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Sleepy Hallow

Tegan 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

1999 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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Calm 3

Single • 2025

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

Single • 2024

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Yes Freestyle (feat. Sheff G)

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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Winners In Paris

Single • 2024

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Girls Like Girls

Single • 2025

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All Mine

Single • 2024

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MARGARET

Single • 2025

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Nostalgia (feat. Gray Hawken)

Single • 2024

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Calm 3

Sleepy Hallow • 691K views

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

Sleepy Hallow • 36M views

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Mmm (Official Video)

Sleepy Hallow • 6M views

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Woke Up

Sheff G & Sleepy Hallow • 902K views

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Deep End Freestyle

Fousheé & Sleepy Hallow • 72M views

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Winners In Paris (Official Video)

Sleepy Hallow • 9.5M views

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2055 (Official Video)

Sleepy Hallow • 188M views

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Sleepy Hallow - Lowkey (Lyric Video)

Sleepy Hallow • 42M views

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1999

Sleepy Hallow • 55M views

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A N X I E T Y (feat. Doechii)

Sleepy Hallow • 4.6M 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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Laid-Back Hip Hop

Playlist • YouTube Music

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Real Talk

Playlist • YouTube Music

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Drill Team

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 • 582K views

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Boy Meets World

Playlist • Sleepy Hallow • 1.7M views

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Read This When You Wake Up

Playlist • Sleepy Hallow • 339K 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

1.92M monthly audience

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Lil Tjay

13.4M monthly audience

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DDG

4.89M monthly audience

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Sheff G

2.17M monthly audience

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Eli Fross

548K monthly audience

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NLE Choppa

17.2M monthly audience

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A Boogie Wit da Hoodie

9.27M monthly audience

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YNW Melly

17.7M monthly audience

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J.I the Prince of N.Y

1.65M monthly audience

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2KBABY

561K monthly audience