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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

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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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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2055 (Official Video)

Sleepy Hallow • 197M views

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ANXIETY (Official Video) (feat. Doechii)

Sleepy Hallow • 23M views

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Marie

Sleepy Hallow • 6.8M views

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1999

Sleepy Hallow • 58M views

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Sleepy Hallow - Lowkey (Lyric Video)

Sleepy Hallow • 44M views

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Molly (feat. Sheff G)

Sleepy Hallow • 40M views

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

Sleepy Hallow • 38M views

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Winners In Paris (Official Video)

Sleepy Hallow • 10M views

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Deep End Freestyle

Fousheé & Sleepy Hallow • 75M views

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Mmm (Official Video)

Sleepy Hallow • 7.4M views

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Murda She Wrote (Live Session) | Vevo Ctrl

Sleepy Hallow • 875K views

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Round Midnight

Fousheé & Sleepy Hallow • 20K views

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Chicken (Live Session) | Vevo Ctrl

Sleepy Hallow • 478K 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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Spilled Emotions

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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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 • 588K 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 • 378K 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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JAY-Bezzy

17.9K subscribers

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Bizzy Banks

250K monthly audience

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Jaybandzz

55 subscribers

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DUSTY LOCANE

493K monthly audience

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MaxThaDemon

69.4K monthly audience

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CoachDaGhost

53.7K monthly audience

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Ron Suno

1.29M monthly audience

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Jay Gwuapo

73.2K monthly audience

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Melvoni

64.3K monthly audience

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Sleepy Hollow

464 subscribers