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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" received platinum certification by the Recording Industry Association of America and marked his first entry on the Billboard Hot 100. His 2021 single, "2055" peaked at number 51 on the chart. From Wikipedia (

1

2055 E

2

Weight On Me E

3

Deep End Freestyle E

4

Die Young (feat. 347aidan) E

5

1999 E

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Read This When You Wake Up

2024

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DON'T SLEEP

2019

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Boy Meets World

2023

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Still Sleep?

2021

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Sleepy Hallow Presents: Sleepy For President

2020

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Baby I

Single • 2026

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Woke Up

Single • 2025

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Don't Sleep While It's Lit - Part 1

Single • 2024

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Fightland

Single • 2025

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Girls Like Girls

Single • 2025

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All Mine

Single • 2024

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Lucky (feat. Bay Swag)

Single • 2025

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MARGARET

Single • 2025

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Calm 3

Single • 2025

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Don't Sleep While It's Lit - Part 2

Single • 2024

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Baby I

Sheff G & Sleepy Hallow • 1.5M views

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1999

Sleepy Hallow • 59M views

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Breaking Bad (Okay) (feat. Sheff G)

Sleepy Hallow • 26M views

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2055 (Official Video)

Sleepy Hallow • 201M views

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ANXIETY (Official Video) (feat. Doechii)

Sleepy Hallow • 23M views

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Molly (feat. Sheff G)

Sleepy Hallow • 40M views

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Deep End Freestyle

Fousheé & Sleepy Hallow • 77M views

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Sleepy Hallow - Lowkey (Lyric Video)

Sleepy Hallow • 45M views

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Die Young (Official Video) (feat. 347aidan)

Sleepy Hallow • 38M views

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Winners In Paris (Official Video)

Sleepy Hallow • 11M views

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Murda She Wrote (Live Session) | Vevo Ctrl

Sleepy Hallow • 879K views

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Round Midnight

Fousheé & Sleepy Hallow • 20K views

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Chicken (Live Session) | Vevo Ctrl

Sleepy Hallow • 480K views

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New York State of Mind

Playlist • YouTube Music

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Laid-Back Hip Hop

Playlist • YouTube Music

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Sad Rap

Playlist • YouTube Music

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Alt Icons

Playlist • YouTube Music

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Drill Team

Playlist • YouTube Music

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Real Talk

Playlist • YouTube Music

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Spilled Emotions

Playlist • YouTube Music

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Still Sleep? Album

Playlist • Sleepy Hallow • 3.9M views

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Sleepy For President

Playlist • Sleepy Hallow • 590K views

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Boy Meets World

Playlist • Sleepy Hallow • 1.8M views

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Read This When You Wake Up

Playlist • Sleepy Hallow • 391K views

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Don't Sleep Album

Playlist • Sleepy Hallow • 1.7M views

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The Black House

Playlist • Sleepy Hallow • 203K views

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Sleepy Hallow Official Video Playlist

Playlist • Sleepy Hallow • 1.6M views

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Jay Gwuapo

76.3K monthly audience

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Ron Suno

1.65M monthly audience

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YSN Flow

144K monthly audience

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22Gz

1.9M monthly audience

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Melvoni

61.5K monthly audience

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2KBABY

635K monthly audience

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Sleepy Hollow

489 subscribers

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Jaybandzz

55 subscribers

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JAY-Bezzy

18K subscribers

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Dthang Gz

274K monthly audience