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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

Baby I E

3

Weight On Me E

4

Deep End Freestyle E

5

Die Young (feat. 347aidan) 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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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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Nostalgia (feat. Gray Hawken)

Single • 2024

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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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Woke Up

Single • 2025

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

Single • 2024

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Baby I

Sheff G & Sleepy Hallow • 1.2M 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 • 200M views

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ANXIETY (Official Video) (feat. Doechii)

Sleepy Hallow • 23M views

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Winners In Paris (Official Video)

Sleepy Hallow • 10M views

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Deep End Freestyle

Fousheé & Sleepy Hallow • 76M views

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Sleepy Hallow - Lowkey (Lyric Video)

Sleepy Hallow • 44M views

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

Sleepy Hallow • 38M views

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Calm 3

Sleepy Hallow • 1.9M views

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Murda She Wrote (Live Session) | Vevo Ctrl

Sleepy Hallow • 878K views

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Round Midnight

Fousheé & Sleepy Hallow • 20K views

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Chicken (Live Session) | Vevo Ctrl

Sleepy Hallow • 479K 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 • 388K 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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Kay Flock

2.58M monthly audience

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JAY-Bezzy

18K subscribers

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Dthang Gz

269K monthly audience

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J.I the Prince of N.Y

1.6M monthly audience

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Jay Gwuapo

73.3K monthly audience

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Ron Suno

1.33M monthly audience

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Scorey

347K monthly audience

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Jaybandzz

55 subscribers

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Bizzy Banks

257K monthly audience

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CoachDaGhost

53.7K monthly audience