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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

Young & Dumb E

4

Die Young (feat. 347aidan) E

5

Deep End Freestyle 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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Young & Dumb

Single • 2026

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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

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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Lucky (feat. Bay Swag)

Single • 2025

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MARGARET

Single • 2025

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Young & Dumb

Sleepy Hallow • 705K views

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Deep End Freestyle

Fousheé & Sleepy Hallow • 77M views

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Breaking Bad (Okay) (feat. Sheff G)

Sleepy Hallow • 27M views

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Baby I

Sheff G & Sleepy Hallow • 1.6M views

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1999

Sleepy Hallow • 60M views

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Winners In Paris (Official Video)

Sleepy Hallow • 11M views

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2055 (Official Video)

Sleepy Hallow • 202M views

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ANXIETY (Official Video) (feat. Doechii)

Sleepy Hallow • 24M views

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

Sleepy Hallow • 39M views

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Sleepy Hallow - Lowkey (Lyric Video)

Sleepy Hallow • 45M views

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Murda She Wrote (Live Session) | Vevo Ctrl

Sleepy Hallow • 881K 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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Alt Icons

Playlist • YouTube Music

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Sad Rap

Playlist • YouTube Music

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Laid-Back Hip Hop

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 • 591K 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 • 395K 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 • 204K 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

1.41M monthly audience

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Superstar Pride

643K monthly audience

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Ron Suno

1.45M monthly audience

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Fivio Foreign

2.43M monthly audience

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DUSTY LOCANE

492K monthly audience

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Bizzy Banks

213K monthly audience

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Stunna Gambino

296K monthly audience

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JAY-Bezzy

18K subscribers

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Calboy

1.52M monthly audience

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Jay Gwuapo

76.9K monthly audience