes:
WTW? Freestyle — 2:49
First Day Out — featuring Annalise Azadian — 2:45
The release marked an important return following Sleepy's recent incarceration.
Listen: WTW? First Day Out on Spotify.
Is Sleepy Hallow releasing another album?
Yes, a follow-up project titled Still Sleep? 2 was announced in September 2026.
His publicity team described it as the sequel to his successful 2021 album Still Sleep?, with plans for an arrival around Halloween 2026.
However, as of October 27, the verified Apple Music catalogue still lists Loaded as his most recent release. The follow-up album should therefore be treated as announced, not yet confirmed as released.
The announcement appears in Audible Treats' September 25, 2026 press release.
Audible Treats
Yes, a follow-up project titled Still Sleep? 2 was announced in September 2026.
His publicity team described it as the sequel to his successful 2021 album Still Sleep?, with plans for an arrival around Halloween 2026.
However, as of October 27, the verified Apple Music catalogue still lists Loaded as his most recent release. The follow-up album should therefore be treated as announced, not yet confirmed as released.
The announcement appears in Audible Treats' September 25, 2026 press release.
Sleepy Hallow's biggest songs and Spotify streaming records
7Sleepy Hallow has released dozens of songs, but a few have become especially important to his career.
2055 remains his biggest Spotify hit, followed by popular recordings such as Deep End Freestyle, Die Young and ANXIETY.
His catalogue had accumulated more than 5.19 billion Spotify streams across lead and featured recordings by October 22, 2026.
Sleepy Hallow's most-streamed songsCumulative Spotify streams in millions, October 22, 2026.
Streaming figures are from Kworb's Sleepy Hallow song rankings, updated October 22, 2026. Weight On Me is a Sheff G-led collaboration.
Spotify Top Songs
Sleepy Hallow has released dozens of songs, but a few have become especially important to his career.
2055 remains his biggest Spotify hit, followed by popular recordings such as Deep End Freestyle, Die Young and ANXIETY.
His catalogue had accumulated more than 5.19 billion Spotify streams across lead and featured recordings by October 22, 2026.
Cumulative Spotify streams in millions, October 22, 2026.
Streaming figures are from Kworb's Sleepy Hallow song rankings, updated October 22, 2026. Weight On Me is a Sheff G-led collaboration.
Which Sleepy Hallow album has the most streams?
Album or edition
Spotify streams
Still Sleep? (Deluxe)
2.18 billion
Still Sleep?
1.98 billion
Boy Meets World
868.2 million
Sleepy for President
787.2 million
DON'T SLEEP — leading edition
377.4 million
Read This When You Wake Up
123.2 million
The Black House
94.3 million
These are individual album-edition totals, so songs appearing on both standard and deluxe versions can be counted in multiple edition totals.
You can explore additional rankings through Sleepy Hallow's Spotify album statistics.
Spotify Top Albums
Album or edition | Spotify streams |
|---|---|
Still Sleep? (Deluxe) | 2.18 billion |
Still Sleep? | 1.98 billion |
Boy Meets World | 868.2 million |
Sleepy for President | 787.2 million |
DON'T SLEEP — leading edition | 377.4 million |
Read This When You Wake Up | 123.2 million |
The Black House | 94.3 million |
These are individual album-edition totals, so songs appearing on both standard and deluxe versions can be counted in multiple edition totals.
You can explore additional rankings through Sleepy Hallow's Spotify album statistics.
Sleepy Hallow's collaborations with other rappers
Sleepy Hallow's collaborations are a big part of his catalogue, particularly his work with Sheff G and producer Great John.
He has also recorded music with artists from outside Brooklyn, showing how flexible his sound can be.
Song
Artists
Molly
Sleepy Hallow and Sheff G
Tip Toe
Sheff G and Sleepy Hallow
Breakin Bad (Okay)
Sleepy Hallow featuring Sheff G
Don't Panic
Sleepy Hallow featuring Sheff G
Baddie Betty Boop
Sleepy Hallow and Fivio Foreign
Nauseous
Sleepy Hallow and Jay Critch
Deep End Freestyle
Sleepy Hallow and Fousheé
2 Sauce (Remix)
Sleepy Hallow and Skillibeng
Die Young
Sleepy Hallow featuring 347aidan
ANXIETY
Sleepy Hallow featuring Doechii
Top Tier
Sleepy Hallow featuring Babyface Ray
Call Me
Sleepy Hallow featuring Sheff G
Fightland
50 Cent, Sheff G and Sleepy Hallow
Fine
Sleepy Hallow featuring Kyle Richh
First Day Out
Sleepy Hallow featuring Annalise Azadian
The 2025 collaboration Fightland was released with 50 Cent and Sheff G, connecting the pair with one of New York's most commercially successful rappers.
