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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

Lucky (feat. Bay Swag) E

4

1999 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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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 • 189K views

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Deep End Freestyle

Fousheé & Sleepy Hallow • 73M views

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Winners In Paris (Official Video)

Sleepy Hallow • 9.7M views

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Calm 3

Sleepy Hallow • 930K views

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

Sleepy Hallow • 36M views

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Mmm (Official Video)

Sleepy Hallow • 6.3M views

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2055 (Official Video)

Sleepy Hallow • 190M views

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ANXIETY (Official Video) (feat. Doechii)

Sleepy Hallow • 22M views

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1999

Sleepy Hallow • 56M views

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Sleepy Hallow - Lowkey (Lyric Video)

Sleepy Hallow • 42M 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 • 583K 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 • 346K 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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YSN Flow

363K monthly audience

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Jay Gwuapo

65.5K subscribers

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Jontae

66.1K subscribers

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CoachDaGhost

56.5K subscribers

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Melvoni

63K monthly audience

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Eli Fross

451K monthly audience

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DUSTY LOCANE

493K monthly audience

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MaxThaDemon

79.8K subscribers

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Bizzy Banks

267K monthly audience

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Stunna Gambino

266K monthly audience