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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

Deep End Freestyle E

3

Weight On Me 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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Loaded

Single • 2026

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Baby I

Single • 2026

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Girls Like Girls

Single • 2025

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Fine (feat. Kyle Richh)

Single • 2026

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Lucky (feat. Bay Swag)

Single • 2025

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MARGARET

Single • 2025

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WTW? First Day Out

Single • 2026

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Calm 3

Single • 2025

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Young & Dumb

Single • 2026

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Woke Up

Single • 2025

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Fine (Official Video) (feat. Kyle Richh)

Sleepy Hallow • 350K views

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

Sleepy Hallow • 40M views

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Breaking Bad (Okay) (feat. Sheff G)

Sleepy Hallow • 28M views

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WTW? Freestyle/First Day Out (Official Video)

Sleepy Hallow • 793K views

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1999

Sleepy Hallow • 62M views

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Winners In Paris (Official Video)

Sleepy Hallow • 11M views

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2055 (Official Video)

Sleepy Hallow • 210M views

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Sleepy Hallow - Lowkey (Lyric Video)

Sleepy Hallow • 47M views

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Deep End Freestyle

Fousheé & Sleepy Hallow • 80M views

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ANXIETY (Official Video) (feat. Doechii)

Sleepy Hallow • 24M views

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Murda She Wrote (Live Session) | Vevo Ctrl

Sleepy Hallow • 888K views

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Round Midnight

Fousheé & Sleepy Hallow • 21K views

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Chicken (Live Session) | Vevo Ctrl

Sleepy Hallow • 483K views

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New York State of Mind

Playlist • YouTube Music

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Clout Rising: New Hip-Hop

Playlist • YouTube Music

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Real Talk

Playlist • YouTube Music

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Sad Rap

Playlist • YouTube Music

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Rap Star Status

Playlist • YouTube Music

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Drill Team

Playlist • YouTube Music

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Alt Icons

Playlist • YouTube Music

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Spilled Emotions

Playlist • YouTube Music

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Laid-Back Hip Hop

Playlist • YouTube Music

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Still Sleep? Album

Playlist • Sleepy Hallow • 4M views

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Sleepy For President

Playlist • Sleepy Hallow • 595K 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 • 417K views

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Don't Sleep Album

Playlist • Sleepy Hallow • 1.8M views

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The Black House

Playlist • Sleepy Hallow • 205K views

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Sleepy Hallow Official Video Playlist

Playlist • Sleepy Hallow • 1.6M views

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J.I the Prince of N.Y

1.28M monthly audience

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TJ Porter

79.9K subscribers

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Jay Gwuapo

83.2K monthly audience

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A Boogie wit da Hoodie

11.1M monthly audience

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26AR

101K monthly audience

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Ron Suno

762K monthly audience

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Bizzy Banks

238K monthly audience

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CoachDaGhost

51.5K monthly audience

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YNW Melly

17.4M monthly audience

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JAY-Bezzy

18K subscribers