For more credits and featured performances, explore AllMusic and Apple Music.
Sleepy Hallow's collaborations are a big part of his catalogue, particularly his work with Sheff G and producer Great John.
He has also recorded music with artists from outside Brooklyn, showing how flexible his sound can be.
Song | Artists |
|---|---|
Molly | Sleepy Hallow and Sheff G |
Tip Toe | Sheff G and Sleepy Hallow |
Breakin Bad (Okay) | Sleepy Hallow featuring Sheff G |
Don't Panic | Sleepy Hallow featuring Sheff G |
Baddie Betty Boop | Sleepy Hallow and Fivio Foreign |
Nauseous | Sleepy Hallow and Jay Critch |
Deep End Freestyle | Sleepy Hallow and Fousheé |
2 Sauce (Remix) | Sleepy Hallow and Skillibeng |
Die Young | Sleepy Hallow featuring 347aidan |
ANXIETY | Sleepy Hallow featuring Doechii |
Top Tier | Sleepy Hallow featuring Babyface Ray |
Call Me | Sleepy Hallow featuring Sheff G |
Fightland | 50 Cent, Sheff G and Sleepy Hallow |
Fine | Sleepy Hallow featuring Kyle Richh |
First Day Out | Sleepy Hallow featuring Annalise Azadian |
The 2025 collaboration Fightland was released with 50 Cent and Sheff G, connecting the pair with one of New York's most commercially successful rappers.
For more credits and featured performances, explore AllMusic and Apple Music.
Sleepy Hallow's official music videos
Deep End Freestyle
The viral breakthrough that introduced Sleepy to a much wider audience.
Watch the video![ANXIETY (feat. Doechii) [Lyric Video] - Music Video by Sleepy Hallow - Apple Music](https://images.openai.com/static-rsc-4/4eLJnOJI_x4Nex4y8tqaHm938qEIcCVgR0j6IaICW6HS7w6ySXEgJTKVqU_p_i8u5ZkX10xNhbFf2D-rZ3YS7LEhINzDHt9LFcYvYPyNMdD0Gfncu3t2ei8eC11FSPRKrGq66d74jOBixMdDVthe_wxPaitnUtGVFv03XXRJqsg?purpose=inline)
ANXIETY — featuring Doechii
A popular song that combines Sleepy's melodic rap with Doechii's distinctive voice.
Find the video
Loaded (2026)
A Miami-set video accompanying his latest release, produced by Great John.
Listen and watchYou can also watch videos for Scrub, 2 Sauce, Winners In Paris, Mmm, All Mine, Upgrade My Life and Nostalgia on his YouTube channel.
Deep End Freestyle
The viral breakthrough that introduced Sleepy to a much wider audience.
Watch the videoANXIETY — featuring Doechii
A popular song that combines Sleepy's melodic rap with Doechii's distinctive voice.
Find the videoLoaded (2026)
A Miami-set video accompanying his latest release, produced by Great John.
Listen and watchYou can also watch videos for Scrub, 2 Sauce, Winners In Paris, Mmm, All Mine, Upgrade My Life and Nostalgia on his YouTube channel.
Sleepy Hallow's Instagram, TikTok, YouTube and other social profiles
5Want to follow Sleepy Hallow outside music streaming? His artist-linked Instagram, TikTok and YouTube profiles are among the places where fans can discover videos, photographs and new music.
Platform
Profile
Instagram
TikTok
YouTube
Spotify
Apple Music
SoundCloud
Audiomack
Amazon Music
Shazam
These principal social handles match his Chartmetric artist profile.
Chartmetric
Want to follow Sleepy Hallow outside music streaming? His artist-linked Instagram, TikTok and YouTube profiles are among the places where fans can discover videos, photographs and new music.
Platform | Profile |
|---|---|
TikTok | |
YouTube | |
Spotify | |
Apple Music | |
SoundCloud | |
Audiomack | |
Amazon Music | |
Shazam |
These principal social handles match his Chartmetric artist profile.
How many followers does Sleepy Hallow have?
Audience snapshot from October 26, 2026.
Spotify monthly listeners
Audience snapshot from October 26, 2026.
Spotify monthly listeners
5.6M
Spotify followers
Spotify followers
2.8M
Instagram followers
Instagram followers
911.7K
TikTok followers
TikTok followers
598.3K
YouTube subscribers
YouTube subscribers
1.6M
YouTube total views
YouTube total views
1.4B
Figures reported by Chartmetric. Social and streaming totals change regularly. Chartmetric
Sleepy Hallow photos: Early career, performances and recent appearances
Sleepy Hallow at the Fightland premiere, 2026
New York, July 21, 2026. Photography credited to Arturo Holmes/WireImage. View Getty Images collection.His Instagram account is another destination for public photographs and reels. The publication dates of individual Instagram images have not been independently confirmed here.
