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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

1999 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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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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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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Girls Like Girls

Single • 2025

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All Mine

Single • 2024

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Lucky (feat. Bay Swag)

Sheff G & Sleepy Hallow • 405K views

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

Sleepy Hallow • 37M views

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Mmm (Official Video)

Sleepy Hallow • 6.7M views

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2055 (Official Video)

Sleepy Hallow • 192M views

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ANXIETY (Official Video) (feat. Doechii)

Sleepy Hallow • 22M views

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Calm 3

Sleepy Hallow • 1.2M views

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1999

Sleepy Hallow • 57M views

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Sleepy Hallow - Lowkey (Lyric Video)

Sleepy Hallow • 43M views

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Deep End Freestyle

Fousheé & Sleepy Hallow • 74M views

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Winners In Paris (Official Video)

Sleepy Hallow • 10M 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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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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Laid-Back Hip Hop

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 • 585K 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 • 358K 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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22Gz

2.03M monthly audience

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2KBABY

410K monthly audience

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A Boogie Wit da Hoodie

10.7M monthly audience

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Eli Fross

400K monthly audience

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J.I the Prince of N.Y

1.73M monthly audience

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StaySolidRocky

5.02M monthly audience

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DUSTY LOCANE

488K monthly audience

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Bizzy Banks

179K monthly audience

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Stunna Gambino

285K monthly audience

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Sheff G

2.34M monthly audience