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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

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Calm 3 E

3

Weight On Me E

4

1999 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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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 • 340K views

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

Sleepy Hallow • 36M views

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Mmm (Official Video)

Sleepy Hallow • 5.7M views

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Woke Up

Sheff G & Sleepy Hallow • 769K views

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Deep End Freestyle

Fousheé & Sleepy Hallow • 71M views

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Winners In Paris (Official Video)

Sleepy Hallow • 9.4M views

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2055 (Official Video)

Sleepy Hallow • 187M views

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

Sleepy Hallow • 4.6M views

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1999

Sleepy Hallow • 55M views

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Sleepy Hallow - Lowkey (Lyric Video)

Sleepy Hallow • 41M 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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Sleepy Hallow Official Video Playlist

Playlist • Sleepy Hallow • 1.6M views

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Don't Sleep Album

Playlist • Sleepy Hallow • 1.7M views

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Boy Meets World

Playlist • Sleepy Hallow • 1.7M views

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The Black House

Playlist • Sleepy Hallow • 203K views

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Read This When You Wake Up

Playlist • Sleepy Hallow • 332K views

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Sleepy For President

Playlist • Sleepy Hallow • 581K views

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Still Sleep? Album

Playlist • Sleepy Hallow • 3.9M views

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Fivio Foreign

3.16M monthly audience

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Kay Flock

2.18M monthly audience

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CoachDaGhost

56.3K subscribers

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SimxSantana

878K monthly audience

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Bizzy Banks

314K monthly audience

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Jay Gwuapo

65.4K subscribers

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2KBABY

896K monthly audience

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MaxThaDemon

79.6K subscribers

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DUSTY LOCANE

539K monthly audience

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Ron Suno

443K monthly audience