Sleepy Hallow at the Fightland premiere, 2026
New York, July 21, 2026. Photography credited to Arturo Holmes/WireImage. View Getty Images collection.
His Instagram account is another destination for public photographs and reels. The publication dates of individual Instagram images have not been independently confirmed here.
Is Sleepy Hallow in jail in 2026?
Sleepy Hallow has faced legal difficulties during his career, including charges connected to a New York gang-conspiracy case.
He served time in custody before returning to music activity in 2026. His July release WTW? First Day Out marked that return, followed by his August performance at Hot 97 Summer Jam.
His September 2026 publicity materials also describe his active return to recording and performances.
As of October 2026, he is no longer serving the incarceration that interrupted his career, according to the recent music-industry reporting available.
Audible Treats+1
Sleepy Hallow has faced legal difficulties during his career, including charges connected to a New York gang-conspiracy case.
He served time in custody before returning to music activity in 2026. His July release WTW? First Day Out marked that return, followed by his August performance at Hot 97 Summer Jam.
His September 2026 publicity materials also describe his active return to recording and performances.
As of October 2026, he is no longer serving the incarceration that interrupted his career, according to the recent music-industry reporting available.
Does Sleepy Hallow have a girlfriend or children?
Sleepy Hallow has kept much of his personal and romantic life away from major public interviews.
He has been publicly described as a father, with a daughter named Melina mentioned in biographical sources. However, his current relationship status has not been reliably established through recent, direct confirmation.
Although he regularly makes music about relationships and attraction, lyrics shouldn't automatically be treated as confirmed information about his private life.
For more personal updates, fans can visit his Instagram profile.
Sleepy Hallow has kept much of his personal and romantic life away from major public interviews.
He has been publicly described as a father, with a daughter named Melina mentioned in biographical sources. However, his current relationship status has not been reliably established through recent, direct confirmation.
Although he regularly makes music about relationships and attraction, lyrics shouldn't automatically be treated as confirmed information about his private life.
For more personal updates, fans can visit his Instagram profile.
What is Sleepy Hallow's net worth in 2026?
There isn't a publicly verified figure for Sleepy Hallow's personal net worth.
He has a substantial music catalogue, a major recording relationship with RCA Records, billions of streams, live-performance opportunities and a growing online audience.
His possible sources of income include recording royalties, songwriting, live shows, merchandise, licensing and brand partnerships.
However, without reliable information about his contracts, expenses, assets and debts, any exact net-worth figure would be speculation.
His streaming success is clear; the exact amount of money he personally owns is not publicly established.
There isn't a publicly verified figure for Sleepy Hallow's personal net worth.
He has a substantial music catalogue, a major recording relationship with RCA Records, billions of streams, live-performance opportunities and a growing online audience.
His possible sources of income include recording royalties, songwriting, live shows, merchandise, licensing and brand partnerships.
However, without reliable information about his contracts, expenses, assets and debts, any exact net-worth figure would be speculation.
His streaming success is clear; the exact amount of money he personally owns is not publicly established.
Sleepy Hallow concerts and live performances
10Sleepy Hallow has appeared on stages across New York and at major hip-hop events.
His return to Hot 97 Summer Jam in August 2026 was a notable milestone following his incarceration.
For future events and concert announcements, visit Sleepy Hallow on Live Nation.
Sleepy Hallow has appeared on stages across New York and at major hip-hop events.
His return to Hot 97 Summer Jam in August 2026 was a notable milestone following his incarceration.
For future events and concert announcements, visit Sleepy Hallow on Live Nation.
Frequently asked questions about Sleepy Hallow
What is Sleepy Hallow's real name?
His full name is Tegan Joshua Anthony Chambers.
How old is Sleepy Hallow in 2026?
He is 26 years old. He was born December 20, 1999.
Where is Sleepy Hallow from?
He was born in Jamaica and raised in East Flatbush, Brooklyn, New York.
Is Sleepy Hallow Jamaican?
Yes. He was born in Jamaica and moved to the United States with his family during childhood.
Is Sleepy Hallow related to Sheff G?
They are longtime friends and musical collaborators, not publicly confirmed biological brothers.
What is Sleepy Hallow's most popular song?
2055 is his most-streamed song on Spotify, having surpassed 1.13 billion streams by October 2026.
What is his latest song?
Loaded, released September 25, 2026.
Is Sleepy Hallow releasing a new album?
A follow-up titled Still Sleep? 2 was announced for around Halloween 2026. As of October 27, its release has not yet been verified.
What was his first studio album?
Still Sleep? released in June 2021.
Who produced 2055?
Great John, one of Sleepy Hallow's most important musical collaborators.
What is Sleepy Hallow's Instagram username?
His artist-linked account is @_sleepyhallow_.
Is Sleepy Hallow alive?
Yes. He is alive and has been releasing music and appearing publicly in 2026.
How many Spotify monthly listeners does Sleepy Hallow have?
Approximately 5.6 million as of October 26, 2026, according to Chart metric.
Is Sleepy Hallow still making music?
Yes. His 2026 releases include Young & Dumb, WTW? First Day Out, Fine and Loaded.
What is Sleepy Hallow's real name?
His full name is Tegan Joshua Anthony Chambers.
How old is Sleepy Hallow in 2026?
He is 26 years old. He was born December 20, 1999.
Where is Sleepy Hallow from?
He was born in Jamaica and raised in East Flatbush, Brooklyn, New York.
Is Sleepy Hallow Jamaican?
Yes. He was born in Jamaica and moved to the United States with his family during childhood.
Is Sleepy Hallow related to Sheff G?
They are longtime friends and musical collaborators, not publicly confirmed biological brothers.
What is Sleepy Hallow's most popular song?
2055 is his most-streamed song on Spotify, having surpassed 1.13 billion streams by October 2026.
What is his latest song?
Loaded, released September 25, 2026.
Is Sleepy Hallow releasing a new album?
A follow-up titled Still Sleep? 2 was announced for around Halloween 2026. As of October 27, its release has not yet been verified.
What was his first studio album?
Still Sleep? released in June 2021.
Who produced 2055?
Great John, one of Sleepy Hallow's most important musical collaborators.
What is Sleepy Hallow's Instagram username?
His artist-linked account is @_sleepyhallow_.
Is Sleepy Hallow alive?
Yes. He is alive and has been releasing music and appearing publicly in 2026.
How many Spotify monthly listeners does Sleepy Hallow have?
Approximately 5.6 million as of October 26, 2026, according to Chart metric.
Is Sleepy Hallow still making music?
Yes. His 2026 releases include Young & Dumb, WTW? First Day Out, Fine and Loaded.
More about Sleepy Hallow: Music, interviews, releases and artist news
Website
What you'll find
Songs, albums and top recordings
Full catalogue and recent singles
Official music videos
Photos, reels and announcements
Short videos and music clips
Songs and earlier recordings
Music releases and streaming
Albums and singles
Popular recordings and song discovery
Discography and biography
Music and artist images
Streaming and social audience statistics
Song streaming rankings
Album streaming rankings
Early life and career interview
Career, Brooklyn drill and personal story
New songs and reviews
Release announcements and artist publicity
Concert and event listings
Listener community and music history
Website | What you'll find |
|---|---|
Songs, albums and top recordings | |
Full catalogue and recent singles | |
Official music videos | |
Photos, reels and announcements | |
Short videos and music clips | |
Songs and earlier recordings | |
Music releases and streaming | |
Albums and singles | |
Popular recordings and song discovery | |
Discography and biography | |
Music and artist images | |
Streaming and social audience statistics | |
Song streaming rankings | |
Album streaming rankings | |
Early life and career interview | |
Career, Brooklyn drill and personal story | |
New songs and reviews | |
Release announcements and artist publicity | |
Concert and event listings | |
Listener community and music history |
Final thoughts: Why Sleepy Hallow's music stands out
Sleepy Hallow's journey is bigger than one viral song.
He was born in Jamaica, raised in Brooklyn and helped develop a sound that became an important part of modern New York hip-hop.
What makes him interesting isn't just the heavy drill beats or his deep voice. It's the way he makes serious stories sound smooth, emotional and surprisingly easy to listen to.
From the early Panic recordings with Sheff G to Deep End Freestyle, 2055, Die Young and ANXIETY, his music has steadily reached new audiences.
Now, with Loaded and his other 2026 releases, he appears focused on rebuilding his momentum and continuing the sound that made him famous.
Whether you've followed him since the early Brooklyn days or discovered him through 2055, there is plenty in his catalogue worth exploring.
Listen to Sleepy Hallow on Spotify, watch his videos on YouTube, or follow his Instagram for more of his music and public updates.
Sleepy Hallow's journey is bigger than one viral song.
He was born in Jamaica, raised in Brooklyn and helped develop a sound that became an important part of modern New York hip-hop.
What makes him interesting isn't just the heavy drill beats or his deep voice. It's the way he makes serious stories sound smooth, emotional and surprisingly easy to listen to.
From the early Panic recordings with Sheff G to Deep End Freestyle, 2055, Die Young and ANXIETY, his music has steadily reached new audiences.
Now, with Loaded and his other 2026 releases, he appears focused on rebuilding his momentum and continuing the sound that made him famous.
Whether you've followed him since the early Brooklyn days or discovered him through 2055, there is plenty in his catalogue worth exploring.
Listen to Sleepy Hallow on Spotify, watch his videos on YouTube, or follow his Instagram for more of his music and public updates.